WO2011006886A2 - Azole compounds carrying a sulfur substituent xiv - Google Patents

Azole compounds carrying a sulfur substituent xiv Download PDF

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WO2011006886A2
WO2011006886A2 PCT/EP2010/060046 EP2010060046W WO2011006886A2 WO 2011006886 A2 WO2011006886 A2 WO 2011006886A2 EP 2010060046 W EP2010060046 W EP 2010060046W WO 2011006886 A2 WO2011006886 A2 WO 2011006886A2
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formula
compounds
combination
row
case
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PCT/EP2010/060046
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WO2011006886A3 (en
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Jochen Dietz
Thomas Grote
Egon Haden
Bernd Müller
Jan Klaas Lohmann
Jens Renner
Sarah Ulmschneider
Alice GLÄTTLI
Marianna Vrettou-Schultes
Wassilios Grammenos
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Basf Se
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Publication of WO2011006886A3 publication Critical patent/WO2011006886A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/84—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Definitions

  • the present invention relates to novel azole compounds of the formulae I and Il as defined below which carry a sulfur substituent, to agricultural compositions containing them, to their use as fungicides and to intermediate compounds used in the method of producing them.
  • the control of plant diseases caused by phythopathogenic fungi is extremely important for achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer.
  • 97/44332 and WO 99/05149 describe sulfurized triazolyl derivatives.
  • the compounds are used for combating harmful fungi.
  • the present invention relates to azole compounds of the formulae I and and to agriculturally useful salts thereof
  • X is N or CH
  • R 1 is a group of formula III, a group of formula IV, a group of formula V, a group of formula Vl or a group of formula VII
  • # is the attachment point to the remainder of the molecule
  • a 1 and A 2 are independently linear Ci-C4-alkylene bridges which may be substituted by 1 , 2, 3 or 4 substituents R 9 ;
  • W is O or S
  • Y is O or S
  • R 2 is hydrogen, Ci-Cio-alkyl which may carry 1 or 2 substituents R 10 , or C1-C10- haloalkyl which may carry 1 or 2 substituents R 10
  • R 3 is selected from hydrogen, Ci-Cio-alkyl which may carry 1 or 2 substituents R 11 , Ci-Cio-haloalkyl which may carry 1 or 2 substituents R 11 , C 3 -C 8 - cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, where the cycloalkyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3 or 4 substituents R 12 , aryl and aryl-Ci-C4-alkyl, where the aryl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R 13 ; each R 4 , independently of one another, is selected from halogen, CN, nitro, Ci- C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, Ci-C4-alkoxy,
  • R 5 is phenyl which is optionally substituted with n substituents R 4 , or hetaryl which is optionally substituted with 1 , 2 or 3 substituents R 4 ; each R 6 , independently of one another, is selected from halogen, CN, nitro, Ci- C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, Ci-C4-alkoxy,
  • R 7 is selected from hydrogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl,
  • R 8 is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl,
  • # is the attachment point to the remainder of the molecule
  • R 8a is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl,
  • each R 9 is independently selected from halogen, OH, SH, NR 20 R 21 , Ci-C 4 -alkyl,
  • Ci-C 4 -haloalkyl C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 - haloalkynyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio and CrC 4 - haloalkylthio, where the aliphatic moieties in the above radicals may carry 1 , 2 or 3 substituents R 22 ; or two radicals R 9 bound on two adjacent carbon atoms, together with the car- bon atoms to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or maximum unsaturated carbocyclic ring or a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or maximum unsaturated heterocyclic ring containing 1 , 2, or 3 heteroatoms selected
  • each R 16 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy and NR 20 R 21 ;
  • R 17 is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, Ci-Cio-alkoxy, Ci- Cio-haloalkoxy, Ci-Cio-aminoalkyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, phenyl, phenoxy, phenyl-Ci-C4-alkyl, where the phenyl moiety in the 3 last- mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R 13 , a 5- or 6- membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may carry 1 , 2 or 3 substituents R 13 , and NR 20 R 21 ;
  • R 18 and R 19 are selected from Ci-Cio-alkyl, Ci-Cio- haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-C10- haloalkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, Ci-Cio-alkoxy, C1-C10- haloalkoxy, Ci-C4-alkoxy-Ci-Cio-alkyl, Ci-C4-alkoxy-Ci-Cio-alkoxy, C1-C10- alkylthio, Ci-Cio-haloalkylthio, C2-Cio-alkenyloxy, C2-Cio-alkenylthio, C2-C10- alkynyloxy, C2-Cio-alkynylthio
  • R 20 and R 21 together form a linear C4- or Cs-alkylene bridge or a group
  • each R 22 is independently selected from nitro, CN, OH, SH, COR 17 , NR 20 R 21 , C 3 - C ⁇ -cycloalkyl, Cs-C ⁇ -halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C 3 -C ⁇ - cycloaloxy, phenyl and phenoxy; each R 23 is independently selected from hydrogen and Ci-C4-alkyl;
  • Q is O or S
  • M is a metal cation equivalent or an ammonium cation of formula
  • R a , R b , R c and R d independently of each other, are selected from hydrogen, Ci-Cio-alkyl, phenyl and benzyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2 or 3 substituents independently selected from halogen, CN, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy and NR 20 R 21 ; m is 0, 1 , 2 or 3; n is 0, 1 , 2, 3, 4 or 5; p is 0, 1 , 2, 3 or 4; preferably
  • variable A 1 is not 1 ,3- propandiyl if (R 4 ) n is 2,4-Cl 2 or 4-CI;
  • variable A 1 is not 1 ,2- ethandiyl if (R 4 ) n is 2,4-Cl 2 ;
  • variable A 1 is not 1 ,2-n- pentandiyl if (R 4 ) n is 4-CF 3 , 4-F, 4-OCF 3 , 2,4-F 2 , 2-OCHF 2 , 2,4,6-Cl 3 or 2,4-Cl 2 , or n is
  • variable A 1 is not 1 ,2-n- butandiyl if (R 4 ) n is 2,4-Cl 2 ;
  • variable A 1 is not fluoro-1 ,2- ethandiyl if (R 4 ) n is 2,4-Cl 2 ;
  • (R 4 )n is 2,4-CI 2 or 4-CI; with the proviso that for R 1 being a group of formula VII the variable R 3 is not tert-butyl if (R 4 ) n is 4-Br, 4-tert-butyl, 2-CI, 3-CI, 4-F, 4-phenyl, 2-phenyl, 2,4-Cl 2 , 2-Me-4-CI, 3,4- Me 2 , 2,4,5-Cl 3 , 4-CF 3 , 4-OCF 3 , 2-OCHF 2 or 4-OMe, or n is O;
  • R 1 being a group of formula VII (R 4 ) n is not 4-CI if R 3 is benzyl, methyl, fluoro-tert-butyl or 1 ,1-di-fluoromethyl-ethyl;
  • the present invention also provides the use of azole compounds of the formulae I and Il and/or their agriculturally useful salts for controlling harmful fungi.
  • the invention further provides fungicidal compositions comprising these azole com- pounds of the formulae I and/or 11 (and/or also of the formula IX; see below) and/or their agriculturally acceptable salts and suitable carriers. Suitable agriculturally acceptable carriers are described below.
  • the compounds I and Il can exist as one or more stereoisomers.
  • the various stereoi- somers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the compounds of the invention may be present as a mixture of stereoisomers, e.g. a racemate, individual stereoisomers, or as an optically active form.
  • Suitable agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I and II.
  • suitable cations are in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammo- nium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium and sulfoxonium
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen- sulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting I or Il with an acid of the corresponding anion, prefera- bly hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • C n -Cm indicates the number of carbon atoms possible in each case in the substituent or sub- stitutent moiety in question:
  • Halogen fluorine, chlorine, bromine and iodine
  • Ci-C 3 - Alkyl is ethyl, n-propyl or isopropyl.
  • Ci-C 2 -alkyl is methyl or ethyl.
  • Ci-C4-alkyl is methyl, ethyl, propyl, isopropyl, butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1 ,1-dimethylethyl (tert-butyl).
  • Ci-C ⁇ -Alkyl is additionally also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl,
  • d-Cs-Alkyl is additionally also, for example, heptyl, octyl, 2-ethylhexyl and positional isomers thereof.
  • Ci-Cio-Alkyl is additionally also, for example, nonyl, decyl, 2-propylheptyl, 3-propylheptyl and positional isomers thereof.
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2 (Ci-C 2 -haloalkyl), 1 to 3 (Ci-C 3 -haloalkyl), 1 to 4 (Ci-C 4 -haloalkyl), 1 to 6 (Ci-C 6 -haloalkyl), 1 to 8 (CrC 8 - haloalkyl), 1 to 10 (Ci-Cio-haloalkyl) or 2 to 10 (C 2 -Cio-haloalkyl) carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above: in particular Ci-C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoro- methyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-
  • Ci-C3-Haloalkyl is additionally, for example, 1 ,1 ,1-trifluoroprop-2-yl, 3,3,3-trifluoropropyl or heptafluoropropyl.
  • CrC 4 - Haloalkyl is additionally, for example, 1-chlorobuty, 2-chlorobutyl, 3-chlorobutyl or 4- chlorobutyl.
  • Ci-Cio-Hydroxyalkyl straight-chain or branched alkyl groups having 1 to 2 (Ci-C 2 - hydroxyalkyl), 1 to 4 (Ci-C 4 -hydroxyalkyl), 2 to 4 (C 2 -C 4 -hydroxyalkyl), 1 to 6 (Ci-C 6 - hydroxyalkyl), 2 to 6 (C 2 -C 6 -hydroxyalkyl), 1 to 8 (d-Cs-hydroxyalkyl), 2 to 8 (C 2 -C 8 - hydroxyalkyl), 1 to 10 (Ci-Cio-hydroxyalkyl) or 2 to 10 (C 2 -Cio-hydroxyalkyl) carbon atoms (as mentioned above), where at least one of the hydrogen atoms is replaced by a hydroxyl group, such as in 2-hydroxyethyl or 3-hydroxypropyl.
  • C 3 -C6-cycloalkyl-Ci-C2-alkyl a Ci-C2-alkyl residue, as decribed above, wherein one of the hydrogen atoms is replaced by a C 3 -C6-cycloalkyl group.
  • Examples are cyclopro- pylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyl-1 -ethyl, cyclobutyl-1 -ethyl, cyclopentyl-1 -ethyl, cyclohexyl-1 -ethyl, cyclopropyl-2-ethyl, cyclobu- tyl-2-ethyl, cyclopentyl-2-ethyl, cyclohexyl-2-ethyl and the like.
  • C 3 -Cio-cycloalkyl-Ci-C4- alkyl is a Ci-C4-alkyl residue, as decribed above, wherein one of the hydrogen atoms is replaced by a C 3 -Cio-cycloalkyl group.
  • Examples are, apart those mentioned above for C 3 -C6-cycloalkyl-Ci-C4-alkyl, cycloheptylmethyl, cyclooctylmethyl, cyclononylmethyl, cyclodecylmethyl, cycloheptyl-1 -ethyl, cyclooctyl-1 -ethyl, cyclononyl-1 -ethyl, cyclode- cyl-1 -ethyl, cycloheptyl-2 -ethyl, cyclooctyl-2 -ethyl, cyclononyl-2 -ethyl, cyclodecylmethyl, cyclopropyl-1 -propyl, cyclopropyl-2-propyl, cyclopropyl-3-propyl, cyclobutyl-1 - propyl, cyclobutyl-2-propyl, cyclobutyl-3-prop
  • C3-C6-halocycloalkyl-Ci-C2-alkyl a Ci-C2-alkyl residue, as decribed above, wherein one of the hydrogen atoms is replaced by a Cs-C ⁇ -halocycloalkyl group.
  • Examples are 1- chlorocyclopropylmethyl, 1-chlorocyclobutylmethyl, 1-chlorocyclopentylmethyl, 1- chlorocyclohexylmethyl, 1-chlorocyclopropyl-i -ethyl, 1-chlorocyclobutyl-1 -ethyl, 1- chlorocyclopentyl-1 -ethyl, 1-chlorocyclohexyl-i -ethyl, 1-chlorocyclopropyl-2-ethyl, 1- chlorocyclobutyl-2 -ethyl, 1-chlorocyclopentyl-2-ethyl, 1-chlorocyclohexyl-2-ethyl, 2- chlorocyclopropylmethyl, 2-chlorocyclobutylmethyl, 2-chlorocyclopentylmethyl, 2- chlorocyclohexylmethyl, 2-chlorocyclopropyl-1 -ethyl, 2-chlorocyclobutyl-1 -eth
  • C3-Cio-halocycloalkyl-Ci-C4-alkyl is a Ci-C4-alkyl residue, as decribed above, wherein one of the hydrogen atoms is replaced by a C3-Cio-halocycloalkyl group.
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • C1-C3- Alkoxy is additionally, for example, n-propoxy or 1-methylethoxy (isopropoxy).
  • C1-C4- Alkoxy is additionally, for example, butoxy, 1-methylpropoxy (sec-butoxy), 2- methylpropoxy (isobutoxy) or 1 ,1-dimethylethoxy (tert-butoxy).
  • d-C ⁇ -Alkoxy is additionally, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1 ,1- dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1- dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3- dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2- trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1 -ethyl-2- methylpropoxy.
  • Ci-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2- ethylhexyloxy and positional isomers thereof. Ci-Cio-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof. C2-Cio-Alkoxy is like Ci-Cio-alkoxy with the exception of methoxy.
  • Haloalkoxy an alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine.
  • Ci-C2-Haloalkoxy is, for example, OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCHCI 2 , OCCI 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy,
  • Ci-C4-Haloalkoxy is additionally, for example,
  • Ci-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy,
  • Alkenyloxy alkenyl as mentioned above which is attached via an oxygen atom, for example C 2 -Cio-alkenyloxy, such as 1-ethenyloxy, 1-propenyloxy, 2-propenyloxy, 1- methylethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propenyloxy, 2-methyl-1-propenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 1- pentenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-1-butenyloxy, 2- methyl-1-butenyloxy, 3-methyl-1-butenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-1-butenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2- butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3
  • Haloalkenyloxy an alkenyloxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine.
  • Alkynyloxy alkynyl as mentioned above which is attached via an oxygen atom, for ex- ample C2-Cio-alkynyloxy, such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl- 2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-2-butynyloxy, 1- methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1 -ethyl-2-propynyloxy, 2-hexynyloxy, 3- hexynyloxy, 4-hexynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl-3- pentynyloxy and the like;
  • Haloalkynyloxy an alkynyloxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine.
  • Cycloalkoxy cycloalkyl as mentioned above which is attached via an oxygen atom, for example C3-Cio-cycloalkoxy or Cs-Cs-cycloalkoxy, such as cyclopropoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cyclononyloxy, cyclodecyloxy and the like;
  • Halocycloalkoxy a cycloalkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine.
  • Cycloalkenyloxy cycloalkenyl as mentioned above which is attached via an oxygen atom, for example C3-Cio-cycloalkenyloxy, Cs-Cs-cycloalkenyloxy or, preferably, Cs-C ⁇ - cycloalkenyloxy, such as cyclopent-1-enoxy, cyclopent-2-enoxy, cyclohex-1-enoxy and cyclohex-2-enoxy;
  • Alkoxyalkyl alkyl as defined above having 1 to 10, 1 to 8, 1 to 6 or 1 to 4, in particular 1 to 3, carbon atoms, in which one hydrogen atom is replaced by an alkoxy group having 1 to 8, 1 to 6, 1 to 4 or 1 to 3 carbon atoms, for example methoxymethyl, 2- methoxyethyl, ethoxymethyl, 3-methoxypropyl, 3-ethoxypropyl and the like.
  • Alkoxyalkoxy alkoxy as defined above having 1 to 10, 1 to 8, 1 to 6 or 1 to 4, in particular 1 to 3, carbon atoms, in which one hydrogen atom is replaced by an alkoxy group having 1 to 8, 1 to 6 or in particular 1 to 4 carbon atoms, for example 2-methoxyethoxy, 2-ethoxyethoxy, 3-methoxypropoxy, 3-ethoxypropoxy and the like.
  • Alkylcarbonyl group of the formula R-CO- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-Cs-alkyl, Ci-C ⁇ -alkyl, Ci-C4-alkyl, Ci-C2-alkyl or C3- C4-alkyl.
  • Examples are acetyl, propionyl and the like.
  • Examples for C3-C4-alkylcarbonyl are propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, sec-butylcarbonyl, isobutylcar- bonyl and tert-butylcarbonyl.
  • Haloalkylcarbonyl group of the formula R-CO- in which R is a haloalkyl group as defined above, for example Ci-Cio-haloalkyl, Ci-Cs-haloalkyl, Ci-C ⁇ -haloalkyl, C1-C4- haloalkyl, Ci-C2-haloalkyl or C3-C4-haloalkyl.
  • R is a haloalkyl group as defined above, for example Ci-Cio-haloalkyl, Ci-Cs-haloalkyl, Ci-C ⁇ -haloalkyl, C1-C4- haloalkyl, Ci-C2-haloalkyl or C3-C4-haloalkyl.
  • Examples are difluoromethylcarbonyl, trifluoromethylcarbonyl, 2,2-difluoroethylcarbony, 2,2,3-trifluoroethylcarbonyl and the like.
  • Alkoxycarbonyl group of the formula R-CO- in which R is an alkoxy group as defined above, for example Ci-Cio-alkoxy, Ci-Cs-alkoxy, Ci-C ⁇ -alkoxy, Ci-C4-alkoxy or C1-C2- alkoxy.
  • Ci-C4-alkoxycarbonyl are methoxycarbonyl, ethoxycarbonyl, pro- poxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, isobutoxy- carbonyl and tert-butoxycarbonyl.
  • Haloalkoxycarbonyl group of the formula R-CO- in which R is a haloalkoxy group as defined above, for example Ci-Cio-haloalkoxy, d-Cs-haloalkoxy, Ci-C6-haloalkoxy, Ci- C4-haloalkoxy or Ci-C2-haloalkoxy.
  • Ci-d-haloalkoxycarbonyl are di- fluoromethoxycarbonyl, trifluoromethoxycarbonyl, 2,2-difluoroethoxycarbony, 2,2,3- trifluoroethoxycarbonyl and the like.
  • Alkylaminocarbonyl group of the formula R-NH-CO- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, d-Cs-alkyl, Ci-C ⁇ -alkyl, Ci-d-alkyl, C1-C2- alkyl or C3-C4-alkyl.
  • Ci-d-alkylaminocarbonyl are methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocarbonyl, butylaminocar- bonyl, sec-butylaminocarbonyl, isobutylaminocarbonyl and tert-butylaminocarbonyl.
  • Dialkylaminocarbonyl group of the formula RR'N-CO- in which R and R', independently of each other, are an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-Cs- alkyl, d-Ce-alkyl, Ci-d-alkyl, Ci-C 2 -alkyl or drd-alkyl.
  • R and R' independently of each other, are an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-Cs- alkyl, d-Ce-alkyl, Ci-d-alkyl, Ci-C 2 -alkyl or drd-alkyl.
  • Examples for di-(Ci-d-alkyl)- aminocarbonyl are dimethylaminocarbonyl, diethylaminocarbonyl, dipropylaminocar- bonyl, diisopropylaminocarbonyl and dibutylaminocarbonyl.
  • Aminoalkyl group of the formula R-NH2 in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-C 8 -alkyl, d-Ce-alkyl, Ci-d-alkyl, Ci-C 2 -alkyl or C 3 -C 4 - alkyl.
  • R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-C 8 -alkyl, d-Ce-alkyl, Ci-d-alkyl, Ci-C 2 -alkyl or C 3 -C 4 - alkyl.
  • Examples are aminomethyl, 1- and 2-aminoethyl, 1-, 2- and 3-aminopropyl, 1- and 2-amino1-methylethyl, 1-, 2-, 3- and 4-aminobutyl and the like.
  • Alkylsulfonyl group of the formula R-S(O)2- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-Cs-alkyl, d-C ⁇ -alkyl, Ci-C4-alkyl or Ci-C2-alkyl.
  • Ci-C4-alkylsulfonyl examples include methylsulfonyl, ethylsulfonyl, propylsulfonyl, iso- propylsulfonyl, n-butylsulfonyl, sec-butylsulfonyl, isobutylsulfonyl and tert-butylsulfonyl.
  • Alkylthio alkyl as defined above which is attached via a sulfur atom.
  • Haloalkylthio haloalkyl as defined above which is attached via a sulfur atom.
  • Alkenylthio alkenyl as defined above which is attached via a sulfur atom.
  • Haloalkenylthio haloalkenyl as defined above which is attached via a sulfur atom.
  • Alkynylthio alkynyl as defined above which is attached via a sulfur atom.
  • Haloalkynylthio haloalkynyl as defined above which is attached via a sulfur atom.
  • Cycloalkylthio cycloalkyl as defined above which is attached via a sulfur atom.
  • Aryl is a carbocyclic aromatic monocyclic or polycyclic ring containing 6 to 16 carbon atoms as ring members. Examples are phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl and azulenyl. Preferably, aryl is phenyl or naphthyl, and especially phenyl.
  • Aryl-Ci-C4-alkyl Ci-C4-alkyl (as defined above), where a hydrogen atom is replaced by an aryl group as defined above, such as benzyl, phenethyl, naphthylmethyl, 2- naphthylethyl and the like.
  • Phenyl-Ci-C4-alkyl Ci-C4-alkyl (as defined above), where a hydrogen atom is replaced by a phenyl group, such as benzyl, phenethyl and the like.
  • Phenyl-Ci-C4-alkoxy Ci-C4-alkoxy (as defined above), where one hydrogen atom is replaced by a phenyl group, such as benzyloxy, phenethyloxy and the like.
  • phenyl is also included in this definition, but as it is also encompassed in the term aryl, it is not listed here.
  • 3-pyrrolidin-2-onyl 4-pyrrolidin-2-onyl, 5-pyrrolidin-2-onyl, 1 -pyrrolidin-3-onyl, 2-pyrrolidin-3-onyl, 4-pyrrolidin-3-onyl, 5-pyrrolidin-3-onyl, 1-pyrrolidin-2,5-dionyl,
  • a seven-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur as ring members: for example mono- and bicyclic heterocycles having 7 ring members which, in addition to carbon ring members, contain one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, for example tetra- and hexahydroazepinyl, such as
  • hexahydroazepin-1-, -2-, -3- or -4-yl tetra- and hexahydrooxepinyl, such as 2,3,4,5-tetrahydro[1 H]oxepin-2-, -3-, -A-, -5-, -6- or -7-yl,
  • 5-membered heteroaryl which is attached via nitrogen and contains one to three nitrogen atoms as ring members, such as pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, 1 ,2,3-triazol-1-yl and 1 ,2,4-triazol- 1-yl; 6-membered heteroaryl, which contains one, two or three nitrogen atoms as ring members, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, 3-pyridazinyl, 4- pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1 ,3,5-triazin-2- yl and 1 ,2,4-triazin-3-yl;
  • Linear C2-alkylene divalent unbranched chains having 2 carbon atoms, namely CH 2 CH 2 .
  • Linear C 2 - or C3-alkylene divalent unbranched chains having 2 or 3 carbon atoms, namely CH 2 CH 2 and CH 2 CH 2 CH 2 .
  • Linear C4-alkylene divalent unbranched chains having 4 carbon atoms, namely CH 2 CH 2 CH 2 CH 2 .
  • Linear Cs-alkylene divalent unbranched chains having 5 carbon atoms, namely CH 2 CH 2 CH 2 CH 2 CH 2 .
  • Linear d-Cs-alkylene divalent unbranched chains having 1 to 5 carbon atoms, namely CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 and CH 2 CH 2 CH 2 CH 2 CH 2 .
  • C 2 -C5-Alkylene divalent branched or preferably unbranched chains having 2 to 5 car- bon atoms, for example CH 2 CH 2 , -CH(CH 3 )-, CH 2 CH 2 CH 2 , CH(CH 3 )CH 2 , CH 2 CH(CH 3 ), CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 .
  • C4-C5-Alkylene divalent branched or preferably unbranched chains having 4 to 5 carbon atoms, for example CH 2 CH 2 CH 2 CH 2 or CH 2 CH 2 CH 2 CH 2 CH 2 .
  • the group -SM is more correctly spoken a group -S " M + , where M + is a metal cation equivalent or an ammonium cation as defined above.
  • a metal cation equivalent is more correctly spoken 1/a M a+ , where a is the valence of the metal and is in general 1 , 2 or 3.
  • R 17 is specifically Ci-C 4 -alkyl, such as methyl, ethyl, propyl, isopropyl, n- butyl, sec-butyl, isobutyl or tert-butyl, preferably methyl, or is Ci-C 4 -alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy, preferably methoxy, and is more specifically methyl, and in the group -S(O) 2 R 17 , R 17 is specifically methyl.
  • R 20 is hydrogen and R 21 is selected from hydrogen, Ci- C 4 -alkyl and phenyl, preferably from hydrogen and Ci-C 4 -alkyl, or the two of R 20 and R 21 are Ci-C 4 -alkyl.
  • R 8 is selected from hydrogen, CN, methyl- carbonyl, methoxycarbonyl and methyl.
  • R 8 is hydrogen.
  • M is preferably selected from an alkali metal cation, an earth alkaline metal cation equivalent, a cation equivalent of Cu, Zn, Fe or Ni or an ammonium cation of formula (NR a R b R c R d ) + , wherein one of R a , R b , R c and R d is hydrogen and three of R a , R b , R c and R d , independently of each other, are selected from Ci-Cio-alkyl.
  • M is selected from Li + , Na + , K + , /4Mg 2+ , a cation equivalent of Cu, Zn, Fe or Ni and an ammonium cation of formula (NR a R b R c R d ) + , wherein one of R a , R b , R c and R d is hydrogen and three of R a , R b , R c and R d , independently of each other, are selected from C1-C10- alkyl.
  • M is selected from Na + , K + , /4Mg 2+ , /4Cu 2+ , /4Zn 2+ , /4Fe 2+ , /4Ni 2+ , triethylammonium and trimethylammonium.
  • m is preferably 0 or 2 and more preferably 0.
  • Each R 4 and each R 6 is preferably selected from halogen, CN, nitro, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkylthio, CrC 4 - haloalkoxy, Ci-C4-haloalkylthio and phenyl, where the phenyl moiety may carry 1 , 2, 3, 4 or 5 substituents R 14 .
  • each substituent R 14 independently of one an- other, is preferably selected from halogen, nitro, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio. More preferably each R 4 and each R 6 , independently of one another, is selected from chlorine, fluorine, methyl, methoxy, trifluoromethyl and phenyl, and preferably from chlorine, fluorine and phenyl. n is preferably 0, 1 , 2 or 3 and more preferably 0, 1 or 2.
  • R 3 is preferably selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cs-cycloalkyl, C3-C5-cycloalkyl-Ci-C4-alkyl, where the cycloalkyl moiety in the two last-mentioned radicals may carry 1 , 2, 3 or 4 substituents R 12 , and phenyl, where the phenyl moiety may carry 1 , 2, 3, 4 or 5 substituents R 13 .
  • each R 12 independently of one another, is preferably selected from halogen and Ci-C4-alkyl and each R 13 , independ- ently of one another, is preferably selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and phenyl; where the phenyl moiety may carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, substituents R 14 .
  • each R 14 is preferably selected from halogen, nitro, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio.
  • R 3 is selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, 1-methyl-cycloproyl, 1-chloro-cyclopropyl, cyclopro- pylmethyl, 2-cyclopropyl-ethyl and 1-cyclopropyl-ethyl.
  • R 1 is a group of formula III and more preferably of formula III 1 ,
  • R 1 is a group of formula IN 1 , where
  • X is N
  • R 2 is hydrogen or Ci-C4-alkyl
  • R 3 , R 4 , R 8 /R 8a , n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings.
  • R 1 is a group of formula III 1 , where
  • X is N
  • R 2 is hydrogen
  • R 3 is Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 3 -C 5 -cycloalkyl, C 3 -C 5 -cycloalkyl-Ci-C 4 -alkyl, where the cycloalkyl moiety in the two last-mentioned radicals may carry 1 or 2 substituents selected from halogen and Ci-C 4 -alkyl, or phenyl, where the phenyl moiety may carry 1 , 2 or 3 substituents selected from halogen, CN, nitro, C1-C4- alkyl and Ci-C4-haloalkyl; and
  • R 4 , R 8 /R 8a , n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings.
  • R 1 is a group of formula IN 1 , where
  • X is N
  • R 2 is hydrogen
  • R 3 is tert-butyl
  • each R 4 is independently selected from methyl, F, Cl, methoxy, trifuoromethyl, trifuoro- methoxy, difuoromethyl, difuoromethoxy, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, phenoxy, 2- chlorophenoxy, 3-chlorophenoxy and 4-chlorophenoxy;
  • n 1 , 2 or 3;
  • R 8 /R 8a and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings.
  • the substituent R 4 is preferably bound in position 2, 4 or 6, if n is 2 the substituents R 4 are preferably bound in positions 2 and 4, 3 and 5, or 4 and 6, and if n is 3 the substituents R 4 are preferably bound in positions 2, 4 and 6, relative to the 1 -position, which is the attachment point of the phenyl ring of the group IN 1 to the remainder of the molecule.
  • Examples for preferred compounds I and Il of embodiment A are compounds of formulae I.A1 to I.A28 and II.A1 to II.A14, where the variables R 41 , R 42 , R 43 , R 44 and R 45 are hydrogen or have one of the general meanings or, in particular, one of the preferred meanings given above for R 4 and where the variables R 2 , R 8 and R 8a have one of the general meanings or, in particular, one of the preferred meanings given above in context with embodiment A.
  • Examples of preferred compounds are the individual compounds compiled in the tables 1 to 2492 below. Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combi- nation in which they are mentioned, a particularly preferred embodiment of the sub- stituents in question.
  • R 2 is hydrogen
  • R 2 is hydrogen
  • R 8 for a compound is as defined in any of tables 1 to 50 and R 2 is methyl
  • R 8a for a compound is as defined in any of tables 1429 to 1466 and R 2 is methyl
  • R 1 is a group of formula IV, where
  • X is N
  • a 1 is 1 ,2-ethandiyl or 1 ,3-propandiyl, each of which may be substituted by 1 , 2, 3 or
  • each R 9 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-alkoxy and C1-C4- alkoxy-Ci-C4-alkoxy; or two radicals R 9 bound to two adjacent carbon atoms, to- gether with the carbon atoms to which they are bound, form a 5- or 6-membered saturated carbocyclic ring; and
  • R 4 , R 8 /R 8a , n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings;
  • a 1 is 1 ,2-n-pentandiyl and (R 4 ) n is 4-CF 3 , 4-F, 4-OCF 3 , 2,4-F 2 , 2-OCHF 2 , 2,4,6-Cl 3 or 2,4-Cb, or n is 0;
  • R 1 is a group of formula IV, where
  • X is N
  • a 1 is -CH2CH2-, -CH2CH2CH2-, -CH 2 CH(CH 3 )-, -CH 2 CH(OCH 3 )-, or
  • each R 4 is independently selected from methyl, F, Cl, methoxy, trifuoromethyl, trifuoro- methoxy, difuoromethyl, difuoromethoxy, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl and 4-chlorophenyl; and
  • R 8 /R 8a , n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings;
  • R 1 is a group of formula IV, where
  • X is N
  • a 1 is -CH 2 CH 2 -;
  • each R 4 is independently selected from methyl, F, Cl, methoxy, trifuoromethyl, trifuoro- methoxy and phenyl;
  • R 8 /R 8a , n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings;
  • the substituent R 4 is preferably bound in position 2, 4 or 6, if n is 2 the substituents R 4 are preferably bound in positions 2 and 4, 3 and 5, or 4 and 6, and if n is 3 the substituents R 4 are preferably bound in positions 2, 4 and 6, relative to the 1 -position, which is the attachment point of the phenyl ring of the group IV to the remainder of the molecule.
  • Examples for preferred compounds I and Il of embodiment B are compounds of formulae I.B1 to I.B24 and II. B1 to II.B12, where the variables R 41 , R 42 , R 43 , R 44 and R 45 are hydrogen or have one of the general meanings or, in particular, one of the preferred meanings given above for R 4 and where the variables R 8 and R 8a have one of the general meanings or, in particular, one of the preferred meanings given above in context with embodiment B.
  • Examples of preferred compounds are the individual compounds compiled in the tables 1 to 1068 below. Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
  • R 8 for a compound is as defined in any of tables 1 to 50
  • R 8 for a compound is as defined in any of tables 1 to 50
  • R 8 for a compound is as defined in any of tables 1 to 50
  • R 8 for a compound is as defined in any of tables 1 to 50
  • R 8 for a compound is as defined in any of tables 1 to 50
  • R 8 for a compound is as defined in any of tables 1 to 50
  • R 8 for a compound is as defined in any of tables 1 to 50 Tables 451 to 500
  • R 8 for a compound is as defined in any of tables 1 to 50
  • R 8 for a compound is as defined in any of tables 1 to 50
  • R 8 for a compound is as defined in any of tables 1 to 50
  • R 8a for a compound is as defined in any of tables 613 to 650 Tables 689 to 726
  • R 8a for a compound is as defined in any of tables 613 to 650
  • R 8a for a compound is as defined in any of tables 613 to 650
  • R 8a for a compound is as defined in any of tables 613 to 650
  • R 8a for a compound is as defined in any of tables 613 to 650
  • R 8a for a compound is as defined in any of tables 613 to 650
  • R 8a for a compound is as defined in any of tables 613 to 650
  • R 8a for a compound is as defined in any of tables 613 to 650
  • R 8a for a compound is as defined in any of tables 613 to 650
  • R 1 is a group of formula V, where
  • X is CH
  • Y is O or S
  • a 2 is 1 ,2-ethandiyl or 1 ,3-propandiyl, each of which may be substituted by 1 , 2 or 3 radicals R 9 ; where each R 9 is independently selected from Ci-C4-alkyl, C1-C4- alkoxy and Ci-C4-alkoxy-Ci-C4-alkoxy; or two radicals R 9 bound to two adjacent carbon atoms, together with the carbon atoms to which they are bound, form a 5- or 6-membered saturated carbocyclic ring;
  • R 7 is hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C 3 -C5-cycloalkyl, where the cycloalkyl moiety may carry 1 , 2, 3 or 4 substituents R 12 , or phenyl, where the phenyl moiety may carry 1 , 2, 3, 4 or 5 substituents R 13 ; where
  • each R 12 independently of one another, is selected from halogen and Ci-C4-alkyl; each R 13 , independently of one another, is selected from halogen, nitro, CN, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio and phenyl; where the phenyl moiety may carry 1 , 2, 3, 4 or 5 sub- stituents R 14 ; where each R 14 , independently of one another, is selected from halogen, nitro, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy,
  • Ci-C4-alkylthio and Ci-C4-haloalkylthio are Ci-C4-alkylthio and Ci-C4-haloalkylthio.
  • R 4 , R 8 /R 8a , n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings.
  • R 1 is a group of formula V, where
  • X is CH
  • Y is O
  • a 2 is -CH2CH2-, -CH2CH2CH2-, -CH 2 CH(CH 3 )-, -CH 2 CH(OCH 3 )- or
  • R 7 is Ci-C 4 -alkyl
  • each R 4 is independently selected from methyl, F, Cl, methoxy, trifuoromethyl, trifuoro- methoxy, difuoromethyl, difuoromethoxy, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, phenoxy, 2- chlorophenoxy, 3-chlorophenoxy and 4-chlorophenoxy; and
  • R 8 /R 8a , n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings.
  • R 1 is a group of formula V, where
  • X is CH
  • Y is O
  • a 2 is -CH 2 CH 2 -;
  • R 7 is n-propyl
  • each R 4 is independently selected from methyl, F, Cl, methoxy, trifuoromethyl, trifuoro- methoxy and phenyl;
  • R 4 , R 8 /R 8a , n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings.
  • Ca and Ca.1 if n is 1 the substituent R 4 is preferably bound in position 2, 4 or 6, if n is 2 the substituents R 4 are preferably bound in positions 2 and 4, 3 and 5, or 4 and 6, and if n is 3 the substituents R 4 are preferably bound in positions 2, 4 and 6, relative to the 1 -position, which is the attachment point of the phenyl ring of the group V to the remainder of the molecule.
  • Examples for preferred compounds I and Il of embodiment C are compounds of formulae I.C1 to I.C72 and II.C1 to II.C36, where the variables R 41 , R 42 , R 43 , R 44 and R 45 are hydrogen or have one of the general meanings or, in particular, one of the preferred meanings given above for R 4 and where the variables R 7 , R 8 and R 8a have one of the general meanings or, in particular, one of the preferred meanings given above in context with embodiment C
  • Examples of preferred compounds are the individual compounds compiled in the tables 1 to 41652 below. Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
  • R 7 is hydrogen
  • R 7 is hydrogen
  • R 7 is hydrogen
  • R 8 for a compound is as defined in any of tables 1 to 50 and R 7 is methyl
  • R 8 for a compound is as defined in any of tables 1 to 50 and R 7 is ethyl
  • R 8 for a compound is as defined in any of tables 1 to 50 and R 7 is propyl
  • R 8 for a compound is as defined in any of tables 1 to 50 and R 7 is isopropyl
  • R 8 for a compound is as defined in any of tables 1 to 50 and R 7 is sec-butyl Tables 351 to 400
  • R 8 for a compound is as defined in any of tables 1 to 50 and R 7 is isobutyl
  • R 8 for a compound is as defined in any of tables 1 to 50 and R 7 is tert-butyl
  • R 8 for a compound is as defined in any of tables 1 to 50 and R 7 is phenyl
  • R 8 for a compound is as defined in any of tables 1 to 50 and R 7 is 4-methylphenyl
  • R 8 for a compound is as defined in any of tables 1 to 50 and R 7 is CN

Abstract

The present invention relates to novel azole compounds of the formulae I and Il as defined below which carry a sulfur substituent, to agricultural compositions containing them, to their use as fungicides and to intermediate compounds used in the method of producing them.

Description

Azole compounds carrying a sulfur substituent XIV Description The present invention relates to novel azole compounds of the formulae I and Il as defined below which carry a sulfur substituent, to agricultural compositions containing them, to their use as fungicides and to intermediate compounds used in the method of producing them. The control of plant diseases caused by phythopathogenic fungi is extremely important for achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. WO 96/16048, WO 97/43269, WO 97/41 107, WO97/42178, WO 97/44331 , WO
97/44332 and WO 99/05149 describe sulfurized triazolyl derivatives. The compounds are used for combating harmful fungi.
There is a continuous need for new compounds which are more effective, less costly, less toxic, environmentally safer and/or have different modes of action.
Accordingly, it is an object of the present invention to provide compounds having a better fungicidal activity and/or a better crop plant compatibility. Surprisingly, these objects are achieved by azole compounds of the general formulae I and II, defined below, and by the agriculturally acceptable salts of the compounds I and
Accordingly, the present invention relates to azole compounds of the formulae I and and to agriculturally useful salts thereof
Figure imgf000002_0001
(I) (H) wherein
X is N or CH;
R1 is a group of formula III, a group of formula IV, a group of formula V, a group of formula Vl or a group of formula VII
Figure imgf000003_0001
(III) (IV) (V)
Figure imgf000003_0002
(Vl) (VII) wherein
# is the attachment point to the remainder of the molecule;
A1 and A2 are independently linear Ci-C4-alkylene bridges which may be substituted by 1 , 2, 3 or 4 substituents R9;
W is O or S;
Y is O or S;
R2 is hydrogen, Ci-Cio-alkyl which may carry 1 or 2 substituents R10, or C1-C10- haloalkyl which may carry 1 or 2 substituents R10
R3 is selected from hydrogen, Ci-Cio-alkyl which may carry 1 or 2 substituents R11, Ci-Cio-haloalkyl which may carry 1 or 2 substituents R11, C3-C8- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, where the cycloalkyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3 or 4 substituents R12, aryl and aryl-Ci-C4-alkyl, where the aryl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R13; each R4, independently of one another, is selected from halogen, CN, nitro, Ci- C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, Ci-C4-alkoxy,
Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and phenyl which may carry 1 , 2, 3, 4 or 5 substituents R14, and, in case R1 is a group of formula III, a group of formula V, a group of formula Vl or a group of formula VII, may also be phenoxy which may carry 1 , 2, 3, 4 or 5 substituents R14;
R5 is phenyl which is optionally substituted with n substituents R4, or hetaryl which is optionally substituted with 1 , 2 or 3 substituents R4; each R6, independently of one another, is selected from halogen, CN, nitro, Ci- C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, Ci-C4-alkoxy,
Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, phenyl and phenoxy, where the phenyl moiety in the two last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R14; R7 is selected from hydrogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl,
C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, phenyl and phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R15; R8 is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl,
C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, phenyl, phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R16 and a 5- or 6-membered saturated, partially unsaturated or aromatic het- erocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may carry 1 , 2 or 3 substituents R16 or, in case m is 0, may also be selected from -C(=O)R17, -C(=S)R17, -S(O)2R17, -CN, -P(=Q)R18R19, M and a group of the formula VIII
Figure imgf000004_0001
wherein X and R1 are as defined for formulae I and II; and
# is the attachment point to the remainder of the molecule;
R8a is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl,
C3-Cio-halocycloalkyl, phenyl, phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R16, a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may carry 1 , 2 or 3 substituents R16,
-C(=O)R17, -C(=S)R17, -S(O)2R17, -CN, -P(=Q)R18R19 and M; each R9 is independently selected from halogen, OH, SH, NR20R21, Ci-C4-alkyl,
Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and CrC4- haloalkylthio, where the aliphatic moieties in the above radicals may carry 1 , 2 or 3 substituents R22; or two radicals R9 bound on two adjacent carbon atoms, together with the car- bon atoms to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or maximum unsaturated carbocyclic ring or a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or maximum unsaturated heterocyclic ring containing 1 , 2, or 3 heteroatoms selected from O, S and N as ring members, where the carbocyclic or heterocyclic ring may carry 1 , 2 or 3 substituents R16; each R10 is independently selected from nitro, CN, OH, SH, Ci-C4-alkoxy, CrC4- haloalkoxy and NR20R21; each R11 is independently selected from nitro, CN, OH, SH, Ci-C4-alkoxy, CrC4- haloalkoxy and NR20R21; each R12 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, CrC4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR20R21; each R13 is independently selected from halogen, CN, nitro, Ci-C4-alkyl, CrC4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, CrC4- haloalkylthio and phenyl, where the phenyl moiety may carry 1 , 2, 3, 4 or 5 substituents R14; each R14 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy,
Ci-C4-alkylthio, Ci-C4-haloalkylthio and NR20R21; each R15 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy,
Ci-C4-alkylthio, Ci-C4-haloalkylthio and NR20R21; each R16 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR20R21;
R17 is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, Ci-Cio-alkoxy, Ci- Cio-haloalkoxy, Ci-Cio-aminoalkyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, phenyl, phenoxy, phenyl-Ci-C4-alkyl, where the phenyl moiety in the 3 last- mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R13, a 5- or 6- membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may carry 1 , 2 or 3 substituents R13, and NR20R21;
R18 and R19, independently of each other, are selected from Ci-Cio-alkyl, Ci-Cio- haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-C10- haloalkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, Ci-Cio-alkoxy, C1-C10- haloalkoxy, Ci-C4-alkoxy-Ci-Cio-alkyl, Ci-C4-alkoxy-Ci-Cio-alkoxy, C1-C10- alkylthio, Ci-Cio-haloalkylthio, C2-Cio-alkenyloxy, C2-Cio-alkenylthio, C2-C10- alkynyloxy, C2-Cio-alkynylthio, C3-Cio-cycloalkoxy, C3-Cio-cycloalkylthio, phenyl, phenyl-Ci-C4-alkyl, phenylthio, phenyl-Ci-C4-alkoxy, and NR20R21; each R20 is independently selected from hydrogen and Ci-Cs-alkyl; each R21 is independently selected from hydrogen, Ci-Cs-alkyl, phenyl, and
phenyl-Ci-C4-alkyl; or R20 and R21 together form a linear C4- or Cs-alkylene bridge or a group
-CH2CH2OCH2CH2- or -CH2CH2NR23CH2CH2-; each R22 is independently selected from nitro, CN, OH, SH, COR17, NR20R21, C3- Cβ-cycloalkyl, Cs-Cβ-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-Cβ- cycloaloxy, phenyl and phenoxy; each R23 is independently selected from hydrogen and Ci-C4-alkyl;
Q is O or S;
M is a metal cation equivalent or an ammonium cation of formula
(NRaRbRcRd)+, wherein Ra, Rb, Rc and Rd, independently of each other, are selected from hydrogen, Ci-Cio-alkyl, phenyl and benzyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2 or 3 substituents independently selected from halogen, CN, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR20R21; m is 0, 1 , 2 or 3; n is 0, 1 , 2, 3, 4 or 5; p is 0, 1 , 2, 3 or 4; preferably
with the proviso that for R1 being a group of formula IV the variable A1 is not 1 ,3- propandiyl if (R4)n is 2,4-Cl2 or 4-CI;
with the proviso that for R1 being a group of formula IV the variable A1 is not 1 ,2- ethandiyl if (R4)n is 2,4-Cl2;
with the proviso that for R1 being a group of formula IV the variable A1 is not
1 ,2-n-propandiyl if (R4)n is 4-CI or 2,4-F2;
with the proviso that for R1 being a group of formula IV the variable A1 is not 1 ,2-n- pentandiyl if (R4)n is 4-CF3, 4-F, 4-OCF3, 2,4-F2, 2-OCHF2, 2,4,6-Cl3 or 2,4-Cl2, or n is
0;
with the proviso that for R1 being a group of formula IV the variable A1 is not 1 ,2-n- butandiyl if (R4)n is 2,4-Cl2;
with the proviso that for R1 being a group of formula IV the variable A1 is not
2,3-n-butandiyl if (R4)n is 2,4-Cl2;
with the proviso that for R1 being a group of formula IV the variable A1 is not fluoro-1 ,2- ethandiyl if (R4)n is 2,4-Cl2;
with the proviso that for R1 being a group of formula VII the variable R3 is not phenyl if
(R4)n is 2,4-CI2 or 4-CI; with the proviso that for R1 being a group of formula VII the variable R3 is not tert-butyl if (R4)n is 4-Br, 4-tert-butyl, 2-CI, 3-CI, 4-F, 4-phenyl, 2-phenyl, 2,4-Cl2, 2-Me-4-CI, 3,4- Me2, 2,4,5-Cl3, 4-CF3, 4-OCF3, 2-OCHF2 or 4-OMe, or n is O;
with the proviso that for R1 being a group of formula VII (R4)n is not 4-CI if R3 is benzyl, methyl, fluoro-tert-butyl or 1 ,1-di-fluoromethyl-ethyl;
wherein the given positions of the substituents R4 on the phenyl ring (e.g. 4-CI) are to be understood as relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule (2,4-Cl2 = 2,4-dichloro, 4-CI = 4-chloro, 4-(4-CI-OPh) = 4-(4-chlorophenoxy, 2-Me = 2-methyl, 3,4-Me2 = 3,4-dimethyl, 4-OMe = 4-methoxy).
The present invention also provides the use of azole compounds of the formulae I and Il and/or their agriculturally useful salts for controlling harmful fungi.
The invention further provides fungicidal compositions comprising these azole com- pounds of the formulae I and/or 11 (and/or also of the formula IX; see below) and/or their agriculturally acceptable salts and suitable carriers. Suitable agriculturally acceptable carriers are described below.
The compounds I and Il can exist as one or more stereoisomers. The various stereoi- somers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, e.g. a racemate, individual stereoisomers, or as an optically active form.
Compounds I and Il can be understood as positional/double bond isomers of each other, at least in case the radicals R8/R8a are identical. In case R8 (and of course also R8a) is hydrogen, the respective compounds I and Il are tautomers.
Suitable agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I and II. Thus, suitable cations are in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammo- nium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulf- oxonium. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen- sulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting I or Il with an acid of the corresponding anion, prefera- bly hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
In the definitions of the variables given in the formulae above, collective terms are used which are generally representative for the substituents in question. The term Cn-Cm indicates the number of carbon atoms possible in each case in the substituent or sub- stitutent moiety in question:
Halogen: fluorine, chlorine, bromine and iodine;
Alkyl and the alkyl moieties in alkoxy, alkoxyalkyl, alkoxyalkoxy, alkylcarbonyl, alkyl- thiocarbonyl, aminoalkyl, alkylamino, dialkylamino, alkylaminocarbonyl, dialkylamino- carbonyl, alkylthio, alkylsulfonyl and the like: saturated straight-chain or branched hydrocarbon radicals having 1 to 2 (Ci-C2-alkyl), 2 or 3 (C2-C3-alkyl), 1 to 4 (Ci-C4-alkyl), 1 to 6 (d-Ce-alkyl), 1 to 8 (Ci-C8-alkyl) or 1 to 10 (Ci-Cio-alkyl) carbon atoms. C2-C3- Alkyl is ethyl, n-propyl or isopropyl. Ci-C2-alkyl is methyl or ethyl. Ci-C4-alkyl is methyl, ethyl, propyl, isopropyl, butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1 ,1-dimethylethyl (tert-butyl). Ci-Cβ-Alkyl is additionally also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl,
1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl,
3-methylpentyl, 4-methylpentyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2- methylpropyl. d-Cs-Alkyl is additionally also, for example, heptyl, octyl, 2-ethylhexyl and positional isomers thereof. Ci-Cio-Alkyl is additionally also, for example, nonyl, decyl, 2-propylheptyl, 3-propylheptyl and positional isomers thereof.
Haloalkyl: straight-chain or branched alkyl groups having 1 to 2 (Ci-C2-haloalkyl), 1 to 3 (Ci-C3-haloalkyl), 1 to 4 (Ci-C4-haloalkyl), 1 to 6 (Ci-C6-haloalkyl), 1 to 8 (CrC8- haloalkyl), 1 to 10 (Ci-Cio-haloalkyl) or 2 to 10 (C2-Cio-haloalkyl) carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above: in particular Ci-C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoro- methyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2- fluoroethyl, 2,2,2-trichloroethyl, or pentafluoroethyl. Ci-C3-Haloalkyl is additionally, for example, 1 ,1 ,1-trifluoroprop-2-yl, 3,3,3-trifluoropropyl or heptafluoropropyl. CrC4- Haloalkyl is additionally, for example, 1-chlorobuty, 2-chlorobutyl, 3-chlorobutyl or 4- chlorobutyl.
Ci-Cio-Hydroxyalkyl: straight-chain or branched alkyl groups having 1 to 2 (Ci-C2- hydroxyalkyl), 1 to 4 (Ci-C4-hydroxyalkyl), 2 to 4 (C2-C4-hydroxyalkyl), 1 to 6 (Ci-C6- hydroxyalkyl), 2 to 6 (C2-C6-hydroxyalkyl), 1 to 8 (d-Cs-hydroxyalkyl), 2 to 8 (C2-C8- hydroxyalkyl), 1 to 10 (Ci-Cio-hydroxyalkyl) or 2 to 10 (C2-Cio-hydroxyalkyl) carbon atoms (as mentioned above), where at least one of the hydrogen atoms is replaced by a hydroxyl group, such as in 2-hydroxyethyl or 3-hydroxypropyl.
Alkenyl and the alkenyl moieties in alkenyloxy, alkenylthio, alkenylcarbonyl and the like: monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 (C2- C4-alkenyl), 2 to 6 (C2-C6-alkenyl), 2 to 8 (C2-C8-alkenyl), 3 to 8 (C3-C8-alkenyl), 2 to 10 (C2-Cio-alkenyl) or 3 to 10 (C3-Cio-alkenyl) carbon atoms and a double bond in any position, for example C2-C4-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1- methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1- propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl, or, for example, C2-C6-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3- butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2- propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl- 1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2- butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1-dimethyl-2- propenyl, 1 ,2-dimethyl-1-propenyl, 1 ,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl- 2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1- pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2- pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3- pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4- pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 ,1-dimethyl- 2-butenyl, 1 ,1-dimethyl-3-butenyl, 1 ,2-dimethyl-1-butenyl, 1 ,2-dimethyl-2-butenyl, 1 ,2- dimethyl-3-butenyl, 1 ,3-dimethyl-1-butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-3- butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3- dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1- ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3- butenyl, 1 ,1 ,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1- propenyl, 1-ethyl-2-methyl-2-propenyl and the like; Haloalkenyl and the haloalkenyl moieties in haloalkenyloxy, haloalkenylcarbonyl and the like: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 (C2- C4-haloalkenyl), 2 to 6 (C2-C6-haloalkenyl), 2 to 8 (C2-C8-haloalkenyl) or 2 to 10 (C2- Cio-haloalkenyl) carbon atoms and a double bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like;
Alkynyl and the alkynyl moieties in alkynyloxy, alkynylthio, alkynylcarbonyl and the like: straight-chain or branched hydrocarbon groups having 2 to 4 (C2-C4-alkynyl), 2 to 6 (C2-C6-alkynyl), 2 to 8 (C2-C8-alkynyl), 3 to 8 (C3-C8-alkynyl), 2 to 10 (C2-Cio-alkynyl) or 3 to 10 (C3-Cio-alkynyl) carbon atoms and one or two triple bonds in any position, for example C2-C4-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3- butynyl, or 1-methyl-2-propynyl, or, for example, C2-C6-alkynyl, such as ethynyl, 1- propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3- butynyl, 3-methyl-1-butynyl, 1 ,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2- hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1- methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3- methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1 ,1-dimethyl-2-butynyl, 1 ,1-dimethyl-3-butynyl, 1 ,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1- butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2- propynyl and the like;
Haloalkynyl and the haloalkynyl moieties in haloalkynyloxy, haloalkynylcarbonyl and the like: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 (C2- C4-haloalkynyl), 2 to 6 (C2-C6-haloalkynyl), 2 to 8 (C2-C8-haloalkynyl) or 2 to 10 (C2-Ci0- haloalkynyl) carbon atoms and one or two triple bonds in any position (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;
Cycloalkyl and the cycloalkyl moieties in cycloalkoxy, cycloalkylcarbonyl and the like; monocyclic saturated hydrocarbon groups having 3 to 6 (Cs-Cβ-cycloalkyl), 3 to 8 (C3- C8-cycloalkyl) or 3 to 10 (C3-Cio-cycloalkyl) carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl; Halocycloalkyl and the halocycloalkyl moieties in halocycloalkoxy, halocycloalkylcar- bonyl and the like: monocyclic saturated hydrocarbon groups having 3 to 6 (C3-C6- halocycloalkyl), 3 to 8 (C3-C8-halocycloalkyl) or 3 to 10 (C3-Cio-halocycloalkyl) carbon ring members (as mentioned above) in which some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;
Cycloalkenyl and the cycloalkenyl moieties in cycloalkenyloxy, cycloalkenylcarbonyl and the like; monocyclic monounsaturated hydrocarbon groups having 3 to 6 (C3-C6- cycloalkenyl), 3 to 8 (C3-C8-cycloalkenyl) or 3 to 10 (C3-Cio-cycloalkenyl) carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclohep- tenyl, cyclooctenyl, cyclononenyl and cyclodecenyl; Halocycloalkenyl and the halocycloalkenyl moieties in halocycloalkenyloxy, halo- cycloalkenylcarbonyl and the like: monocyclic monounsaturated hydrocarbon groups having 3 to 6 (C3-C6-halocycloalkenyl), 3 to 8 (C3-C8-halocycloalkenyl) or 3 to 10 (C3- Cio-halocycloalkenyl) carbon ring members (as mentioned above) in which some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, in par- ticular fluorine, chlorine and bromine;
C3-C6-cycloalkyl-Ci-C2-alkyl: a Ci-C2-alkyl residue, as decribed above, wherein one of the hydrogen atoms is replaced by a C3-C6-cycloalkyl group. Examples are cyclopro- pylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyl-1 -ethyl, cyclobutyl-1 -ethyl, cyclopentyl-1 -ethyl, cyclohexyl-1 -ethyl, cyclopropyl-2-ethyl, cyclobu- tyl-2-ethyl, cyclopentyl-2-ethyl, cyclohexyl-2-ethyl and the like. C3-Cio-cycloalkyl-Ci-C4- alkyl is a Ci-C4-alkyl residue, as decribed above, wherein one of the hydrogen atoms is replaced by a C3-Cio-cycloalkyl group. Examples are, apart those mentioned above for C3-C6-cycloalkyl-Ci-C4-alkyl, cycloheptylmethyl, cyclooctylmethyl, cyclononylmethyl, cyclodecylmethyl, cycloheptyl-1 -ethyl, cyclooctyl-1 -ethyl, cyclononyl-1 -ethyl, cyclode- cyl-1 -ethyl, cycloheptyl-2 -ethyl, cyclooctyl-2 -ethyl, cyclononyl-2 -ethyl, cyclodecylmethyl, cyclopropyl-1 -propyl, cyclopropyl-2-propyl, cyclopropyl-3-propyl, cyclobutyl-1 - propyl, cyclobutyl-2-propyl, cyclobutyl-3-propyl, cyclopentyl-1 -propyl, cyclopentyl-2- propyl, cyclopentyl-3-propyl, cyclohexyl-1 -propyl, cyclohexyl-2-propyl, cyclohexyl-3- propyl, cycloheptyl-1 -propyl, cycloheptyl-2-propyl, cycloheptyl-3-propyl, cyclooctyl-1 - propyl, cyclooctyl-2-propyl, cyclooctyl-3-propyl, cyclononyl-1 -propyl, cyclononyl-2- propyl, cyclononyl-3-propyl, cyclodecyl-1 -propyl, cyclodecyl-2-propyl, cyclodecyl-3- propy, cyclopropyl-1 -butyl, cyclopropyl-2-butyl, cyclopropyl-3-butyl, cyclopropyl-4-butyl, cyclobutyl-1 -butyl, cyclobutyl-2-butyl, cyclobutyl-3-butyl, cyclobutyl-4-butyl, cyclopentyl- 1 -butyl, cyclopentyl-2-butyl, cyclopentyl-3-butyl, cyclopentyl-4-butyl, cyclohexyl-1 -butyl, cyclohexyl-2-butyl, cyclohexyl-3-butyl, cyclohexyl-4-butyl, cycloheptyl-1 -butyl, cyclohep- tyl-2-butyl, cycloheptyl-3-butyl, cycloheptyl-4-butyl, cyclooctyl-1 -butyl, cyclooctyl-2- butyl, cyclooctyl-3-butyl, cyclooctyl-4-butyl, cyclononyl-1 -butyl, cyclononyl-2-butyl, cyc- lononyl-3-butyl, cyclononyl-4-butyl, cyclodecyl-1 -butyl, cyclodecyl-2-butyl, cyclodecyl-3- butyl, cyclodecyl-4-butyl, and the like.
C3-C6-halocycloalkyl-Ci-C2-alkyl: a Ci-C2-alkyl residue, as decribed above, wherein one of the hydrogen atoms is replaced by a Cs-Cβ-halocycloalkyl group. Examples are 1- chlorocyclopropylmethyl, 1-chlorocyclobutylmethyl, 1-chlorocyclopentylmethyl, 1- chlorocyclohexylmethyl, 1-chlorocyclopropyl-i -ethyl, 1-chlorocyclobutyl-1 -ethyl, 1- chlorocyclopentyl-1 -ethyl, 1-chlorocyclohexyl-i -ethyl, 1-chlorocyclopropyl-2-ethyl, 1- chlorocyclobutyl-2 -ethyl, 1-chlorocyclopentyl-2-ethyl, 1-chlorocyclohexyl-2-ethyl, 2- chlorocyclopropylmethyl, 2-chlorocyclobutylmethyl, 2-chlorocyclopentylmethyl, 2- chlorocyclohexylmethyl, 2-chlorocyclopropyl-1 -ethyl, 2-chlorocyclobutyl-1 -ethyl, 2- chlorocyclopentyl-1 -ethyl, 2-chlorocyclohexyl-1 -ethyl, 2-chlorocyclopropyl-2-ethyl, 2- chlorocyclobutyl-2 -ethyl, 2-chlorocyclopentyl-2-ethyl, 2-chlorocyclohexyl-2-ethyl, 1- fluorocyclopropylmethyl, 1-fluorocyclobutylmethyl, 1-fluorocyclopentylmethyl, 1- fluorocyclohexylmethyl, 1-fluorocyclopropyl-1 -ethyl, 1-fluorocyclobutyl-1 -ethyl, 1- fluorocyclopentyl-1 -ethyl, 1-fluorocyclohexyl-1 -ethyl, 1-fluorocyclopropyl-2-ethyl, 1- fluorocyclobutyl-2 -ethyl, 1-fluorocyclopentyl-2-ethyl, 1-fluorocyclohexyl-2-ethyl, 2- fluorocyclopropylmethyl, 2-fluorocyclobutylmethyl, 2-fluorocyclopentylmethyl, 2- fluorocyclohexylmethyl, 2-fluorocyclopropyl-1 -ethyl, 2-fluorocyclobutyl-1 -ethyl, 2- fluorocyclopentyl-1 -ethyl, 2-fluorocyclohexyl-1 -ethyl, 2-fluorocyclopropyl-2-ethyl, 2- fluorocyclobutyl-2-ethyl, 2-fluorocyclopentyl-2-ethyl, 2-fluorocyclohexyl-2-ethyl, and the like. C3-Cio-halocycloalkyl-Ci-C4-alkyl is a Ci-C4-alkyl residue, as decribed above, wherein one of the hydrogen atoms is replaced by a C3-Cio-halocycloalkyl group.
Alkoxy: an alkyl group attached via oxygen. Ci-C2-Alkoxy is methoxy or ethoxy. C1-C3- Alkoxy is additionally, for example, n-propoxy or 1-methylethoxy (isopropoxy). C1-C4- Alkoxy is additionally, for example, butoxy, 1-methylpropoxy (sec-butoxy), 2- methylpropoxy (isobutoxy) or 1 ,1-dimethylethoxy (tert-butoxy). d-Cβ-Alkoxy is additionally, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1 ,1- dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1- dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3- dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2- trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1 -ethyl-2- methylpropoxy. Ci-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2- ethylhexyloxy and positional isomers thereof. Ci-Cio-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof. C2-Cio-Alkoxy is like Ci-Cio-alkoxy with the exception of methoxy. Haloalkoxy: an alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine. Ci-C2-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy,
2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2- fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
2,2,2-trichloroethoxy or OC2Fs. Ci-C4-Haloalkoxy is additionally, for example,
2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,
2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy,
3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2- C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2CI)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. Ci-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy,
5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.
Alkenyloxy: alkenyl as mentioned above which is attached via an oxygen atom, for example C2-Cio-alkenyloxy, such as 1-ethenyloxy, 1-propenyloxy, 2-propenyloxy, 1- methylethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propenyloxy, 2-methyl-1-propenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 1- pentenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-1-butenyloxy, 2- methyl-1-butenyloxy, 3-methyl-1-butenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2- butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3- methyl-3-butenyl, 1 ,1-dimethyl-2-propenyloxy, 1 ,2-dimethyl-1-propenyloxy, 1 ,2- dimethyl-2-propenyloxy, 1-ethyl-1-propenyloxy, 1-ethyl-2-propenyloxy, 1-hexenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy, 1-methyl-1 -pentenyloxy,
2-methyl-1 -pentenyloxy, 3-methyl-1 -pentenyloxy, 4-methyl-1 -pentenyloxy, 1-methyl-2- pentenyloxy, 2-methyl-2-pentenyloxy, 3-methyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pentenyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3- pentenyloxy, 1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy, 4-methyl-4-pentenyloxy, 1 ,1-dimethyl-2-butenyloxy, 1 ,1-dimethyl-3-butenyloxy,
1 ,2-dimethyl-1-butenyloxy, 1 ,2-dimethyl-2-butenyloxy, 1 ,2-dimethyl-3-butenyloxy, 1 ,3-dimethyl-1-butenyloxy, 1 ,3-dimethyl-2-butenyloxy, 1 ,3-dimethyl-3-butenyloxy, 2,2-dimethyl-3-butenyloxy, 2,3-dimethyl-1 -butenyloxy, 2,3-dimethyl-2-butenyloxy, 2,3-dimethyl-3-butenyloxy, 3,3-dimethyl-1 -butenyloxy, 3,3-dimethyl-2-butenyloxy, 1 -ethyl-1 -butenyloxy, 1-ethyl-2-butenyloxy, 1-ethyl-3-butenyloxy, 2-ethyl-1-butenyloxy, 2-ethyl-2-butenyloxy, 2-ethyl-3-butenyloxy, 1 ,1 ,2-trimethyl-2-propenyloxy, 1 -ethyl-1 - methyl-2-propenyloxy, 1-ethyl-2-methyl-1-propenyloxy and 1-ethyl-2-methyl-2- propenyloxy and the like;
Haloalkenyloxy: an alkenyloxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine.
Alkynyloxy: alkynyl as mentioned above which is attached via an oxygen atom, for ex- ample C2-Cio-alkynyloxy, such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl- 2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-2-butynyloxy, 1- methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1 -ethyl-2-propynyloxy, 2-hexynyloxy, 3- hexynyloxy, 4-hexynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl-3- pentynyloxy and the like;
Haloalkynyloxy: an alkynyloxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine.
Cycloalkoxy: cycloalkyl as mentioned above which is attached via an oxygen atom, for example C3-Cio-cycloalkoxy or Cs-Cs-cycloalkoxy, such as cyclopropoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cyclononyloxy, cyclodecyloxy and the like;
Halocycloalkoxy: a cycloalkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine.
Cycloalkenyloxy: cycloalkenyl as mentioned above which is attached via an oxygen atom, for example C3-Cio-cycloalkenyloxy, Cs-Cs-cycloalkenyloxy or, preferably, Cs-Cβ- cycloalkenyloxy, such as cyclopent-1-enoxy, cyclopent-2-enoxy, cyclohex-1-enoxy and cyclohex-2-enoxy;
Alkoxyalkyl: alkyl as defined above having 1 to 10, 1 to 8, 1 to 6 or 1 to 4, in particular 1 to 3, carbon atoms, in which one hydrogen atom is replaced by an alkoxy group having 1 to 8, 1 to 6, 1 to 4 or 1 to 3 carbon atoms, for example methoxymethyl, 2- methoxyethyl, ethoxymethyl, 3-methoxypropyl, 3-ethoxypropyl and the like.
Alkoxyalkoxy: alkoxy as defined above having 1 to 10, 1 to 8, 1 to 6 or 1 to 4, in particular 1 to 3, carbon atoms, in which one hydrogen atom is replaced by an alkoxy group having 1 to 8, 1 to 6 or in particular 1 to 4 carbon atoms, for example 2-methoxyethoxy, 2-ethoxyethoxy, 3-methoxypropoxy, 3-ethoxypropoxy and the like. Alkylcarbonyl: group of the formula R-CO- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-Cs-alkyl, Ci-Cβ-alkyl, Ci-C4-alkyl, Ci-C2-alkyl or C3- C4-alkyl. Examples are acetyl, propionyl and the like. Examples for C3-C4-alkylcarbonyl are propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, sec-butylcarbonyl, isobutylcar- bonyl and tert-butylcarbonyl.
Haloalkylcarbonyl: group of the formula R-CO- in which R is a haloalkyl group as defined above, for example Ci-Cio-haloalkyl, Ci-Cs-haloalkyl, Ci-Cβ-haloalkyl, C1-C4- haloalkyl, Ci-C2-haloalkyl or C3-C4-haloalkyl. Examples are difluoromethylcarbonyl, trifluoromethylcarbonyl, 2,2-difluoroethylcarbony, 2,2,3-trifluoroethylcarbonyl and the like.
Alkoxycarbonyl: group of the formula R-CO- in which R is an alkoxy group as defined above, for example Ci-Cio-alkoxy, Ci-Cs-alkoxy, Ci-Cβ-alkoxy, Ci-C4-alkoxy or C1-C2- alkoxy. Examples for Ci-C4-alkoxycarbonyl are methoxycarbonyl, ethoxycarbonyl, pro- poxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, isobutoxy- carbonyl and tert-butoxycarbonyl. Haloalkoxycarbonyl: group of the formula R-CO- in which R is a haloalkoxy group as defined above, for example Ci-Cio-haloalkoxy, d-Cs-haloalkoxy, Ci-C6-haloalkoxy, Ci- C4-haloalkoxy or Ci-C2-haloalkoxy. Examples for Ci-d-haloalkoxycarbonyl are di- fluoromethoxycarbonyl, trifluoromethoxycarbonyl, 2,2-difluoroethoxycarbony, 2,2,3- trifluoroethoxycarbonyl and the like.
Alkylaminocarbonyl: group of the formula R-NH-CO- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, d-Cs-alkyl, Ci-Cβ-alkyl, Ci-d-alkyl, C1-C2- alkyl or C3-C4-alkyl. Examples for Ci-d-alkylaminocarbonyl are methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocarbonyl, butylaminocar- bonyl, sec-butylaminocarbonyl, isobutylaminocarbonyl and tert-butylaminocarbonyl.
Dialkylaminocarbonyl: group of the formula RR'N-CO- in which R and R', independently of each other, are an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-Cs- alkyl, d-Ce-alkyl, Ci-d-alkyl, Ci-C2-alkyl or drd-alkyl. Examples for di-(Ci-d-alkyl)- aminocarbonyl are dimethylaminocarbonyl, diethylaminocarbonyl, dipropylaminocar- bonyl, diisopropylaminocarbonyl and dibutylaminocarbonyl.
Aminoalkyl: group of the formula R-NH2 in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-C8-alkyl, d-Ce-alkyl, Ci-d-alkyl, Ci-C2-alkyl or C3-C4- alkyl. Examples are aminomethyl, 1- and 2-aminoethyl, 1-, 2- and 3-aminopropyl, 1- and 2-amino1-methylethyl, 1-, 2-, 3- and 4-aminobutyl and the like.
Alkylsulfonyl: group of the formula R-S(O)2- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-Cs-alkyl, d-Cε-alkyl, Ci-C4-alkyl or Ci-C2-alkyl. Examples for Ci-C4-alkylsulfonyl are methylsulfonyl, ethylsulfonyl, propylsulfonyl, iso- propylsulfonyl, n-butylsulfonyl, sec-butylsulfonyl, isobutylsulfonyl and tert-butylsulfonyl.
Alkylthio: alkyl as defined above which is attached via a sulfur atom.
Haloalkylthio: haloalkyl as defined above which is attached via a sulfur atom.
Alkenylthio: alkenyl as defined above which is attached via a sulfur atom. Haloalkenylthio: haloalkenyl as defined above which is attached via a sulfur atom. Alkynylthio: alkynyl as defined above which is attached via a sulfur atom.
Haloalkynylthio: haloalkynyl as defined above which is attached via a sulfur atom.
Cycloalkylthio: cycloalkyl as defined above which is attached via a sulfur atom.
Aryl is a carbocyclic aromatic monocyclic or polycyclic ring containing 6 to 16 carbon atoms as ring members. Examples are phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl and azulenyl. Preferably, aryl is phenyl or naphthyl, and especially phenyl.
Aryl-Ci-C4-alkyl: Ci-C4-alkyl (as defined above), where a hydrogen atom is replaced by an aryl group as defined above, such as benzyl, phenethyl, naphthylmethyl, 2- naphthylethyl and the like.
Phenyl-Ci-C4-alkyl: Ci-C4-alkyl (as defined above), where a hydrogen atom is replaced by a phenyl group, such as benzyl, phenethyl and the like.
Phenyl-Ci-C4-alkoxy: Ci-C4-alkoxy (as defined above), where one hydrogen atom is replaced by a phenyl group, such as benzyloxy, phenethyloxy and the like.
3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated carbocyclic radical: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclo- propenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclobutadienyl, cyclopentadienyl, cyclohexadienyl, cycloheptadienyl or cycloheptatrienyl. Formally, phenyl is also included in this definition, but as it is also encompassed in the term aryl, it is not listed here. 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms or heteroatom containing groups selected from oxygen, nitrogen (as N or NR) and sulfur (as S, SO or SO2) and optionally 1 or 2 groups selected from C(=O) and C(=S) as ring members: - three- or four-membered saturated or partially unsaturated heterocycle (hereinbe- low also referred to as heterocyclyl) which contains 1 , 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen (as N or NR) and sulfur (as S, SO or SO2) and optionally 1 or 2 groups selected from C(=O) and C(=S) as ring members: for example monocyclic saturated or partially unsaturated hetero- cycles which, in addition to carbon ring members, contain one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms and optionally 1 or 2 groups selected from C(=O) and C(=S), for example 2- oxiranyl, 2-thiiranyl, 1- or 2-aziridinyl, 1-, 2- or 3-azetidinyl, - five- or six-membered saturated or partially unsaturated heterocycle (hereinbelow also referred to as heterocyclyl) which contains 1 , 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen (as N or NR) and sulfur (as S, SO or SO2) and optionally 1 or 2 groups selected from C(=O) and C(=S) as ring members: for example monocyclic saturated or partially unsaturated heterocycles which, in addition to carbon ring members, contain one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms and optionally 1 or 2 groups selected from C(=O) and C(=S), for example
2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 3-tetrahydrofuran-2-onyl,
4-tetrahydrofuran-2-onyl, 5-tetrahydrofuran-2-onyl, 2-tetrahydrofuran-3-onyl, 4-tetrahydrofuran-3-onyl, 5-tetrahydrofuran-3-onyl, 2-tetrahydrothienyl,
3-tetrahydrothienyl, 3-tetrahydrothien-2-onyl, 4-tetrahydrothien-2-onyl,
5-tetrahydrothien-2-onyl, 2-tetrahydrothien-3-onyl, 4-tetrahydrothien-3-onyl, 5-tetrahydrothien-3-onyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 1 -pyrrolidin-2-onyl,
3-pyrrolidin-2-onyl, 4-pyrrolidin-2-onyl, 5-pyrrolidin-2-onyl, 1 -pyrrolidin-3-onyl, 2-pyrrolidin-3-onyl, 4-pyrrolidin-3-onyl, 5-pyrrolidin-3-onyl, 1-pyrrolidin-2,5-dionyl,
3-pyrrolidin-2,5-dionyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl,
3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl,
4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1 ,2,4-thiadiazolidin-3-yl,
1 ,2,4-thiadiazolidin-5-yl, 1 ,2,4-triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4-thiadiazolidin-2-yl, 1 ,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur- 3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl,
2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl,
2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl,
3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-i-yl,
3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1 -yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,
2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,
3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,
3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,
2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1 ,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl,
4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and
1 ,2,4-hexahydrotriazin-3-yl and also the corresponding -ylidene radicals; a seven-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur as ring members: for example mono- and bicyclic heterocycles having 7 ring members which, in addition to carbon ring members, contain one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, for example tetra- and hexahydroazepinyl, such as
2,3,4,5-tetrahydro[1 H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,
3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -A-, -5-, -6- or -7-yl,
2,3,4,7-tetrahydro[1 H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,
2,3,6,7-tetrahydro[1 H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,
hexahydroazepin-1-, -2-, -3- or -4-yl, tetra- and hexahydrooxepinyl, such as 2,3,4,5-tetrahydro[1 H]oxepin-2-, -3-, -A-, -5-, -6- or -7-yl,
2,3,4,7-tetrahydro[1 H]oxepin-2-, -3-, -A-, -5-, -6- or -7-yl,
2,3,6,7-tetrahydro[1 H]oxepin-2-, -3-, -A-, -5-, -6- or -7-yl,
hexahydroazepin-1-, -2-, -3- or -4-yl, tetra- and hexahydro-1 ,3-diazepinyl, tetra- and hexahydro-1 ,4-diazepinyl, tetra- and hexahydro-1 ,3-oxazepinyl,
tetra- and hexahydro-1 ,4-oxazepinyl, tetra- and hexahydro-1 ,3-dioxepinyl, tetra- and hexahydro-1 ,4-dioxepinyl and the corresponding -ylidene radicals. a five- or six-membered aromatic (= maximum unsaturated) heterocycle (= het- eroaromatic radical) which contains 1 , 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, for example 5-membered het- eroaryl which is attached via carbon and contains one to three nitrogen atoms or one or two nitrogen atoms and one sulfur or oxygen atom as ring members, such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4- isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4- pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5- thiazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl, 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thiadiazol-5-yl, 1 ,2,4-triazol-3-yl, 1 ,3,4-oxadiazol-2-yl,
1 ,3,4-thiadiazol-2-yl and 1 ,3,4-triazol-2-yl; 5-membered heteroaryl which is attached via nitrogen and contains one to three nitrogen atoms as ring members, such as pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, 1 ,2,3-triazol-1-yl and 1 ,2,4-triazol- 1-yl; 6-membered heteroaryl, which contains one, two or three nitrogen atoms as ring members, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, 3-pyridazinyl, 4- pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1 ,3,5-triazin-2- yl and 1 ,2,4-triazin-3-yl;
Linear C2-alkylene: divalent unbranched chains having 2 carbon atoms, namely CH2CH2.
Linear C2- or C3-alkylene: divalent unbranched chains having 2 or 3 carbon atoms, namely CH2CH2 and CH2CH2CH2. Linear C4-alkylene: divalent unbranched chains having 4 carbon atoms, namely CH2CH2CH2CH2.
Linear Cs-alkylene: divalent unbranched chains having 5 carbon atoms, namely CH2CH2CH2CH2CH2.
Linear d-Cs-alkylene: divalent unbranched chains having 1 to 5 carbon atoms, namely CH2, CH2CH2, CH2CH2CH2, CH2CH2CH2CH2 and CH2CH2CH2CH2CH2.
C2-C5-Alkylene: divalent branched or preferably unbranched chains having 2 to 5 car- bon atoms, for example CH2CH2, -CH(CH3)-, CH2CH2CH2, CH(CH3)CH2, CH2CH(CH3), CH2CH2CH2CH2, CH2CH2CH2CH2CH2.
C4-C5-Alkylene: divalent branched or preferably unbranched chains having 4 to 5 carbon atoms, for example CH2CH2CH2CH2 or CH2CH2CH2CH2CH2. The group -SM is more correctly spoken a group -S"M+, where M+ is a metal cation equivalent or an ammonium cation as defined above. A metal cation equivalent is more correctly spoken 1/a Ma+, where a is the valence of the metal and is in general 1 , 2 or 3. The statements made below with respect to suitable and preferred features of the compounds according to the invention, especially with respect to their substituents R1, R2, R3, R4, R5, R5a, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, Ra, Rb, Rc, Rd, A1, A2 W, Y, Q, M and the indices m and n, and to their use, are valid both per se and, in particular, in every possible combination with one another.
R17 in the groups -C(=O)R17 and -S(O)2R17 is preferably selected from Ci-C4-alkyl, Ci- C2-haloalkyl, Ci-C4-alkoxy, Ci-C2-haloalkoxy, phenyl, phenoxy and NR20R21, more preferably from Ci-C4-alkyl, Ci-C2-haloalkyl, Ci-C4-alkoxy, Ci-C2-haloalkoxy and NR20R21 and even more preferably from Ci-C4-alkyl, Ci-C4-alkoxy and NR20R21. In the group -C(=O)R17, R17 is specifically Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl, n- butyl, sec-butyl, isobutyl or tert-butyl, preferably methyl, or is Ci-C4-alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy, preferably methoxy, and is more specifically methyl, and in the group -S(O)2R17, R17 is specifically methyl. Preferably, R20 is hydrogen and R21 is selected from hydrogen, Ci- C4-alkyl and phenyl, preferably from hydrogen and Ci-C4-alkyl, or the two of R20 and R21 are Ci-C4-alkyl.
R8 is preferably selected from hydrogen, Ci-C4-alkyl, -C(=O)R17, -S(O)2R17, -CN, M and a group of the formula VIII, where R17 has one of the above general meanings or, in particular, one of the above preferred meanings and M has one of the above general meanings or, in particular, one of the below-given preferred meanings.
R8 is more preferably selected from hydrogen, Ci-C4-alkyl, C3-C4-alkylcarbonyl, CrC4- alkoxycarbonyl, -C(=O)N(H)Ci-C4-alkyl, -C(=O)N(Ci-C4-alkyl)2, Ci-C4-alkylsulfonyl, CN and a group of the formula III. In particular, R8 is selected from hydrogen, CN, methyl- carbonyl, methoxycarbonyl and methyl. Specifically, R8 is hydrogen.
M is preferably selected from an alkali metal cation, an earth alkaline metal cation equivalent, a cation equivalent of Cu, Zn, Fe or Ni or an ammonium cation of formula (NRaRbRcRd)+, wherein one of Ra, Rb, Rc and Rd is hydrogen and three of Ra, Rb, Rc and Rd, independently of each other, are selected from Ci-Cio-alkyl. More preferably, M is selected from Li+, Na+, K+, /4Mg2+, a cation equivalent of Cu, Zn, Fe or Ni and an ammonium cation of formula (NRaRbRcRd)+, wherein one of Ra, Rb, Rc and Rd is hydrogen and three of Ra, Rb, Rc and Rd, independently of each other, are selected from C1-C10- alkyl. Even more preferably, M is selected from Na+, K+, /4Mg2+, /4Cu2+, /4Zn2+, /4Fe2+, /4Ni2+, triethylammonium and trimethylammonium.
In the group of formula VIII, the variables preferably have the same meanings as in the remainder of the molecule I. Thus, the remarks made above as to preferred meanings of the radicals apply to this moiety, too.
R8a is preferably selected from hydrogen, Ci-Cio-alkyl, Ci-C4-haloalkyl, phenyl, phenyl- Ci-C4-alkyl, -C(=O)R17 and -S(O)2R17, where R17 has one of the above given general or, in particular, one of the above-given preferred meanings. More preferably, R8a is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, phenyl, benzyl, -C(=O)R17 and -S(O)2R17, where R17 has one of the above given general or, in particular, one of the above-given preferred meanings, and more preferably from hydrogen, Ci-C4-alkyl, Ci- C4-haloalkyl, -C(=O)R17 and -S(O)2R17, where R17 has one of the above given general or, in particular, one of the above-given preferred meanings. In particular, R8a is hydrogen, Ci-C4-alkyl, preferably methyl, or -C(=O)R17, more particularly hydrogen, C1-C4- alkyl, preferably methyl, methylcarbonyl or methoxycarbonyl, even more particularly hydrogen or Ci-C4-alkyl, preferably methyl, and is specifically hydrogen. If m is 1 , the oxygen atom is preferably bound via a double bond to the sulfur atom, the radical -S(O)m-R8 thus resulting in a group -S(=O)-R8. If m is 2, the two oxygen atoms are preferably both bound via a double bond to the sulfur atom, the radical -S(O)m-R8 thus resulting in a group -S(=O)2-R8. If m is 3, the radical -S(O)m-R8 is a group -S(=O)2- O-R8. m is preferably 0 or 2 and more preferably 0.
In a particularly preferred embodiment, in compounds I, m is 0 and R8 is H (or, alternatively, in compounds II, R8a is H).
Each R4 and each R6, independently of one another, is preferably selected from halogen, CN, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, CrC4- haloalkoxy, Ci-C4-haloalkylthio and phenyl, where the phenyl moiety may carry 1 , 2, 3, 4 or 5 substituents R14. In this context each substituent R14, independently of one an- other, is preferably selected from halogen, nitro, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio. More preferably each R4 and each R6, independently of one another, is selected from chlorine, fluorine, methyl, methoxy, trifluoromethyl and phenyl, and preferably from chlorine, fluorine and phenyl. n is preferably 0, 1 , 2 or 3 and more preferably 0, 1 or 2. p is preferably 0, 1 , 2 or 3 and more preferably 0, 1 or 2. R3 is preferably selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cs-cycloalkyl, C3-C5-cycloalkyl-Ci-C4-alkyl, where the cycloalkyl moiety in the two last-mentioned radicals may carry 1 , 2, 3 or 4 substituents R12, and phenyl, where the phenyl moiety may carry 1 , 2, 3, 4 or 5 substituents R13. In this context each R12, independently of one another, is preferably selected from halogen and Ci-C4-alkyl and each R13, independ- ently of one another, is preferably selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and phenyl; where the phenyl moiety may carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, substituents R14. In this context each R14, independently of one another, is preferably selected from halogen, nitro, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio.
More preferably R3 is selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, 1-methyl-cycloproyl, 1-chloro-cyclopropyl, cyclopro- pylmethyl, 2-cyclopropyl-ethyl and 1-cyclopropyl-ethyl.
In a preferred embodiment of the invention (embodiment A), R1 is a group of formula III and more preferably of formula III1,
Figure imgf000023_0001
(III1) where R2, R3, R4, and n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings.
Even more preferably (embodiment A.a), R1 is a group of formula IN1, where
X is N;
R2 is hydrogen or Ci-C4-alkyl; and
R3, R4, R8/R8a, n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings. Particularly preferably (embodiment A.a.1 ), R1 is a group of formula III1, where
X is N;
R2 is hydrogen;
R3 is Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C5-cycloalkyl, C3-C5-cycloalkyl-Ci-C4-alkyl, where the cycloalkyl moiety in the two last-mentioned radicals may carry 1 or 2 substituents selected from halogen and Ci-C4-alkyl, or phenyl, where the phenyl moiety may carry 1 , 2 or 3 substituents selected from halogen, CN, nitro, C1-C4- alkyl and Ci-C4-haloalkyl; and
R4, R8/R8a, n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings.
In particular (embodiment A.a.1.1 ), R1 is a group of formula IN1, where
X is N;
R2 is hydrogen;
R3 is tert-butyl; and
each R4 is independently selected from methyl, F, Cl, methoxy, trifuoromethyl, trifuoro- methoxy, difuoromethyl, difuoromethoxy, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, phenoxy, 2- chlorophenoxy, 3-chlorophenoxy and 4-chlorophenoxy;
n is 1 , 2 or 3; and
R8/R8a and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings. In the context of embodiments A, A.a, A.a.1 and A.a.1.1 if n is 1 the substituent R4 is preferably bound in position 2, 4 or 6, if n is 2 the substituents R4 are preferably bound in positions 2 and 4, 3 and 5, or 4 and 6, and if n is 3 the substituents R4 are preferably bound in positions 2, 4 and 6, relative to the 1 -position, which is the attachment point of the phenyl ring of the group IN1 to the remainder of the molecule.
Examples for preferred compounds I and Il of embodiment A are compounds of formulae I.A1 to I.A28 and II.A1 to II.A14, where the variables R41, R42, R43, R44 and R45 are hydrogen or have one of the general meanings or, in particular, one of the preferred meanings given above for R4 and where the variables R2, R8 and R8a have one of the general meanings or, in particular, one of the preferred meanings given above in context with embodiment A. Examples of preferred compounds are the individual compounds compiled in the tables 1 to 2492 below. Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combi- nation in which they are mentioned, a particularly preferred embodiment of the sub- stituents in question.
Figure imgf000025_0001
(I.A1 1 ) (I.A12) (I.A13) (I.A14)
Figure imgf000025_0002
Figure imgf000026_0001
Figure imgf000027_0001
I A6) (Il A7) I A8) (Il A9) (Il A10)
Figure imgf000027_0002
Table 1
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is hydrogen and R2 is hydrogen
Table 2
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is methyl and R2 is hydrogen
Table 3
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is ethyl and R2 is hydrogen
Table 4
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is propyl and R2 is hydrogen
Table 5
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isopropyl and R2 is hydrogen
Table 6
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is n-butyl and R2 is hydrogen
Table 7
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is sec-butyl and R2 is hydrogen
Table 8
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isobutyl and R2 is hydrogen
Table 9
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is tert-butyl and R2 is hydrogen
Table 10
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is phenyl and R2 is hydrogen Table 11
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is benzyl and R2 is hydrogen
Table 12
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is Li+ and R2 is hydrogen
Table 13
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is Na+ and R2 is hydrogen
Table 14
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is K+ and R2 is hydrogen
Table 15
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is YiMg2+ and R2 is hydrogen
Table 16
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is /4Cu2+ and R2 is hydrogen
Table 17
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is /4Zn2+ and R2 is hydrogen
Table 18
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is /4Fe2+ and R2 is hydrogen
Table 19
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is VzNi2+ and R2 is hydrogen
Table 20
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is NH(CH3)3+ and
R2 is hydrogen
Table 21
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is NH(C2H5)3+ and
R2 is hydrogen
Table 22
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is
NH(CH2CH2CH2)S+ and R2 is hydrogen
Table 23
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is NH(CH(CHs)2)3+ and R2 is hydrogen
Table 24
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is
NH(CH2CH2CH2CH2)S+ and R2 is hydrogen
Table 25
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is methylcarbonyl and R2 is hydrogen
Table 26
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is ethylcarbonyl and R2 is hydrogen
Table 27
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is propylcarbonyl and R2 is hydrogen
Table 28
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isopropylcar- bonyl and R2 is hydrogen
Table 29
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is phenylcarbonyl and R2 is hydrogen Table 30
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is methoxycarbonyl and R2 is hydrogen
Table 31
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is ethoxycarbonyl and R2 is hydrogen
Table 32
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is propoxycarbonyl and R2 is hydrogen
Table 33
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isopropoxycar- bonyl and R2 is hydrogen
Table 34
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is phenoxycarbonyl and R2 is hydrogen
Table 35
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is methylaminocar- bonyl and R2 is hydrogen
Table 36
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is ethylaminocar- bonyl and R2 is hydrogen
Table 37
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is propylaminocar- bonyl and R2 is hydrogen
Table 38
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isopropylamino- carbonyl and R2 is hydrogen
Table 39
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is phenylaminocar- bonyl and R2 is hydrogen
Table 40
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is methylsulfonyl and R2 is hydrogen
Table 41
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is ethylsulfonyl and R2 is hydrogen
Table 42
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is propylsulfonyl and R2 is hydrogen
Table 43
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isopropylsulfonyl and R2 is hydrogen
Table 44
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is phenylsulfonyl and R2 is hydrogen
Table 45
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is methoxysulfonyl and R2 is hydrogen
Table 46
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is ethoxysulfonyl and R2 is hydrogen
Table 47
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is propoxysulfonyl and R2 is hydrogen
Table 48
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isopropoxysul- fonyl and R2 is hydrogen Table 49
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is phenoxysulfonyl and R2 is hydrogen
Table 50
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is CN and R2 is hydrogen
Tables 51 to 100
Compounds of the formula I.A1 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50 and R2 is methyl
Tables 101 to 200
Compounds of the formula I.A2 in which the combination of R41, R42, R43, R44, R45, R2 and R8 for a compound is as defined in any of tables 1 to 100
Tables 201 to 300
Compounds of the formula I. A3 in which the combination of R41, R42, R43, R44, R45, R2 and R8 for a compound is as defined in any of tables 1 to 100
Tables 301 to 400
Compounds of the formula I.A4 in which the combination of R41, R42, R43, R44, R45, R2 and R8 for a compound is as defined in any of tables 1 to 100
Tables 401 to 500
Compounds of the formula I.A5 in which the combination of R41, R42, R43, R44, R45, R2 and R8 for a compound is as defined in any of tables 1 to 100
Tables 501 to 600
Compounds of the formula I.A6 in which the combination of R41, R42, R43, R44, R45, R2 and R8 for a compound is as defined in any of tables 1 to 100
Tables 601 to 700
Compounds of the formula I.A7 in which the combination of R41, R42, R43, R44, R45, R2 and R8 for a compound is as defined in any of tables 1 to 100
Tables 701 to 800
Compounds of the formula I.A8 in which the combination of R41, R42, R43, R44, R45, R2 and R8 for a compound is as defined in any of tables 1 to 100
Tables 801 to 900
Compounds of the formula I.A9 in which the combination of R41, R42, R43, R44, R45, R2 and R8 for a compound is as defined in any of tables 1 to 100
Tables 901 to 1000
Compounds of the formula I.A10 in which the combination of R41, R42, R43, R44, R45, R2 and R8 for a compound is as defined in any of tables 1 to 100 Tables 1001 to 1 100
Compounds of the formula I.A1 1 in which the combination of R41, R42, R43, R44, R45, R2 and R8 for a compound is as defined in any of tables 1 to 100
Tables 1101 to 1200
Compounds of the formula I.A12 in which the combination of R41, R42, R43, R44, R45, R2 and R8 for a compound is as defined in any of tables 1 to 100
Tables 1201 to 1300
Compounds of the formula I.A13 in which the combination of R41, R42, R43, R44, R45, R2 and R8 for a compound is as defined in any of tables 1 to 100
Tables 1301 to 1400
Compounds of the formula I.A14 in which the combination of R41, R42, R43, R44, R45, R2 and R8 for a compound is as defined in any of tables 1 to 100
Tables 1401 and 1402
Compounds of the formula I.A15 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Tables 1403 and 1404
Compounds of the formula I.A16 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Tables 1405 and 1406
Compounds of the formula I.A17 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Tables 1407 and 1408
Compounds of the formula I.A18 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Tables 1409 and 1410
Compounds of the formula I.A19 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Tables 1411 and 1412
Compounds of the formula I.A20 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Tables 1413 and 1414
Compounds of the formula I.A21 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Tables 1415 and 1416
Compounds of the formula I.A22 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Tables 1417 and 1418
Compounds of the formula I.A23 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Tables 1419 and 1420
Compounds of the formula I.A24 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Tables 1421 and 1422
Compounds of the formula I.A25 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Tables 1423 and 1424
Compounds of the formula I.A26 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Tables 1425 and 1426
Compounds of the formula I.A27 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Tables 1427 and 1428
Compounds of the formula I.A28 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R2 is as defined in table 1 or table 51
Table 1429
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is hydrogen and R2 is hydrogen
Table 1430
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is methyl and R2 is hydrogen Table 1431
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is ethyl and R2 is hydrogen
Table 1432
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is propyl and R2 is hydrogen
Table 1433
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isopropyl and R2 is hydrogen
Table 1434
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is n-butyl and R2 is hydrogen
Table 1435
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is sec-butyl and R2 is hydrogen
Table 1436
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isobutyl and R2 is hydrogen
Table 1437
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is tert-butyl and R2 is hydrogen
Table 1438
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is phenyl and R2 is hydrogen
Table 1439
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is 4-methylphenyl and R2 is hydrogen
Table 1440
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is benzyl and R2 is hydrogen
Table 1441
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is methylcarbonyl and R2 is hydrogen
Table 1442
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is ethylcarbonyl and R2 is hydrogen
Table 1443
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is propylcarbonyl and R2 is hydrogen
Table 1444
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isopropylcar- bonyl and R2 is hydrogen
Table 1445
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is phenylcarbonyl and R2 is hydrogen
Table 1446
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is methoxycar- bonyl and R2 is hydrogen
Table 1447
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is ethoxycarbonyl and R2 is hydrogen
Table 1448
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is propoxycar- bonyl and R2 is hydrogen
Table 1449
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isopropoxycar- bonyl and R2 is hydrogen Table 1450
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is phenoxycar- bonyl and R2 is hydrogen
Table 1451
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is methylamino- carbonyl and R2 is hydrogen
Table 1452
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is ethylaminocar- bonyl and R2 is hydrogen
Table 1453
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is propylamino- carbonyl and R2 is hydrogen
Table 1454
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isopropylamino- carbonyl and R2 is hydrogen
Table 1455
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is phenylamino- carbonyl and R2 is hydrogen
Table 1456
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is methylsulfonyl and R2 is hydrogen
Table 1457
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is ethylsulfonyl and R2 is hydrogen
Table 1458
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is propylsulfonyl and R2 is hydrogen
Table 1459
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isopropylsul- fonyl and R2 is hydrogen
Table 1460
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is phenylsulfonyl and R2 is hydrogen
Table 1461
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is methoxysulfonyl and R2 is hydrogen
Table 1462
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is ethoxysulfonyl and R2 is hydrogen
Table 1463
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is propoxysulfonyl and R2 is hydrogen
Table 1464
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isopropoxysul- fonyl and R2 is hydrogen
Table 1465
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is phenoxysulfonyl and R2 is hydrogen
Table 1466
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is CN and R2 is hydrogen
Tables 1467 to 1504
Compounds of the formula II.A1 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 1429 to 1466 and R2 is methyl
Tables 1505 to 1580
Compounds of the formula II.A2 in which the combination of R41, R42, R43, R44, R45, R2 and R8a for a compound is as defined in any of tables 1429 to 1504
Tables 1581 to 1656
Compounds of the formula 11. A3 in which the combination of R41, R42, R43, R44, R45, R2 and R8a for a compound is as defined in any of tables 1429 to 1504 Tables 1657 to 1732
Compounds of the formula II.A4 in which the combination of R41, R42, R43, R44, R45, R2 and R8a for a compound is as defined in any of tables 1429 to 1504
Tables 1733 to 1808
Compounds of the formula II.A5 in which the combination of R41, R42, R43, R44, R45, R2 and R8a for a compound is as defined in any of tables 1429 to 1504
Tables 1809 to 1884
Compounds of the formula II.A6 in which the combination of R41, R42, R43, R44, R45, R2 and R8a for a compound is as defined in any of tables 1429 to 1504
Tables 1885 to 1960
Compounds of the formula II.A7 in which the combination of R41, R42, R43, R44, R45, R2 and R8a for a compound is as defined in any of tables 1429 to 1504
Tables 1961 to 2036
Compounds of the formula II.A8 in which the combination of R41, R42, R43, R44, R45, R2 and R8a for a compound is as defined in any of tables 1429 to 1504
Tables 2037 to 2112
Compounds of the formula II.A9 in which the combination of R41, R42, R43, R44, R45, R2 and R8a for a compound is as defined in any of tables 1429 to 1504
Tables 21 13 to 2188
Compounds of the formula II.A10 in which the combination of R41, R42, R43, R44, R45, R2 and R8a for a compound is as defined in any of tables 1429 to 1504
Tables 2189 to 2264
Compounds of the formula II.A11 in which the combination of R41, R42, R43, R44, R45, R2 and R8a for a compound is as defined in any of tables 1429 to 1504
Tables 2265 to 2340
Compounds of the formula II.A12 in which the combination of R41, R42, R43, R44, R45, R2 and R8a for a compound is as defined in any of tables 1429 to 1504
Tables 2341 to 2416
Compounds of the formula II.A13 in which the combination of R41, R42, R43, R44, R45, R2 and R8a for a compound is as defined in any of tables 1429 to 1504
Tables 2417 to 2492
Compounds of the formula II.A14 in which the combination of R41, R42, R43, R44, R45, R2 and R8a for a compound is as defined in any of tables 1429 to 1504 Table A
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000055_0001
Figure imgf000056_0001
Figure imgf000057_0001
Figure imgf000058_0001
Figure imgf000059_0001
Figure imgf000060_0001
Figure imgf000061_0001
In another preferred embodiment of the invention (embodiment B), R1 is a group of formula IV, where
X is N;
A1 is 1 ,2-ethandiyl or 1 ,3-propandiyl, each of which may be substituted by 1 , 2, 3 or
4 radicals R9; where
each R9 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-alkoxy and C1-C4- alkoxy-Ci-C4-alkoxy; or two radicals R9 bound to two adjacent carbon atoms, to- gether with the carbon atoms to which they are bound, form a 5- or 6-membered saturated carbocyclic ring; and
R4, R8/R8a, n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings;
except for compounds wherein A1 is 1 ,3-propandiyl and (R4)n is 2,4-Cb or 4-CI;
except for compounds wherein A1 is 1 ,2-ethandiyl and (R4)n is 2,4-Cb;
except for compounds wherein A1 is 1 ,2-propandiyl and (R4)n is 4-CI or 2,4-F2;
except for compounds wherein A1 is 1 ,2-n-pentandiyl and (R4)n is 4-CF3, 4-F, 4-OCF3, 2,4-F2, 2-OCHF2, 2,4,6-Cl3 or 2,4-Cb, or n is 0;
except for compounds wherein A1 is 1 ,2-n-butandiyl and (R4)n is 2,4-Cb; and except for compounds wherein A1 is 2,3-n-butandiyl and (R4)n is 2,4-Cb;
wherein the given positions of the substituents R4 on the phenyl ring (e.g. 4-CI) are to be understood as relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule (2,4-Cl2 = 2,4-dichloro, 4-CI = 4-chloro, 4-(4-CI-OPh) = 4-(4-chlorophenoxy)).
More preferably (embodiment B. a), R1 is a group of formula IV, where
X is N;
A1 is -CH2CH2-, -CH2CH2CH2-, -CH2CH(CH3)-, -CH2CH(OCH3)-, or
-CH2CH2CH(CH3)-;
each R4 is independently selected from methyl, F, Cl, methoxy, trifuoromethyl, trifuoro- methoxy, difuoromethyl, difuoromethoxy, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl and 4-chlorophenyl; and
R8/R8a, n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings;
except for compounds wherein A1 is 1 ,3-propandiyl and (R4)n is 2,4-Cl2 or 4-CI;
except for compounds wherein A1 is 1 ,2-ethandiyl and (R4)n is 2,4-Cl2; and except for compounds wherein A1 is 1 ,2-propandiyl and (R4)n is 4-CI or 2,4-F2.
Even more preferably (embodiment B.a.1 ), R1 is a group of formula IV, where
X is N;
A1 is -CH2CH2-;
each R4 is independently selected from methyl, F, Cl, methoxy, trifuoromethyl, trifuoro- methoxy and phenyl; and
R8/R8a, n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings;
except for compounds wherein A1 is 1 ,2-ethandiyl and (R4)n is 2,4-Cl2.
In the context of embodiments B, B. a and B.a.1 if n is 1 the substituent R4 is preferably bound in position 2, 4 or 6, if n is 2 the substituents R4 are preferably bound in positions 2 and 4, 3 and 5, or 4 and 6, and if n is 3 the substituents R4 are preferably bound in positions 2, 4 and 6, relative to the 1 -position, which is the attachment point of the phenyl ring of the group IV to the remainder of the molecule.
Examples for preferred compounds I and Il of embodiment B are compounds of formulae I.B1 to I.B24 and II. B1 to II.B12, where the variables R41, R42, R43, R44 and R45 are hydrogen or have one of the general meanings or, in particular, one of the preferred meanings given above for R4 and where the variables R8 and R8a have one of the general meanings or, in particular, one of the preferred meanings given above in context with embodiment B. Examples of preferred compounds are the individual compounds compiled in the tables 1 to 1068 below. Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
Figure imgf000062_0001
Figure imgf000063_0001
Figure imgf000064_0001
Figure imgf000065_0001
Table 1
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is hydrogen
Table 2
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is methyl Table 3
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is ethyl Table 4
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is propyl
Table 5
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isopropyl
Table 6
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is n-butyl Table 7
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is sec-butyl
Table 8
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isobutyl
Table 9
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is tert-butyl
Table 10
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is phenyl
Table 11
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is benzyl Table 12
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is Li+
Table 13
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is Na+
Table 14
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is K+
Table 15
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is YiMg2+
Table 16
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is /4Cu2+ Table 17
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is /4Zn2+
Table 18
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is YiFe2+
Table 19
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is !4Ni2+ Table 20
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is NH(CH3)3+
Table 21
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is NH(C2H5)3+
Table 22
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is
Figure imgf000067_0001
Table 23
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is
Figure imgf000067_0002
Table 24
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is
Figure imgf000067_0003
Table 25
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is methylcar- bonyl
Table 26
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is ethylcarbonyl Table 27
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is propylcar- bonyl Table 28
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isopropylcar- bonyl
Table 29
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is phenylcar- bonyl
Table 30
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is methoxycar- bonyl
Table 31
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is ethoxycar- bonyl
Table 32
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is propoxycar- bonyl
Table 33
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isopropoxy- carbonyl
Table 34
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is phenoxycar- bonyl
Table 35
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is methylami- nocarbonyl
Table 36
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is ethylamino- carbonyl
Table 37
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is propylamino- carbonyl
Table 38
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isopro- pylaminocarbonyl
Table 39
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is phenylami- nocarbonyl
Table 40
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is methylsul- fonyl
Table 41
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is ethylsulfonyl
Table 42
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is propylsul- fonyl
Table 43
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isopropylsul- fonyl
Table 44
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is phenylsul- fonyl
Table 45
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is methoxysul- fonyl
Table 46
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is ethoxysul- fonyl
Table 47
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is propoxysul- fonyl
Table 48
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isopropoxy- sulfonyl
Table 49
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is phenoxysul- fonyl
Table 50
Compounds of the formula I.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is CN
Tables 51 to 100
Compounds of the formula I.B2 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 101 to 150
Compounds of the formula I.B3 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 151 to 200
Compounds of the formula I.B4 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 201 to 250
Compounds of the formula I.B5 in which the combination of R41, R42, R43, R44, R45 and R8 for a compound is as defined in any of tables 1 to 50
Tables 251 to 300
Compounds of the formula I.B6 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 301 to 350
Compounds of the formula I.B7 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 351 to 400
Compounds of the formula I.B8 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 401 to 450
Compounds of the formula I.B9 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50 Tables 451 to 500
Compounds of the formula I.B10 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 501 to 550
Compounds of the formula I.B1 1 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 551 to 600
Compounds of the formula I.B12 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Table 601
Compounds of the formula I.B13 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 602
Compounds of the formula I.B14 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 603
Compounds of the formula I.B15 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 604
Compounds of the formula I.B16 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 605
Compounds of the formula I.B17 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 606
Compounds of the formula I.B18 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 607
Compounds of the formula I.B19 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 608
Compounds of the formula I.B20 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 609
Compounds of the formula I.B21 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A Table 610
Compounds of the formula I.B22 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 61 1
Compounds of the formula I.B23 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 612
Compounds of the formula I.B24 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 613
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is hydrogen
Table 614
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is methyl
Table 615
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is ethyl Table 616
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is propyl
Table 617
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isopropyl
Table 618
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is n-butyl
Table 619
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is sec-butyl
Table 620
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isobutyl Table 621
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is tert-butyl Table 622
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is phenyl
Table 623
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is 4- methylphenyl
Table 624
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is benzyl
Table 625
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is methylcar- bonyl
Table 626
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is ethylcar- bonyl
Table 627
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is propylcar- bonyl
Table 628
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isopropyl- carbonyl
Table 629
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is phenylcar- bonyl
Table 630
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is methoxy- carbonyl
Table 631
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is ethoxycar- bonyl Table 632
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is propoxycar- bonyl
Table 633
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isopropoxy- carbonyl
Table 634
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is phenoxy- carbonyl
Table 635
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is methylami- nocarbonyl
Table 636
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is ethylamino- carbonyl
Table 637
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is propylami- nocarbonyl
Table 638
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isopro- pylaminocarbonyl
Table 639
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is phenylami- nocarbonyl
Table 640
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is methylsul- fonyl
Table 641
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is ethylsulfonyl Table 642
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is propylsul- fonyl
Table 643
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isopropylsul- fonyl
Table 644
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is phenylsul- fonyl
Table 645
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is methoxysul- fonyl
Table 646
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is ethoxysul- fonyl
Table 647
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is propoxysul- fonyl
Table 648
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isopropoxy- sulfonyl
Table 649
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is phenoxysul- fonyl
Table 650
Compounds of the formula II.B1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is CN
Tables 651 to 688
Compounds of the formula II.B2 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 613 to 650 Tables 689 to 726
Compounds of the formula II.B3 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 613 to 650
Tables 727 to 764
Compounds of the formula II.B4 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 613 to 650
Tables 765 to 802
Compounds of the formula II.B5 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 613 to 650
Tables 803 to 840
Compounds of the formula II.B6 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 613 to 650
Tables 841 to 878
Compounds of the formula II.B7 in which the combination of R41, R42, R43, R44, R45 and R8a for a compound is as defined in any of tables 613 to 650
Tables 879 to 916
Compounds of the formula II.B8 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 613 to 650
Tables 917 to 954
Compounds of the formula II.B9 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 613 to 650
Tables 955 to 992
Compounds of the formula II.B10 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 613 to 650
Tables 993 to 1030
Compounds of the formula II.B11 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 613 to 650
Tables 1031 to 1068
Compounds of the formula II.B12 in which the combination of R41, R42, R43, R44, R45 and R8a for a compound is as defined in any of tables 613 to 650
In another preferred embodiment of the invention (embodiment C), R1 is a group of formula V, where
X is CH;
Y is O or S;
A2 is 1 ,2-ethandiyl or 1 ,3-propandiyl, each of which may be substituted by 1 , 2 or 3 radicals R9; where each R9 is independently selected from Ci-C4-alkyl, C1-C4- alkoxy and Ci-C4-alkoxy-Ci-C4-alkoxy; or two radicals R9 bound to two adjacent carbon atoms, together with the carbon atoms to which they are bound, form a 5- or 6-membered saturated carbocyclic ring;
R7 is hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C5-cycloalkyl, where the cycloalkyl moiety may carry 1 , 2, 3 or 4 substituents R12, or phenyl, where the phenyl moiety may carry 1 , 2, 3, 4 or 5 substituents R13; where
each R12, independently of one another, is selected from halogen and Ci-C4-alkyl; each R13, independently of one another, is selected from halogen, nitro, CN, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio and phenyl; where the phenyl moiety may carry 1 , 2, 3, 4 or 5 sub- stituents R14; where each R14, independently of one another, is selected from halogen, nitro, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy,
Ci-C4-alkylthio and Ci-C4-haloalkylthio; and
R4, R8/R8a, n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings.
More preferably (embodiment Ca), R1 is a group of formula V, where
X is CH;
Y is O;
A2 is -CH2CH2-, -CH2CH2CH2-, -CH2CH(CH3)-, -CH2CH(OCH3)- or
-CH2CH2CH(CH3)-;
R7 is Ci-C4-alkyl;
each R4 is independently selected from methyl, F, Cl, methoxy, trifuoromethyl, trifuoro- methoxy, difuoromethyl, difuoromethoxy, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, phenoxy, 2- chlorophenoxy, 3-chlorophenoxy and 4-chlorophenoxy; and
R8/R8a, n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings.
Even more preferably (embodiment C.a.1), R1 is a group of formula V, where
X is CH;
Y is O;
A2 is -CH2CH2-;
R7 is n-propyl;
each R4 is independently selected from methyl, F, Cl, methoxy, trifuoromethyl, trifuoro- methoxy and phenyl; and
R4, R8/R8a, n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings. In the context of embodiments C, Ca and Ca.1 if n is 1 the substituent R4 is preferably bound in position 2, 4 or 6, if n is 2 the substituents R4 are preferably bound in positions 2 and 4, 3 and 5, or 4 and 6, and if n is 3 the substituents R4 are preferably bound in positions 2, 4 and 6, relative to the 1 -position, which is the attachment point of the phenyl ring of the group V to the remainder of the molecule.
Examples for preferred compounds I and Il of embodiment C are compounds of formulae I.C1 to I.C72 and II.C1 to II.C36, where the variables R41, R42, R43, R44 and R45 are hydrogen or have one of the general meanings or, in particular, one of the preferred meanings given above for R4 and where the variables R7, R8 and R8a have one of the general meanings or, in particular, one of the preferred meanings given above in context with embodiment C Examples of preferred compounds are the individual compounds compiled in the tables 1 to 41652 below. Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
Figure imgf000078_0001
(I.C1 ) (I.C2) (I.C3) (I.C4)
Figure imgf000078_0002
(I.C5) (I.C6) (I.C7) (I.C8)
Figure imgf000079_0001
(I.C9) (I.C10) (I.C11) (I.C12)
Figure imgf000079_0002
(I.C15) (I.C16)
Figure imgf000079_0003
(I.C17) (I.C18)
Figure imgf000080_0001
(I.C19) (I.C20) (I.C21 ) (I.C22)
Figure imgf000080_0002
(I.C23) (I.C24) (I.C25) (I.C26)
Figure imgf000080_0003
(I.C27) (I.C28) (I.C29) (I.C30)
Figure imgf000081_0001
(I.C33) (I.C34)
Figure imgf000081_0002
(I.C37) (I.C38)
Figure imgf000082_0001
(I.C39) (I.C40)
Figure imgf000082_0002
(I C41) (I C42)
Figure imgf000082_0003
(I.C43) (I.C44)
Figure imgf000082_0004
(I.C45) (I.C46)
Figure imgf000083_0001
(I.C47) (I.C48)
Figure imgf000083_0002
(I.C49) (I.C50)
Figure imgf000083_0003
(IC51) (I C52)
Figure imgf000084_0001
(I C53) (I C54)
Figure imgf000084_0002
(I.C55) (I.C56)
Figure imgf000084_0003
(I.C57) (I.C58)
Figure imgf000084_0004
(I C59) (I C60)
Figure imgf000085_0001
(I.C61 ) (I.C62)
Figure imgf000085_0002
(I.C63) (I.C64)
Figure imgf000085_0003
(I.C65) (I.C66)
Figure imgf000086_0001
(I.C67)
(I.C68)
Figure imgf000086_0002
(I C69) (I C70)
Figure imgf000086_0003
(IC71) (I C72)
Figure imgf000087_0001
II.C1) IC2) (Il C3) IC4)
Figure imgf000087_0002
II.C5) II.C6) (Il C7) II.C8)
Figure imgf000087_0003
II.C9) IC10) IC11) (Il C12)
Figure imgf000088_0001
(Il C 15) (Il C 16)
Figure imgf000088_0002
II.C17) II.C18)
Figure imgf000088_0003
II.C19) (Il C20) I C21) I.C22)
Figure imgf000089_0001
II.C23) IC24) IC25) (Il C26)
Figure imgf000089_0002
II.C27) (Il C28) (Il C29) IC30)
Figure imgf000089_0003
(Il C33) I C34)
Figure imgf000090_0001
II.C35) II.C36)
Table 1
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is hydrogen and R7 is hydrogen
Table 2
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is methyl and R7 is hydrogen
Table 3
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is ethyl and R7 is hydrogen
Table 4
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is propyl and R7 is hydrogen
Table 5
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isopropyl and R7 is hydrogen
Table 6
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is n-butyl and R7 is hydrogen
Table 7
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is sec-butyl and R7 is hydrogen Table 8
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isobutyl and R7 is hydrogen
Table 9
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is tert-butyl and R7 is hydrogen
Table 10
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is phenyl and R2 is hydrogen
Table 11
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is benzyl and R7 is hydrogen
Table 12
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is Li+ and R7 is hy- drogen
Table 13
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is Na+ and R7 is hydrogen
Table 14
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is K+ and R7 is hydrogen
Table 15
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is YiMg2+ and R7 is hydrogen
Table 16
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is YiCu2+ and R7 is hydrogen
Table 17
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is /4Zn2+ and R7 is hydrogen
Table 18
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is YiFe2+ and R7 is hydrogen
Table 19
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is !4Ni2+ and R7 is hydrogen
Table 20
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is NH(CH3)3+ and
R7 is hydrogen
Table 21
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is NH(C2H5)3+ and
R7 is hydrogen
Table 22
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is
NH(CH2CH2CH2)S+ and R7 is hydrogen
Table 23
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is NH(CH(CHs)2)3+ and R7 is hydrogen
Table 24
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is
NH(CH2CH2CH2CH2)S+ and R7 is hydrogen
Table 25
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is methylcarbonyl and R7 is hydrogen
Table 26
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is ethylcarbonyl and R7 is hydrogen Table 27
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is propylcarbonyl and R7 is hydrogen
Table 28
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isopropylcar- bonyl and R7 is hydrogen
Table 29
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is phenylcarbonyl and R7 is hydrogen
Table 30
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is methoxycarbonyl and R7 is hydrogen
Table 31
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is ethoxycarbonyl and R7 is hydrogen
Table 32
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is propoxycarbonyl and R7 is hydrogen
Table 33
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isopropoxycar- bonyl and R7 is hydrogen
Table 34
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is phenoxycarbonyl and R7 is hydrogen
Table 35
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is methylaminocar- bonyl and R7 is hydrogen
Table 36
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is ethylaminocar- bonyl and R7 is hydrogen
Table 37
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is propylaminocar- bonyl and R7 is hydrogen
Table 38
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isopropylamino- carbonyl and R7 is hydrogen
Table 39
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is phenylaminocar- bonyl and R7 is hydrogen
Table 40
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is methylsulfonyl and R7 is hydrogen
Table 41
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is ethylsulfonyl and
R7 is hydrogen
Table 42
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is propylsulfonyl and R7 is hydrogen
Table 43
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isopropylsulfonyl and R7 is hydrogen
Table 44
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is phenylsulfonyl and R7 is hydrogen
Table 45
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is methoxysulfonyl and R7 is hydrogen Table 46
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is ethoxysulfonyl and R7 is hydrogen
Table 47
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is propoxysulfonyl and R7 is hydrogen
Table 48
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is isopropoxysul- fonyl and R7 is hydrogen
Table 49
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is phenoxysulfonyl and R7 is hydrogen
Table 50
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8 is CN and R7 is hydrogen
Tables 51 to 100
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50 and R7 is methyl
Tables 101 to 150
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50 and R7 is ethyl
Tables 151 to 200
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50 and R7 is propyl
Tables 201 to 250
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50 and R7 is isopropyl
Tables 251 to 300
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44, R45 and R8 for a compound is as defined in any of tables 1 to 50 and R7 is n-butyl
Tables 301 to 350
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50 and R7 is sec-butyl Tables 351 to 400
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50 and R7 is isobutyl
Tables 401 to 450
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50 and R7 is tert-butyl
Tables 451 to 500
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50 and R7 is phenyl
Tables 501 to 550
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50 and R7 is 4-methylphenyl
Tables 551 to 600
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44, R45 and R8 for a compound is as defined in any of tables 1 to 50 and R7 is benzyl
Tables 601 to 650
Compounds of the formula I.C1 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50 and R7 is CN
Tables 651 to 1300
Compounds of the formula I.C2 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 1301 to 1950
Compounds of the formula I.C3 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 1951 to 2600
Compounds of the formula I.C4 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 2601 to 3250
Compounds of the formula I.C5 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 3251 to 3900
Compounds of the formula I.C6 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 3901 to 4550
Compounds of the formula I.C7 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 4551 to 5200
Compounds of the formula I.C8 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650 Tables 5201 to 5850
Compounds of the formula I.C9 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 5851 to 6500
Compounds of the formula I.C10 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 100
Tables 6501 to 7150
Compounds of the formula I.C11 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 7151 to 7800
Compounds of the formula I.C12 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 7801 to 8450
Compounds of the formula I.C13 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 8451 to 9100
Compounds of the formula I.C14 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 9101 and 9750
Compounds of the formula I.C15 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 9751 and 10400
Compounds of the formula I.C16 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 10401 and 1 1050
Compounds of the formula I.C17 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 11051 and 1 1700
Compounds of the formula I.C18 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 11701 and 12350
Compounds of the formula I.C19 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 12351 and 13000
Compounds of the formula I.C20 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 13001 and 13650
Compounds of the formula I.C21 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650 Tables 13651 and 14300
Compounds of the formula I.C22 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 14301 and 14950
Compounds of the formula I.C23 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 14951 and 15600
Compounds of the formula I.C24 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 15601 and 16250
Compounds of the formula I.C25 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 16251 and 16900
Compounds of the formula I.C26 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 16901 and 17550
Compounds of the formula I.C27 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 17551 and 18200
Compounds of the formula I.C28 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 18201 and 18850
Compounds of the formula I.C29 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 18851 and 19500
Compounds of the formula I.C30 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 19501 and 20150
Compounds of the formula I.C31 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 20151 and 20800
Compounds of the formula I.C32 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 20801 and 21450
Compounds of the formula I.C33 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 21451 and 22100
Compounds of the formula I.C34 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650 Tables 22101 and 22750
Compounds of the formula I.C35 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 22751 and 23400
Compounds of the formula I.C36 in which the combination of R41, R42, R43, R44, R45, R7 and R8 for a compound is as defined in any of tables 1 to 650
Tables 23401 and 23413
Compounds of the formula I.C37 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1 , 51 , 101 , 151 , 201 , 251 , 301 , 351 , 401 , 451 , 501 , 551 and 601
Tables 23414 and 23426
Compounds of the formula I.C38 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23427 and 23439
Compounds of the formula I.C39 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23440 and 23452
Compounds of the formula I.C40 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23453 and 23465
Compounds of the formula I.C41 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23466 and 23478
Compounds of the formula I.C42 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23479 and 23491
Compounds of the formula I.C43 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23492 and 23504
Compounds of the formula I.C44 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1 , 51 , 101 , 151 , 201 , 251 , 301 , 351 , 401 , 451 , 501 , 551 and 601 Tables 23505 and 23517
Compounds of the formula I.C45 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23518 and 23530
Compounds of the formula I.C46 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23531 and 23543
Compounds of the formula I.C47 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23544 and 23556
Compounds of the formula I.C48 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23557 and 23569
Compounds of the formula I.C49 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23570 and 23582
Compounds of the formula I.C50 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23583 and 23595
Compounds of the formula I.C51 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23596 and 23608
Compounds of the formula I.C52 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23609 and 23621
Compounds of the formula I.C53 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23622 and 23634
Compounds of the formula I.C54 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23635 and 23647
Compounds of the formula I.C55 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23648 and 23660
Compounds of the formula I.C56 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23661 and 23673
Compounds of the formula I.C57 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in anyoftables1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23674 and 23686
Compounds of the formula I.C58 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1 , 51 , 101 , 151 , 201 , 251 , 301 , 351 , 401 , 451 , 501 , 551 and 601
Tables 23687 and 23699
Compounds of the formula I.C59 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23700 and 23712
Compounds of the formula I.C60 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23713 and 23725
Compounds of the formula I.C61 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23726 and 23738
Compounds of the formula I.C62 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23739 and 23751
Compounds of the formula I.C63 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1 , 51 , 101 , 151 , 201 , 251 , 301 , 351 , 401 , 451 , 501 , 551 and 601 Tables 23752 and 23764
Compounds of the formula I.C64 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23765 and 23777
Compounds of the formula I.C65 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23778 and 23790
Compounds of the formula I.C66 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23791 and 23803
Compounds of the formula I.C67 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23804 and 23816
Compounds of the formula I.C68 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23817 and 23829
Compounds of the formula I.C69 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23830 and 23842
Compounds of the formula I.C70 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23843 and 23855
Compounds of the formula I.C71 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Tables 23856 and 23868
Compounds of the formula I.C72 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R7 is as defined in any of tables 1,51, 101, 151,201,251,301,351,401,451,501,551 and 601
Table 23869
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is hydrogen and
R7 is hydrogen
Table 23870
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is methyl and R7 is hydrogen
Table 23871
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is ethyl and R7 is hydrogen
Table 23872
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is propyl and R7 is hydrogen
Table 23873
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isopropyl and R7 is hydrogen
Table 23874
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is n-butyl and R7 is hydrogen
Table 23875
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is sec-butyl and R7 is hydrogen
Table 23876
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isobutyl and R7 is hydrogen
Table 23877
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is tert-butyl and R7 is hydrogen
Table 23878
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is phenyl and R7 is hydrogen Table 23879
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is 4-methylphenyl and R7 is hydrogen
Table 23880
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is benzyl and R7 is hydrogen
Table 23881
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is methylcarbonyl and R7 is hydrogen
Table 23882
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is ethylcarbonyl and R7 is hydrogen
Table 23883
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is propylcarbonyl and R7 is hydrogen
Table 23884
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isopropylcar- bonyl and R7 is hydrogen
Table 23885
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is phenylcarbonyl and R7 is hydrogen
Table 23886
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is methoxycar- bonyl and R7 is hydrogen
Table 23887
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is ethoxycarbonyl and R7 is hydrogen
Table 23888
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is propoxycar- bonyl and R7 is hydrogen
Table 23889
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isopropoxycar- bonyl and R7 is hydrogen
Table 23890
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is phenoxycar- bonyl and R7 is hydrogen
Table 23891
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is methylamino- carbonyl and R7 is hydrogen
Table 23892
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is ethylaminocar- bonyl and R7 is hydrogen
Table 23893
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is propylamino- carbonyl and R7 is hydrogen
Table 23894
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isopropylamino- carbonyl and R7 is hydrogen
Table 23895
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is phenylamino- carbonyl and R7 is hydrogen
Table 23896
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is methylsulfonyl and R7 is hydrogen
Table 23897
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is ethylsulfonyl and R7 is hydrogen Table 23898
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is propylsulfonyl and R7 is hydrogen
Table 23899
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isopropylsul- fonyl and R7 is hydrogen
Table 23900
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is phenylsulfonyl and R7 is hydrogen
Table 23901
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is methoxysulfonyl and R7 is hydrogen
Table 23902
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is ethoxysulfonyl and R7 is hydrogen
Table 23903
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is propoxysulfonyl and R7 is hydrogen
Table 23904
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is isopropoxysul- fonyl and R7 is hydrogen
Table 23905
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is phenoxysulfonyl and R7 is hydrogen
Table 23906
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A, R8a is CN and R7 is hydrogen
Tables 23907 to 23944
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 23869 to 23906 and R7 is methyl Tables 23945 to 23982
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 23869 to 23906 and R7 is ethyl
Tables 23983 to 24020
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 23869 to 23906 and R7 is propyl
Tables 24021 to 24058
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 23869 to 23906 and R7 is isopropyl Tables 24059 to 24096
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 23869 to 23906 and R7 is n-butyl
Tables 24097 to 24134
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44, R45 and R8a for a compound is as defined in any of tables 23869 to 23906 and R7 is sec-butyl
Tables 24135 to 24172
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 23869 to 23906 and R7 is isobutyl
Tables 24173 to 24210
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 23869 to 23906 and R7 is tert-butyl
Tables 2421 1 to 24248
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 23869 to 23906 and R7 is phenyl Tables 24249 to 24286
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 23869 to 23906 and R7 is 4- methylphenyl
Tables 24287 to 24324
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 23869 to 23906 and R7 is benzyl
Tables 24325 to 24362
Compounds of the formula II.C1 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 23869 to 23906 and R7 is CN Tables 24363 to 24856
Compounds of the formula II.C2 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362 Tables 24857 to 25350
Compounds of the formula II.C3 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 25351 to 25844
Compounds of the formula II.C4 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 25845 to 26338
Compounds of the formula II.C5 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 26339 to 26832
Compounds of the formula II.C6 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 26833 to 27326
Compounds of the formula II.C7 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 27327 to 27820
Compounds of the formula II.C8 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 27821 to 28314
Compounds of the formula II.C9 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 28315 to 28808
Compounds of the formula II.C10 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 28809 to 29302
Compounds of the formula II.C1 1 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 29303 to 29796
Compounds of the formula II.C12 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 29797 to 30290
Compounds of the formula II.C13 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 30291 to 30784
Compounds of the formula II.C14 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 30785 to 31278
Compounds of the formula II.C15 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362 Tables 31279 to 31772
Compounds of the formula II.C16 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 31773 to 32266
Compounds of the formula II.C17 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 32267 to 32760
Compounds of the formula II.C18 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 32761 to 33254
Compounds of the formula II.C19 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 33255 to 33748
Compounds of the formula II.C20 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 33749 to 34242
Compounds of the formula II.C21 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 34243 to 34736
Compounds of the formula II.C22 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 34737 to 35230
Compounds of the formula II.C23 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 35231 to 35724
Compounds of the formula II.C24 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 35725 to 36218
Compounds of the formula II.C25 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 36219 to 36712
Compounds of the formula II.C26 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 36713 to 37206
Compounds of the formula II.C27 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 37207 to 37700
Compounds of the formula II.C28 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362 Tables 37701 to 38194
Compounds of the formula II.C29 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 38195 to 38688
Compounds of the formula II.C30 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 38689 to 39182
Compounds of the formula II.C31 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 39183 to 39676
Compounds of the formula II.C32 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 39677 to 40170
Compounds of the formula II.C33 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 40171 to 40664
Compounds of the formula II.C34 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 40665 to 41 158
Compounds of the formula II.C35 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
Tables 41 159 to 41652
Compounds of the formula II.C36 in which the combination of R41, R42, R43, R44, R45, R7 and R8a for a compound is as defined in any of tables 23869 to 24362
In another preferred embodiment of the invention (embodiment D), R1 is a group of formula Vl, where
X is N;
W is O or S; and
R4, R5, R8/R8a, n, p and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings.
More preferably (embodiment D. a), R1 is a group of formula Vl, where
X is N;
W is O;
each R4 and each R6 is independently selected from methyl, F, Cl, methoxy, trifuoro- methyl, trifuoromethoxy, difuoromethyl, difuoromethoxy, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, phenoxy, 2-chlorophenoxy, 3-chlorophenoxy and 4-chlorophenoxy;
p is 1 , 2 or 3; and
R8/R8a, n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings.
Even more preferably (embodiment D.a.1 ), R1 is a group of formula Vl, where
X is N;
W is O;
R5 is phenyl which may carry 1 or 2 radicals R4;
each R4 and each R6 is independently selected from methyl, F, Cl, methoxy, trifuoro- methyl, trifuoromethoxy and phenyl;
p is 1 or 2; and
R8/R8a and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings.
In the context of embodiments D, D. a and D.a.1 if n is 1 the substituent R4 is preferably bound in position 2, 4 or 6, if n is 2 the substituents R4 are preferably bound in positions 2 and 4, 3 and 5, or 4 and 6, and if n is 3 the substituents R4 are preferably bound in positions 2, 4 and 6, relative to the 1 -position, which is the attachment point of the phenyl ring of the group Vl to the remainder of the molecule.
Examples for preferred compounds I and Il of embodiment D are compounds of formulae I.D1 to I.D4, II. D1 and II. D2, where the variables R61, R62, R63 and R64 are hydrogen or have one of the general meanings or, in particular, one of the preferred meanings given above for R6 and where the variables R5, n, R8 and R8a have one of the general meanings or, in particular, one of the preferred meanings given above in context with embodiment D. Examples of preferred compounds are the individual compounds compiled in the tables 1 to 86760 below. Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
Figure imgf000112_0001
(I.D1) (I.D2)
Figure imgf000112_0002
(I.D3)
Figure imgf000112_0003
(I.D4)
Figure imgf000113_0001
(II.D1) (II.D2)
Table 1
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is phenyl
Table 2
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- fluorophenyl
Table 3
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- fluorophenyl
Table 4
Compounds of the formula I. D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 4- fluorophenyl
Table 5
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- chlorophenyl
Table 6
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- chlorophenyl
Table 7
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 4- chlorophenyl Table 8
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- bromophenyl
Table 9
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- bromophenyl
Table 10
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 4- bromophenyl
Table 11
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methylphenyl
Table 12
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- methylphenyl
Table 13
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 4- methylphenyl
Table 14
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-
(difluoromethyl)-phenyl
Table 15
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-
(difluoromethyl)-phenyl
Table 16
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 4-
(difluoromethyl)-phenyl
Table 17
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-
(trifluoromethyl)-phenyl
Table 18
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-
(trifluoromethyl)-phenyl
Table 19
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 4- (trifluoromethyl)-phenyl
Table 20
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxyphenyl
Table 21
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- methoxyphenyl
Table 22
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 4- methoxyphenyl
Table 23
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-
(difluoromethoxy)-phenyl
Table 24
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- (difluoromethoxy)-phenyl
Table 25
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 4-
(difluoromethoxy)-phenyl
Table 26
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-
(trifluoromethoxy)-phenyl Table 27
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-
(trifluoromethoxy)-phenyl
Table 28
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 4-
(trifluoromethoxy)-phenyl
Table 29
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3- difluorophenyl
Table 30
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4- difluorophenyl
Table 31
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,5- difluorophenyl
Table 32
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- difluorophenyl
Table 33
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4- difluorophenyl
Table 34
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,5- difluorophenyl
Table 35
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3- dichlorophenyl
Table 36
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4- dichlorophenyl
Table 37
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,5- dichlorophenyl
Table 38
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- dichlorophenyl
Table 39
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4- dichlorophenyl
Table 40
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,5- dichlorophenyl
Table 41
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3- dibromophenyl
Table 42
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4- dibromophenyl
Table 43
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,5- dibromophenyl
Table 44
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- dibromophenyl
Table 45
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4- dibromophenyl Table 46
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,5- dibromophenyl
Table 47
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3- dimethylphenyl
Table 48
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4- dimethylphenyl
Table 49
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,5- dimethylphenyl
Table 50
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- dimethylphenyl
Table 51
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4- dimethylphenyl
Table 52
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,5- dimethylphenyl
Table 53
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3-di-
(difluoromethyl)-phenyl
Table 54
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4-di-
(difluoromethyl)-phenyl
Table 55
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,5-di-
(difluoromethyl)-phenyl
Table 56
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6-di-
(difluoromethyl)-phenyl
Table 57
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4-di- (difluoromethyl)-phenyl
Table 58
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,5-di-
(difluoromethyl)-phenyl
Table 59
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3-di-
(trifluoromethyl)-phenyl
Table 60
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4-di-
(trifluoromethyl)-phenyl
Table 61
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,5-di-
(trifluoromethyl)-phenyl
Table 62
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6-di- (trifluoromethyl)-phenyl
Table 63
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4-di-
(trifluoromethyl)-phenyl
Table 64
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,5-di-
(trifluoromethyl)-phenyl Table 65
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3- dimethoxyphenyl
Table 66
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4- dimethoxyphenyl
Table 67
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,5- dimethoxyphenyl
Table 68
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- dimethoxyphenyl
Table 69
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4- dimethoxyphenyl
Table 70
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,5- dimethoxyphenyl
Table 71
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3-di-
(difluoromethoxy)-phenyl
Table 72
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4-di-
(difluoromethoxy)-phenyl
Table 73
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,5-di-
(difluoromethoxy)-phenyl
Table 74
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6-di-
(difluoromethoxy)-phenyl
Table 75
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4-di-
(difluoromethoxy)-phenyl
Table 76
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,5-di- (difluoromethoxy)-phenyl
Table 77
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3-di-
(trifluoromethoxy)-phenyl
Table 78
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4-di-
(trifluoromethoxy)-phenyl
Table 79
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,5-di-
(trifluoromethoxy)-phenyl
Table 80
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6-di-
(trifluoromethoxy)-phenyl
Table 81
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4-di- (trifluoromethoxy)-phenyl
Table 82
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,5-di-
(trifluoromethoxy)-phenyl
Table 83
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-3- chlorophenyl Table 84
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-4- chlorophenyl
Table 85
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-5- chlorophenyl
Table 86
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-6- chlorophenyl
Table 87
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-4- chlorophenyl
Table 88
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-5- chlorophenyl
Table 89
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
3-fluorophenyl
Table 90
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
4-fluorophenyl
Table 91
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
5-fluorophenyl
Table 92
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro-
4-fluorophenyl
Table 93
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-3- bromophenyl
Table 94
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-4- bromophenyl
Table 95
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-5- bromophenyl
Table 96
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-6- bromophenyl
Table 97
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-4- bromophenyl
Table 98
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-5- bromophenyl
Table 99
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
3-fluorophenyl
Table 100
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo- 4-fluorophenyl
Table 101
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
5-fluorophenyl
Table 102
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo-
4-fluorophenyl Table 103
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-3- methylphenyl
Table 104
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-4- methylphenyl
Table 105
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-5- methylphenyl
Table 106
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-6- methylphenyl
Table 107
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-4- methylphenyl
Table 108
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-5- methylphenyl
Table 109
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
3-fluorophenyl
Table 110
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
4-fluorophenyl
Table 11 1
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
5-fluorophenyl
Table 112
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-methyl-
4-fluorophenyl
Table 113
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-3- difluoromethylphenyl
Table 114
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-4- difluoromethylphenyl
Table 115
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-5- difluoromethylphenyl
Table 116
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-6- difluoromethylphenyl
Table 117
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-4- difluoromethylphenyl
Table 118
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-5- difluoromethylphenyl
Table 119
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-3-fluorophenyl
Table 120
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-4-fluorophenyl
Table 121
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-5-fluorophenyl Table 122
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethyl-4-fluorophenyl
Table 123
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-3- trifluoromethylphenyl
Table 124
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-4- trifluoromethylphenyl
Table 125
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-5- trifluoromethylphenyl
Table 126
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-6- trifluoromethylphenyl
Table 127
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-4- trifluoromethylphenyl
Table 128
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-5- trifluoromethylphenyl
Table 129
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-3-fluorophenyl
Table 130
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-4-fluorophenyl
Table 131
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-5-fluorophenyl
Table 132
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethyl-4-fluorophenyl
Table 133
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-3- methoxyphenyl
Table 134
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-4- methoxyphenyl
Table 135
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-5- methoxyphenyl
Table 136
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-6- methoxyphenyl
Table 137
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-4- methoxyphenyl
Table 138
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-5- methoxyphenyl
Table 139
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-3-fluorophenyl
Table 140
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-4-fluorophenyl Table 141
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-5-fluorophenyl
Table 142
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- methoxy-4-fluorophenyl
Table 143
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-3- difluoromethoxyphenyl
Table 144
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-4- difluoromethoxyphenyl
Table 145
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-5- difluoromethoxyphenyl
Table 146
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-6- difluoromethoxyphenyl
Table 147
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-4- difluoromethoxyphenyl
Table 148
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-5- difluoromethoxyphenyl
Table 149
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-3-fluorophenyl
Table 150
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-4-fluorophenyl
Table 151
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-5-fluorophenyl
Table 152
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethoxy-4-fluorophenyl
Table 153
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-3- trifluoromethoxyphenyl
Table 154
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-4- trifluoromethoxyphenyl
Table 155
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-5- trifluoromethoxyphenyl
Table 156
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-fluoro-6- trifluoromethoxyphenyl
Table 157
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-4- trifluoromethoxyphenyl
Table 158
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-fluoro-5- trifluoromethoxyphenyl
Table 159
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-3-fluorophenyl Table 160
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-4-fluorophenyl
Table 161
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-5-fluorophenyl
Table 162
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethoxy-4-fluorophenyl
Table 163
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
3-bromophenyl
Table 164
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro- 4-bromophenyl
Table 165
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
5-bromophenyl
Table 166
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
6-bromophenyl
Table 167
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro-
4-bromophenyl
Table 168
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro-
5-bromophenyl
Table 169
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
3-chlorophenyl
Table 170
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
4-chlorophenyl
Table 171
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo- 5-chlorophenyl
Table 172
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo-
4-chlorophenyl
Table 173
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
3-methylphenyl
Table 174
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
4-methylphenyl
Table 175
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
5-methylphenyl
Table 176
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro- 6-methylphenyl
Table 177
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro-
4-methylphenyl
Table 178
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro-
5-methylphenyl Table 179
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
3-chlorophenyl
Table 180
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
4-chlorophenyl
Table 181
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
5-chlorophenyl
Table 182
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-methyl-
4-chlorophenyl
Table 183
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro- 3-difluoromethylphenyl
Table 184
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
4-difluoromethylphenyl
Table 185
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
5-difluoromethylphenyl
Table 186
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
6-difluoromethylphenyl
Table 187
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is H and R5 is 3-chloro-
4-difluoromethylphenyl
Table 188
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro-
5-difluoromethylphenyl
Table 189
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is H and R5 is 2- difluoromethyl-3-chlorophenyl
Table 190
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-4-chlorophenyl
Table 191
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-5-chlorophenyl
Table 192
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is H and R5 is 3- difluoromethyl-4-chlorophenyl
Table 193
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
3-trifluoromethylphenyl
Table 194
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
4-trifluoromethylphenyl
Table 195
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro- 5-trifluoromethylphenyl
Table 196
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
6-trifluoromethylphenyl
Table 197
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro-
4-trifluoromethylphenyl Table 198
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro-
5-trifluoromethylphenyl
Table 199
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-3-chlorophenyl
Table 200
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-4-chlorophenyl
Table 201
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-5-chlorophenyl
Table 202
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethyl-4-chlorophenyl
Table 203
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
3-methoxyphenyl
Table 204
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
4-methoxyphenyl
Table 205
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
5-methoxyphenyl
Table 206
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
6-methoxyphenyl
Table 207
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro-
4-methoxyphenyl
Table 208
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro-
5-methoxyphenyl
Table 209
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-3-chlorophenyl
Table 210
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-4-chlorophenyl
Table 21 1
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-5-chlorophenyl
Table 212
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- methoxy-4-chlorophenyl
Table 213
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
3-difluoromethoxyphenyl
Table 214
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro- 4-difluoromethoxyphenyl
Table 215
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
5-difluoromethoxyphenyl
Table 216
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
6-difluoromethoxyphenyl Table 217
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro-
4-difluoromethoxyphenyl
Table 218
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro-
5-difluoromethoxyphenyl
Table 219
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-3-chlorophenyl
Table 220
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-4-chlorophenyl
Table 221
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-5-chlorophenyl
Table 222
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethoxy-4-chlorophenyl
Table 223
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
3-trifluoromethoxyphenyl
Table 224
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
4-trifluoromethoxyphenyl
Table 225
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
5-trifluoromethoxyphenyl
Table 226
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-chloro-
6-trifluoromethoxyphenyl
Table 227
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro-
4-trifluoromethoxyphenyl
Table 228
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-chloro- 5-trifluoromethoxyphenyl
Table 229
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-3-chlorophenyl
Table 230
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-4-chlorophenyl
Table 231
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-5-chlorophenyl
Table 232
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethoxy-4-chlorophenyl
Table 233
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo- 3-methylphenyl
Table 234
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
4-methylphenyl
Table 235
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
5-methylphenyl Table 236
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
6-methylphenyl
Table 237
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo-
4-methylphenyl
Table 238
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo-
5-methylphenyl
Table 239
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
3-bromophenyl
Table 240
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl- 4-bromophenyl
Table 241
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
5-bromophenyl
Table 242
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-methyl-
4-bromophenyl
Table 243
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
3-difluoromethylphenyl
Table 244
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
4-difluoromethylphenyl
Table 245
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
5-difluoromethylphenyl
Table 246
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
6-difluoromethylphenyl
Table 247
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo- 4-difluoromethylphenyl
Table 248
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo-
5-difluoromethylphenyl
Table 249
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-3-bromophenyl
Table 250
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-4-bromophenyl
Table 251
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-5-bromophenyl
Table 252
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethyl-4-bromophenyl
Table 253
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
3-trifluoromethylphenyl
Table 254
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
4-trifluoromethylphenyl Table 255
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
5-trifluoromethylphenyl
Table 256
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
6-trifluoromethylphenyl
Table 257
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo-
4-trifluoromethylphenyl
Table 258
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo-
5-trifluoromethylphenyl
Table 259
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-3-bromophenyl
Table 260
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-4-bromophenyl
Table 261
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-5-bromophenyl
Table 262
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethyl-4-bromophenyl
Table 263
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
3-methoxyphenyl
Table 264
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
4-methoxyphenyl
Table 265
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
5-methoxyphenyl
Table 266
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo- 6-methoxyphenyl
Table 267
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo-
4-methoxyphenyl
Table 268
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo-
5-methoxyphenyl
Table 269
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-3-bromophenyl
Table 270
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-4-bromophenyl
Table 271
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-5-bromophenyl
Table 272
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- methoxy-4-bromophenyl
Table 273
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
3-difluoromethoxyphenyl Table 274
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
4-difluoromethoxyphenyl
Table 275
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
5-difluoromethoxyphenyl
Table 276
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
6-difluoromethoxyphenyl
Table 277
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo-
4-difluoromethoxyphenyl
Table 278
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo- 5-difluoromethoxyphenyl
Table 279
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-3-bromophenyl
Table 280
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-4-bromophenyl
Table 281
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-5-bromophenyl
Table 282
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethoxy-4-bromophenyl
Table 283
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
3-trifluoromethoxyphenyl
Table 284
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
4-trifluoromethoxyphenyl
Table 285
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo- 5-trifluoromethoxyphenyl
Table 286
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-bromo-
6-trifluoromethoxyphenyl
Table 287
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo-
4-trifluoromethoxyphenyl
Table 288
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-bromo-
5-trifluoromethoxyphenyl
Table 289
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-3-bromophenyl
Table 290
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-4-bromophenyl
Table 291
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-5-bromophenyl
Table 292
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethoxy-4-bromophenyl Table 293
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
3-difluoromethylphenyl
Table 294
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
4-difluoromethylphenyl
Table 295
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
5-difluoromethylphenyl
Table 296
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
6-difluoromethylphenyl
Table 297
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-methyl- 4-difluoromethylphenyl
Table 298
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-methyl-
5-difluoromethylphenyl
Table 299
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-3-methylphenyl
Table 300
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-4-methylphenyl
Table 301
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-5-methylphenyl
Table 302
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethyl-4-methylphenyl
Table 303
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
3-trifluoromethylphenyl
Table 304
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl- 4-trifluoromethylphenyl
Table 305
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
5-trifluoromethylphenyl
Table 306
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
6-trifluoromethylphenyl
Table 307
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-methyl-
4-trifluoromethylphenyl
Table 308
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-methyl-
5-trifluoromethylphenyl
Table 309
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-3-methylphenyl
Table 310
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-4-methylphenyl
Table 31 1
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-5-methylphenyl Table 312
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethyl-4-methylphenyl
Table 313
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
3-methoxyphenyl
Table 314
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
4-methoxyphenyl
Table 315
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
5-methoxyphenyl
Table 316
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl- 6-methoxyphenyl
Table 317
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-methyl-
4-methoxyphenyl
Table 318
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-methyl-
5-methoxyphenyl
Table 319
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-3-methylphenyl
Table 320
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-4-methylphenyl
Table 321
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-5-methylphenyl
Table 322
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- methoxy-4-methylphenyl
Table 323
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl- 3-difluoromethoxyphenyl
Table 324
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
4-difluoromethoxyphenyl
Table 325
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
5-difluoromethoxyphenyl
Table 326
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
6-difluoromethoxyphenyl
Table 327
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-methyl-
4-difluoromethoxyphenyl
Table 328
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-methyl- 5-difluoromethoxyphenyl
Table 329
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-3-methylphenyl
Table 330
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-4-methylphenyl Table 331
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-5-methylphenyl
Table 332
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethoxy-4-methylphenyl
Table 333
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
3-trifluoromethoxyphenyl
Table 334
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
4-trifluoromethoxyphenyl
Table 335
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl- 5-trifluoromethoxyphenyl
Table 336
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2-methyl-
6-trifluoromethoxyphenyl
Table 337
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-methyl-
4-trifluoromethoxyphenyl
Table 338
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3-methyl-
5-trifluoromethoxyphenyl
Table 339
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-3-methylphenyl
Table 340
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-4-methylphenyl
Table 341
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-5-methylphenyl
Table 342
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethoxy-4-methylphenyl
Table 343
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-3-trifluoromethylphenyl
Table 344
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-4-trifluoromethylphenyl
Table 345
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-5-trifluoromethylphenyl
Table 346
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-6-trifluoromethylphenyl
Table 347
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethyl-4-trifluoromethylphenyl
Table 348
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethyl-5-trifluoromethylphenyl
Table 349
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-3-difluoromethylphenyl Table 350
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-4-difluoromethylphenyl
Table 351
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-5-difluoromethylphenyl
Table 352
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethyl-4-difluoromethylphenyl
Table 353
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-3-methoxyphenyl
Table 354
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-4-methoxyphenyl
Table 355
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-5-methoxyphenyl
Table 356
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-6-methoxyphenyl
Table 357
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethyl-4-methoxyphenyl
Table 358
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethyl-5-methoxyphenyl
Table 359
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-3-difluoromethylphenyl
Table 360
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-4-difluoromethylphenyl
Table 361
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-5-difluoromethylphenyl
Table 362
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- methoxy-4-difluoromethylphenyl
Table 363
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-3-difluoromethoxyphenyl
Table 364
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-4-difluoromethoxyphenyl
Table 365
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-5-difluoromethoxyphenyl
Table 366
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-6-difluoromethoxyphenyl
Table 367
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethyl-4-difluoromethoxyphenyl
Table 368
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethyl-5-difluoromethoxyphenyl Table 369
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-3-difluoromethylphenyl
Table 370
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-4-difluoromethylphenyl
Table 371
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-5-difluoromethylphenyl
Table 372
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethoxy-4-difluoromethylphenyl
Table 373
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-3-trifluoromethoxyphenyl
Table 374
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-4-trifluoromethoxyphenyl
Table 375
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-5-trifluoromethoxyphenyl
Table 376
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethyl-6-trifluoromethoxyphenyl
Table 377
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethyl-4-trifluoromethoxyphenyl
Table 378
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethyl-5-trifluoromethoxyphenyl
Table 379
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-3-difluoromethylphenyl
Table 380
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-4-difluoromethylphenyl
Table 381
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-5-difluoromethylphenyl
Table 382
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethoxy-4-difluoromethylphenyl
Table 383
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-3-methoxyphenyl
Table 384
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-4-methoxyphenyl
Table 385
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-5-methoxyphenyl
Table 386
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-6-methoxyphenyl
Table 387
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethyl-4-methoxyphenyl Table 388
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethyl-5-methoxyphenyl
Table 389
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-3-trifluoromethylphenyl
Table 390
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-4-trifluoromethylphenyl
Table 391
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-5-trifluoromethylphenyl
Table 392
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- methoxy-4-trifluoromethylphenyl
Table 393
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-3-difluoromethoxyphenyl
Table 394
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-4-difluoromethoxyphenyl
Table 395
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-5-difluoromethoxyphenyl
Table 396
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-6-difluoromethoxyphenyl
Table 397
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethyl-4-difluoromethoxyphenyl
Table 398
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethyl-5-difluoromethoxyphenyl
Table 399
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-3-trifluoromethylphenyl
Table 400
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-4-trifluoromethylphenyl
Table 401
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-5-trifluoromethylphenyl
Table 402
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethoxy-4-trifluoromethylphenyl
Table 403
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-3-trifluoromethoxyphenyl
Table 404
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-4-trifluoromethoxyphenyl
Table 405
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-5-trifluoromethoxyphenyl
Table 406
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethyl-6-trifluoromethoxyphenyl Table 407
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethyl-4-trifluoromethoxyphenyl
Table 408
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethyl-5-trifluoromethoxyphenyl
Table 409
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-3-trifluoromethylphenyl
Table 410
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-4-trifluoromethylphenyl
Table 41 1
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-5-trifluoromethylphenyl
Table 412
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethoxy-4-trifluoromethylphenyl
Table 413
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-3-difluoromethoxyphenyl
Table 414
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-4-difluoromethoxyphenyl
Table 415
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-5-difluoromethoxyphenyl
Table 416
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-6-difluoromethoxyphenyl
Table 417
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- methoxy-4-difluoromethoxyphenyl
Table 418
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- methoxy-5-difluoromethoxyphenyl
Table 419
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-3-methoxyphenyl
Table 420
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-4-methoxyphenyl
Table 421
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-5-methoxyphenyl
Table 422
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethoxy-4-methoxyphenyl
Table 423
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-3-trifluoromethoxyphenyl
Table 424
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-4-trifluoromethoxyphenyl
Table 425
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-5-trifluoromethoxyphenyl Table 426
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- methoxy-6-trifluoromethoxyphenyl
Table 427
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- methoxy-4-trifluoromethoxyphenyl
Table 428
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- methoxy-5-trifluoromethoxyphenyl
Table 429
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-3-methoxyphenyl
Table 430
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-4-methoxyphenyl
Table 431
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-5-methoxyphenyl
Table 432
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethoxy-4-methoxyphenyl
Table 433
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-3-trifluoromethoxyphenyl
Table 434
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-4-trifluoromethoxyphenyl
Table 435
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-5-trifluoromethoxyphenyl
Table 436
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- difluoromethoxy-6-trifluoromethoxyphenyl
Table 437
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethoxy-4-trifluoromethoxyphenyl
Table 438
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- difluoromethoxy-5-trifluoromethoxyphenyl
Table 439
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-3-difluoromethoxyphenyl
Table 440
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-4-difluoromethoxyphenyl
Table 441
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2- trifluoromethoxy-5-difluoromethoxyphenyl
Table 442
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3- trifluoromethoxy-4-difluoromethoxyphenyl
Table 443
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,4- trifluorophenyl
Table 444
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,5- trifluorophenyl Table 445
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,6- trifluorophenyl
Table 446
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4,5- trifluorophenyl
Table 447
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4,6- trifluorophenyl
Table 448
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4,5- trifluorophenyl
Table 449
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,4- trichlorophenyl
Table 450
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,5- trichlorophenyl
Table 451
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,6- trichlorophenyl
Table 452
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4,5- trichlorophenyl
Table 453
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4,6- trichlorophenyl
Table 454
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4,5- trichlorophenyl
Table 455
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,4- tribromophenyl
Table 456
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,5- tribromophenyl
Table 457
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,6- tribromophenyl
Table 458
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4,5- tribromophenyl
Table 459
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4,6- tribromophenyl
Table 460
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4,5- tribromophenyl
Table 461
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,4- trimethylphenyl
Table 462
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,5- trimethylphenyl
Table 463
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,6- trimethylphenyl Table 464
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4,5- trimethylphenyl
Table 465
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4,6- trimethylphenyl
Table 466
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4,5- trimethylphenyl
Table 467
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,4-tri-
(trifluoromethyl)-phenyl
Table 468
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,5-tri- (trifluoromethyl)-phenyl
Table 469
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,3,6-tri-
(trifluoromethyl)-phenyl
Table 470
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4,5-tri-
(trifluoromethyl)-phenyl
Table 471
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,4,6-tri-
(trifluoromethyl)-phenyl
Table 472
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 3,4,5-tri-
(trifluoromethyl)-phenyl
Table 473
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- difluoro-4-chlorophenyl
Table 474
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- difluoro-4-methylphenyl
Table 475
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- difluoro-4-trifluoromethylphenyl
Table 476
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- difluoro-4-methoxyphenyl
Table 477
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- difluoro-4-trifluoromethoxyphenyl
Table 478
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- dichloro-4-fluorophenyl
Table 479
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- dichloro-4-methylphenyl
Table 480
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- dichloro-4-trifluoromethylphenyl
Table 481
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- dichloro-4-methoxyphenyl
Table 482
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is 2,6- dichloro-4-trifluoromethoxyphenyl Table 483
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2-phenylphenyl
Table 484
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
3-phenylphenyl
Table 485
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
4-phenylphenyl
Table 486
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2-fluoro-4-phenylphenyl
Table 487
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2-chloro-4-phenylphenyl
Table 488
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2-methyl-4-phenylphenyl
Table 489
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2-trifluoromethyl-4-phenylphenyl
Table 490
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2-methoxy-4-phenylphenyl
Table 491
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2-trifluoromethoxy-4-phenylphenyl
Table 492
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2,6-difluoro-4-phenylphenyl
Table 493
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2,6-dichloro-4-phenylphenyl
Table 494
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2,6-dimethyl-4-phenylphenyl
Table 495
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2,6-di-(trifluoromethyl)-4-phenylphenyl
Table 496
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2,6-dimethoxy-4-phenylphenyl
Table 497
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2,6-di-(trifluoromethoxy)-4-phenylphenyl
Table 498
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2-fluoro-6-chloro-4-phenylphenyl
Table 499
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2-fluoro-6-methyl-4-phenylphenyl
Table 500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R8 is H and R5 is
2-chloro-6-methyl-4-phenylphenyl
Tables 501 to 1000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is methyl Tables 1001 to 1500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is ethyl
Tables 1501 to 2000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is propyl
Tables 2001 to 2500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is isopropyl
Tables 2501 to 3000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is n-butyl
Tables 3001 to 3500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is sec-butyl
Tables 3501 to 4000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is isobutyl
Tables 4001 to 4500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is tert-butyl
Tables 4501 to 5000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is phenyl
Tables 5001 to 5500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is 4-methylphenyl
Tables 5501 to 6000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is benzyl
Tables 6001 to 6500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is Li+
Tables 6501 to 7000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is Na+
Tables 7001 to 7500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is K+
Tables 7501 to 8000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is Y2Mg2+
Tables 8001 to 8500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is 1/2Cu2+
Tables 8501 to 9000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is 1/2Zn2+
Tables 9001 to 9500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is 1/2Fe2+
Tables 9501 to 10000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is 1/2Ni2+
Tables 10001 to 10500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is NH(CHs)3 + Tables 10501 to 11000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is NH(C2Hs)3 +
Tables 11001 to 11500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is NH(CH2CH2CH2)S+
Tables 11501 to 12000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is NH(CH(CH3)2)3 +
Tables 12001 to 12500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is NH(CH2CH2CH2CH2)3 +
Tables 12501 to 13000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is methylcarbonyl
Tables 13001 to 13500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is ethylcarbonyl
Tables 13501 to 14000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is propylcarbonyl
Tables 14001 to 14500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is isopropylcarbonyl
Tables 14501 to 15000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is phenylcarbonyl
Tables 15001 to 15500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is methoxycarbonyl
Tables 15501 to 16000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is ethoxycarbonyl
Tables 16001 to 16500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is propoxycarbonyl
Tables 16501 to 17000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is isopropoxycarbonyl
Tables 17001 to 17500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is phenoxycarbonyl
Tables 17501 to 18000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is methylaminocarbonyl
Tables 18001 to 18500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is ethylaminocarbonyl
Tables 18501 to 19000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is propylaminocarbonyl
Tables 19001 to 19500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is isopropylaminocarbonyl
Tables 19501 to 20000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is phenylaminocarbonyl Tables 20001 to 20500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is methylsulfonyl
Tables 20501 to 21000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is ethylsulfonyl
Tables 21001 to 21500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is propylsulfonyl
Tables 21501 to 22000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is isopropylsulfonyl
Tables 22001 to 22500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is phenylsulfonyl
Tables 22501 to 23000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is methoxysulfonyl
Tables 23001 to 23500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is ethoxysulfonyl
Tables 23501 to 24000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is propoxysulfonyl
Tables 24001 to 24500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is isopropoxysulfonyl
Tables 24501 to 25000
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is phenoxysulfonyl
Tables 25001 to 25500
Compounds of the formula I.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8 is CN
Tables 25501 to 51000
Compounds of the formula I.D2 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B and the combination of R5 and R8 is as defined in any of tables 1 to 25500
Tables 51001 to 51500
Compounds of the formula I.D3 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B and R5 is as defined in any of tables 1 to 500
Tables 51501 to 52000
Compounds of the formula I.D4 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B and R5 is as defined in any of tables 1 to 500
Tables 52001 to 52500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is H
Tables 52501 to 53000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is methyl
Tables 53001 to 53500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is ethyl
Tables 53501 to 54000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is propyl
Tables 54001 to 54500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is isopropyl
Tables 54501 to 55000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is n-butyl
Tables 55001 to 55500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is sec-butyl
Tables 55501 to 56000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is isobutyl
Tables 56001 to 56500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is tert-butyl
Tables 56501 to 57000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is phenyl
Tables 57001 to 57500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is 4-methylphenyl
Tables 57501 to 58000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is benzyl
Tables 58001 to 58500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is methylcarbonyl
Tables 58501 to 59000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is ethylcarbonyl Tables 59001 to 59500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is propylcarbonyl
Tables 59501 to 60000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is isopropylcarbonyl
Tables 60001 to 60500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is phenylcarbonyl
Tables 60501 to 61000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is methoxycarbonyl
Tables 61001 to 61500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is ethoxycarbonyl
Tables 61501 to 62000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is propoxycarbonyl
Tables 62001 to 62500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is isopropoxycarbonyl
Tables 62501 to 63000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is phenoxycarbonyl
Tables 63001 to 63500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is methylaminocarbonyl
Tables 63501 to 64000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is ethylaminocarbonyl
Tables 64001 to 64500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is propylaminocarbonyl
Tables 64501 to 65000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is isopropylaminocarbonyl
Tables 65001 to 65500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is phenylaminocarbonyl
Tables 65501 to 66000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is methylsulfonyl
Tables 66001 to 66500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is ethylsulfonyl
Tables 66501 to 67000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is propylsulfonyl
Tables 67001 to 67500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is isopropylsulfonyl
Tables 67501 to 68000
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is phenylsulfonyl
Tables 68001 to 68500
Compounds of the formula II.D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is methoxysulfonyl Tables 68501 to 69000
Compounds of the formula II. D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is ethoxysulfonyl
Tables 69001 to 69500
Compounds of the formula II. D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is propoxysulfonyl
Tables 69501 to 70000
Compounds of the formula II. D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is isopropoxysulfonyl
Tables 70001 to 70500
Compounds of the formula II. D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is phenoxysulfonyl
Tables 70501 to 71000
Compounds of the formula II. D1 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B, R5 is as defined in any of tables 1 to 500 and R8a is CN
Tables 71001 to 90000
Compounds of the formula II.D2 in which the combination of R61, R62, R63 and R64 for a compound corresponds in each case to one row of table B and the combination of R5 and R8a is as defined in any of tables 52001 to 71000
In the above tables 1 to 500, the given positions of the substituents on the phenyl ring (e.g. 2-fluoro) are to be understood as relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
Table B
Figure imgf000175_0001
Figure imgf000176_0001
Figure imgf000178_0001
Figure imgf000179_0001
Figure imgf000180_0001
Figure imgf000181_0001
Figure imgf000182_0001
Figure imgf000183_0001
Figure imgf000184_0001
Figure imgf000185_0001
Figure imgf000186_0001
Figure imgf000187_0001
Figure imgf000188_0001
Figure imgf000189_0001
Figure imgf000190_0001
Figure imgf000191_0001
Figure imgf000192_0001
Figure imgf000193_0001
Figure imgf000194_0001
Figure imgf000195_0001
Figure imgf000196_0001
Figure imgf000197_0001
Figure imgf000198_0001
Figure imgf000199_0001
Figure imgf000200_0001
Figure imgf000201_0001
In another preferred embodiment of the invention (embodiment E), R1 is a group of formula VII, where
X is N; and
R3 is Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C5-cycloalkyl, C3-C5-cyclohaloalkyl, benzyl or phenyl, where the phenyl moiety of the two last-mentioned radicals may carry 1 ,
2 or 3 substituents selected from halogen, CN, nitro, Ci-C4-alkyl and C1-C4- haloalkyl;
R4, R8/R8a, n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings;
except for compounds wherein R3 is phenyl and (R4)n is 2,4-Cb or 4-CI;
except for compounds wherein R3 is tert-butyl and (R4)n is 4-Br, 4-tert-butyl, 2-CI, 3-CI, 4-F, 4-phenyl, 2-phenyl, 2,4-Cl2, 2-Me and 4-CI, 3,4-Me2, 2,4,5-Cl3, 4-CF3, 4-OCF3, 2- OCHF2 or 4-OMe, or n is O;
except for compounds wherein (R4)n is 4-CI and R3 is benzyl, methyl, fluoro-tert-butyl or 1 ,1-di-fluoromethyl-ethyl;
wherein the given positions of the substituents R4 on the phenyl ring (e.g. 4-CI) are to be understood as relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule (2,4-Cb = 2,4-dichloro, 4-CI = 4-chloro, 2-Me = 2-methyl, 3,4-Me2 = 3,4-dimethyl, 4-OMe = 4-methoxy).
More preferably (embodiment E. a), R1 is a group of formula VII, where
X is N;
R3 is Ci-C4-alkyl, Ci-C4-haloalkyl or phenyl;
R3 is Ci-C4-alkyl;
each R4 is independently selected from methyl, F, Cl, methoxy, trifuoromethyl, trifuoro- methoxy, difuoromethyl, difuoromethoxy, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, phenoxy, 2- chlorophenoxy, 3-chlorophenoxy and 4-chlorophenoxy; and
R8/R8a, n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings;
except for compounds wherein R3 is phenyl and (R4)n is 2,4-Cb or 4-CI;
except for compounds wherein R3 is tert-butyl and (R4)n is 4-Br, 4-tert-butyl, 2-CI, 3-CI,
4-F, 4-phenyl, 2-phenyl, 2,4-Cb, 2-Me and 4-CI, 3,4-Me2, 2,4,5-Cl3, 4-CF3, 4-OCF3,
2-OCHF2 or 4-OMe, or n is 0;
except for compounds wherein (R4)n is 4-CI and R3 is methyl, fluoro-tert-butyl or 1 ,1-di- fluoromethyl-ethyl.
Even more preferably (embodiment E.a.1 ), R1 is a group of formula VII, where
X is N;
R3 is tert-butyl;
each R4 is independently selected from methyl, F, Cl, methoxy, trifuoromethyl, trifuoro- methoxy and phenyl; and
R4, R8/R8a, n and m have one of the above given general meanings or, preferably, one of the above-given preferred meanings;
except for compounds wherein R3 is tert-butyl and (R4)n is 2-CI, 3-CI, 4-F, 4-phenyl, 2- phenyl, 2,4-Cl2, 2-Me and 4-CI, 3,4-Me2, 2,4,5-Cl3, 4-CF3, 4-OCF3 or 4-OMe, or n is 0;
In the context of embodiments E, E. a and E.a.1 if n is 1 the substituent R4 is preferably bound in position 2, 4 or 6, if n is 2 the substituents R4 are preferably bound in positions 2 and 4, 3 and 5, or 4 and 6, and if n is 3 the substituents R4 are preferably bound in positions 2, 4 and 6, relative to the 1 -position, which is the attachment point of the phenyl ring of the group VII to the remainder of the molecule.
Examples for preferred compounds I and Il of embodiment E are compounds of formulae I.E1 to I.E28 and II. E1 to II.E14, where the variables R41, R42, R43, R44 and R45 are hydrogen or have one of the general meanings or, in particular, one of the preferred meanings given above for R4 and where the variables R8 and R8a have one of the general meanings or, in particular, one of the preferred meanings given above in context with embodiment E. Examples of preferred compounds are the individual compounds compiled in the tables 1 to 1246 below. Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
Figure imgf000203_0001
(I E1 ) (I E2) (I E3) (I E4) (I.E5)
Figure imgf000203_0002
Figure imgf000204_0001
Figure imgf000205_0001
Figure imgf000206_0001
Table 1
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is hydrogen
Table 2
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is methyl
Table 3
Compounds of the formula I. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is ethyl
Table 4
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is propyl Table 5
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isopropyl
Table 6
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is n-butyl
Table 7
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is sec-butyl
Table 8
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isobutyl
Table 9
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is tert-butyl Table 10
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is phenyl Table 11
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is benzyl
Table 12
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is Li+
Table 13
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is Na+ Table 14
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is K+
Table 15
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is /4Mg2+
Table 16
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is YiCu2+
Table 17
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is /4Zn2+
Table 18
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is /4Fe2+ Table 19
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is /4Ni2+
Table 20
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is NH(CH3)3+
Table 21
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is NH(C2H5)3+
Table 22
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is
Figure imgf000207_0001
Table 23
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is
Figure imgf000208_0001
Table 24
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is
Figure imgf000208_0002
Table 25
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is methylcar- bonyl
Table 26
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is ethylcarbonyl
Table 27
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is propylcar- bonyl
Table 28
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isopropylcar- bonyl
Table 29
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is phenylcar- bonyl
Table 30
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is methoxycar- bonyl
Table 31
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is ethoxycar- bonyl
Table 32
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is propoxycar- bonyl
Table 33
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isopropoxy- carbonyl
Table 34
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is phenoxycar- bonyl
Table 35
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is methylami- nocarbonyl
Table 36
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is ethylamino- carbonyl
Table 37
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is propylamino- carbonyl
Table 38
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isopro- pylaminocarbonyl
Table 39
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is phenylami- nocarbonyl
Table 40
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is methylsul- fonyl
Table 41
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is ethylsulfonyl
Table 42
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is propylsul- fonyl
Table 43
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isopropylsul- fonyl
Table 44
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is phenylsul- fonyl
Table 45
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is methoxysul- fonyl
Table 46
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is ethoxysul- fonyl
Table 47
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is propoxysul- fonyl
Table 48
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is isopropoxy- sulfonyl
Table 49
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is phenoxysul- fonyl
Table 50
Compounds of the formula I.E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8 is CN
Tables 51 to 100
Compounds of the formula I.E2 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 101 to 150
Compounds of the formula I.E3 in which the combination of R41, R42, R43, R44, R45 and R8 for a compound is as defined in any of tables 1 to 50
Tables 151 to 200
Compounds of the formula I.E4 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50 Tables 201 to 250
Compounds of the formula I.E5 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 251 to 300
Compounds of the formula I.E6 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 301 to 350
Compounds of the formula I.E7 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 351 to 400
Compounds of the formula I.E8 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 401 to 450
Compounds of the formula I.E9 in which the combination of R41, R42, R43, R44, R45 and R8 for a compound is as defined in any of tables 1 to 50
Tables 451 to 500
Compounds of the formula I.E10 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 501 to 550
Compounds of the formula I.E1 1 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 551 to 600
Compounds of the formula I.E12 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 601 to 650
Compounds of the formula I.E13 in which the combination of R41, R42, R43, R44, R45 and
R8 for a compound is as defined in any of tables 1 to 50
Tables 651 to 700
Compounds of the formula I.E14 in which the combination of R41, R42, R43, R44, R45 and R8 for a compound is as defined in any of tables 1 to 50
Table 701
Compounds of the formula I.E15 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 702
Compounds of the formula I.E16 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A Table 703
Compounds of the formula I.E17 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 704
Compounds of the formula I.E18 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 705
Compounds of the formula I.E19 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 706
Compounds of the formula I.E20 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 707
Compounds of the formula I.E21 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 708
Compounds of the formula I.E22 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 709
Compounds of the formula I.E23 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 710
Compounds of the formula I.E24 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 71 1
Compounds of the formula I.E25 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 712
Compounds of the formula I.E26 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 713
Compounds of the formula I.E27 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A
Table 714
Compounds of the formula I.E28 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A Table 715
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is hydrogen
Table 716
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is methyl
Table 717
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is ethyl Table 718
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is propyl
Table 719
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isopropyl
Table 720
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is n-butyl
Table 721
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is sec-butyl
Table 722
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isobutyl Table 723
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is tert-butyl
Table 724
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is phenyl
Table 725
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is 4- methylphenyl
Table 726
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is benzyl
Table 727
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is methylcar- bonyl
Table 728
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is ethylcar- bonyl
Table 729
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is propylcar- bonyl
Table 730
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isopropyl- carbonyl
Table 731
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is phenylcar- bonyl
Table 732
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is methoxy- carbonyl
Table 733
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is ethoxycar- bonyl
Table 734
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is propoxycar- bonyl
Table 735
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isopropoxy- carbonyl
Table 736
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is phenoxy- carbonyl Table 737
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is methylami- nocarbonyl
Table 738
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is ethylamino- carbonyl
Table 739
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is propylami- nocarbonyl
Table 740
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isopro- pylaminocarbonyl
Table 741
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is phenylami- nocarbonyl
Table 742
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is methylsul- fonyl
Table 743
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is ethylsulfonyl
Table 744
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is propylsul- fonyl
Table 745
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isopropylsul- fonyl
Table 746
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is phenylsul- fonyl Table 747
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is methoxysul- fonyl
Table 748
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is ethoxysul- fonyl
Table 749
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is propoxysul- fonyl
Table 750
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is isopropoxy- sulfonyl
Table 751
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is phenoxysul- fonyl
Table 752
Compounds of the formula II. E1 in which the combination of R41, R42, R43, R44 and R45 for a compound corresponds in each case to one row of table A and R8a is CN
Tables 753 to 790
Compounds of the formula II.E2 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 715 to 752
Tables 791 to 828
Compounds of the formula II.E3 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 715 to 752
Tables 829 to 866
Compounds of the formula II.E4 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 715 to 752
Tables 867 to 904
Compounds of the formula II.E5 in which the combination of R41, R42, R43, R44, R45 and R8a for a compound is as defined in any of tables 715 to 752
Tables 905 to 942
Compounds of the formula II.E6 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 715 to 752 Tables 943 to 980
Compounds of the formula II.E7 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 715 to 752
Tables 981 to 1018
Compounds of the formula II.E8 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 715 to 752
Tables 1019 to 1056
Compounds of the formula II.E9 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 715 to 752
Tables 1057 to 1094
Compounds of the formula II.E10 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 715 to 752
Tables 1095 to 1 132
Compounds of the formula II.E11 in which the combination of R41, R42, R43, R44, R45 and R8a for a compound is as defined in any of tables 715 to 752
Tables 1133 to 1 170
Compounds of the formula II.E12 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 715 to 752
Tables 1171 to 1208
Compounds of the formula II.E13 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 715 to 752
Tables 1209 to 1246
Compounds of the formula II.E14 in which the combination of R41, R42, R43, R44, R45 and
R8a for a compound is as defined in any of tables 715 to 752
Compounds of formulae I and Il can be prepared by one or more of the following methods and variations as described in schemes 1 to 24 and in the syntheses descriptions below. The variables are as defined above for formulae I and II.
Compounds of formula I, wherein R8 is H and m is 0 (or compounds II, wherein R8a is H), can be prepared by sulfurizing the corresponding azole derivative IX as outlined in scheme 1. Sulfurization can be carried out in analogy to known processes, for example as described in WO 96/16048, WO 97/06152 or DE-A-19620407. For instance, the triazolyl ring can be first deprotonated with a strong base, e.g. an organolithium base, such as n-butyllithium, tert-butyllithium or sec-butyllithium, lithium diisopropyl amide, sodium hydride, sodium amide or potassium tert-butylate mixed with tetramethylethyl- ene diamine (TMEDA), and then the resulting anion is reacted with elemental sulfur. Sulfur is generally used in powdered form. The reaction is generally carried out in an inert solvent, such as ethers, e.g. diethylether, methyl-tert-butylether, tetrahydrofuran or dioxane, dimethoxyethane, liquid ammonia, dimethylsulfoxide or dimethylformamide. The reaction temperature is not very critical and can range, for example, from -70 to +50 0C, preferably from -70 to 00C. Alternatively, sulfurization can be carried out in the absence of a base by reacting IX with elemental sulfur in a high-boiling solvent, such as N-methylpyrrolidinone, dimethylsulfoxide or N,N-dimethylformamide, while heating, e.g. to 160 to 250 0C. After completion of the reaction, the resulting mixture is hydro- lyzed, e.g. by the addition of water or an aqueous acid, such as a mineral acid (e.g. dilute sulfuric acid or hydrochloric acid), acetic acid or ammoniumchloride, to give com- pound I.
Scheme 1
Figure imgf000218_0001
IX I
(R8/R8a = H; m = 0)
The azole compound IX, wherein R1 is a group III, can be prepared in analogy to known methods, as outlined in scheme 2. For instance, the carbonyl compounds 1 and 2a, wherein LG is a good leaving group, such as Cl, Br, I, tosylate or triflate, can be subjected to an aldol condensation for example in the presense of an acid, such as methansulfonic acid, or in an inert reaction medium at elevated temperatures. In a subsequent step the obtained olefine 3 can be converted to a compound 5 by reacting it with the azole compound 4 in the presence of a base, such as an alkali metal hydride (e.g. sodium hydride, potassium hydride), an alkali metal hydroxide (e.g. sodium hydroxide, potassium hydroxide), or an alkali metal carbonate (e.g. sodium carbonate, potassium carbonate, caesium carbonate). The latter reaction is suitably carried out in a solvent. Suitable solvents are, for example, toluene, N-methypyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran), alcohols (e.g. methanol, ethanol, isopropanol or tert-butanol), acetonitrile, or N,N-dimethylformamide. The reduction of ketone 5 is depicted in scheme 4.
Scheme 2
Figure imgf000219_0001
As an alternative to the aldol condensation described in scheme 2, the carbonyl compound 1 can be reacted, in analogy to methods described in Nongyao, 40(12), 12-14, 2001 and Nongyao, 41 (2), 10-12, 2002, with a carbonyl comopound 2b that in place of the leaving group LG already carries the azole moiety. This way compound 5 can be obtained in one step starting from compound 1 , as shown in scheme 3. If desired it may be possible to obtain predominantely the E-isomer (in relation to the phenyl group and the azole group) of compound 5 by carrying out the aldol condensation in the presence of bromine and bromo-succinimide or by heating the initial product of the aldol condensation in an inert solvent, as also described in the above cited references.
Scheme 3
Figure imgf000219_0002
Scheme 4 depicts a subsequent reduction of the carbonyl compound 5 to the desired azole compound IX, wherein R1 is a group III, in analogy to methods described in Nongyao, 40(12), 12-14, 2001 and Nongyao, 41 (2), 10-12, 2002, using customary procedures, such as reduction with sodium borohydride or potassium borohydride in a polar solvent, preferably an alkanol, such as methanol, ethanol, butanol or isopropanol, or ethers, such as diethyl ether or tetrahydrofurane.
Scheme 4
Figure imgf000220_0001
(R1 = group III)
The carbonyl compounds 1 are either commercially available, in particular the benzal- dehyde derivatives 1 with R2 being hydrogen, or can be produced by known proce- dures. Thus, compounds 1 can be prepared by a Friedel-Crafts acylation of benzene that optionally carries n substituents R4 with R2-C(=O)-CI in the presence of a Lewis acid, such as AICb or FeCb, under reaction conditions customary for this reaction type.
The carbonyl compound 2a is either commercially available or can be obtained for in- stance from the halide 6 by a Grignard reaction with the aldehyde 7, or from the halide 61 by a Grignard reaction with the aldehyde T, as outlined in scheme 5 below. Oxidation of the obtained alcohol 8 via known methods, such as oxidation with the Swern reagent, hypervalent iodine compounds (IBX, Dess-Martin reagent), chromine compounds (e.g. pyridinium dichromate, pyridinium chlorochromate, dipyridinium chromine trioxide), sodium hypochlorite and the like, yields the carbonyl compound 9. Subsequent halogenation of the carbonyl compound 9 results in carbonyl compound 2a, wherein LG is a halogen atom, which, if desired, can be converted into a compound 2a, wherein LG is a leaving group LG other than halogen. In case R3 is an aryl group carbonyl compound 9 can also be produced for instance by a Friedel-Crafts acylation of R3-H with acetylchloride in the presence of a Lewis acid, as described before.
Scheme 5
1.) Mg
Figure imgf000221_0001
(Hal = halogen )
The halides 6 and 6\ the aldehydes 7 and T and the starting materials for the preparation of compound 1 , as described herein before, are either commercially available or can be produced by standard methods known to the skilled
person.
The compound 2b can be prepared from compound 2a using a procedure analogous to that described for the second reaction step depicted in scheme 2.
The azole compound IX, wherein R1 is a group IV, can be prepared in analogy to known methods described, for example, in DE-A-255156, EP-A-0065485, Nongyao, 40(3), 9-10, 2001 or Pesticide Science, 1 1 (1 ), 95-99, 1980, as outlined in scheme 6. For instance, the compound 10, wherein LG is a good leaving group, such as a halo- gen atom, in particular Cl, Br or I, phenylsulfonyloxy, p-tosyloxy, trifluoroacetyloxy or alkylsulfonyloxy, such as mesyloxy, can be reacted with the azole compound 41, wherein M is a hydrogen atom or a metal atom, in particular an alkali metal atom, such as Li, Na or K. In case M is H, the reaction is suitably carried out in the presence of a base, such as an alkali metal hydride (e.g. sodium hydride, potassium hydride), an al- kali metal hydroxide (e.g. sodium hydroxide, potassium hydroxide), an alkali metal carbonate (e.g. sodium carbonate, potassium carbonate, caesium carbonate) or a suitable amine (e.g. triethylamine, triethylenediamine, piperidine, pyridine, 4- dimethylaminopyridine, 4-pyrrolidylpyridine). If LG is Cl or Br, the reaction can be accelerated by the addition of an alkali metal iodide, such as NaI or Kl. The reaction is suitably carried out in a solvent. Suitable solvents are inert versus the reacants and products and are rather polar, for example, N,N-dimethylformamide, N,N-dimethylacet- amide, dimethylsulfoxide, acetonitrile, benzonitrile, ethers, such as diethyl ether, dipro- pyl ether, methyl-tert-butyl ether, tetrahydrofuran or dioxane, and the like, and can be used in combination with other inert, less polar solvents, such as benzene, toluene, the xylenes, chlorobenzene, nitrobenzene, hexane, heptane, petrolether and the like. The reaction temperature is not very critical and can range, for example from 0 to 2200C and preferably from 80 to 1700C. Suitably, the reaction is carried out at reflux temperature of the reaction mixture.
Scheme 6
Figure imgf000222_0001
(R1 = a group IV)
Compound 10 in turn can be prepared in analogy to known methods, such as described, for example, in DE-A-255156, EP-A-0065485, Synthesis, 1974, I, 23 or Nongyao, 40(3), 9-10, 2001 , as outlined in scheme 7 below. For instance, the ketone
11 may be reacted with a diol HO-A1-OH for several hours preferably in the presence of an azeotrope-forming compound, such as benzene, toluene, xylene, chloroform or tet- rachloromethane, which can also serve as reaction solvents. Alternatively, a mixture of a solvent which doesn't form an azeotrope with water and an azeotrope-forming solvent, such as ethanol, propanol, butanol or pentanol, is used. The ketalization reaction is accelerated by the presence of a strong acid, such p-toluenesulfonic acid. The reaction is generally carried out at reflux. Subsequent halogenation of the resulting ketale
12 yields ketale 10, wherein LG is a halogen atom, which, if desired, can be converted into a compound 10, wherein LG is a leaving group LG other than halogen.
Scheme 7
Figure imgf000222_0002
As an alternative to the process described in scheme 6, compound IX with R1 being a group IV can be prepared in analogy to the method described in EP-A-0065485 as outlined in scheme 8 below by a ketalization reaction of the ketone 13 with a diol HO-A1- OH. The ketalization reaction can be carried out under reaction conditions described for the process of scheme 7.
Scheme 8
Figure imgf000223_0001
(R1 = a group IV)
The ketone 13 in turn can be prepared in analogy to the method described in EP-A- 0065485 as outlined in scheme 9 below by reacting the compound 14, wherein LG is a good leaving group, such as a halogen atom, in particular Cl, Br or I, phenylsulfonyloxy, p-tosyloxy, trifluoroacetyloxy or alkylsulfonyloxy, such as mesyloxy, with the azole compound 41 under reaction conditions described for the reaction in scheme 6. Compound 14, in turn, is obtainable from the halogenation of the ketone 11 , which can be accomplished by using standard methods customary for this type of reaction.
Scheme 9
Figure imgf000223_0002
Ketone 11 used in the above reactions is either commercially available or can be pro- duced by standard methods known to the skilled person, for instance by a Friedel- Crafts acylation of benzene optionally carrying n substituents R4 with acetylchloride in the presence of a Lewis acid, such as AICb or FeCb, under reaction conditions customary for this reaction type. The azole compound IX, wherein R1 is a group V, can be prepared in analogy to known methods, such as described, for example, in US 3,991 ,071 , Hecheng Huaxue, 10(6), 506-509, 2002 and Huaxue Gongchengshi, 20(6), 62-64, 2006, as outlined in scheme 10. For instance, the compound 15, wherein LG is a good leaving group, such as a halogen atom, in particular Cl, Br or I, phenylsulfonyloxy, p-tosyloxy, trifluoroacetyloxy or alkylsulfonyloxy, such as mesyloxy, can be reacted with azole compound 4\ wherein M is a hydrogen atom or a metal atom, in particular an alkali metal atom, such as Li, Na or K. In case M is H, the reaction is suitably carried out in the presence of an additional base, such as an alkali metal hydride (e.g. sodium hydride, potassium hydride), an alkali metal hydroxide (e.g. sodium hydroxide, potassium hydroxide), an alkali metal carbonate (e.g. sodium carbonate, potassium carbonate, caesium carbonate) or a suitable amine (e.g. triethylamine, triethylenediamine, piperidine, pyridine, 4- dimethylaminopyridine, 4-pyrrolidylpyridine), or alternatively in the presence of excess azole compound 41. The reaction is suitably carried out in a solvent. Suitable solvents are inert versus the reactants and the product and are rather polar, for example, N, N- dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, acetonitrile, benzoni- trile, ethers, such as diethyl ether, dipropyl ether, methyl-tert-butyl ether, tetrahydrofu- ran or dioxane, and the like, and can be used in combination with other inert, less polar solvents, such as benzene, toluene, the xylenes, chlorobenzene, nitrobenzene, hex- ane, heptane, petrolether and the like. The reaction temperature is not very critical and can range, for example from 0 to 2000C and preferably from 80 to 1500C. Suitably, the reaction is carried out at reflux temperature of the reaction mixture.
Scheme 10
R1 = a group V
As shown in scheme 1 1 , compound 15 can be prepared by reacting the amine 16 with the carbonyl compound 17, such as phosgene or bis(trichloromethyl) carbonate, in ac- cordance with methods described in the aforementioned references. The reaction is typically carried out in the presence of an additional base such as described herein before, or alternatively in the presence of excess amine 16. The reaction is suitably carried out in an inert solvents such as described herein before. Scheme 1 1
Figure imgf000225_0001
The amine 16 in turn can be prepared in accordance with any of the methods well known to a skilled person. For example it can be made by reacting the compound 18 with compound 20 or, alternatively, in case R7 is not hydrogen, by reacting the primary amine 19 with compound 21 , as outlined in scheme 12. These amination reactions are typically carried out in the presence of a base. The leaving group LG' in compounds 20 and 21 is typically halogen, in particular bromine. Scheme 12
Figure imgf000225_0002
Figure imgf000225_0003
Figure imgf000225_0004
The compounds 18 to 21 are either commercially available or can be produced using methods well known to a skilled person. The compound 20, wherein Y is O, can for instance be prepared according to Hecheng Huaxue, 10(6), 506-509, 2002 by reacting the phenol 22 with a dihalide 23, as shown in scheme 13 below. The reaction can suitably be carried out in an aqueous medium in the presence of a base, such as sodium hydroxide, under phase transfer catalysis conditions.
Scheme 13
Figure imgf000226_0001
(Y = O, LC = HaI)
A further method for preparing the azole compound IX, wherein R1 is a group V, comprises reacting commercially available carbonyldiazole of formula 24, wherein LG" is azolyl, with amine 16, as shown in scheme 14. The reaction is suitably effected in an inert solvent, such as described before, at a temperature of, for example, from 0° to 1000C, and optionally in the presense of an additional base. Alternatively, compound 24, wherein LG" is a leaving group as described herein before, in particular halogen, can be employed as azolyl carbonyl donor, as also shown in scheme 14. The latter reaction is suitably carried out in the presence of an additional base, such as described before, or in the presense of excess amine 16.
Scheme 14
Figure imgf000226_0002
V
LG" = -NN j or LG, such as Cl
X^
The azole compound IX, wherein R1 is a group Vl, can be prepared in analogy to known methods, such as described, for example, in EP 0 183 458 B1 , as outlined in scheme 15. For instance, the compound 25, wherein LG is a good leaving group, such as a halogen atom, in particular Cl, Br or I, phenylsulfonyloxy, p-tosyloxy, trifluoroacety- loxy or alkylsulfonyloxy, such as mesyloxy, can be reacted with the azole compound 4. The reaction is suitably carried out in the presence of a base, such as an alkali metal hydride (e.g. sodium hydride, potassium hydride), an alkali metal hydroxide (e.g. so- dium hydroxide, potassium hydroxide), an alkali metal carbonate (e.g. sodium carbonate, potassium carbonate, caesium carbonate) or a suitable amine (e.g. triethylamine, triethylenediamine, piperidine, pyridine, 4-dimethylaminopyridine, 4-pyrrolidylpyridine). If LG is Cl or Br, the reaction can be accelerated by the addition of an alkali metal io- dide, such as NaI or Kl. The reaction is suitably carried out in a solvent. Suitable solvents are inert versus the reactants and the product and are rather polar, for example, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, acetonitrile, ben- zonitrile, ethers, such as diethyl ether, dipropyl ether, methyl-tert-butyl ether, tetrahy- drofuran or dioxane, and the like, and can be used in combination with other inert, less polar solvents, such as benzene, toluene, the xylenes, chlorobenzene, nitrobenzene, hexane, heptane, petrolether and the like. The reaction temperature is not very critical and can range, for example from 0 to 2200C and preferably from 80 to 1700C. Suitably, the reaction is carried out at reflux temperature of the reaction mixture.
Scheme 15
Figure imgf000227_0001
Vl
The compound 25 with LG being halogen can be prepared by reaction of compound 26 with Sθ2Hal2, wherein Hal stands for halogen and in particular for bromine or chloride, according to EP 0 183 458 B1 , as shown in scheme 16 below. The reaction is suitably carried out in an inert solvent, such as chloroform, dichlormethane, acetonitrile, pyridine, ether, such as diethyl ether, dipropyl ether, methyl-tert-butyl ether, tetrahydrofu- ran or dioxane, and the like. A compound 25 with LG being a leaving group other than halogen can be obtained by conversion of a compound 25 with LG being halogen according to methods well known to a skilled person.
Scheme 16
SO9 oHl IaClIIo
Figure imgf000227_0002
Figure imgf000227_0003
Aternatively the compound 25 with LG being halogen can be prepared by reaction of compound 27 with POHab, wherein Hal stands in particular for bromine or chlorinde, according to EP 0 183 458 B1 , as shown in scheme 17 below. The reaction is suitably performed in the presence of a base, in particular an organic base such as pyridine. The reaction medium may in addition comprise an inert solvent as described herein before.
Scheme 17
Figure imgf000228_0001
The compound 26, wherein W is O, can be prepared by reaction of the carboxylic acid 28 with the isothiocyanate 29, in accordance with EP 0 183 458 B1 , as outlined in scheme 18 below. The reaction is suitably effected with heating, e.g. to reflux, in an anhydrous aprotic solvent, such as ethanol, ether, chloroform, dichlormethan and the like. If desired a compound 26, wherein W is S, can be obtained from the corresponding compound 26, wherein W is O, by a sulfurization reaction. Examples of suitable sulfurizing agents are organophosphorus sulfides, such as Lawesson's reagent, (2,2- bis(4-methoxyphenyl)-1 ,3,2,4-dithiodiphosphetane 2,4-disulfide, organotin sulfides, such as bis(tricyclohexyltin) sulfide, or phosphorus pentasulfide (see also J. March, Advanced Organic Chemistry, 4th edition, Wiley lnterscience 1992, p.893f and the literature cited therein). Scheme 18
Figure imgf000228_0002
The compound 27, wherein W is O, can be prepared by reaction of the urea derivative 30 in the presence of an acid, in particular an inorganic acid such as hydrochloric acid, in accordance with EP 0 183 458 B1 , as outlined in scheme 19. In general the reaction is carried out in an inert solvent, such as in particular alkanol, e.g. ethanol. A compound 27, wherein W is S, if desired, can be obtained from the corresponding compound 27, wherein W is O, by a sulfurization reaction, as described herein above for compound 26. Scheme 19
As outlined in scheme 20, compound 30 can be prepared by reaction of carboxylic acid 28 with the isocyanate 31 employing reaction conditions customary for this reaction type.
Scheme 20
Figure imgf000229_0002
28 30
Compound 28 in turn is either commercially available or can be produced by standard methods known to the skilled person.
As an alternative to the process depicted in scheme 15 the azole compound IX, wherein R1 is a group Vl and W is O, can also be prepared by reacting the iminophos- phorane 32, which is a derivative of compound 28, in a one-pot reaction with the isocyanate 31 and subsequently with the azole 4 in the presence of a base, such as described herein before, according to method described in Synthetic Communications, 32(19), 3057-3062, 2002, as outlined in scheme 21 below.
Scheme 21
Figure imgf000229_0003
Figure imgf000229_0004
R1 = a group Vl.
W = O The azole compound IX, wherein R1 is a group VII, can be prepared in analogy to known methods, such as described, for example, in GB 1 418 430, Xiamen Daxue Xuebao, Ziran Kexueban, 25(6), 730-733, 1986, Xiamen Daxue Xuebao, Ziran Kexue- ban, 29(3), 305-308, 1990 and Pesticide Biochemsitry and Physiology, 26(1 ), 10-21 , 1986, as outlined in scheme 22. For instance by reduction of the corresponding car- bonyl compound 33 using standard procedures customary for this type of conversion, such as reacting with hydrogen in the presence of a catalyst, reacting with compex hydrides, such as sodium borohydride, or reacting with sodium dithionite, and the like.
10 The reduction is usually carried out in a solvent that is suitable for the particular reaction type employed.
Scheme 22
reduction
Figure imgf000230_0001
H e
Figure imgf000230_0002
R1 = a group VII
The carbonyl compound 33 can be prepared by conventional methods, for instance according to the procedure depicted in scheme 23 below. The compound 34, wherein LG is a good leaving group, such as a halogen atom, in particular Cl, Br or I, phenylsul-
20 fonyloxy, p-tosyloxy, trifluoroacetyloxy or alkylsulfonyloxy, such as mesyloxy, can be reacted with an azole compound 41, wherein M is a hydrogen atom or a metal atom, in particular an alkali metal atom, such as Li, Na or K. In case M is H, the reaction is suitably carried out in the presence of a base, such as an alkali metal hydride (e.g. sodium hydride, potassium hydride), an alkali metal hydroxide (e.g. sodium hydroxide,
25 potassium hydroxide), an alkali metal carbonate (e.g. sodium carbonate, potassium carbonate, caesium carbonate) or a suitable amine (e.g. triethylamine, triethylenedia- mine, piperidine, pyridine, 4-dimethylaminopyridine, 4-pyrrolidylpyridine). If X is Cl or Br, the reaction can be accelerated by the addition of an alkali metal iodide, such as NaI or Kl. The reaction is suitably carried out in a solvent. Suitable solvents are inert
30 versus the reacants and products and are rather polar, for example, N, N- dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, acetonitrile, benzoni- trile, ethers, such as diethyl ether, dipropyl ether, methyl-tert-butyl ether, tetrahydrofu- ran or dioxane, and the like, and can be used in combination with other inert, less polar solvents, such as benzene, toluene, the xylenes, chlorobenzene, nitrobenzene, hex- ane, heptane, petrolether and the like. The reaction temperature is not very critical and can range, for example from 0 to 2200C and preferably from 80 to 1700C. Suitably, the reaction is carried out at reflux temperature of the reaction mixture.
Scheme 23
Figure imgf000231_0001
Compound 34 in turn can be produced for example by the 2-step process shown in scheme 24. In the first step compound 37 is prepared by reacting the phenol 35 with the carbonyl compound 2a1, wherein LG' is a good leaving group, such as described herein before. Typically LG' is a halogen atom, in particular Cl, Br or I. In the second step the carbonyl compound 37 is then converted into compound 34 by introduction of a leaving group LG, such as bromine, according to standard methods well known to a skilled person.
Scheme 24
Figure imgf000231_0002
The phenol 35 and the carbonyl compound 2a1 are either commercially available or can be prepared according to well established processes known to a skilled person. The compound 2a1 is for instance obtainable in analogy to the method for producing the compound 2a that is outlined in scheme 5 and has been described herein before.
Compounds of formula I, wherein R8 is different from hydrogen and m is 0, can be prepared from compounds I (wherein R8 = H and m = 0). Compounds of formula I, wherein m is 0 and R8 is Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2- Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, phenyl, phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last- mentioned radicals may be substituted as described above, and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 het- eroatoms selected from N, O and S as ring members, where the heterocyclic ring may be substituted as described above, may be prepared in analogy to the method described in DE-A-19520098 by reacting a compound I, wherein m is 0 and R8 is H, with a compound R8-LG, where R8 has one of the above meanings and LG is a leaving group, such as a halide (e.g. Cl, Br, I), a tosylate or a mesylate, in the presence of a base. Suitable bases are, for example, alkali metal hydrides (e.g. sodium hydride, potassium hydride), alkali metal hydroxides (e.g. sodium hydroxide, potassium hydroxide), alkali metal carbonates (e.g. sodium carbonate, potassium carbonate, caesium carbonate), alkali metal alkoxides (e.g. sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide) or organolithium bases (e.g. n-butyl lithium, sec-butyl lithium, tert-butyl lithium and lithium diisopropylamine.). The reaction is generally carried out in a suitable solvent. Suitable solvents are, for example, toluene, N-methylpyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane), acetonitrile, N,N-dimethylformamide or dimethylsulfox- ide.
Alternatively, compounds of formula I, wherein m is 0 and R8 is Ci-Cio-alkyl, Ci-Cio- haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-C10- cycloalkyl, C3-Cio-halocycloalkyl, phenyl, phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may be substituted as described above, and a 5- or 6- membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may be substituted as described above, may be prepared in analogy to the method described in Heterocycles, 23(7), 1645-1649, 1985 by reacting compound IX with a disulfide R8-S-S-R8 in the presence of a strong base under conditions similar to those described for scheme 1.
Compounds of formulae I, wherein m is 0 and R8 is -C(=O)R17 or -C(=S)R17, may be prepared in analogy to the method described in DE-A-19617461 by reacting a compound I, wherein m is 0 and R8 is H, with a compound R17-C(=O)-W, R17-C(=S)-W, R17'- N=C=O or R17'-N=C=S, wherein R17 has one of the above meanings, R17' is Ci-Cio- alkyl or Ci-Cio-haloalkyl and W is a good leaving group, such as a halide (e.g. Cl, Br, I), an alkoxide (e.g. methoxide, ethoxide) or pentafluorophenoxide, in the presence of a base. Suitable bases are, for example, alkali metal hydrides (e.g. sodium hydride, potassium hydride), alkali metal hydroxides (e.g. sodium hydroxide, potassium hydroxide), alkali metal carbonates (e.g. sodium carbonate, potassium carbonate, caesium carbonate), alkali metal alkoxides (e.g. sodium methoxide, potassium methoxide, so- dium ethoxide, potassium ethoxide, potassium tert-butoxide) or organolithium bases (e.g. n-butyl lithium, sec-butyl lithium, tert-butyl lithium, lithium diisopropylamine). The reaction is generally carried out in a suitable solvent. Suitable solvents are, for example, toluene, N-methylpyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane), acetonitrile, N,N-dimethylformamide or dimethylsulfoxide.
Compounds of formula I, wherein m is 0 and R8 is -SO2R17, may be prepared in analogy to the method described in DE-A-19620590 by reacting a compound I, wherein m is 0 and R8 is H, with a compound R17-Sθ2-W, wherein R17 has one of the above meanings and W is a good leaving group, such as a halide (e.g. Cl, Br, I), an alkoxide (e.g. methoxide, ethoxide) or pentafluorophenoxide, in the presence of a base. Suitable bases are, for example, alkali metal hydrides (e.g. sodium hydride, potassium hydride), alkali metal hydroxides (e.g. sodium hydroxide, potassium hydroxide), alkali metal carbonates (e.g. sodium carbonate, potassium carbonate, caesium carbonate), alkali metal alkoxides (e.g. sodium methoxide, potassium methoxide, sodium ethoxide, po- tassium ethoxide, potassium tert-butoxide) or organolithium bases (e.g. n-butyl lithium, sec-butyl lithium, tert-butyl lithium, lithium diisopropylamine). The reaction is generally carried out in a suitable solvent. Suitable solvents are, for example, toluene, N- methylpyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2- dimethoxyethane), acetonitrile, N,N-dimethylformamide or dimethylsulfoxide.
Compounds of formula I, wherein m is 0 and R8 is -CN, may be prepared in analogy to the method described in DE-A-19620407 by reacting a compound I, wherein m is 0 and R8 is H, with a compound CN-W, wherein W is a good leaving group, such as a halide (e.g. Cl, Br, I), in the presence of a base. Suitable bases are, for example, alkali metal hydrides (e.g. sodium hydride, potassium hydride), alkali metal hydroxides (e.g. sodium hydroxide, potassium hydroxide), alkali metal carbonates (e.g. sodium carbonate, potassium carbonate, caesium carbonate), alkali metal alkoxides (e.g. sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide) or organolithium bases (e.g. n-butyl lithium, sec-butyl lithium, tert-butyl lithium, lithium diisopropylamine). The reaction is generally carried out in a suitable solvent. Suitable solvents are, for example, toluene, N-methylpyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane), acetonitrile, N,N-dimethylformamide or dimethylsulfoxide. Compounds of formula I, wherein m is 0 and R8 is M, may be prepared in analogy to the method described in DE-A-19617282 by reacting a compound I with an amine NRaRbRc, wherein Ra, Rb and Rc are as defined above, or with a metal salt, such as sodium hydroxide, potassium hydroxide or copper acetate.
Compounds of formula I, wherein m is 0 and R8 is a group of formula III, may be prepared in analogy to the method described in WO 97/43269 by reacting a compound I, wherein m is 0 and R8 is H, with a halogen, especially iodine, in the presence of a base. Suitable bases are, for example, alkali metal hydrides (e.g. sodium hydride, po- tassium hydride), alkali metal hydroxides (e.g. sodium hydroxide, potassium hydroxide), alkali metal carbonates (e.g. sodium carbonate, potassium carbonate, caesium carbonate), alkali metal alkoxides (e.g. sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide) or organolithium bases (e.g. n-butyl lithium, sec-butyl lithium, tert-butyl lithium, lithium diisopropylamine). The reaction is generally carried out in a suitable solvent. Suitable solvents are, for example, toluene, N-methylpyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane), acetonitrile, N,N-dimethylformamide or dimethylsulfoxide.
Compounds of formula I, wherein m is 0 and R8 is -P(=Q)R18R19, may be prepared in analogy to the method described in WO 99/05149.
Compounds of formula II, wherein R8a is different from hydrogen, can be prepared by reacting the NR8a group, wherein R8a is H, in analogy to the above-described conversion of compounds I, wherein R8 is H, into compounds, wherein R8 is different from H.
Compounds I, wherein m is 1 or 2, can be prepared from respective compounds I, wherein m is 0, by oxidation. Alternatively, compounds I, wherein m is 2, can be prepared from compounds IX by first deprotonating the triazolyl ring and then reacting with a sulfonyl chloride R8Sθ2CI. Compounds I, wherein m is 3, can be prepared from com- pounds IX by first deprotonating the triazolyl ring and then reacting with sulfuric acid chloride or a sulfuric ester chloride of formula R8OSθ2CI, wherein R8 is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-C10- alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, phenyl, phenyl-Ci- C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may be substituted as mentioned above, and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S, wherein the heterocyclic ring may be substituted as mentioned above. If individual compounds cannot be prepared via the above-described routes, they can be prepared by derivatization of other compounds I and Il or by customary modifications of the synthesis routes described. The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or silica gel. Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils, which are freed or purified from volatile components under reduced pressure and at moder- ately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or digestion.
A further aspect of the invention relates to compounds of formula IX
R1 (IX) wherein X and R1 have one of the general or, in particular, one of the preferred meanings given above for compounds I and II.
Compounds IX are on the one side valuable intermediates in the preparation of com- pounds I and Il (see above schemes), but on the other side show a remarkable fungicidal activity, too.
The invention further refers to an agricultural composition comprising at least one compound of formula I and/or Il as defined above or an agriculturally acceptable salt thereof and a liquid or solid carrier. Suitable carriers, as well as auxiliaries and further active compounds which may also be contained in the composition of the invention are defined below.
The compounds I and Il and the compositions according to the invention, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomy- cetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomy- cetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants. The compounds I and Il and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e. g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants. Preferably, compounds I and Il and compositions thereof, respectively are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
Preferably, treatment of plant propagation materials with compounds I and Il and com- positions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf.
http://www.bio.org/speeches/pubs/er/agrLproducts.asp). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have been rendered tolerant to applications of specific classes of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e. g. US 6,222,100, WO 01/82685,
WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529,
WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imida- zolinones (see e. g. US 6,222,100, WO 01/82685, WO 00/026390, WO 97/41218, WO 98/002526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/014357, WO 03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate (see e. g. WO 92/00377); glutamine synthetase (GS) inhibitors, such as glufosinate (see e.g. EP-A 242 236, EP-A 242 246) or oxynil herbicides (see e. g. US 5,559,024) as a result of conventional methods of breeding or genetic engineering. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox. Genetic engineering methods have been used to render cultivated plants, such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.) and LibertyLink® (glufosinate- tolerant, Bayer CropScience, Germany).
Furthermore, plants are also covered that, by the use of recombinant DNA techniques, are capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bi ) or Cryθc; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp. or Xenor- habdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Strep- tomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g., in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coleoptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of them are commercially available such as YieldGard® (corn cultivars producing the CryiAb toxin), YieldGard® Plus (corn cultivars producing CryiAb and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Her- culex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphi- nothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the Cry1 Ac toxin), Bollgard® I (cotton cultivars producing the CryiAc toxin), Bollgard® Il (cotton cultivars producing CryiAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt- Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt 1 1 (e. g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CryiAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Mon- santo Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CryiAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme). Furthermore, plants are also covered that, by the use of recombinant DNA techniques, are capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solarium bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the per- son skilled in the art and are described, e. g., in the publications mentioned above.
Furthermore, plants are also covered that, by the use of recombinant DNA techniques, are capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
Furthermore, plants are also covered that, by the use of recombinant DNA techniques, contain a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health- promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sciences, Canada).
Furthermore, plants are also covered that, by the use of recombinant DNA techniques, contain a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany).
The compounds I and Il and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A. tragopogonis); Altemaria spp. (Alternaria leaf spot) on vegetables, rape {A. brassicola or brassicae), sugar beets {A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solanior A. altemata), tomatoes (e. g. A. solanior A. altemata) and wheat; Aphano- myces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight (β. zeicola) on corn, e. g. spot blotch (β. sorokiniana) on cereals and e.g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e. g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad- leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e.g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. beticola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum: leaf mold) and ce- reals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph: B. sorokiniana) and rice (e. g. C. miy- abeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. (an- thracnose) on cotton (e. g. C. gossypii), corn (e. g. C. graminicola: Anthracnose stalk rot), soft fruits, potatoes (e. g. C. coccodes: black dot), beans (e. g. C. lindemuthianum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. sa- sakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. liriodendri, teleomorph: Neonectria liriodendrf. Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeo- acremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyri), soft fruits (E. veneta: anthracnose) and vines (E ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (E. betae), vegetables (e. g. E. pisi), such as cucurbits (e. g. E. cichoracearum), cabbages, rape (e. g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turcicum); Fusarium (teleomorph: Gib- berella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxy- sporum on tomatoes, F. solani on soybeans and F. verticillioides on corn; Gaeumanno- myces graminis (take-all) on cereals (e. g. wheat or barley) and corn; Gibberella spp. on cereals (e. g. G. zeae) and rice (e. g. G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grain- staining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helmintho- sporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., e. g. H. vastatrix (coffee leaf rust) on coffee; lsariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoli) (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica), onions (e. g. P. destructor), tobacco (P. tabacina) and soybeans (e. g. P.
manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad-leaved trees (e. g. P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples; Polymyxa spp., e. g. on cereals, such as barley and wheat (P. graminis) and sugar beets (P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on cereals, e. g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e. g. P. cubensis on cucurbits or P. humili ou hop; Pseudopezicula tracheiphila (red fire disease or , rotbrenner' , anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, and asparagus (e. g. P. asparagi); Pyrenophora (anamorph: Drechslera) tritici- repentis (tan spot) on wheat or P. feres (net blotch) on barley; Pyricularia spp., e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni (Ra mu Ia ria leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. so/an/ (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. rolfsii or S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum
(Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. miliaria: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tilletia spp. (common bunt or stinking smut) on cereals, such as e. g. T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) on barley or wheat; Um- cystis spp., e. g. U. occulta (stem smut) on rye; Ummyces spp. (rust) on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. dahliae on strawberries, rape, potatoes and tomatoes.
The compounds I and Il and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials. The term "protection of materials" is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, colling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria. As to the protection of wood and other materials, the particular attention is paid to the following harmful fungi: Ascomycetes such as Ophio- stoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chae- tomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Po- ria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichorma spp., Altemaria spp., Paecilomyces spp. and Zygomycetes such as /Wucorspp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
The compounds I and Il and compositions thereof, respectively, may be used for improving the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compounds I and/or Il and compositions thereof, respectively.
The term "plant health" is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor [e. g. improved plant growth and/or greener leaves ("greening effect")], quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress. The above identified indicators for the health condition of a plant may be interdependent or may result from each other.
The compounds of formula I and Il can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention. The compounds I and Il are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, mate- rials or rooms by the fungi.
Plant propagation materials may be treated with compounds I and/or Il as such or a composition comprising at least one compound I and/or Il prophylactically either at or before planting or transplanting. The invention also relates to agrochemical compositions comprising a solvent or solid carrier and at least one compound I and/or Il and to the use for controlling harmful fungi.
An agrochemical composition comprises a fungicidally effective amount of a compound I and/or II. The term "effective amount" denotes an amount of the composition or of the compounds I and/or II, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial dam- age to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.
The compounds I and/or Il and salts thereof can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes and granules. The composition type depends on the particular intended purpose; in each case, it should ensure a fine and uniform distribution of the compound according to the invention. Examples for composition types are suspensions (SC, OD, FS), emulsifiable concentrates (EC), emulsions (EW, EO, ES), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG), which can be water- soluble or wettable, as well as gel formulations for the treatment of plant propagation materials such as seeds (GF).
Usually the composition types (e. g. SC, OD, FS, EC, WG, SG, WP, SP, SS, WS, GF) are employed diluted. Composition types such as DP, DS, GR, FG, GG and MG are usually used undiluted. The compositions are prepared in a known manner (cf. US 3,060,084, EP-A 707 445 (for liquid concentrates), Browning: "Agglomeration", Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pp. 8-57 et seq., WO 91/13546, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701 , US 5,208,030, GB 2,095,558, US 3,299,566, Klingman: Weed Control as a Science (J. Wiley & Sons, New York, 1961), Hance et al.: Weed Control Handbook (8th Ed., Blackwell Scientific, Oxford, 1989) and Mollet, H. and Grubemann, A.: Formulation technology (Wiley VCH Verlag, Weinheim, 2001 ). The agrochemical compositions may also comprise auxiliaries which are customary in agrochemical compositions. The auxiliaries used depend on the particular application form and active substance, respectively. Examples for suitable auxiliaries are solvents, solid carriers, dispersants or emulsifiers (such as further solubilizers, protective colloids, surfactants and adhesion agents), organic and inorganic thickeners, bactericides, anti-freezing agents, anti-foaming agents, if appropriate colorants and tackifiers or binders (e. g. for seed treatment formulations). Suitable solvents are water, organic solvents such as mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, glycols, ke- tones such as cyclohexanone and gamma-butyrolactone, fatty acid dimethylamides, fatty acids and fatty acid esters and strongly polar solvents, e. g. amines such as N- methylpyrrolidone.
Solid carriers are mineral earths such as silicates, silica gels, talc, kaolins, limestone, lime, chalk, bole, loess, clays, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, e. g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
Suitable surfactants (adjuvants, wtters, tackifiers, dispersants or emulsifiers) are alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, such as ligninsoulfonic acid (Borresperse® types, Borregard, Norway) phenolsulfonic acid, naphthalenesulfonic acid (Morwet® types, Akzo Nobel, U.S.A.), dibutylnaphthalene- sulfonic acid (Nekal® types, BASF, Germany), and fatty acids, alkylsulfonates, alkyl- arylsulfonates, alkyl sulfates, laurylether sulfates, fatty alcohol sulfates, and sulfated hexa-, hepta- and octadecanolates, sulfated fatty alcohol glycol ethers, furthermore condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxy-ethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, tristearyl- phenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and proteins, denatured proteins, polysaccharides (e. g. methylcellulose), hydrophobically modified starches, polyvinyl alcohols (Mowiol® types, Clariant, Switzerland), polycarboxylates (Sokolan® types, BASF, Germany), polyalkoxylates, polyvinyl- amines (Lupasol® types, BASF, Germany), polyvinylpyrrolidone and the copolymers therof.
Examples for thickeners (i. e. compounds that impart a modified flowability to compositions, i. e. high viscosity under static conditions and low viscosity during agitation) are polysaccharides and organic and anorganic clays such as Xanthan gum (Kelzan®, CP Kelco, U.S.A.), Rhodopol® 23 (Rhodia, France), Veegum® (RT. Vanderbilt, U.S.A.) or Attaclay® (Engelhard Corp., NJ, USA).
Bactericides may be added for preservation and stabilization of the composition. Examples for suitable bactericides are those based on dichlorophene and benzylalcohol hemi formal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and ben- zisothiazolinones (Acticide® MBS from Thor Chemie).
Examples for suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Examples for anti-foaming agents are silicone emulsions (such as e. g. Silikon® SRE, Wacker, Germany or Rhodorsil®, Rhodia, France), long chain alcohols, fatty acids, salts of fatty acids, fluoroorganic compounds and mixtures thereof. Suitable colorants are pigments of low water solubility and water-soluble dyes. Examples to be mentioned und the designations rhodamin B, C. I. pigment red 112, C. I. solvent red 1 , pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
Examples for tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols and cellulose ethers (Tylose®, Shin-Etsu, Japan).
Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the compounds I and, if appropriate, further active substances, with at least one solid carrier. Granules, e. g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active substances to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, e. g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
Examples for composition types are:
1. Composition types for dilution with water i) Water-soluble concentrates (SL, LS)
10 parts by weight of a compound I or Il according to the invention are dissolved in 90 parts by weight of water or in a water-soluble solvent. As an alternative, wetting agents or other auxiliaries are added. The active substance dissolves upon dilution with water. In this way, a composition having a content of 10% by weight of active substance is obtained. ii) Dispersible concentrates (DC)
20 parts by weight of a compound I or Il according to the invention are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, e. g. polyvinylpyrrolidone. Dilution with water gives a dispersion. The active substance content is 20% by weight. iii) Emulsifiable concentrates (EC)
15 parts by weight of a compound I or Il according to the invention are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor
011 ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The composition has an active substance content of 15% by weight. iv) Emulsions (EW, EO, ES)
25 parts by weight of a compound I or Il according to the invention are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifying machine (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The composition has an active substance content of 25% by weight. v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20 parts by weight of a compound I or Il according to the invention are comminuted with addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. The active substance content in the composition is 20% by weight. vi) Water-dispersible granules and water-soluble granules (WG, SG)
50 parts by weight of a compound I or Il according to the invention are ground finely with addition of 50 parts by weight of dispersants and wetting agents and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance. The composition has an active substance content of 50% by weight. vii) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS) 75 parts by weight of a compound I or Il according to the invention are ground in a ro- tor-stator mill with addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution of the active substance. The active substance content of the composition is 75% by weight. viii) Gel (GF)
In an agitated ball mill, 20 parts by weight of a compound I or Il according to the invention are comminuted with addition of 10 parts by weight of dispersants, 1 part by weight of a gelling agent wetters and 70 parts by weight of water or of an organic solvent to give a fine suspension of the active substance. Dilution with water gives a stable sus- pension of the active substance, whereby a composition with 20% (w/w) of active substance is obtained.
2. Composition types to be applied undiluted ix) Dustable powders (DP, DS)
5 parts by weight of a compound I or Il according to the invention are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable composition having an active substance content of 5% by weight. x) Granules (GR, FG, GG, MG)
0.5 parts by weight of a compound I or Il according to the invention is ground finely and associated with 99.5 parts by weight of carriers. Current methods are extrusion, spray- drying or the fluidized bed. This gives granules to be applied undiluted having an active substance content of 0.5% by weight. xi) ULV solutions (UL)
10 parts by weight of a compound I or Il according to the invention are dissolved in 90 parts by weight of an organic solvent, e. g. xylene. This gives a composition to be ap- plied undiluted having an active substance content of 10% by weight.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, most preferably between 0.5 and 90%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, prefera- bly from 95% to 100% (according to NMR spectrum).
Water-soluble concentrates (LS), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES) emulsifiable concentrates (EC) and gels (GF) are usually em- ployed for the purposes of treatment of plant propagation materials, particularly seeds. These compositions can be applied to plant propagation materials, particularly seeds, diluted or undiluted. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying or treating agrochemical compounds and compositions thereof, respectively, on to plant propagation material, especially seeds, are known in the art, and include dressing, coating, pelleting, dusting, soaking and in- furrow application methods of the propagation material. In a preferred embodiment, the compounds or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
In a preferred embodiment, a suspension-type (FS) composition is used for seed treatment. Typcially, a FS composition may comprise 1-800 g/l of active substance, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
The active substances can be used as such or in the form of their compositions, e. g. in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading, brushing, immersing or pouring. The application forms depend entirely on the intended purposes; it is intended to ensure in each case the finest possible distribution of the active substances according to the in- vention.
Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water. The active substance concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.001 to 1 % by weight of active substance.
The active substances may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply compositions comprising over 95% by weight of active substance, or even to apply the active substance without additives.
When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, in particular from 0.1 to 0.75 kg per ha.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seed) are generally required.
When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are, e. g., 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
Various types of oils, wetters, adjuvants, herbicides, bactericides, other fungicides and/or pesticides may be added to the active substances or the compositions com- prising them, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1. Adjuvants which can be used are in particular organic modified polysiloxanes such as Break Thru S 240®; alcohol alkoxylates such as Atplus 245®, Atplus MBA 1303®, PIu- rafac LF 300® and Lutensol ON 30®; EO/PO block polymers, e. g. Pluronic RPE 2035® and Genapol B®; alcohol ethoxylates such as Lutensol XP 80®; and dioctyl sulfosucci- nate sodium such as Leophen RA®.
The compositions according to the invention can, in the use form as fungicides, also be present together with other active substances, e. g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as pre-mix or, if appropriate, not until immediately prior to use (tank mix).
Mixing the compounds I and/or Il or the compositions comprising them in the use form as fungicides with other fungicides results in many cases in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, synergistic effects are obtained.
The following list of active substances, in conjunction with which the compounds according to the invention can be used, is intended to illustrate the possible combinations but does not limit them: A) strobilurins
azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, meto- minostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyribencarb, triflox- ystrobin, 2-(2-(6-(3-chloro-2-methyl-phenoxy)-5-fluoro-pyrimidin-4-yloxy)-phenyl)- 2-methoxyimino-N-methyl-acetamide, 3-methoxy-2-(2-(N-(4-methoxy-phenyl)- cyclopropane-carboximidoylsulfanylmethyl)-phenyl)-acrylic acid methyl ester, methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate and 2-(2- (3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2- methoxyimino-N-methyl-acetamide;
B) carboxamides
- carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, me- pronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, pen- thiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4-methyl- thiazole-5-carboxanilide, 2-chloro-N-(1 ,1 ,3-trimethyl-indan-4-yl)-nicotinamide, N- (3\4\5'-trifluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1 H-pyrazole- 4-carboxamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1 -methyl- 1 H-pyrazole-4-carboxamide, N-(2-(1 ,3-dimethyl-butyl)-phenyl)-1 ,3-dimethyl-5- fluoro-1 H-pyrazole-4-carboxamide and N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3- dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide;
carboxylic morpholides: dimethomorph, flumorph, pyrimorph;
benzoic acid amides: flumetover, fluopicolide, fluopyram, zoxamide, N-(3-Ethyl- 3,5,5-trimethyl-cyclohexyl)-3-formylamino-2-hydroxy-benzamide;
other carboxamides: carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofarm and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide;
C) azoles
triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenocona- zole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquincona- zole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metcona- zole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadi- menol, triticonazole, uniconazole, 1-(4-chloro-phenyl)-2-([1 ,2,4]triazol-1-yl)- cycloheptanol;
imidazoles: cyazofamid, imazalil, pefurazoate, prochloraz, triflumizol;
- benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;
others: ethaboxam, etridiazole, hymexazole and 2-(4-chloro-phenyl)-N-[4-(3,4-di- methoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide;
D) heterocyclic compounds
pyridines: fluazinam, pyrifenox, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin- 3-yl]-pyridine, 3-[5-(4-methyl-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,
2,3,5,6-tetra-chloro-4-methanesulfonyl-pyridine, 3,4,5-trichloropyridine-2,6-di- carbonitrile, N-(1-(5-bromo-3-chloro-pyridin-2-yl)-ethyl)-2,4-dichloronicotinamide,
N-[(5-bromo-3-chloro-pyridin-2-yl)-methyl]-2,4-dichloro-nicotinamide;
pyrimidines: bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepani- pyrim, nitrapyrin, nuarimol, pyrimethanil;
piperazines: triforine;
pyrroles: fenpiclonil, fludioxonil;
morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tride- morph;
- piperidines: fenpropidin;
dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;
non-aromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, oc- thilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro- pyrazole-1-carbothioic acid S-allyl ester; others: acibenzolar-S-methyl, amisulbrom, anilazin, blasticidin-S, captafol, cap- tan, chinomethionat, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat- methylsulfate, fenoxanil, Folpet, oxolinic acid, piperalin, proquinazid, pyroquilon, quinoxyfen, triazoxide, tricyclazole, 2-butoxy-6-iodo-3-propylchromen-4-one, 5- chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole, 5-chloro-
7-(4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine and 5-ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidine-7-ylamine;
E) carbamates
thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam, methasulpho- carb, metiram, propineb, thiram, zineb, ziram;
carbamates: benthiavalicarb, diethofencarb, iprovalicarb, propamocarb, propamo- carb hydrochlorid, valiphenal and N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2- yl) carbamic acid-(4-fluorophenyl) ester;
F) other active substances
- guanidines: guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate);
antibiotics: kasugamycin, kasugamycin hydrochloride-hydrate, streptomycin, pol- yoxine, validamycin A;
nitrophenyl derivates: binapacryl, dinobuton, dinocap, nitrthal-isopropyl, tecna- zen,
organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;
sulfur-containing heterocyclyl compounds: dithianon, isoprothiolane;
organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, iproben- fos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;
organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen, flusul- famide, hexachlorobenzene, pencycuron, pentachlorphenole and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanid, N-(4-chloro-2-nitro- phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
- inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
others: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamin, metrafenone, mildiomycin, oxin-copper, prohexadione-calcium, spiroxamine, tolylfluanid, N- (cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2- phenyl acetamide, N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl- phenyl)-N-ethyl-N-methyl formamidine, N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)- 2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N'-(2-methyl-5- trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N- ethyl-N-methyl formamidine,
2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4- carboxylic acid methyl-(1 ,2,3,4-tetrahydro-naphthalen-1-yl)-amide, 2-{1-[2-(5- methyl-S-trifluoromethyl-pyrazole-i-yO-acetyO-piperidin^-ylJ-thiazole^-carboxylic acid methyl-(R)-1 ,2,3,4-tetrahydro-naphthalen-1-yl-amide, acetic acid 6-tert-butyl-
8-fluoro-2,3-dimethyl-quinolin-4-yl ester and methoxy-acetic acid 6-tert-butyl-8- fluoro-2,3-dimethyl-quinolin-4-yl ester.
G) growth regulators
abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
2,3,5-tri-iodobenzoic acid , trinexapac-ethyl and uniconazole;
H) herbicides
acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufen- acet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethox- amid, pretilachlor, propachlor, thenylchlor;
amino acid derivatives: bilanafos, glyphosate, glufosinate, sulfosate;
aryloxyphenoxypropionates: clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;
Bipyridyls: diquat, paraquat;
- (thio)carbamates: asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;
cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim;
- dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, triflu- ralin;
diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;
hydroxybenzonitriles: bomoxynil, dichlobenil, ioxynil;
- imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;
phenoxy acetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-
DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, Mecoprop;
pyrazines: chloridazon, flufenpyr-ethyl, fluthiacet, norflurazon, pyridate; pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;
sulfonyl ureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, fluce- tosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfu- ron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfu- ron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1-((2- chloro-6-propyl-imidazo[1 ,2-b]pyridazin-3-yl)sulfonyl)-3-(4,6-dimethoxy-pyrimidin- 2-yl)urea;
triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam; ureas: chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, metha- benzthiazuron,tebuthiuron;
- other acetolactate synthase inhibitors: bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam;
others: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, bencar- bazone,benfluresate, benzofenap, bentazone, benzobicyclon, bromacil, bromo- butide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethlyl, chlor- thal, cinmethylin, clomazone, cumyluron, cyprosulfamide, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanid, fen- trazamide, flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfo- tole, pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione, sulfentra- zone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, 4- hydroxy-3-[2-(2-methoxy-ethoxymethyl)-6-trifluoromethyl-pyridine-3-carbonyl]- bicyclo[3.2.1]oct-3-en-2-one, (3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4- trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenoxy]-pyridin-2-yloxy)-acetic a- cid ethyl ester, 6-amino-5-chloro-2-cyclopropyl-pyrimidine-4-carboxylic acid methyl ester, 6-chloro-3-(2-cyclopropyl-6-methyl-phenoxy)-pyridazin-4-ol, 4- amino-3-chloro-6-(4-chloro-phenyl)-5-fluoro-pyridine-2-carboxylic acid, 4-amino-
3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)-pyridine-2-carboxylic acid methyl ester, and 4-amino-3-chloro-6-(4-chloro-3-dimethylamino-2-fluoro-phenyl)- pyridine-2-carboxylic acid methyl ester.
I) insecticides organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoa- te, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamido- phos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton- methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetra- chlorvinphos, terbufos, triazophos, trichlorfon;
carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate;
pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cyperme- thrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda- cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau- fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimeflu- thrin;
insect growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazu- ron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenu- ron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozi- de, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat; nicotinic receptor agonists/antagonists compounds: clothianidin, dinotefuran, imi- dacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1-(2-chloro- thiazol-5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1 ,3,5]triazinane;
GABA antagonist compounds: endosulfan, ethiprole, fipronil, vaniliprole, pyraflu- prole, pyriprole, 5-amino-1 -(2,6-dichloro-4-methyl-phenyl)-4-sulfinamoyl-
1 H-pyrazole-3-carbothioic acid amide;
macrocyclic lactone insecticides: abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram;
mitochondrial electron transport inhibitor (METI) I acaricides: fenazaquin, pyrida- ben, tebufenpyrad, tolfenpyrad, flufenerim;
METI Il and III compounds: acequinocyl, fluacyprim, hydramethylnon;
Uncouplers: chlorfenapyr;
oxidative phosphorylation inhibitors: cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
moulting disruptor compounds: cryomazine;
mixed function oxidase inhibitors: piperonyl butoxide;
sodium channel blockers: indoxacarb, metaflumizone; others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, flubendiamide, chlorantraniliprole, cyazypyr (HGW86), cyenopyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron, and pyrifluquina- zon.
The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I and/or Il (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to I) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to F), as described above, and if desired one suitable solvent or solid carrier. Those mixtures are of particular interest, since many of them at the same application rate show higher efficiencies against harmful fungi. Furthermore, combating harmful fungi with a mixture of compounds I and/or Il and at least one fungicide from groups A) to F), as described above, is more efficient than combating those fungi with individual compounds I or Il or individual fungicides from groups A) to F). By applying compounds
1 and/or Il together with at least one active substance from groups A) to I) a synergistic effect can be obtained, i.e. more then simple addition of the individual effects is obtained (synergistic mixtures). According to this invention, applying the compounds I and/or Il together with at least one further active substance is to be understood to denote that at least one compound of formula I and/or Il and at least one further active substance occur simultaneously at the site of action (i.e. the harmful fungi to be controlled or their habitats such as infected plants, plant propagation materials, particularly seeds, surfaces, materials or the soil as well as plants, plant propagation materials, particularly seeds, soil, surfaces, materials or rooms to be protected from fungal attack) in a fungicidally effective amount. This can be obtained by applying the compounds I and/or Il and at least one further active substance simultaneously, either jointly (e. g. as tank-mix) or sperately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s). The order of application is not essential for working of the present invention.
In binary mixtures, i.e. compositions according to the invention comprising one com- pound I or Il (component 1 ) and one further active substance (component 2), e. g. one active substance from groups A) to I), the weight ratio of component 1 and component
2 generally depends from the properties of the active substances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :3 to 3:1.
In ternary mixtures, i.e. compositions according to the invention comprising one com- pound I (component 1 ) and a first further active substance (component 2) and a second further active substance (component 3), e. g. two active substances from groups A) to I), the weight ratio of component 1 and component 2 depends from the properties of the active substances used, preferably it is in the range of from 1 :50 to 50:1 and particularly in the range of from 1 :10 to 10:1 , and the weight ratio of component 1 and component 3 preferably is in the range of from 1 :50 to 50:1 and particularly in the range of from 1 :10 to 10:1.
The components can be used individually or already partially or completely mixed with one another to prepare the composition according to the invention. It is also possible for them to be packaged and used further as combination composition such as a kit of parts.
In one embodiment of the invention, the kits may include one or more, including all, components that may be used to prepare a subject agrochemical composition. E. g., kits may include one or more fungicide component(s) and/or an adjuvant component and/or an insecticide component and/or a growth regulator component and/or a her- bicde. One or more of the components may already be combined together or pre- formulated. In those embodiments where more than two components are provided in a kit, the components may already be combined together and as such are packaged in a single container such as a vial, bottle, can, pouch, bag or canister. In other embodiments, two or more components of a kit may be packaged separately, i. e., not pre- formulated. As such, kits may include one or more separate containers such as vials, cans, bottles, pouches, bags or canisters, each container containing a separate component for an agrochemical composition. In both forms, a component of the kit may be applied separately from or together with the further components or as a component of a combination composition according to the invention for preparing the composition according to the invention.
The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank or a spray plane. Here, the agrochemical composition is made up with water and/or buffer to the desired application concentration, it being possible, if appropriate, to add further auxiliaries, and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus ob- tained. Usually, 50 to 500 liters of the ready-to-use spray liquor are applied per hectare of agricultural useful area, preferably 100 to 400 liters.
According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate (tank mix).
In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e. g. components comprising compounds I and/or Il and/or active substances from the groups A) to I), may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate (tank mix). In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e. g. components comprising compounds I and/or Il and/or active substances from the groups A) to I), can be applied jointly (e. .g. after tankmix) or consecutively. Preference is also given to mixtures comprising a compound I and/or Il (component 1 ) and at least one active substance selected from the strobilurines of group A) (component 2) and particularly selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin. Preference is also given to mixtures comprising a compound I and/or Il (component 1 ) and at least one active substance selected from the carboxamides of group B) (component 2) and particularly selected from bixafen, boscalid, sedaxane, fenhexamid, metalaxyl, isopyrazam, mefenoxam, ofurace, dimethomorph, flumorph, fluopicolid (pi- cobenzamid), zoxamide, carpropamid, mandipropamid and N-(3',4',5'-trifluorobiphenyl- 2-yl)-3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide.
Preference is given to mixtures comprising a compound of formula I and/or Il (component 1 ) and at least one active substance selected from the azoles of group C) (component 2) and particularly selected from cyproconazole, difenoconazole, epoxicona- zole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamid, benomyl, carbendazim and ethaboxam. Preference is also given to mixtures comprising a compound I and/or Il (component 1 ) and at least one active substance selected from the heterocyclic compounds of group D) (component 2) and particularly selected from fluazinam, cyprodinil, fenarimol, me- panipyrim, pyrimethanil, triforine, fludioxonil, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, vinclozolin, famoxadone, fenamidone, probenazole, proquina- zid, acibenzolar-S-methyl, captafol, folpet, fenoxanil, quinoxyfen and 5-ethyl-6-octyl- [1 ,2,4]triazolo[1 ,5-a]pyrimidine-7-ylamine.
Preference is also given to mixtures comprising a compound I and/or Il (component 1 ) and at least one active substance selected from the carbamates of group E) (component 2) and particularly selected from mancozeb, metiram, propineb, thiram, iprovali- carb, benthiavalicarb and propamocarb.
Preference is also given to mixtures comprising a compound I and/or Il (component 1 ) and at least one active substance selected from the fungicides given in group F) (component 2) and particularly selected from dithianon, fentin salts, such as fentin acetate, fosetyl, fosetyl-aluminium, H3PO3 and salts thereof, chlorthalonil, dichlofluanid, thio- phanat-methyl, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, cymoxanil, metrafenone and spiroxamine.
Accordingly, the present invention furthermore relates to compositions comprising one compound I and/or Il (component 1 ) and one further active substance (component 2), which further active substance is selected from the column "Component 2" of the lines C-1 to C-346 of Table C.
A further embodiment relates to the compositions C-1 to C-346 listed in Table C, where a row of Table C corresponds in each case to a fungicidal composition comprising one of the in the present specification individualized compounds of formula I or Il (component 1 ) and the respective further active substance from groups A) to I) (component 2) stated in the row in question. Preferably, the compositions described comprise the active substances in synergistically effective amounts.
Table C: Composition comprising one indiviualized compound I or Il and one further active substance from groups A) to I)
Figure imgf000260_0001
Figure imgf000261_0001
Figure imgf000262_0001
Figure imgf000263_0001
Figure imgf000264_0001
Figure imgf000265_0001
Figure imgf000266_0001
Figure imgf000267_0001
Figure imgf000268_0001
Mixture Component 1 Component 2
N'-(2-methyl-5-trifluoromethyl-4-
(3-trimethylsilanyl-propoxy)-
C-241 one individualized compound I or Il
phenyl)-N-ethyl-N-methyl forma- midine
N'-(5-difluoromethyl-2-methyl-4-
(3-trimethylsilanyl-propoxy)-
C-242 one individualized compound I or Il
phenyl)-N-ethyl-N-methyl forma- midine
2-{1-[2-(5-Methyl-3- trifluoromethyl-pyrazole-1 -yl)-
C-243 one individualized compound I or Il acetyl]-piperidin-4-yl}-thiazole-4- carboxylic acid methyl-(1 , 2,3,4- tetrahydro-naphthalen-1-yl)-amide
2-{1 -[2-(5-Methyl-3-trifluoro- methyl-pyrazole-1-yl)-acetyl]-pipe-
C-244 one individualized compound I or Il ridin-4-yl}-thiazole-4-carboxylic acid methyl-(R)-1 , 2,3,4- tetrahydro-naphthalen-1-yl-amide
Acetic acid 6-tert-butyl-8-fluoro-
C-245 one individualized compound I or Il
2,3-dimethyl-quinolin-4-yl ester
Methoxy-acetic acid 6-tert-butyl-8-
C-246 one individualized compound I or Il fluoro-2,3-dimethyl-quinolin-4-yl ester
C-247 one individualized compound I or Il Carbaryl
C-248 one individualized compound I or Il Carbofuran
C-249 one individualized compound I or Il Carbosulfan
C-250 one individualized compound I or Il Methomylthiodicarb
C-251 one individualized compound I or Il Bifenthrin
C-252 one individualized compound I or Il Cyfluthrin
C-253 one individualized compound I or Il Cypermethrin
C-254 one individualized compound I or Il alpha-Cypermethrin
C-255 one individualized compound I or Il zeta-Cypermethrin
C-256 one individualized compound I or Il Deltamethrin
C-257 one individualized compound I or Il Esfenvalerate
C-258 one individualized compound I or Il Lambda-cyhalothrin
C-259 one individualized compound I or Il Permethrin
C-260 one individualized compound I or Il Tefluthrin
C-261 one individualized compound I or Il Diflubenzuron
Figure imgf000270_0001
Figure imgf000271_0001
Figure imgf000272_0001
The active substances referred to as component 2, their preparation and their activity against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by IUPAC nomencla- ture, their preparation and their fungicidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122;
EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358; WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853;
WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609;
WO 03/74491 ; WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689;
WO 05/123690; WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866;
WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624).
The mixtures of active substances can be prepared as compositions comprising besides the active ingredients at least one inert ingredient by usual means, e. g. by the means given for the compositions of compounds I and/or II.
Concerning usual ingredients of such compositions reference is made to the explanations given for the compositions containing compounds I and/or II.
The mixtures of active substances according to the present invention are suitable as fungicides, as are the compounds of formula I and II. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, especially from the classes of the Ascomycetes, Basidiomycetes, Deuteromycetes and Perono- sporomycetes (syn. Oomycetes ). In addition, it is referred to the explanations regarding the fungicidal activity of the compounds and the compositions containing compounds I and/or Il respectively.
The compounds 1, 11 and IX and pharmaceutically acceptable salts thereof are also suitable for treating diseases in men and animals, especially as antimycotics, for treating cancer and for treating virus infections. The term "antimycotic", as distinguished from the term "fungicide", refers to a medicament for combating zoopathogenic or hu- manpathogenic fungi, i.e. for combating fungi in animals, especially in mammals (including humans) and birds.
Thus, a further aspect of the present invention relates to a medicament comprising at least one compound of the formulae I, Il and/or IX and/or at least one pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
Suitable pharmaceutically acceptable salts are especially physiologically tolerated salts of the compound I, Il and/or IX, in particular the acid addition salts with physiologically acceptable acids. Examples of suitable organic and inorganic acids are hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, Ci-C4-alkylsulfonic acids, such as methanesulfonic acid, aromatic sulfonic acids, such as benzenesulfonic acid and toluenesulfonic acid, oxalic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, adipic acid and benzoic acid. Further suitable acids are described, for example, in Fortschritte der Arzneimittelforschung, Volume 10, pages 224 ff., Birkhauser Verlag, Basle and Stuttgart, 1966, the entire contents of which is expressly incorporated herein by way of reference.
Suitable carriers are, for example, solvents, carriers, excipients, binders and the like customarily used for pharmaceutical formulations, which are described below in an exemplary manner for individual types of administration.
A further aspect of the present invention relates to the use of compounds I, Il and IX or of pharmaceutically acceptable salts thereof for preparing an antimycotic medicament; i.e. for preparing a medicament for the treatment and/or prophylaxis of infections with humanpathogenic and/or zoopathogenic fungi. Another aspect of the present invention relates to the use of compounds of formulae I, Il and/or IX or of pharmaceutically acceptable salts thereof for preparing a medicament for the treatment of cancer. Another aspect of the present invention relates to the use of compounds of formulae I, Il and/or IX or of pharmaceutically acceptable salts thereof for preparing a medicament for the treatment or prophylaxis of virus infections.
The compounds of formulae 1, 11 and IX and/or their pharmaceutically acceptable salts are suitable for the treatment, inhibiton or control of growth and/or propagation of tumor cells and the disorders associated therewith. Accordingly, they are suitable for cancer therapy in warm-blooded vertebrates, for example mammals and birds, in particular man, but also other mammals, in particular useful and domestic animals, such as dogs, cats, pigs, ruminants (cattle, sheep, goats, bison, etc.), horses and birds, such as chicken, turkey, ducks, geese, guineafowl and the like.
The compounds of formulae I, Il and IX and/or their pharmaceutically acceptable salts are suitable for the therapy of cancer or cancerous disorders of the following organs: breast, lung, intestine, prostate, skin (melanoma), kidney, bladder, mouth, larynx, oe- sophagus, stomach, ovaries, pancreas, liver and brain or CNS.
The compounds of formulae I, Il and IX and/or their pharmaceutically acceptable salts are suitable for the treatment of virus infections in warm-blooded vertebrates, for example mammals and birds, in particular man, but also other mammals, in particular useful and domestic animals, such as dogs, cats, pigs, ruminants (cattle, sheep, goats, bison, etc.), horses and birds, such as chicken, turkey, ducks, geese, guineafowl and the like. They are suitable for treating virus infections like retrovirus infections such as HIV and HTLV, influenza virus infection, rhinovirus infections, herpes and the like. The compounds according to the invention can be administered in a customary manner, for example orally, intravenously, intramuscularly or subcutaneously. For oral administration, the active compound can be mixed, for example, with an inert diluent or with an edible carrier; it can be embedded into a hard or soft gelatin capsule, it can be compressed to tablets or it can be mixed directly with the food/feed. The active com- pound can be mixed with excipients and administered in the form of indigestible tablets, buccal tablets, pastilles, pills, capsules, suspensions, potions, syrups and the like. Such preparations should contain at least 0.1 % of active compound. The composition of the preparation may, of course, vary. It usually comprises from 2 to 60% by weight of active compound, based on the total weight of the preparation in question (dosage unit). Preferred preparations of the compound I according to the invention comprise from 10 to 1000 mg of active compound per oral dosage unit.
The tablets, pastilles, pills, capsules and the like may furthermore comprise the following components: binders, such as traganth, gum arabic, corn starch or gelatin, excipi- ents, such as dicalcium phosphate, disintegrants, such as corn starch, potato starch, alginic acid and the like, glidants, such as magnesium stearate, sweeteners, such as sucrose, lactose or saccharin, and/or flavors, such as peppermint, vanilla and the like. Capsules may furthermore comprise a liquid carrier. Other substances which modify the properties of the dosage unit may also be used. For example, tablets, pills and capsules may be coated with schellack, sugar or mixtures thereof. In addition to the active compound, syrups or potions may also comprise sugar (or other sweeteners), methyl- or propylparaben as preservative, a colorant and/or a flavor. The components of the active compound preparations must, of course, be pharmaceutically pure and nontoxic at the quantities employed. Furthermore, the active compounds can be formulated as preparations with a controlled release of active compound, for example as delayed-release preparations.
The active compounds can also be administered parenterally or intraperitoneally. SoIu- tions or suspensions of the active compounds or their salts can be prepared with water using suitable wetting agents, such as hydroxypropylcellulose. Dispersions can also be prepared using glycerol, liquid polyethylene glycols and mixtures thereof in oils. Frequently, these preparations furthermore comprise a preservative to prevent the growth of microorganisms.
Preparations intended for injections comprise sterile aqueous solutions and dispersions and also sterile powders for preparing sterile solutions and dispersions. The preparation has to be sufficiently liquid for injection. It has to be stable under the preparation and storage conditions and it has to be protected against contamination by microorgan- isms. The carrier may be a solvent or a dispersion medium, for example, water, etha- nol, a polyol (for example glycerol, propylene glycol or liquid polyethylene glycol), a mixture thereof and/or a vegetable oil.
The invention is further illustrated by the following, non-limiting examples.
I. Synthesis examples
II. Examples of the action against harmful fungi
The fungicidal action of the compounds of the formulae I and Il was demonstrated by the following experiments:
A) Microtiter tests The active substances were formulated separately as a stock solution in dimethyl sulfoxide (DMSO) at a concentration of 10 000 ppm. Use example 1 : Activity against the late blight pathogen Phytophthora infestans in the microtiter test
The stock solution was pipetted into a microtiter plate (MTP) and diluted to the stated active substance concentration using a pea juice-based aqueous nutrient medium for fungi. An aqueous zoospore suspension of Phytophthora infestans was then added. The plates were placed in a water vapor-saturated chamber at temperatures of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation. The measured parameters were compared to the growth of the active substance-free control variant (= 100 %) and the fungus- and active substance-free blank value to determine the relative growth in % of the pathogens in the individual active substances.
Use example 2: Activity against the rice blast pathogen caused by Pyricularia oryzae in the microtiter test
The stock solution was pipetted into a microtiter plate (MTP) and diluted to the stated active substance concentration using a malt-based aqueous nutrient medium for fungi. An aqueous spore suspension of Pyricularia oryzae was then added. The plates were placed in a water vapor-saturated chamber at temperatures of 18°C. Using an absorp- tion photometer, the microtiter plates were measured at 405 nm on day 7 after the inoculation. The measured parameters were compared to the growth of the active substance-free control variant (= 100%) and the fungus- and active substance-free blank value to determine the relative growth in % of the pathogens in the individual active substances.
Use example 3: Activity against the Septoria blotch pathogen caused by Septoria tritici in the microtiter test
The stock solution was pipetted into a microtiter plate (MTP) and diluted to the stated active substance concentration using a malt-based aqueous nutrient medium for fungi. An aqueous spore suspension of Septoria tritici was then added. The plates were placed in a water vapor-saturated chamber at temperatures of 18°C. Using an absorption photometer, the microtiter plates were measured at 405 nm on day 7 after the inoculation. The measured parameters were compared to the growth of the active sub- stance-free control variant (= 100%) and the fungus- and active substance-free blank value to determine the relative growth in % of the pathogens in the individual active substances. B) Greenhouse tests
The active substances were formulated separately or together as a stock solution comprising 25 mg of active substance which was made up to 10 ml using a mixture of acetone and/or dimethyl sulfoxide (DMSO) and the emulsifier Wettol EM 31 (wetting agent having emulsifying and dispersing action based on ethoxylated alkylphenols) in a volume ratio of solvent/emulsifier of 99 to 1. This solution was then made up to 100 ml using water. This stock solution was diluted with the solvent/emulsifier/water mixture described to the active substance concentration given below. Use example 4: Activity against early blight on tomatoes caused by Phytophthora in- festans with protective application
Young seedlings of tomato plants were grown in pots. The plants were sprayed to runoff with an aqueous suspension containing the concentration of active substance stated below. The next day, the treated plants were inoculated with an aqueous suspension of sporangia of Phytophthora infestans. After inoculation, the trial plants were immediately transferred to a humid chamber. After 6 days at 18 to 200C and a relative humidity close to 100%, the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
Use example 5: Curative action against Puccinia recondita on wheat (brown rust of wheat)
Leaves of potted wheat seedlings of the cultivar "Kanzler" were dusted with a suspen- sion of spores of brown rust of wheat (Puccinia recondita). The plants were then placed in a chamber with high atmospheric humidity (90 to 95%), at 20-220C, for 24 hours. During this time, the spores germinated and the germinal tubes penetrated into the leaf tissue. The next day, the infected plants were sprayed to runoff point with an aqueous suspension having the concentration of active substance stated below. After drying of the sprayed suspension, the test plants were returned into the greenhouse and cultivated at temperatures between 20 and 22°C and at 65 to 70% relative atmospheric humidity for a further 7 days. The extent of the rust development on the leaves was then determined visually. Use example 6: Protective action against Puccinia recondita on wheat (brown rust of wheat)
Leaves of potted wheat seedlings of the cultivar "Kanzler" were sprayed to runoff point with an aqueous suspension having the concentration of active substance stated below. The next day, the treated plants were dusted with a suspension of spores of brown rust of wheat (Puccinia recondita). The plants were then placed in a chamber with high atmospheric humidity (90 to 95%), at 20-220C, for 24 hours. During this time, the spores germinated and the germinal tubes penetrated into the leaf tissue. The next day, the test plants were returned into the greenhouse and cultivated at temperatures between 20 and 22°C and at 65 to 70% relative atmospheric humidity for a further 7 days. The extent of the rust development on the leaves was then determined visually.
Use example 7: Protective action against Blumeria graminis tritici on wheat (mildew of wheat)
Leaves of potted wheat seedlings of the cultivar "Kanzler" were sprayed to runoff point with an aqueous suspension having the concentration of active substance stated below. The next day, the treated plants were dusted with a suspension of spores of mil- dew of wheat (Blumeria graminis tritici). The plants were then returned into the greenhouse and cultivated at temperatures between 20 and 24°C and at 60 to 90% relative atmospheric humidity for a further 7 days. The extent of the mildew development on the leaves was then determined visually. Use example 8: Protective action against Sphaerotheca fuliginea on cucumber (mildew of cucumber)
Leaves of potted cucumber seedlings (in the germ layer stage) were sprayed to runoff point with an aqueous suspension having the concentration of active substance stated below. The next day, the treated plants were dusted with a suspension of spores of mildew of cucumber (Sphaerotheca fuliginea). The plants were then returned into the greenhouse and cultivated at temperatures between 20 and 24°C and at 60 to 80% relative atmospheric humidity for a further 7 days. The extent of the mildew development on the seed leaves was then determined visually.

Claims

We claim:
1. Azole compounds of the formulae I and Il
Figure imgf000279_0001
(I) (H) wherein
X is N or CH;
R1 is a group of formula III, a group of formula IV, a group of formula V, group of formula Vl or a group of formula VII
Figure imgf000279_0002
(III) (IV) (V)
Figure imgf000279_0003
(Vl) (VII)
wherein
# is the attachment point to the remainder of the molecule;
A1 and A2 are independently linear Ci-C4-alkylene bridges which may be substituted by 1 , 2, 3 or 4 substituents R9; W is O or S; Y is O or S; R2 is hydrogen, Ci-Cio-alkyl which may carry 1 or 2 substituents R10, or C1-C10- haloalkyl which may carry 1 or 2 substituents R10
R3 is selected from hydrogen, Ci-Cio-alkyl which may carry 1 or 2 substituents
R11, Ci-Cio-haloalkyl which may carry 1 or 2 substituents R11, C3-C8- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, where the cycloalkyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3 or 4 substituents R12, aryl and aryl-Ci-C4-alkyl, where the aryl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R13; each R4, independently of one another, is selected from halogen, CN, nitro, Ci-
C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and phenyl which may carry 1 , 2, 3, 4 or 5 substituents R14, and, in case R1 is a group of formula III, a group of formula V, a group of formula Vl or a group of formula VII, may also be phenoxy which may carry 1 , 2, 3, 4 or 5 substituents R14;
R5 is phenyl which is optionally substituted with n substituents R4, or hetaryl which is optionally substituted with 1 , 2 or 3 substituents R4; each R6, independently of one another, is selected from halogen, CN, nitro, Ci-
C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, phenyl and phenoxy, where the phenyl moiety in the two last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R14;
R7 is selected from hydrogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, phenyl and phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R15;
R8 is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, phenyl, phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R16 and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may carry 1 , 2 or 3 substituents R16 or, in case m is 0, may also be selected from -C(=O)R17, -C(=S)R17, -S(O)2R17, -CN, -P(=Q)R18R19, M and a group of the formula VIII
Figure imgf000281_0001
wherein
X and R1 are as defined for formulae I and II; and
# is the attachment point to the remainder of the molecule;
R8a is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, phenyl, phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R16, a
5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may carry 1 , 2 or 3 substituents R16, -C(=O)R17, -C(=S)R17, -S(O)2R17, -CN, -P(=Q)R18R19 and M; each R9 is independently selected from halogen, OH, SH, NR20R21, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and C1-C4- haloalkylthio, where the aliphatic moieties in the above radicals may carry 1 , 2 or 3 substituents R22; or two radicals R9 bound on two adjacent carbon atoms, together with the carbon atoms to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or maximum unsaturated carbocyclic ring or a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or maximum unsaturated heterocyclic ring containing 1 , 2, or 3 heteroatoms selected from O, S and N as ring members, where the carbocyclic or heterocyclic ring may carry 1 , 2 or 3 substituents R16; each R10 is independently selected from nitro, CN, OH, SH, Ci-C4-alkoxy, Ci-C4- haloalkoxy and NR20R21; each R11 is independently selected from nitro, CN, OH, SH, Ci-C4-alkoxy, C1-C4- haloalkoxy and NR20R21; each R12 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR20R21; each R13 is independently selected from halogen, CN, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio and phenyl, where the phenyl moiety may carry 1 , 2, 3, 4 or 5 substituents R14; each R14 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and NR20R21; each R15 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio and NR20R21; each R16 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR20R21;
R17 is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, Ci-Cio-alkoxy, Ci- Cio-haloalkoxy, Ci-Cio-aminoalkyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, phenyl, phenoxy, phenyl-Ci-C4-alkyl, where the phenyl moiety in the 3 last- mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R13, a 5- or 6- membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring mem- bers, where the heterocyclic ring may carry 1 , 2 or 3 substituents R13, and
NR20R21;
R18 and R19, independently of each other, are selected from Ci-Cio-alkyl, Ci-Cio- haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-C10- haloalkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, Ci-Cio-alkoxy, C1-C10- haloalkoxy, Ci-C4-alkoxy-Ci-Cio-alkyl, Ci-C4-alkoxy-Ci-Cio-alkoxy, C1-C10- alkylthio, Ci-Cio-haloalkylthio, C2-Cio-alkenyloxy, C2-Cio-alkenylthio, C2-C10- alkynyloxy, C2-Cio-alkynylthio, C3-Cio-cycloalkoxy, C3-Cio-cycloalkylthio, phenyl, phenyl-Ci-C4-alkyl, phenylthio, phenyl-Ci-C4-alkoxy, and NR20R21; each R20 is independently selected from hydrogen and Ci-Cs-alkyl; each R21 is independently selected from hydrogen, Ci-Cs-alkyl, phenyl, and
phenyl-Ci-C4-alkyl; or R20 and R21 together form a linear C4- or Cs-alkylene bridge or a group -CH2CH2OCH2CH2- or -CH2CH2NR23CH2CH2-; each R22 is independently selected from nitro, CN, OH, SH, COR17, NR20R21, C3-
Cβ-cycloalkyl, Cs-Cβ-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6- cycloaloxy, phenyl and phenoxy; each R23 is independently selected from hydrogen and Ci-C4-alkyl;
Q is O or S;
M is a metal cation equivalent or an ammonium cation of formula
(NRaRbRcRd)+, wherein Ra, Rb, Rc and Rd, independently of each other, are selected from hydrogen, Ci-Cio-alkyl, phenyl and benzyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2 or 3 substituents independently selected from halogen, CN, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR20R21; m is 0, 1 , 2 or 3; n is 0, 1 , 2, 3, 4 or 5; p is 0, 1 , 2, 3 or 4; and the agriculturally acceptable salts thereof.
2. The compounds of formulae I and Il as claimed in claim 1 , where
each R4 and each R6, independently of one another, is selected from halogen, CN, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4- haloalkoxy, Ci-C4-haloalkylthio and phenyl which may carry 1 , 2, 3, 4 or 5 substituents R14, and, in case R1 is a group of formula III, a group of formula V, a group of formula Vl or a group of formula VII, may also be phenoxy which may carry 1 , 2, 3, 4 or 5 substituents R14; and each R14 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and C1-C4- haloalkylthio. 3. The compounds of formulae I and Il as claimed in claim 2, where
each R4 and each R6, independently of each other, is selected from chlorine, fluorine, methyl, methoxy, trifluoromethyl and phenyl, and preferably from chlorine, fluorine and phenyl. 4. The compounds of formulae I and Il as claimed in any one of the preceding
claims, where R1 is a group of formula III or a group of formula VII, where X is N;
R3 is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cs-cycloalkyl, where the cycloalkyl moiety may carry 1 , 2, 3 or 4 substituents R12, benzyl and phenyl, where the phenyl moiety in the two last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R13;
each R12 is independently selected from halogen and Ci-C4-alkyl;
each R13 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio and phenyl; where the phenyl moiety may carry 1 , 2,
3,
4 or 5 substituents R14;
each R14 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and C1-C4- haloalkylthio.
5. The compounds of formulae I and Il as claimed in claim 4, where
R3 is Ci-C4-alkyl and preferably fe/t-butyl.
6. The compounds of formulae I and Il as claimed in any one of claims 1 to 3, where R1 is a group of formula IV, where
X is N; and
A1 is 1 ,2-ethandiyl or 1 ,3-propandiyl, and preferably is 1 ,2-ethandiyl, where 1 ,2-ethandiyl or 1 ,3-propandiyl may be substituted by 1 , 2, 3 or 4 substituents R9; where
each R9 is independently selected from halogen, Ci-C4-alkyl and Ci-C4-alkoxy.
7. The compounds of formulae I and Il as claimed in claim 6, where A1 is 1 ,2-ethandiyl or 1 ,3-propandiyl, and preferably is 1 ,2-ethandiyl, where 1 ,2-ethandiyl or 1 ,3-propandiyl may be substituted by 1 , 2 or 3 substituents independently selected from fluorine, methyl and methoxy.
8. The compounds of formulae I and Il as claimed in any one of claims 1 to 3, where R1 is a group of formula V, where
X is CH;
R7 is Ci-C4-alkyl and preferably n-propyl;
Y is O; and
A2 is 1 ,2-ethandiyl or 1 ,3-propandiyl, and preferably is 1 ,2-ethandiyl, where
1 ,2-ethandiyl or 1 ,3-propandiyl may be substituted by 1 , 2, 3 or 4 substituents R9; where
each R9 is independently selected from Ci-C4-alkyl and Ci-C4-alkoxy.
9. The compounds of formulae I and Il as claimed in claim 8, where
A2 is 1 ,2-ethandiyl or 1 ,3-propandiyl, and preferably is 1 ,2-ethandiyl, where 1 ,2-ethandiyl or 1 ,3-propandiyl may be substituted by 1 , 2 or 3 substituents independently selected from methyl and methoxy.
10. The compounds of formulae I and Il as claimed in any one of claims 1 to 3, where R1 is a group of formula Vl, where
X is N;
W is O; and
each R4 and each R6 is independently selected from methyl, F, Cl, methoxy, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, phenyl, 2- fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3- chlorophenyl, 4-chlorophenyl, phenoxy, 2-chlorophenoxy, 3-chlorophenoxy and 4-chlorophenoxy.
1 1. The compounds of formulae I and Il as claimed in claim 10, where
R5 is phenyl which may carry 1 or 2 radicals R4, where
each R4 and each R6 is independently selected from methyl, F, Cl, methoxy, trifluoromethyl, trifluoromethoxy and phenyl.
12. The compounds of formulae I and Il as claimed in any of the preceding claims, where R17 is selected from Ci-C4-alkyl, Ci-C2-haloalkyl, Ci-C4-alkoxy, C1-C2- haloalkoxy, phenyl, phenoxy and NR20R21, where R20 is hydrogen and R21 is selected from hydrogen, Ci-C4-alkyl and phenyl or the two of R20 and R21 are C1-C4- alkyl.
13. The compounds of formulae I and Il as claimed in any of the preceding claims, where R8 is selected from hydrogen, Ci-C4-alkyl, -C(=O)R17, -S(O)2R17, -CN, M and a group of the formula VIII and preferably from hydrogen, CN, -C(=O)CH3,
-C(=O)OCH3 and methyl.
14. The compounds of formulae I and Il as claimed in any of the preceding claims, where R8a is selected from hydrogen, Ci-C4-alkyl and -C(=O)R17.
15. The compounds of formulae I and Il as claimed in any of the preceding claims, where m is 0.
16. Compounds of formula IX
Figure imgf000286_0001
where R1 and X are as defined in any of claims 1 to 11.
17. An agricultural composition comprising at least one compound of formula I, Il and/or IX as defined in any of claims 1 to 16 or an agriculturally acceptable salt thereof and a liquid or solid carrier.
18. The use of a compound of formula I, Il and/or IX as defined in any of claims 1 to 16 for controlling harmful fungi.
19. A method for controlling harmful fungi, wherein the fungi, their habitat or the materials or plants to be protected against fungal attack, or the soil or propagation material are treated with an effective amount of at least compound of formula I, Il and/or IX, where compounds I, Il and IX are as defined in any of claims 1 to 16.
20. Seed, comprising at least compound of formula I, Il and/or IX, where compounds 1 , 11 and IX are as defined in any of claims 1 to 16, in an amount of from 0.1 g to
10 kg per 100 kg of seeds.
21. A pharmaceutical composition comprising at least one compound of formula I, Il and/or IX as defined in any of claims 1 to 16 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable carrier.
22. The use of a compound of formula I, Il or IX as defined in any of claims 1 to 16 or a pharmaceutically acceptable salt thereof for preparing a medicament for the treatment of cancer or virus infections or for preparing an antimycotic medicament.
23. A method for treating cancer or virus infections or for combating zoopathogenic or humanpathogenic fungi, which comprises treating an individual in need thereof with at least one compound of formula IJI and/or IX as defined in any of claims 1 to 16, with at least one pharmaceutically acceptable salt thereof or with a pharmaceutical composition as defined in claim 21.
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