WO2010149758A1 - Antifungal 1, 2, 4-triazolyl derivatives - Google Patents

Antifungal 1, 2, 4-triazolyl derivatives Download PDF

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WO2010149758A1
WO2010149758A1 PCT/EP2010/059037 EP2010059037W WO2010149758A1 WO 2010149758 A1 WO2010149758 A1 WO 2010149758A1 EP 2010059037 W EP2010059037 W EP 2010059037W WO 2010149758 A1 WO2010149758 A1 WO 2010149758A1
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compounds
formula
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combination
case
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PCT/EP2010/059037
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French (fr)
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Jochen Dietz
Alice GLÄTTLI
Thomas Grote
Wassilios Grammenos
Bernd Müller
Jan Klaas Lohmann
Jens Renner
Sarah Ulmschneider
Marianna Vrettou-Schultes
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Basf Se
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/101,2,4-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
    • C07D249/12Oxygen or sulfur atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10Antimycotics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents

Definitions

  • the present invention relates to novel triazole 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.
  • 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.
  • triazole compounds of the general formulae I and II defined below, and by the agriculturally acceptable salts of the compounds I and II.
  • the present invention relates to triazole compounds of the formulae I and Il and to agriculturally useful salts thereof
  • R 1 is group of formula V or
  • # is the attachment point to the remainder of the molecule
  • A is a linear d-Cs-alkylene bridge which may be substituted by 1 , 2, 3 or 4 sub- stituents R 6 ;
  • R 2 is aryl which may carry 1 , 2, 3, 4 or 5 substituents R 7 , or is a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heteroaromatic ring may carry 1 , 2, 3 or 4 substituents R 8 ;
  • R 3 is selected from Ci-Cio-alkyl which may carry 1 or 2 substituents R 9 , C1-C10- haloalkyl which may carry 1 or 2 substituents R 9 , Cs-Cs-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 10 , 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 11 ;
  • R 4 is hydrogen, OH or CN
  • R 1 is as defined for formulae I and II; and # is the attachment point to the remainder of the molecule;
  • each R 6 is independently selected from halogen, OH, SH, NR 16 R 17 , Ci-C 4 -alkyl, Ci-C 4 - haloalkyl, C2-C 4 -alkenyl, C2-C 4 -haloalkenyl, C2-C 4 -alkynyl, C2-C 4 -haloalkynyl, Ci- C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio and Ci-C 4 -haloalkylthio, where the aliphatic moieties in the above radicals may carry 1 , 2 or 3 substituents R 18 ; or
  • each R 7 is independently selected from halogen, nitro, CN, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy and NR 16 R 17 ;
  • each R 8 is independently selected from halogen, nitro, CN, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy and NR 16 R 17 ;
  • each R 9 is independently selected from nitro, CN, OH, SH, Si(R 20 ) 3 , NR 16 R 17 , CrC 4 - alkoxy, Ci-C 4 -haloalkoxy, Cs-C ⁇ -cycloalkyl, Cs-C ⁇ -halocycloalkyl and C3-C6- cycloaloxy; each R 10 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, CrC 4 - haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy and NR 16 R 17 ;
  • each R 11 is independently selected from halogen, nitro, CN, Ci-C 4 -alkyl, C1-C4- haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy and NR 16 R 17 ;
  • each R 12 is independently selected from halogen, nitro, CN, Ci-C 4 -alkyl, C1-C4- haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy and NR 16 R 17 ;
  • R 13 is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, Ci-Cio-alkoxy, C1-C10- haloalkoxy, Ci-Cio-aminoalkyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, phenyl, phenyl-Ci-C 4 -alkyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R 12 , 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 12 , and NR 16 R 17 ;
  • R 14 and R 15 are selected from Ci-Cio-alkyl, Ci-Cio- haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, Ci-Cio-alkoxy, Ci-Cio-haloalkoxy, C1-C4- alkoxy-Ci-Cio-alkyl, Ci-C4-alkoxy-Ci-Cio-alkoxy, Ci-Cio-alkylthio, C1-C10- haloalkylthio, C2-Cio-alkenyloxy, C2-Cio-alkenylthio, C2-Cio-alkynyloxy, C2-C10- alkynylthi
  • each R 16 is independently selected from hydrogen and Ci-Cs-alkyl
  • each R 17 is independently selected from hydrogen, Ci-Cs-alkyl, phenyl, and phenyl-Ci-
  • R 16 and R 17 together form a linear C 4 - or Cs-alkylene bridge or a group -CH2CH2OCH2CH2- or -CH 2 CH 2 NR 19 CH 2 CH 2 -;
  • each R 18 is independently selected from nitro, CN, OH, SH, COR 13 , NR 16 R 17 , C 3 -C 6 - cycloalkyl, Cs-C ⁇ -halocycloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, C3-C6- cycloaloxy, phenyl and phenoxy;
  • each R 19 is independently selected from hydrogen and Ci-C 4 -alkyl; each R 20 is independently selected from d-C ⁇ -alkyl, C-i-C ⁇ -haloalkyl, phenyl, phenyl- Ci-C4-alkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
  • Q is O or S
  • M is a metal cation equivalent or an ammonium cation of formula (NR a R b R c R d ) + , wherein 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-C4-alkoxy, Ci-C4-haloalkoxy and NR 16 R 17 ; and
  • n 0, 1 , 2 or 3;
  • R 2 is not 2-fluorophenyl if R 3 is 4-fluorophenyl and R 4 is OH; with the proviso that R 3 is not 2-fluorophenyl if R 2 is 4-fluorophenyl and R 4 is OH; with the proviso that R 3 is not n-butyl if R 2 is 4-fluorophenyl, 2-chlorophenyl, 4- chlorophenyl, 2,4-dichlorophenyl, 4-bromophenyl, 4-tert-butylphenyl or 4-biphenyl and R 4 is CN; with the proviso that R 3 is not tert-butyl if R 2 is 2-chlorophenyl, 4-chlorophenyl, 2,4- dichlorophenyl, 2,4,6-trichlorophenyl, 4-trifluoromethylphenyl or 2- difluoromethoxyphenyl and R 4 is CN; with the proviso that R
  • the present invention also provides the use of triazole 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 triazole compounds of the formulae I and/or Il (and/or also of the formula IV; 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 stereoisomers 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, preferably 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
  • C 2 -C 3 - Alkyl is ethyl, n-propyl or isopropyl.
  • Ci-C 2 -Alkyl is methyl or ethyl.
  • CrC 4 -AIkVl 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, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl,
  • 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-propyl heptyl, 3-propylheptyl and positional isomers thereof.
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2 (Ci-C 2 -haloalkyl), 1 to 3 (d-Cs-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-C 2 -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 (Ci-C 8 -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.
  • Haloalkenyl and the haloalkenyl moieties in haloalkenyloxy, haloalkenylcarbonyl and the like unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 (C 2 - C 4 -haloalkenyl), 2 to 6 (C 2 -C 6 -haloalkenyl), 2 to 8 (C 2 -C 8 -haloalkenyl) or 2 to 10 (C 2 - 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;
  • 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, i-chlorocyclobutylmethyl, i-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
  • 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, 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 OC 2 Fs.
  • 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, OCH 2 -C 2 F 5 , OCF 2 - C 2 F 5 , 1-(CH 2 F)-2-fluoroethoxy, 1-(CH 2 CI)-2-chloroethoxy, 1-(CH 2 Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
  • Ci-C ⁇ -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 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 example 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, Ci-Cs-haloalkoxy, Ci-C ⁇ -haloalkoxy, Ci- C4-haloalkoxy or Ci-C2-haloalkoxy.
  • Ci-C4-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, Ci-Cs-alkyl, Ci-C ⁇ -alkyl, Ci-C4-alkyl, C1-C2- alkyl or C3-C4-alkyl.
  • R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-Cs-alkyl, Ci-C ⁇ -alkyl, Ci-C4-alkyl, C1-C2- alkyl or C3-C4-alkyl.
  • Ci-C4-alkylaminocarbonyl are methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocarbonyl, butylaminocar- bonyl, sec-butylaminocarbonyl, isobutylaminocarbonyl and tert-but
  • 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-C 4 -alkyl)- aminocarbonyl are dimethylaminocarbonyl, diethylaminocarbonyl, dipropylaminocar- bonyl, diisopropylaminocarbonyl and dibutylaminocarbony
  • Aminoalkyl group of the formula R-NH2 in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-Cs-alkyl, Ci-Ce-alkyl, Ci-C 4 -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-Cs-alkyl, Ci-Ce-alkyl, Ci-C 4 -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-2,5-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,
  • 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,
  • 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 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 carbon 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 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.
  • 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 7 , R 8 , R 10 , R 11 and R 12 are independently of each other and independently of each occurrence preferably selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy and more preferably from F, Cl, Br, methyl, difluoromethyl, trifluoromethyl, methoxy, difluoromethoxy and trifluoromethoxy.
  • R 16 is hydrogen and R 17 is selected from hydrogen, Ci-C4-alkyl and phenyl, preferably from hydrogen and Ci-C4-alkyl, or the two of R 16 and R 17 are Ci-C4-alkyl.
  • R 19 is hydrogen or methyl and in particular methyl.
  • R 20 is Ci-C4-alkyl and in particular methyl.
  • R 13 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) 2 R 13 , R 13 is specifically methyl.
  • Ci-C4-alkyl such as methyl, ethyl, propyl, isopropyl, n- butyl, sec-butyl, isobutyl or tert-butyl, preferably methyl
  • Ci-C4-alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-but
  • R 16 is hydrogen and R 17 is selected from hydrogen, Ci- C4-alkyl and phenyl, preferably from hydrogen and Ci-C4-alkyl, or the two of R 16 and R 17 are Ci-C 4 -alkyl.
  • R 5 is selected from hydrogen, CN, methyl- carbonyl, methoxycarbonyl and methyl.
  • R 5 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 + , YiMg 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.
  • R 1 is a group of formula V, where
  • R 2 is phenyl which may carry 1 , 2, 3, 4 or 5 substituents R 7 ;
  • R 3 is phenyl which may carry 1 , 2, 3, 4 or 5 substituents R 11 ;
  • R 4 is OH;
  • R 5 /R 5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R 2 is 2-fluorophenyl, R 3 is 4-fluorophenyl and R 4 is OH; and except for compounds wherein R 2 is 4-fluorophenyl, R 3 is 2-fluorophenyl and R 4 is OH.
  • R 1 is a group of formula V, where R 2 is phenyl which may carry 1 , 2 or 3 substituents R 7 ; R 3 is phenyl which may carry 1 , 2 or 3 substituents R 11 ; R 4 is OH; each R 7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3,
  • each R 11 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH 3 , CHF2, CF 3 ,
  • R 5 /R 5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R 2 is 2-fluorophenyl, R 3 is 4-fluorophenyl and R 4 is OH; and except for compounds wherein R 2 is 4-fluorophenyl, R 3 is 2-fluorophenyl and R 4 is OH.
  • R 1 is a group of formula V, where R 2 is phenyl which may carry 1 or 2 substituents R 7 ; R 3 is phenyl which may carry 1 or 2 substituents R 11 ; R 4 is OH; each R 7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH 3 , CHF 2 , CF 3 , OCH 3 , OCHF 2 and OCF 3 ; each R 11 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH 3 , CHF 2 , CF 3 ,
  • R 5 /R 5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R 2 is 2-fluorophenyl, R 3 is 4-fluorophenyl and R 4 is OH; and except for compounds wherein R 2 is 4-fluorophenyl, R 3 is 2-fluorophenyl and R 4 is OH.
  • R 2 is phenyl which carries 1 substituent R 7 , this is preferably bound in 2- or 4- position, more preferably in 2-position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
  • R 3 is phenyl which carries 1 substituent R 11 , this is preferably bound in 2- opposition, more preferably in 2-position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
  • R 2 is phenyl which carries 2 substituents R 7 , these are preferably bound in 2,4- position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
  • R 3 is phenyl which carries 2 substituents R 11 , these are preferably bound in 2,4- position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
  • Examples for preferred compounds I and Il of embodiment A are compounds of formulae I.A1 , IA.2 and II.A1 , where the variables R 71 , R 72 , R 73 , R 74 and R 75 are hydrogen or have one of the general or, in particular, one of the preferred meanings given above for R 7 and where the variables R 3 , R 5 and R 5a have one of the general 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 43380 below.
  • the meanings mentioned below for the individual variables in the ta- bles are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
  • Table 81 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 3,4- di-(trifluoromethoxy)-phenyl
  • Table 145 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 2- fluoro-5-difluoromethoxyphenyl
  • Table 152 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 3- difluoromethoxy-4-fluorophenyl
  • Table 164 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 2- chloro-4-bromophenyl
  • Table 171 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 2- bromo-5-chlorophenyl
  • Table 190 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 2- difluoromethyl-4-chlorophenyl
  • Table 202 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 3- trifluoromethyl-4-chlorophenyl
  • Table 240 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 2- methyl-4-bromophenyl
  • Table 271 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 2- methoxy-5-bromophenyl
  • Table 304 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 2- methyl-4-trifluoromethylphenyl
  • Table 354 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 2- difluoromethyl-4-methoxyphenyl
  • Table 380 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 2- trifluoromethoxy-4-difluoromethylphenyl
  • Table 404 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 2- trifluoromethyl-4-trifluoromethoxyphenyl
  • Table 41 1 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 2- trifluoromethoxy-5-trifluoromethylphenyl
  • Table 456 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is
  • Table 480 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 5 is H and R 3 is 2,6- dichloro-4-trifluoromethylphenyl
  • Tables 2411 to 2892 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 3 is as defined in any of tables 1 to 482 and R 5 is n-butyl
  • Tables 5785 to 6266 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 3 is as defined in any of tables 1 to 482 and R 5 is Li +
  • Tables 8195 to 8676 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 3 is as defined in any of tables 1 to 482 and R 5 is Y 2 Zn 2+
  • Tables 11569 to 12050 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 3 is as defined in any of tables 1 to 482 and R 5 is NH(CH 2 CH 2 CH 2 CH 2 ) 3 +
  • Tables 14943 to 15424 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 3 is as defined in any of tables 1 to 482 and R 5 is ethoxycarbonyl
  • Tables 17353 to 17834 Compounds of the formula I.A1 in which the combination of R 71 , R 72 , R 73 , R 74 and R 75 for a compound corresponds in each case to one row of Table A, R 3 is as defined in any of tables 1 to 482 and R 5 is ethylaminocarbonyl

Abstract

The present invention relates to novel triazole compounds of the formulae (I), ( II ) and ( IV) as defined below, to agricultural and pharmaceutical compositions containing them and to their use as fungicides, antimycotic, anticancer and antiviral agents.

Description

ANTIFUNGAL 1, 2, 4-TRIAZOLYL DERIVATIVES
Description
The present invention relates to novel triazole 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.
DE 19528046, DE 19529089, DE 19528300, DE 19617461 , DE 19617282, DE
19620407, DE 19620590, WO96/16048 and WO 97/43269 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 triazole compounds of the general formulae I and II, defined below, and by the agriculturally acceptable salts of the compounds I and II.
Accordingly, the present invention relates to triazole compounds of the formulae I and Il and to agriculturally useful salts thereof
5a
R
Figure imgf000002_0001
(I) (H)
wherein R1 is group of formula V or
Figure imgf000003_0001
(V) (Vl) wherein
# is the attachment point to the remainder of the molecule;
A is a linear d-Cs-alkylene bridge which may be substituted by 1 , 2, 3 or 4 sub- stituents R6;
R2 is aryl which may carry 1 , 2, 3, 4 or 5 substituents R7, or is a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heteroaromatic ring may carry 1 , 2, 3 or 4 substituents R8;
R3 is selected from Ci-Cio-alkyl which may carry 1 or 2 substituents R9, C1-C10- haloalkyl which may carry 1 or 2 substituents R9, Cs-Cs-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 R10, 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 R11;
R4 is hydrogen, OH or CN;
R5 is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-C10- haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl, C3-C10- 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 R12, 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 R12; or, in case m is 0, may also be selected from -C(=O)R13, -C(=S)R13, -S(O)2R13, -CN, -P(=Q)R14R15, M and a group of the formula III
Figure imgf000004_0001
wherein
R1 is as defined for formulae I and II; and # is the attachment point to the remainder of the molecule;
R5a is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-C10- haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl, C3-C10- 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 R12, 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 R12, -C(=O)R13, -C(=S)R13, -S(O)2R13, -CN, -P(=Q)R14R15 and M;
each R6 is independently selected from halogen, OH, SH, NR16R17, 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 Ci-C4-haloalkylthio, where the aliphatic moieties in the above radicals may carry 1 , 2 or 3 substituents R18; or
two radicals R6 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 R12;
each R7 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR16R17;
each R8 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR16R17;
each R9 is independently selected from nitro, CN, OH, SH, Si(R20)3, NR16R17, CrC4- alkoxy, Ci-C4-haloalkoxy, Cs-Cβ-cycloalkyl, Cs-Cβ-halocycloalkyl and C3-C6- cycloaloxy; each R10 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, CrC4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR16R17;
each R11 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR16R17;
each R12 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR16R17;
R13 is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, Ci-Cio-alkoxy, C1-C10- haloalkoxy, Ci-Cio-aminoalkyl, 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 R12, 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 R12, and NR16R17;
R14 and R15, independently of each other, are selected from Ci-Cio-alkyl, Ci-Cio- haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, Ci-Cio-alkoxy, Ci-Cio-haloalkoxy, C1-C4- alkoxy-Ci-Cio-alkyl, Ci-C4-alkoxy-Ci-Cio-alkoxy, Ci-Cio-alkylthio, C1-C10- haloalkylthio, C2-Cio-alkenyloxy, C2-Cio-alkenylthio, C2-Cio-alkynyloxy, C2-C10- alkynylthio, C3-Cio-cycloalkoxy, C3-Cio-cycloalkylthio, phenyl, phenyl-Ci-C4-alkyl, phenylthio, phenyl-Ci-C4-alkoxy, and NR16R17;
each R16 is independently selected from hydrogen and Ci-Cs-alkyl;
each R17 is independently selected from hydrogen, Ci-Cs-alkyl, phenyl, and phenyl-Ci-
CU-alkyl;
or R16 and R17 together form a linear C4- or Cs-alkylene bridge or a group -CH2CH2OCH2CH2- or -CH2CH2NR19CH2CH2-;
each R18 is independently selected from nitro, CN, OH, SH, COR13, NR16R17, C3-C6- cycloalkyl, Cs-Cβ-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6- cycloaloxy, phenyl and phenoxy;
each R19 is independently selected from hydrogen and Ci-C4-alkyl; each R20 is independently selected from d-Cε-alkyl, C-i-Cβ-haloalkyl, phenyl, phenyl- Ci-C4-alkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
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 NR16R17; and
m is 0, 1 , 2 or 3;
preferably with the proviso that R2 is not 2-fluorophenyl if R3 is 4-fluorophenyl and R4 is OH; with the proviso that R3 is not 2-fluorophenyl if R2 is 4-fluorophenyl and R4 is OH; with the proviso that R3 is not n-butyl if R2 is 4-fluorophenyl, 2-chlorophenyl, 4- chlorophenyl, 2,4-dichlorophenyl, 4-bromophenyl, 4-tert-butylphenyl or 4-biphenyl and R4 is CN; with the proviso that R3 is not tert-butyl if R2 is 2-chlorophenyl, 4-chlorophenyl, 2,4- dichlorophenyl, 2,4,6-trichlorophenyl, 4-trifluoromethylphenyl or 2- difluoromethoxyphenyl and R4 is CN; with the proviso that R2 is not 4-chlorophenyl if R3 is 2-fluoromethylprop-2-yl, 1 ,3- difluoro-2-methylprop-2-yl, 4-chlorophenyl, 4-chlorophenyl-methyl, 4-chlorophenyl-1- ethyl, 4-chlorophenyl-2-ethyl or 4-fluorophenyl-2-ethyl and R4 is CN; with the proviso that R2 is not 2,4-dichlorophenyl if R3 is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2,2,2-trifluoroethyl, pentafluoroethyl, trifluoro- methoxymethyl, 1 ,1-difluoroethoxymethyl, 1 ,1 ,2,2-tetrafluoroethoxymethyl, cyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-cyclopropylethyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, 4-fluorophenyl, 4-chlorophenyl, 4-fluorophenylmethyl or 4- chlorophenylmethyl and R4 is H; with the proviso that R3 is not n-propyl if R2 is 4-fluorophenyl, 2-chlorophenyl, 4- chlorophenyl, 2,4,6-trichlorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl or 2- trifluoromethoxyphenyl and R4 is H; with the proviso that R3 is not 1 ,1 ,2,2-tetrafluoroethoxymethyl if R2 is 4-fluorophenyl, 2- chlorophenyl or 4-chlorophenyl and R4 is H; with the proviso that R2 is not 2,4-dichlorophenyl if R3 is n-butyl, R4 is OH and R5 is H, methyl or CN, preferably with the proviso that R2 is not 2,4-dichlorophenyl if R3 is n- Butyl and R4 is OH; with the proviso that in case R1 is a group Vl, R2 is not phenyl, 4-fluorophenyl, 2,4- difluorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,4,6-trichlorophenyl, 4- trifluoromethylphenyl, 2-difluoromethoxyphenyl or 4-trifluoromethoxyphenyl.
The present invention also provides the use of triazole 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 triazole compounds of the formulae I and/or Il (and/or also of the formula IV; 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 stereoisomers 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 R5/R5a are identical. In case R5 (and of course also R5a) 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, preferably 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. CrC4-AIkVl 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-propyl heptyl, 3-propylheptyl and positional isomers thereof.
Haloalkyl: straight-chain or branched alkyl groups having 1 to 2 (Ci-C2-haloalkyl), 1 to 3 (d-Cs-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 (Ci-C8-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 particular 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, i-chlorocyclobutylmethyl, i-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-i -ethyl, 1-fluorocyclopropyl-2-ethyl, 1- fluorocyclobutyl-2 -ethyl, 1-fluorocyclopentyl-2-ethyl, i-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-Cβ-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 example 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, Ci-Cs-haloalkoxy, Ci-Cβ-haloalkoxy, Ci- C4-haloalkoxy or Ci-C2-haloalkoxy. Examples for Ci-C4-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, Ci-Cs-alkyl, Ci-Cβ-alkyl, Ci-C4-alkyl, C1-C2- alkyl or C3-C4-alkyl. Examples for Ci-C4-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-C4-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-Cs-alkyl, Ci-Ce-alkyl, Ci-C4-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 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 carbon 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 com- pounds 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, Ra, Rb, Rc, Rd, Q, M and the index m, and to their use, are valid both per se and, in particular, in every possible combination with one another.
Unless specified otherwise in specific embodiments of the invention, R7, R8, R10, R11 and R12 are independently of each other and independently of each occurrence preferably selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy and more preferably from F, Cl, Br, methyl, difluoromethyl, trifluoromethyl, methoxy, difluoromethoxy and trifluoromethoxy.
Unless specified otherwise in specific embodiments of the invention, preferably, R16 is hydrogen and R17 is selected from hydrogen, Ci-C4-alkyl and phenyl, preferably from hydrogen and Ci-C4-alkyl, or the two of R16 and R17 are Ci-C4-alkyl.
Unless specified otherwise in specific embodiments of the invention, preferably, R19 is hydrogen or methyl and in particular methyl.
Unless specified otherwise in specific embodiments of the invention, preferably, R20 is Ci-C4-alkyl and in particular methyl.
R13 in the groups -C(=O)R13 and -S(O)2R13 is preferably selected from Ci-C4-alkyl, Ci- C2-haloalkyl, Ci-C4-alkoxy, Ci-C2-haloalkoxy, phenyl, phenoxy and NR16R17, more preferably from Ci-C4-alkyl, Ci-C2-haloalkyl, Ci-C4-alkoxy, Ci-C2-haloalkoxy and NR16R17 and even more preferably from Ci-C4-alkyl, Ci-C4-alkoxy and NR16R17. In the group -C(=O)R13, R13 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)2R13, R13 is specifically methyl. Preferably, R16 is hydrogen and R17 is selected from hydrogen, Ci- C4-alkyl and phenyl, preferably from hydrogen and Ci-C4-alkyl, or the two of R16 and R17 are Ci-C4-alkyl.
R5 is preferably selected from hydrogen, Ci-C4-alkyl, -C(=O)R13, -S(O)2R13, -CN, M and a group of the formula III, where R13 has one of the above general meanings or, in par- ticular, 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.
R5 is more preferably selected from hydrogen, Ci-C4-alkyl, C3-C4-alkylcarbonyl, C1-C4- 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, R5 is selected from hydrogen, CN, methyl- carbonyl, methoxycarbonyl and methyl. Specifically, R5 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+, YiMg2+, 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 III, 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.
R5a is preferably selected from hydrogen, Ci-Cio-alkyl, Ci-C4-haloalkyl, phenyl, phenyl- Ci-C4-alkyl, -C(=O)R13 and -S(O)2R13, where R13 has one of the above given general or, in particular, one of the above-given preferred meanings. More preferably, R5a is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, phenyl, benzyl, -C(=O)R13 and -S(O)2R13, where R13 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)R13 and -S(O)2R13, where R13 has one of the above given general or, in particular, one of the above-given preferred meanings. In particular, R5a is hydrogen, Ci-C4-alkyl, preferably methyl, or -C(=O)R13, 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-R5 thus resulting in a group -S(=O)-R5. 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-R5 thus resulting in a group -S(=O)2-R5. If m is 3, the radical -S(O)m-R5 is a group -S(=O)2- O-R5.
m is preferably 0 or 2 and more preferably 0.
In a particularly preferred embodiment, in compounds I, m is 0 and R5 is H (or, alternatively, in compounds II, R5a is H). In a preferred embodiment of the invention (embodiment A), R1 is a group of formula V, where
R2 is phenyl which may carry 1 , 2, 3, 4 or 5 substituents R7; R3 is phenyl which may carry 1 , 2, 3, 4 or 5 substituents R11; R4 is OH; and
R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R2 is 2-fluorophenyl, R3 is 4-fluorophenyl and R4 is OH; and except for compounds wherein R2 is 4-fluorophenyl, R3 is 2-fluorophenyl and R4 is OH.
More preferably (embodiment A.1 ), R1 is a group of formula V, where R2 is phenyl which may carry 1 , 2 or 3 substituents R7; R3 is phenyl which may carry 1 , 2 or 3 substituents R11; R4 is OH; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3,
OCH3, OCHF2 and OCF3; each R11 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3,
OCH3, OCHF2 and OCF3; and
R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R2 is 2-fluorophenyl, R3 is 4-fluorophenyl and R4 is OH; and except for compounds wherein R2 is 4-fluorophenyl, R3 is 2-fluorophenyl and R4 is OH.
Even more preferably (embodiment A.1.1 ), R1 is a group of formula V, where R2 is phenyl which may carry 1 or 2 substituents R7; R3 is phenyl which may carry 1 or 2 substituents R11; R4 is OH; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3; each R11 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3,
OCH3, OCHF2 and OCF3; and R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R2 is 2-fluorophenyl, R3 is 4-fluorophenyl and R4 is OH; and except for compounds wherein R2 is 4-fluorophenyl, R3 is 2-fluorophenyl and R4 is OH.
If R2 is phenyl which carries 1 substituent R7, this is preferably bound in 2- or 4- position, more preferably in 2-position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
If R3 is phenyl which carries 1 substituent R11, this is preferably bound in 2- opposition, more preferably in 2-position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
If R2 is phenyl which carries 2 substituents R7, these are preferably bound in 2,4- position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
If R3 is phenyl which carries 2 substituents R11, these are preferably bound in 2,4- position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
Examples for preferred compounds I and Il of embodiment A are compounds of formulae I.A1 , IA.2 and II.A1 , where the variables R71, R72, R73, R74 and R75 are hydrogen or have one of the general or, in particular, one of the preferred meanings given above for R7 and where the variables R3, R5 and R5a have one of the general 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 43380 below. Moreover, the meanings mentioned below for the individual variables in the ta- bles are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
Figure imgf000024_0001
Table 1
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is phenyl
Table 2
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluorophenyl
Table 3
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluorophenyl Table 4
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 4- fluorophenyl
Table 5 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chlorophenyl
Table 6
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chlorophenyl
Table 7
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 4- chlorophenyl
Table 8
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromophenyl
Table 9
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromophenyl
Table 10
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 4- bromophenyl Table 11
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methylphenyl
Table 12 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methylphenyl
Table 13
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 4- methylphenyl
Table 14
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- (difluoromethyl)-phenyl
Table 15
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3-
(difluoromethyl)-phenyl Table 16
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 4-
(difluoromethyl)-phenyl Table 17
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2-
(trifluoromethyl)-phenyl Table 18
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3-
(trifluoromethyl)-phenyl
Table 19 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 4-
(trifluoromethyl)-phenyl
Table 20
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxyphenyl
Table 21
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methoxyphenyl
Table 22
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 4- methoxyphenyl Table 23
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2-
(difluoromethoxy)-phenyl
Table 24 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3-
(difluoromethoxy)-phenyl
Table 25
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 4-
(difluoromethoxy)-phenyl
Table 26
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2-
(trifluoromethoxy)-phenyl
Table 27
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3-
(trifluoromethoxy)-phenyl
Table 28
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 4- (trifluoromethoxy)-phenyl
Table 29
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,3- difluorophenyl Table 30
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,4- difluorophenyl
Table 31 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,5- difluorophenyl
Table 32
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- difluorophenyl
Table 33
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,4- difluorophenyl
Table 34
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,5- difluorophenyl Table 35
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,3- dichlorophenyl Table 36
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,4- dichlorophenyl Table 37
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,5- dichlorophenyl
Table 38 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- dichlorophenyl
Table 39
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,4- dichlorophenyl
Table 40
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,5- dichlorophenyl
Table 41
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,3- dibromophenyl Table 42
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,4- dibromophenyl
Table 43 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,5- dibromophenyl
Table 44
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- dibromophenyl
Table 45
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,4- dibromophenyl
Table 46
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,5- dibromophenyl
Table 47
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,3- dimethylphenyl
Table 48
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,4- dimethylphenyl Table 49
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,5- dimethylphenyl
Table 50 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- dimethylphenyl
Table 51
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,4- dimethylphenyl
Table 52
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,5- dimethylphenyl
Table 53
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,3- di-(difluoromethyl)-phenyl Table 54
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,4- di-(difluoromethyl)-phenyl Table 55
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,5- di-(difluoromethyl)-phenyl Table 56
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- di-(difluoromethyl)-phenyl
Table 57 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,4- di-(difluoromethyl)-phenyl
Table 58
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,5- di-(difluoromethyl)-phenyl
Table 59
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,3- di-(trifluoromethyl)-phenyl
Table 60
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,4- di-(trifluoromethyl)-phenyl Table 61
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,5- di-(trifluoromethyl)-phenyl
Table 62 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- di-(trifluoromethyl)-phenyl
Table 63
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,4- di-(trifluoromethyl)-phenyl
Table 64
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,5- di-(trifluoromethyl)-phenyl
Table 65
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,3- dimethoxyphenyl
Table 66
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,4- dimethoxyphenyl
Table 67
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,5- dimethoxyphenyl Table 68
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- dimethoxyphenyl
Table 69 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,4- dimethoxyphenyl
Table 70
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,5- dimethoxyphenyl
Table 71
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,3- di-(difluoromethoxy)-phenyl
Table 72
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,4- di-(difluoromethoxy)-phenyl Table 73
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,5- di-(difluoromethoxy)-phenyl Table 74
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- di-(difluoromethoxy)-phenyl Table 75
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,4- di-(difluoromethoxy)-phenyl
Table 76 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,5- di-(difluoromethoxy)-phenyl
Table 77
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,3- di-(trifluoromethoxy)-phenyl
Table 78
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,4- di-(trifluoromethoxy)-phenyl
Table 79
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,5- di-(trifluoromethoxy)-phenyl Table 80
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- di-(trifluoromethoxy)-phenyl
Table 81 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,4- di-(trifluoromethoxy)-phenyl
Table 82
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3,5- di-(trifluoromethoxy)-phenyl
Table 83
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-3-chlorophenyl
Table 84
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-4-chlorophenyl
Table 85
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-5-chlorophenyl
Table 86
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-6-chlorophenyl Table 87
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-4-chlorophenyl
Table 88 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-5-chlorophenyl
Table 89
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-3-fluorophenyl
Table 90
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-4-fluorophenyl
Table 91
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-5-fluorophenyl Table 92
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-4-fluorophenyl Table 93
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-3-bromophenyl Table 94
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-4-bromophenyl
Table 95 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-5-bromophenyl
Table 96
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-6-bromophenyl
Table 97
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-4-bromophenyl
Table 98
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-5-bromophenyl Table 99
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-3-fluorophenyl
Table 100 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-4-fluorophenyl
Table 101
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-5-fluorophenyl
Table 102
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-4-fluorophenyl
Table 103
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-3-methylphenyl
Table 104
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-4-methylphenyl
Table 105
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-5-methylphenyl Table 106
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-6-methylphenyl
Table 107 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-4-methylphenyl
Table 108
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-5-methylphenyl
Table 109
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-3-fluorophenyl
Table 110
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-4-fluorophenyl Table 11 1
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-5-fluorophenyl Table 112
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methyl-4-fluorophenyl Table 113
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-3-difluoromethylphenyl
Table 114 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-4-difluoromethylphenyl
Table 115
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-5-difluoromethylphenyl
Table 116
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-6-difluoromethylphenyl
Table 117
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-4-difluoromethylphenyl Table 118
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-5-difluoromethylphenyl
Table 119 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-3-fluorophenyl
Table 120
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-4-fluorophenyl
Table 121
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-5-fluorophenyl
Table 122
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethyl-4-fluorophenyl
Table 123
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-3-trifluoromethylphenyl
Table 124
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-4-trifluoromethylphenyl Table 125
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-5-trifluoromethylphenyl
Table 126 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-6-trifluoromethylphenyl
Table 127
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-4-trifluoromethylphenyl
Table 128
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-5-trifluoromethylphenyl
Table 129
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-3-fluorophenyl Table 130
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-4-fluorophenyl Table 131
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-5-fluorophenyl Table 132
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethyl-4-fluorophenyl
Table 133 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-3-methoxyphenyl
Table 134
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-4-methoxyphenyl
Table 135
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-5-methoxyphenyl
Table 136
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-6-methoxyphenyl Table 137
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-4-methoxyphenyl
Table 138 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-5-methoxyphenyl
Table 139
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-3-fluorophenyl
Table 140
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-4-fluorophenyl
Table 141
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-5-fluorophenyl
Table 142
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methoxy-4-fluorophenyl
Table 143
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-3-difluoromethoxyphenyl Table 144
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-4-difluoromethoxyphenyl
Table 145 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-5-difluoromethoxyphenyl
Table 146
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-6-difluoromethoxyphenyl
Table 147
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-4-difluoromethoxyphenyl
Table 148
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-5-difluoromethoxyphenyl Table 149
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-3-fluorophenyl Table 150
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-4-fluorophenyl Table 151
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-5-fluorophenyl
Table 152 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethoxy-4-fluorophenyl
Table 153
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-3-trifluoromethoxyphenyl
Table 154
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-4-trifluoromethoxyphenyl
Table 155
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-5-trifluoromethoxyphenyl Table 156
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- fluoro-6-trifluoromethoxyphenyl
Table 157 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-4-trifluoromethoxyphenyl
Table 158
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- fluoro-5-trifluoromethoxyphenyl
Table 159
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-3-fluorophenyl
Table 160
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-4-fluorophenyl
Table 161
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-5-fluorophenyl
Table 162
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethoxy-4-fluorophenyl Table 163
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-3-bromophenyl
Table 164 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-4-bromophenyl
Table 165
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-5-bromophenyl
Table 166
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-6-bromophenyl
Table 167
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-4-bromophenyl Table 168
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-5-bromophenyl Table 169
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-3-chlorophenyl Table 170
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-4-chlorophenyl
Table 171 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-5-chlorophenyl
Table 172
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-4-chlorophenyl
Table 173
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-3-methylphenyl
Table 174
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-4-methylphenyl Table 175
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-5-methylphenyl
Table 176 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-6-methylphenyl
Table 177
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-4-methylphenyl
Table 178
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-5-methylphenyl
Table 179
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-3-chlorophenyl
Table 180
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-4-chlorophenyl
Table 181
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-5-chlorophenyl Table 182
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methyl-4-chlorophenyl
Table 183 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-3-difluoromethylphenyl
Table 184
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-4-difluoromethylphenyl
Table 185
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-5-difluoromethylphenyl
Table 186
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-6-difluoromethylphenyl Table 187
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-4-difluoromethylphenyl Table 188
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-5-difluoromethylphenyl Table 189
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-3-chlorophenyl
Table 190 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-4-chlorophenyl
Table 191
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-5-chlorophenyl
Table 192
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethyl-4-chlorophenyl
Table 193
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-3-trifluoromethylphenyl Table 194
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-4-trifluoromethylphenyl
Table 195 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-5-trifluoromethylphenyl
Table 196
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-6-trifluoromethylphenyl
Table 197
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-4-trifluoromethylphenyl
Table 198
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-5-trifluoromethylphenyl
Table 199
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-3-chlorophenyl
Table 200
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-4-chlorophenyl Table 201
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-5-chlorophenyl
Table 202 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethyl-4-chlorophenyl
Table 203
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-3-methoxyphenyl
Table 204
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-4-methoxyphenyl
Table 205
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-5-methoxyphenyl Table 206
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-6-methoxyphenyl Table 207
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-4-methoxyphenyl Table 208
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-5-methoxyphenyl
Table 209 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-3-chlorophenyl
Table 210
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-4-chlorophenyl
Table 21 1
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-5-chlorophenyl
Table 212
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methoxy-4-chlorophenyl Table 213
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-3-difluoromethoxyphenyl
Table 214 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-4-difluoromethoxyphenyl
Table 215
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-5-difluoromethoxyphenyl
Table 216
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-6-difluoromethoxyphenyl
Table 217
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-4-difluoromethoxyphenyl
Table 218
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-5-difluoromethoxyphenyl
Table 219
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-3-chlorophenyl Table 220
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-4-chlorophenyl
Table 221 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-5-chlorophenyl
Table 222
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethoxy-4-chlorophenyl
Table 223
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-3-trifluoromethoxyphenyl
Table 224
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-4-trifluoromethoxyphenyl Table 225
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-5-trifluoromethoxyphenyl Table 226
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- chloro-6-trifluoromethoxyphenyl Table 227
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-4-trifluoromethoxyphenyl
Table 228 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- chloro-5-trifluoromethoxyphenyl
Table 229
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-3-chlorophenyl
Table 230
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-4-chlorophenyl
Table 231
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-5-chlorophenyl Table 232
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethoxy-4-chlorophenyl
Table 233 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-3-methylphenyl
Table 234
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-4-methylphenyl
Table 235
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-5-methylphenyl
Table 236
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-6-methylphenyl
Table 237
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-4-methylphenyl
Table 238
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-5-methylphenyl Table 239
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-3-bromophenyl
Table 240 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-4-bromophenyl
Table 241
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-5-bromophenyl
Table 242
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methyl-4-bromophenyl
Table 243
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-3-difluoromethylphenyl Table 244
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-4-difluoromethylphenyl Table 245
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-5-difluoromethylphenyl Table 246
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-6-difluoromethylphenyl
Table 247 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-4-difluoromethylphenyl
Table 248
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-5-difluoromethylphenyl
Table 249
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-3-bromophenyl
Table 250
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-4-bromophenyl Table 251
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-5-bromophenyl
Table 252 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethyl-4-bromophenyl
Table 253
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-3-trifluoromethylphenyl
Table 254
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-4-trifluoromethylphenyl
Table 255
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-5-trifluoromethylphenyl
Table 256
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-6-trifluoromethylphenyl
Table 257
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-4-trifluoromethylphenyl Table 258
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-5-trifluoromethylphenyl
Table 259 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-3-bromophenyl
Table 260
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-4-bromophenyl
Table 261
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-5-bromophenyl
Table 262
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethyl-4-bromophenyl Table 263
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-3-methoxyphenyl Table 264
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-4-methoxyphenyl Table 265
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-5-methoxyphenyl
Table 266 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-6-methoxyphenyl
Table 267
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-4-methoxyphenyl
Table 268
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-5-methoxyphenyl
Table 269
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-3-bromophenyl Table 270
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-4-bromophenyl
Table 271 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-5-bromophenyl
Table 272
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methoxy-4-bromophenyl
Table 273
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-3-difluoromethoxyphenyl
Table 274
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-4-difluoromethoxyphenyl
Table 275
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-5-difluoromethoxyphenyl
Table 276
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-6-difluoromethoxyphenyl Table 277
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-4-difluoromethoxyphenyl
Table 278 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-5-difluoromethoxyphenyl
Table 279
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-3-bromophenyl
Table 280
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-4-bromophenyl
Table 281
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-5-bromophenyl Table 282
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethoxy-4-bromophenyl Table 283
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-3-trifluoromethoxyphenyl Table 284
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-4-trifluoromethoxyphenyl
Table 285 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-5-trifluoromethoxyphenyl
Table 286
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- bromo-6-trifluoromethoxyphenyl
Table 287
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-4-trifluoromethoxyphenyl
Table 288
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- bromo-5-trifluoromethoxyphenyl Table 289
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-3-bromophenyl
Table 290 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-4-bromophenyl
Table 291
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-5-bromophenyl
Table 292
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethoxy-4-bromophenyl
Table 293
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-3-difluoromethylphenyl
Table 294
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-4-difluoromethylphenyl
Table 295
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-5-difluoromethylphenyl Table 296
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-6-difluoromethylphenyl
Table 297 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methyl-4-difluoromethylphenyl
Table 298
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methyl-5-difluoromethylphenyl
Table 299
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-3-methylphenyl
Table 300
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-4-methylphenyl Table 301
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-5-methylphenyl Table 302
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethyl-4-methylphenyl Table 303
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-3-trifluoromethylphenyl
Table 304 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-4-trifluoromethylphenyl
Table 305
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-5-trifluoromethylphenyl
Table 306
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-6-trifluoromethylphenyl
Table 307
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methyl-4-trifluoromethylphenyl Table 308
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methyl-5-trifluoromethylphenyl
Table 309 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-3-methylphenyl
Table 310
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-4-methylphenyl
Table 31 1
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-5-methylphenyl
Table 312
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethyl-4-methylphenyl
Table 313
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-3-methoxyphenyl
Table 314
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-4-methoxyphenyl Table 315
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-5-methoxyphenyl
Table 316 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-6-methoxyphenyl
Table 317
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methyl-4-methoxyphenyl
Table 318
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methyl-5-methoxyphenyl
Table 319
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-3-methylphenyl Table 320
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-4-methylphenyl Table 321
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-5-methylphenyl Table 322
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methoxy-4-methylphenyl
Table 323 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-3-difluoromethoxyphenyl
Table 324
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-4-difluoromethoxyphenyl
Table 325
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-5-difluoromethoxyphenyl
Table 326
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-6-difluoromethoxyphenyl Table 327
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methyl-4-difluoromethoxyphenyl
Table 328 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methyl-5-difluoromethoxyphenyl
Table 329
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-3-methylphenyl
Table 330
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-4-methylphenyl
Table 331
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-5-methylphenyl
Table 332
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethoxy-4-methylphenyl
Table 333
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-3-trifluoromethoxyphenyl Table 334
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-4-trifluoromethoxyphenyl
Table 335 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-5-trifluoromethoxyphenyl
Table 336
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methyl-6-trifluoromethoxyphenyl
Table 337
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methyl-4-trifluoromethoxyphenyl
Table 338
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methyl-5-trifluoromethoxyphenyl Table 339
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-3-methylphenyl Table 340
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-4-methylphenyl Table 341
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-5-methylphenyl
Table 342 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethoxy-4-methylphenyl
Table 343
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-3-trifluoromethylphenyl
Table 344
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-4-trifluoromethylphenyl
Table 345
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-5-trifluoromethylphenyl Table 346
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-6-trifluoromethylphenyl
Table 347 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethyl-4-trifluoromethylphenyl
Table 348
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethyl-5-trifluoromethylphenyl
Table 349
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-3-difluoromethylphenyl
Table 350
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-4-difluoromethylphenyl
Table 351
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-5-difluoromethylphenyl
Table 352
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethyl-4-difluoromethylphenyl Table 353
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-3-methoxyphenyl
Table 354 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-4-methoxyphenyl
Table 355
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-5-methoxyphenyl
Table 356
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-6-methoxyphenyl
Table 357
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethyl-4-methoxyphenyl Table 358
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethyl-5-methoxyphenyl Table 359
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-3-difluoromethylphenyl Table 360
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-4-difluoromethylphenyl
Table 361 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-5-difluoromethylphenyl
Table 362
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methoxy-4-difluoromethylphenyl
Table 363
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-3-difluoromethoxyphenyl
Table 364
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-4-difluoromethoxyphenyl Table 365
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-5-difluoromethoxyphenyl
Table 366 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-6-difluoromethoxyphenyl
Table 367
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethyl-4-difluoromethoxyphenyl
Table 368
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethyl-5-difluoromethoxyphenyl
Table 369
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-3-difluoromethylphenyl
Table 370
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-4-difluoromethylphenyl
Table 371
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-5-difluoromethylphenyl Table 372
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethoxy-4-difluoromethylphenyl
Table 373 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-3-trifluoromethoxyphenyl
Table 374
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-4-trifluoromethoxyphenyl
Table 375
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-5-trifluoromethoxyphenyl
Table 376
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethyl-6-trifluoromethoxyphenyl Table 377
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethyl-4-trifluoromethoxyphenyl Table 378
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethyl-5-trifluoromethoxyphenyl Table 379
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-3-difluoromethylphenyl
Table 380 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-4-difluoromethylphenyl
Table 381
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-5-difluoromethylphenyl
Table 382
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethoxy-4-difluoromethylphenyl
Table 383
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-3-methoxyphenyl Table 384
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-4-methoxyphenyl
Table 385 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-5-methoxyphenyl
Table 386
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-6-methoxyphenyl
Table 387
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethyl-4-methoxyphenyl
Table 388
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethyl-5-methoxyphenyl
Table 389
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-3-trifluoromethylphenyl
Table 390
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-4-trifluoromethylphenyl Table 391
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-5-trifluoromethylphenyl
Table 392 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methoxy-4-trifluoromethylphenyl
Table 393
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-3-difluoromethoxyphenyl
Table 394
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-4-difluoromethoxyphenyl
Table 395
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-5-difluoromethoxyphenyl Table 396
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-6-difluoromethoxyphenyl Table 397
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethyl-4-difluoromethoxyphenyl Table 398
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethyl-5-difluoromethoxyphenyl
Table 399 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-3-trifluoromethylphenyl
Table 400
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-4-trifluoromethylphenyl
Table 401
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-5-trifluoromethylphenyl
Table 402
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethoxy-4-trifluoromethylphenyl Table 403
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-3-trifluoromethoxyphenyl
Table 404 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-4-trifluoromethoxyphenyl
Table 405
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-5-trifluoromethoxyphenyl
Table 406
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethyl-6-trifluoromethoxyphenyl
Table 407
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethyl-4-trifluoromethoxyphenyl
Table 408
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethyl-5-trifluoromethoxyphenyl
Table 409
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-3-trifluoromethylphenyl Table 410
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-4-trifluoromethylphenyl
Table 41 1 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-5-trifluoromethylphenyl
Table 412
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethoxy-4-trifluoromethylphenyl
Table 413
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-3-difluoromethoxyphenyl
Table 414
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-4-difluoromethoxyphenyl Table 415
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-5-difluoromethoxyphenyl Table 416
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-6-difluoromethoxyphenyl Table 417
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methoxy-4-difluoromethoxyphenyl
Table 418 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methoxy-5-difluoromethoxyphenyl
Table 419
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-3-methoxyphenyl
Table 420
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-4-methoxyphenyl
Table 421
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-5-methoxyphenyl Table 422
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethoxy-4-methoxyphenyl
Table 423 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-3-trifluoromethoxyphenyl
Table 424
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-4-trifluoromethoxyphenyl
Table 425
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-5-trifluoromethoxyphenyl
Table 426
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- methoxy-6-trifluoromethoxyphenyl
Table 427
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methoxy-4-trifluoromethoxyphenyl
Table 428
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- methoxy-5-trifluoromethoxyphenyl Table 429
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-3-methoxyphenyl
Table 430 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-4-methoxyphenyl
Table 431
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-5-methoxyphenyl
Table 432
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethoxy-4-methoxyphenyl
Table 433
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-3-trifluoromethoxyphenyl Table 434
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-4-trifluoromethoxyphenyl Table 435
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-5-trifluoromethoxyphenyl Table 436
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- difluoromethoxy-6-trifluoromethoxyphenyl
Table 437 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethoxy-4-trifluoromethoxyphenyl
Table 438
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- difluoromethoxy-5-trifluoromethoxyphenyl
Table 439
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-3-difluoromethoxyphenyl
Table 440
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-4-difluoromethoxyphenyl Table 441
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2- trifluoromethoxy-5-difluoromethoxyphenyl
Table 442 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 3- trifluoromethoxy-4-difluoromethoxyphenyl
Table 443
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,4-trifluorophenyl
Table 444
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,5-trifluorophenyl
Table 445
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,6-trifluorophenyl
Table 446
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,4,5-trifluorophenyl
Table 447
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,4,6-trifluorophenyl Table 448
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
3,4,5-trifluorophenyl
Table 449 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,4-trichlorophenyl
Table 450
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,5-trichlorophenyl
Table 451
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,3,6-trichlorophenyl
Table 452
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,4,5-trichlorophenyl Table 453
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,4,6-trichlorophenyl Table 454
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
3,4,5-trichlorophenyl Table 455
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,4-tribromophenyl
Table 456 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,5-tribromophenyl
Table 457
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,6-tribromophenyl
Table 458
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,4,5-tribromophenyl
Table 459
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,4,6-tribromophenyl Table 460
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
3,4,5-tribromophenyl
Table 461 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,4-trimethylphenyl
Table 462
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,5-trimethylphenyl
Table 463
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,6-trimethylphenyl
Table 464
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,4,5-trimethylphenyl
Table 465
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,4,6-trimethylphenyl
Table 466
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
3,4,5-trimethylphenyl Table 467
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,4-tri-(trifluoromethyl)-phenyl
Table 468 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,5-tri-(trifluoromethyl)-phenyl
Table 469
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,3,6-tri-(trifluoromethyl)-phenyl
Table 470
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,4,5-tri-(trifluoromethyl)-phenyl
Table 471
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
2,4,6-tri-(trifluoromethyl)-phenyl Table 472
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is
3,4,5-tri-(trifluoromethyl)-phenyl Table 473
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- difluoro-4-chlorophenyl Table 474
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- difluoro-4-methylphenyl
Table 475 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- difluoro-4-trifluoromethylphenyl
Table 476
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- difluoro-4-methoxyphenyl
Table 477
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- difluoro-4-trifluoromethoxyphenyl
Table 478
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- dichloro-4-fluorophenyl Table 479
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- dichloro-4-methylphenyl
Table 480 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- dichloro-4-trifluoromethylphenyl
Table 481
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- dichloro-4-methoxyphenyl
Table 482
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is H and R3 is 2,6- dichloro-4-trifluoromethoxyphenyl
Tables 483 to 964
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is methyl
Tables 965 to 1446
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is ethyl
Tables 1447 to 1928
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is propyl Tables 1929 to 2410
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is isopropyl
Tables 2411 to 2892 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is n-butyl
Tables 2893 to 3374
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is sec-butyl
Tables 3375 to 3856
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is isobutyl
Tables 3857 to 4338
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is tert-butyl Tables 4339 to 4820
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is phenyl Tables 4821 to 5302
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is 4-methylphenyl Tables 5303 to 5784
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is benzyl
Tables 5785 to 6266 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is Li+
Tables 6267 to 6748
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is Na+
Tables 6749 to 7230
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is K+
Tables 7231 to 7712
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is Y2Mg2+ Tables 7713 to 8194
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is Y2Cu2+
Tables 8195 to 8676 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is Y2Zn2+
Tables 8677 to 9158
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is Y2Fe2+
Tables 9159 to 9640
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is Y2Ni2+
Tables 9641 to 10122
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is NH(CHs)3 +
Tables 10123 to 10604
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is NH(C2Hs)3 +
Tables 10605 to 11086
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is NH(CH2CH2CH2)3 + Tables 1 1087 to 11568
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is NH(CH(CH3)2)3 +
Tables 11569 to 12050 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is NH(CH2CH2CH2CH2)3 +
Tables 12051 to 12532
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is methylcarbonyl
Tables 12533 to 13014
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is ethylcarbonyl
Tables 13015 to 13496
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is propylcarbonyl Tables 13497 to 13978
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is isopropylcarbonyl Tables 13979 to 14460
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is phenylcarbonyl Tables 14461 to 14942
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is methoxycarbonyl
Tables 14943 to 15424 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is ethoxycarbonyl
Tables 15425 to 15906
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is propoxycarbonyl
Tables 15907 to 16388
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is isopropoxycarbonyl
Tables 16389 to 16870
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is phenoxycarbonyl Tables 16871 to 17352
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is methylaminocarbonyl
Tables 17353 to 17834 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is ethylaminocarbonyl
Tables 17835 to 18316
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is propylaminocarbonyl
Tables 18317 to 18798
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is isopropylaminocarbonyl
Tables 18799 to 19280
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is phenylaminocarbonyl
Tables 19281 to 19762
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is methylsulfonyl
Tables 19763 to 20244
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is ethylsulfonyl Tables 20245 to 20726
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is propylsulfonyl
Tables 20727 to 21208 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is isopropylsulfonyl
Tables 21209 to 21690
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is phenylsulfonyl
Tables 21691 to 22172
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is methoxysulfonyl
Tables 22173 to 22654
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is ethoxysulfonyl Tables 22655 to 23136
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is propoxysulfonyl Tables 23137 to 23618
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is isopropoxysulfonyl Tables 23619 to 24100
Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is phenoxysulfonyl
Tables 24101 to 24582 Compounds of the formula I.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5 is CN
Tables 24583 to 25064
Compounds of the formula I.A2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A and R3 is as defined in any of tables 1 to 482
Tables 25065 to 25546
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is H
Tables 25547 to 26028
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is methyl Tables 26029 to 26510
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is ethyl
Tables 2651 1 to 26992 Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is propyl
Tables 26993 to 27474
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is isopropyl
Tables 27475 to 27956
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is n-butyl
Tables 27957 to 28438
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is sec-butyl
Tables 28439 to 28920
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is isobutyl
Tables 28921 to 29402
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is tert-butyl Tables 29403 to 29884
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is phenyl
Tables 29885 to 30366 Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is 4-methylphenyl
Tables 30367 to 30848
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is benzyl
Tables 30849 to 31330
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is methylcarbonyl
Tables 31331 to 31812
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is ethylcarbonyl Tables 31813 to 32294
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is propylcarbonyl Tables 32295 to 32776
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is isopropylcarbonyl Tables 32777 to 33258
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is phenylcarbonyl
Tables 33259 to 33740 Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is methoxycarbonyl
Tables 33741 to 34222
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is ethoxycarbonyl
Tables 34223 to 34704
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is propoxycarbonyl
Tables 34705 to 35186
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is isopropoxycarbonyl Tables 35187 to 35668
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is phenoxycarbonyl
Tables 35669 to 36150 Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is methylaminocarbonyl
Tables 36151 to 36632
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is ethylaminocarbonyl
Tables 36633 to 37114
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is propylaminocarbonyl
Tables 37115 to 37596
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is isopropylaminocarbonyl
Tables 37597 to 38078
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is phenylaminocarbonyl
Tables 38079 to 38560
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is methylsulfonyl Tables 38561 to 39042
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is ethylsulfonyl
Tables 39043 to 39524 Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is propylsulfonyl
Tables 39525 to 40006
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is isopropylsulfonyl
Tables 40007 to 40488
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is phenylsulfonyl
Tables 40489 to 40970
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is methoxysulfonyl Tables 40971 to 41452
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is ethoxysulfonyl Tables 41453 to 41934
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is propoxysulfonyl
Tables 41935 to 42416
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is isopropoxysulfonyl
Tables 42417 to 42898
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is phenoxysulfonyl
Tables 42899 to 43380
Compounds of the formula II.A1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R3 is as defined in any of tables 1 to 482 and R5a is CN
In the above tables 1 to 482, 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 A
Figure imgf000084_0001
Figure imgf000085_0001
Figure imgf000086_0001
Figure imgf000087_0001
Figure imgf000088_0001
Figure imgf000089_0001
Figure imgf000090_0001
Figure imgf000091_0001
Figure imgf000092_0001
Figure imgf000093_0001
Figure imgf000094_0001
Figure imgf000095_0001
Figure imgf000096_0001
Figure imgf000097_0001
Figure imgf000098_0001
Figure imgf000099_0001
In another preferred embodiment of the invention (embodiment B), R1 is a group of formula V, where
R2 is aryl which may carry 1 , 2, 3, 4 or 5 substituents R7, or is a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heteroaromatic ring may carry 1 , 2, 3 or 4 substituents R8; R3 is selected from Ci-Cio-alkyl, Ci-Cio-haloalkyl, aryl and aryl-Ci-C4-alkyl, where the aryl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substitu- ents R11; R4 is CN; and R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R2 is 4-fluorophenyl, 2-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 4-bromophenyl, 4-tert-butylphenyl or 4-biphenyl, R3 is n-butyl and R4 is CN; except for compounds wherein R2 is 2-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,4,6-trichlorophenyl, 4-trifluoromethylphenyl or 2-difluoromethoxyphenyl, R3 is tert-butyl and R4 is CN; and except for compounds wherein R2 is 4-chlorophenyl, R3 is 2-fluoromethylprop-2-yl, 1 ,3- difluoro-2-methylprop-2-yl, 4-chlorophenyl, 4-chlorophenyl-methyl, 4-chlorophenyl-1- ethyl, 4-chlorophenyl-2-ethyl or 4-fluorophenyl-2-ethyl, and R4 is CN.
In this embodiment B, aryl is preferably phenyl.
In a more preferred embodiment of the invention (embodiment B.1 ), R1 is a group of formula V, where
R2 is aryl, preferably phenyl, which may carry 1 , 2 or 3 substituents R7;
R3 is selected from Ci-Cβ-alkyl, Ci-C4-haloalkyl, phenyl and phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2 or 3 substituents R11; R4 is CN; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3; and each R11 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3,
OCH3, OCHF2 and OCF3; except for compounds wherein R2 is 4-fluorophenyl, 2-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 4-bromophenyl, 4-tert-butylphenyl or 4-biphenyl, R3 is n-butyl and R4 is CN; except for compounds wherein R2 is 2-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,4,6-trichlorophenyl, 4-trifluoromethylphenyl or 2-difluoromethoxyphenyl, R3 is tert-butyl and R4 is CN; and except for compounds wherein R2 is 4-chlorophenyl, R3 is 2-fluoromethylprop-2-yl, 1 ,3- difluoro-2-methylprop-2-yl, 4-chlorophenyl, 4-chlorophenyl-methyl, 4-chlorophenyl-1- ethyl, 4-chlorophenyl-2-ethyl or 4-fluorophenyl-2-ethyl, and R4 is CN.
In an even more preferred embodiment of the invention (embodiment B.1.1 ), R1 is a group of formula V, where
R2 phenyl which may carry 1 , 2 or 3 substituents R7; R3 is selected from Ci-Cβ-alkyl and phenyl-Ci-C4-alkyl, where the phenyl moiety may carry 1 , 2 or 3 substituents R11; R4 is CN; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3; and each R11 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3,
OCH3, OCHF2 and OCF3; except for compounds wherein R2 is 4-fluorophenyl, 2-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 4-bromophenyl, 4-tert-butylphenyl or 4-biphenyl, R3 is n-butyl and R4 is CN; except for compounds wherein R2 is 2-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,4,6-trichlorophenyl, 4-trifluoromethylphenyl or 2-difluoromethoxyphenyl, R3 is tert-butyl and R4 is CN; and except for compounds wherein R2 is 4-chlorophenyl, R3 is 2-fluoromethylprop-2-yl, 1 ,3- difluoro-2-methylprop-2-yl, 4-chlorophenyl, 4-chlorophenyl-methyl, 4-chlorophenyl-1- ethyl, 4-chlorophenyl-2-ethyl or 4-fluorophenyl-2-ethyl, and R4 is CN.
If R2 is phenyl which carries 1 substituent R7, this is preferably bound in 2- or 4- position, more preferably in 2-position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
If R3 is phenyl which carries 1 substituent R11, this is preferably bound in 2- opposition, more preferably in 2-position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule. If R3 is phenyl-Ci-C4-alkyl, where the phenyl moiety carries 1 substituent R11, this is preferably bound in 2- or 4-position, more preferably in 2-position, relative to the 1 -position of the attachment point of the phenyl ring to the Ci-C4-alkyl group. If R2 is phenyl which carries 2 substituents R7, these are preferably bound in 2,4- position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
If R3 is phenyl which carries 2 substituents R11, these are preferably bound in 2,4- position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule. If R3 is phenyl-Ci-C4-alkyl, where the phenyl moiety carries 2 substituents R11, these are preferably bound in 2,4-position, relative to the 1-position of the attachment point of the phenyl ring to the Ci-C4-alkyl group.
Particular compounds of this embodiment B are compounds I or II, wherein
- R5 or R5a are H, m is 0, R4 is CN, R3 is n-butyl and R2 is 2,4-difluorophenyl;
- R5 or R5a are H, m is 0, R4 is CN, R3 is n-butyl and R2 is 3,4-difluorophenyl; - R5 or R5a are H, m is 0, R4 is CN, R3 is n-butyl and R2 is 2-chloro-4-fluorophenyl;
- R5 or R5a are H, m is 0, R4 is CN, R3 is n-butyl and R2 is 4-chloro-2-fluorophenyl.
Examples for preferred compounds I and Il of embodiment B are compounds of formulae I.B1 to I.B8 and II.B1 to II. B4, where the variables R71, R72, R73, R74 and R75 are hydrogen or have one of the general or, in particular, one of the preferred meanings given above for R7, where the variables R5 and R5a have one of the general or, in particular, one of the preferred meanings given above, where the variable R31 has one of the preferred meanings given above for R3 in context with embodiment B, but except for the meaning aryl and aryl-i-C4-alkyl, and the variable R32 is aryl as defined above for R3 in context with embodiment B. Examples of preferred compounds are the individual compounds compiled in the tables 1 to 184092 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 imgf000102_0001
(I B1 ) (I B2) (I B3) (I B4)
Figure imgf000103_0001
R5a R5a R5a R5a
Figure imgf000103_0002
(Il B1 ) (Il B2) (Il B3) (M B4)
Table 1
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is H Table 2
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is methyl
Table 3 Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is ethyl
Table 4
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is propyl
Table 5
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is isopropyl
Table 6
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is n-butyl
Table 7
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is sec-butyl
Table 8
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is isobutyl
Table 9
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is tert-butyl Table 10
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is phenyl
Table 11 Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is 4-methylphenyl
Table 12
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is benzyl
Table 13
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is Li+
Table 14
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is Na+ Table 15
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is K+ Table 16
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is Y2Mg2+ Table 17
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is 1/2Cu2+
Table 18 Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is 1/2Zn2+
Table 19
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is 1/2Fe2+
Table 20
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is 1/2Ni2+
Table 21
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is NH(CHs)3 + Table 22
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is NH(C2Hs)3 +
Table 23 Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is NH(CH2CH2CH2)3 +
Table 24
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is NH(CH(CH3)2)3 +
Table 25 Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is NH(CH2CH2CH2CH2)S+
Table 26 Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is methylcarbonyl
Table 27
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is ethylcarbonyl
Table 28
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is propylcarbonyl
Table 29
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is isopropylcarbonyl Table 30
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is methoxycarbonyl
Table 31 Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is ethoxycarbonyl
Table 32
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is propoxycarbonyl
Table 33
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is isopropoxycarbonyl
Table 34
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is phenoxycarbonyl Table 35
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is methylaminocarbonyl Table 36
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is ethylaminocarbonyl
Table 37 Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is propylaminocarbonyl
Table 38
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is isopropylaminocarbonyl
Table 39
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is phenylaminocarbonyl
Table 40
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is methylsulfonyl Table 41
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is ethylsulfonyl
Table 42 Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is propylsulfonyl
Table 43
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is isopropylsulfonyl
Table 44 Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is phenylsulfonyl
Table 45 Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is methoxysulfonyl
Table 46
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is ethoxysulfonyl
Table 47
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is propoxysulfonyl
Table 48
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is isopropoxysulfonyl Table 49
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is phenoxysulfonyl
Table 50 Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5 is CN
Tables 51 to 100
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R31 is ethyl
Tables 101 to 150
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R31 is propyl
Tables 151 to 200
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R31 is isopropyl Tables 201 to 250
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R31 is n-butyl Tables 251 to 300
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R31 is sec-butyl
Tables 301 to 350 Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R31 is isobutyl
Tables 351 to 400
Compounds of the formula I.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R31 is tert-butyl
Tables 401 to 450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is phenyl
Tables 451 to 500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluorophenyl Tables 501 to 550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluorophenyl
Tables 551 to 600 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 4-fluorophenyl
Tables 601 to 650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chlorophenyl
Tables 651 to 700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chlorophenyl
Tables 701 to 750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 4-chlorophenyl
Tables 751 to 800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromophenyl
Tables 801 to 850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromophenyl Tables 851 to 900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 4-bromophenyl
Tables 901 to 950 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methylphenyl
Tables 951 to 1000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methylphenyl
Tables 1001 to 1050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 4-methylphenyl
Tables 1051 to 1 100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-(difluoromethyl)-phenyl Tables 1 101 to 1150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-(difluoromethyl)-phenyl Tables 1 151 to 1200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 4-(difluoromethyl)-phenyl Tables 1201 to 1250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-(trifluoromethyl)-phenyl
Tables 1251 to 1300 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-(trifluoromethyl)-phenyl
Tables 1301 to 1350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 4-(trifluoromethyl)-phenyl
Tables 1351 to 1400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxyphenyl
Tables 1401 to 1450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methoxyphenyl Tables 1451 to 1500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 4-methoxyphenyl
Tables 1501 to 1550 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-(difluoromethoxy)-phenyl
Tables 1551 to 1600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-(difluoromethoxy)-phenyl
Tables 1601 to 1650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 4-(difluoromethoxy)-phenyl
Tables 1651 to 1700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-(trifluoromethoxy)-phenyl
Tables 1701 to 1750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-(trifluoromethoxy)-phenyl
Tables 1751 to 1800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 4-(trifluoromethoxy)-phenyl Tables 1801 to 1850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,3-difluorophenyl
Tables 1851 to 1900 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,4-difluorophenyl
Tables 1901 to 1950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,5-difluorophenyl
Tables 1951 to 2000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,6-difluorophenyl
Tables 2001 to 2050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,4-difluorophenyl Tables 2051 to 2100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,5-difluorophenyl Tables 2101 to 2150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,3-dichlorophenyl Tables 2151 to 2200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,4-dichlorophenyl
Tables 2201 to 2250 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,5-dichlorophenyl
Tables 2251 to 2300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,6-dichlorophenyl
Tables 2301 to 2350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,4-dichlorophenyl
Tables 2351 to 2400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,5-dichlorophenyl Tables 2401 to 2450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,3-dibromophenyl
Tables 2451 to 2500 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,4-dibromophenyl
Tables 2501 to 2550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,5-dibromophenyl
Tables 2551 to 2600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,6-dibromophenyl
Tables 2601 to 2650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,4-dibromophenyl
Tables 2651 to 2700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,5-dibromophenyl
Tables 2701 to 2750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,3-dimethylphenyl Tables 2751 to 2800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,4-dimethylphenyl
Tables 2801 to 2850 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,5-dimethylphenyl
Tables 2851 to 2900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,6-dimethylphenyl
Tables 2901 to 2950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,4-dimethylphenyl
Tables 2951 to 3000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,5-dimethylphenyl Tables 3001 to 3050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,3-di-(difluoromethyl)-phenyl Tables 3051 to 3100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,4-di-(difluoromethyl)-phenyl Tables 3101 to 3150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,5-di-(difluoromethyl)-phenyl
Tables 3151 to 3200 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,6-di-(difluoromethyl)-phenyl
Tables 3201 to 3250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,4-di-(difluoromethyl)-phenyl
Tables 3251 to 3300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,5-di-(difluoromethyl)-phenyl
Tables 3301 to 3350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,3-di-(trifluoromethyl)-phenyl Tables 3351 to 3400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,4-di-(trifluoromethyl)-phenyl
Tables 3401 to 3450 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,5-di-(trifluoromethyl)-phenyl
Tables 3451 to 3500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,6-di-(trifluoromethyl)-phenyl
Tables 3501 to 3550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,4-di-(trifluoromethyl)-phenyl
Tables 3551 to 3600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,5-di-(trifluoromethyl)-phenyl
Tables 3601 to 3650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,3-dimethoxyphenyl
Tables 3651 to 3700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,4-dimethoxyphenyl Tables 3701 to 3750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,5-dimethoxyphenyl
Tables 3751 to 3800 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,6-dimethoxyphenyl
Tables 3801 to 3850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,4-dimethoxyphenyl
Tables 3851 to 3900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,5-dimethoxyphenyl
Tables 3901 to 3950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,3-di-(difluoromethoxy)-phenyl Tables 3951 to 4000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,4-di-(difluoromethoxy)-phenyl Tables 4001 to 4050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,5-di-(difluoromethoxy)-phenyl Tables 4051 to 4100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,6-di-(difluoromethoxy)-phenyl Tables 4101 to 4150 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,4-di-(difluoromethoxy)-phenyl Tables 4151 to 4200 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,5-di-(difluoromethoxy)-phenyl Tables 4201 to 4250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,3-di-(trifluoromethoxy)-phenyl Tables 4251 to 4300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,4-di-(trifluoromethoxy)-phenyl Tables 4301 to 4350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,5-di-(trifluoromethoxy)-phenyl Tables 4351 to 4400 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2,6-di-(trifluoromethoxy)-phenyl Tables 4401 to 4450 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,4-di-(trifluoromethoxy)-phenyl Tables 4451 to 4500 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3,5-di-(trifluoromethoxy)-phenyl
Tables 4501 to 4550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-3-chlorophenyl
Tables 4551 to 4600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-4-chlorophenyl
Tables 4601 to 4650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-5-chlorophenyl Tables 4651 to 4700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-6-chlorophenyl
Tables 4701 to 4750 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-4-chlorophenyl
Tables 4751 to 4800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-5-chlorophenyl
Tables 4801 to 4850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-3-fluorophenyl
Tables 4851 to 4900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-4-fluorophenyl Tables 4901 to 4950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-5-fluorophenyl Tables 4951 to 5000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-4-fluorophenyl Tables 5001 to 5050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-3-bromophenyl
Tables 5051 to 5100 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-4-bromophenyl
Tables 5101 to 5150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-5-bromophenyl
Tables 5151 to 5200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-6-bromophenyl
Tables 5201 to 5250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-4-bromophenyl Tables 5251 to 5300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-5-bromophenyl
Tables 5301 to 5350 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-3-fluorophenyl
Tables 5351 to 5400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-4-fluorophenyl
Tables 5401 to 5450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-5-fluorophenyl
Tables 5451 to 5500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-4-fluorophenyl
Tables 5501 to 5550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-3-methylphenyl
Tables 5551 to 5600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-4-methylphenyl Tables 5601 to 5650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-5-methylphenyl
Tables 5651 to 5700 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-6-methylphenyl
Tables 5701 to 5750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-4-methylphenyl
Tables 5751 to 5800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-5-methylphenyl
Tables 5801 to 5850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-3-fluorophenyl Tables 5851 to 5900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-4-fluorophenyl Tables 5901 to 5950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-5-fluorophenyl Tables 5951 to 6000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methyl-4-fluorophenyl
Tables 6001 to 6050 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-3-difluoromethylphenyl
Tables 6051 to 6100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-4-difluoromethylphenyl
Tables 6101 to 6150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-5-difluoromethylphenyl
Tables 6151 to 6200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-6-difluoromethylphenyl Tables 6201 to 6250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-4-difluoromethylphenyl
Tables 6251 to 6300 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-5-difluoromethylphenyl
Tables 6301 to 6350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-3-fluorophenyl
Tables 6351 to 6400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-4-fluorophenyl Tables 6401 to 6450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-5-fluorophenyl Tables 6451 to 6500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethyl-4-fluorophenyl Tables 6501 to 6550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-3-trifluoromethylphenyl Tables 6551 to 6600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-4-trifluoromethylphenyl Tables 6601 to 6650 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-5-trifluoromethylphenyl Tables 6651 to 6700 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-6-trifluoromethylphenyl Tables 6701 to 6750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-4-trifluoromethylphenyl Tables 6751 to 6800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-5-trifluoromethylphenyl Tables 6801 to 6850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-3-fluorophenyl Tables 6851 to 6900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-4-fluorophenyl Tables 6901 to 6950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-5-fluorophenyl
Tables 6951 to 7000 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethyl-4-fluorophenyl
Tables 7001 to 7050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-3-methoxyphenyl
Tables 7051 to 7100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-4-methoxyphenyl
Tables 7101 to 7150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-5-methoxyphenyl Tables 7151 to 7200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-6-methoxyphenyl
Tables 7201 to 7250 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-4-methoxyphenyl
Tables 7251 to 7300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-5-methoxyphenyl
Tables 7301 to 7350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-3-fluorophenyl
Tables 7351 to 7400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-4-fluorophenyl
Tables 7401 to 7450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-5-fluorophenyl
Tables 7451 to 7500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methoxy-4-fluorophenyl Tables 7501 to 7550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-3-difluoromethoxyphenyl
Tables 7551 to 7600 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-4-difluoromethoxyphenyl
Tables 7601 to 7650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-5-difluoromethoxyphenyl
Tables 7651 to 7700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-6-difluoromethoxyphenyl
Tables 7701 to 7750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-4-difluoromethoxyphenyl Tables 7751 to 7800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-5-difluoromethoxyphenyl Tables 7801 to 7850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-3-fluorophenyl Tables 7851 to 7900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-4-fluorophenyl Tables 7901 to 7950 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-5-fluorophenyl Tables 7951 to 8000 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethoxy-4-fluorophenyl Tables 8001 to 8050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-3-trifluoromethoxyphenyl Tables 8051 to 8100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-4-trifluoromethoxyphenyl Tables 8101 to 8150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-5-trifluoromethoxyphenyl Tables 8151 to 8200 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-fluoro-6-trifluoromethoxyphenyl Tables 8201 to 8250 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-4-trifluoromethoxyphenyl Tables 8251 to 8300 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-fluoro-5-trifluoromethoxyphenyl
Tables 8301 to 8350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-3-fluorophenyl
Tables 8351 to 8400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-4-fluorophenyl
Tables 8401 to 8450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-5-fluorophenyl Tables 8451 to 8500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethoxy-4-fluorophenyl
Tables 8501 to 8550 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-3-bromophenyl
Tables 8551 to 8600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-4-bromophenyl
Tables 8601 to 8650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-5-bromophenyl
Tables 8651 to 8700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-6-bromophenyl Tables 8701 to 8750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-4-bromophenyl Tables 8751 to 8800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-5-bromophenyl Tables 8801 to 8850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-3-chlorophenyl
Tables 8851 to 8900 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-4-chlorophenyl
Tables 8901 to 8950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-5-chlorophenyl
Tables 8951 to 9000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-4-chlorophenyl
Tables 9001 to 9050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-3-methylphenyl Tables 9051 to 9100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-4-methylphenyl
Tables 9101 to 9150 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-5-methylphenyl
Tables 9151 to 9200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-6-methylphenyl
Tables 9201 to 9250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-4-methylphenyl
Tables 9251 to 9300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-5-methylphenyl
Tables 9301 to 9350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-3-chlorophenyl
Tables 9351 to 9400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-4-chlorophenyl Tables 9401 to 9450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-5-chlorophenyl
Tables 9451 to 9500 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methyl-4-chlorophenyl
Tables 9501 to 9550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-3-difluoromethylphenyl
Tables 9551 to 9600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-4-difluoromethylphenyl
Tables 9601 to 9650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-5-difluoromethylphenyl Tables 9651 to 9700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-6-difluoromethylphenyl Tables 9701 to 9750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-4-difluoromethylphenyl Tables 9751 to 9800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-5-difluoromethylphenyl Tables 9801 to 9850 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-3-chlorophenyl Tables 9851 to 9900 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-4-chlorophenyl Tables 9901 to 9950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-5-chlorophenyl Tables 9951 to 10000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethyl-4-chlorophenyl Tables 10001 to 10050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-3-trifluoromethylphenyl Tables 10051 to 10100 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-4-trifluoromethylphenyl Tables 10101 to 10150 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-5-trifluoromethylphenyl Tables 10151 to 10200 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-6-trifluoromethylphenyl
Tables 10201 to 10250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-4-trifluoromethylphenyl
Tables 10251 to 10300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-5-trifluoromethylphenyl
Tables 10301 to 10350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-3-chlorophenyl Tables 10351 to 10400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-4-chlorophenyl
Tables 10401 to 10450 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-5-chlorophenyl
Tables 10451 to 10500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethyl-4-chlorophenyl
Tables 10501 to 10550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-3-methoxyphenyl
Tables 10551 to 10600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-4-methoxyphenyl Tables 10601 to 10650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-5-methoxyphenyl Tables 10651 to 10700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-6-methoxyphenyl Tables 10701 to 10750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-4-methoxyphenyl
Tables 10751 to 10800 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-5-methoxyphenyl
Tables 10801 to 10850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-3-chlorophenyl
Tables 10851 to 10900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-4-chlorophenyl
Tables 10901 to 10950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-5-chlorophenyl Tables 10951 to 1 1000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methoxy-4-chlorophenyl
Tables 11001 to 11050 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-3-difluoromethoxyphenyl
Tables 11051 to 11 100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-4-difluoromethoxyphenyl
Tables 11 101 to 11 150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-5-difluoromethoxyphenyl Tables 1 1 151 to 11200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-6-difluoromethoxyphenyl Tables 11201 to 11250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-4-difluoromethoxyphenyl Tables 11251 to 11300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-5-difluoromethoxyphenyl Tables 1 1301 to 11350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-3-chlorophenyl Tables 11351 to 11400 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-4-chlorophenyl Tables 11401 to 11450 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-5-chlorophenyl Tables 11451 to 11500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethoxy-4-chlorophenyl Tables 11501 to 11550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-3-trifluoromethoxyphenyl Tables 1 1551 to 11600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-4-trifluoromethoxyphenyl Tables 1 1601 to 11650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-5-trifluoromethoxyphenyl Tables 1 1651 to 11700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-chloro-6-trifluoromethoxyphenyl Tables 11701 to 11750 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-4-trifluoromethoxyphenyl Tables 11751 to 11800 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-chloro-5-trifluoromethoxyphenyl Tables 11801 to 11850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-3-chlorophenyl Tables 11851 to 11900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-4-chlorophenyl Tables 1 1901 to 1 1950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-5-chlorophenyl Tables 11951 to 12000 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethoxy-4-chlorophenyl Tables 12001 to 12050 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-3-methylphenyl Tables 12051 to 12100 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-4-methylphenyl
Tables 12101 to 12150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-5-methylphenyl
Tables 12151 to 12200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-6-methylphenyl
Tables 12201 to 12250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-4-methylphenyl Tables 12251 to 12300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-5-methylphenyl
Tables 12301 to 12350 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-3-bromophenyl
Tables 12351 to 12400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-4-bromophenyl
Tables 12401 to 12450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-5-bromophenyl
Tables 12451 to 12500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methyl-4-bromophenyl Tables 12501 to 12550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-3-difluoromethylphenyl Tables 12551 to 12600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-4-difluoromethylphenyl Tables 12601 to 12650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-5-difluoromethylphenyl Tables 12651 to 12700 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-6-difluoromethylphenyl Tables 12701 to 12750 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-4-difluoromethylphenyl Tables 12751 to 12800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-5-difluoromethylphenyl Tables 12801 to 12850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-3-bromophenyl Tables 12851 to 12900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-4-bromophenyl Tables 12901 to 12950 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-5-bromophenyl Tables 12951 to 13000 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethyl-4-bromophenyl Tables 13001 to 13050 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-3-trifluoromethylphenyl Tables 13051 to 13100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-4-trifluoromethylphenyl Tables 13101 to 13150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-5-trifluoromethylphenyl Tables 13151 to 13200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-6-trifluoromethylphenyl Tables 13201 to 13250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-4-trifluoromethylphenyl Tables 13251 to 13300 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-5-trifluoromethylphenyl Tables 13301 to 13350 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-3-bromophenyl Tables 13351 to 13400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-4-bromophenyl Tables 13401 to 13450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-5-bromophenyl Tables 13451 to 13500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethyl-4-bromophenyl Tables 13501 to 13550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-3-methoxyphenyl Tables 13551 to 13600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-4-methoxyphenyl
Tables 13601 to 13650 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-5-methoxyphenyl
Tables 13651 to 13700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-6-methoxyphenyl
Tables 13701 to 13750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-4-methoxyphenyl
Tables 13751 to 13800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-5-methoxyphenyl Tables 13801 to 13850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-3-bromophenyl
Tables 13851 to 13900 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-4-bromophenyl
Tables 13901 to 13950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-5-bromophenyl
Tables 13951 to 14000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methoxy-4-bromophenyl Tables 14001 to 14050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-3-difluoromethoxyphenyl Tables 14051 to 14100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-4-difluoromethoxyphenyl Tables 14101 to 14150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-5-difluoromethoxyphenyl Tables 14151 to 14200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-6-difluoromethoxyphenyl Tables 14201 to 14250 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-4-difluoromethoxyphenyl Tables 14251 to 14300 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-5-difluoromethoxyphenyl Tables 14301 to 14350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-3-bromophenyl Tables 14351 to 14400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-4-bromophenyl Tables 14401 to 14450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-5-bromophenyl Tables 14451 to 14500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethoxy-4-bromophenyl Tables 14501 to 14550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-3-trifluoromethoxyphenyl Tables 14551 to 14600 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-4-trifluoromethoxyphenyl Tables 14601 to 14650 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-5-trifluoromethoxyphenyl Tables 14651 to 14700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-bromo-6-trifluoromethoxyphenyl Tables 14701 to 14750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-4-trifluoromethoxyphenyl Tables 14751 to 14800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-bromo-5-trifluoromethoxyphenyl Tables 14801 to 14850 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-3-bromophenyl Tables 14851 to 14900 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-4-bromophenyl Tables 14901 to 14950 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-5-bromophenyl Tables 14951 to 15000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethoxy-4-bromophenyl Tables 15001 to 15050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-3-difluoromethylphenyl Tables 15051 to 15100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-4-difluoromethylphenyl Tables 15101 to 15150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-5-difluoromethylphenyl Tables 15151 to 15200 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-6-difluoromethylphenyl Tables 15201 to 15250 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methyl-4-difluoromethylphenyl Tables 15251 to 15300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methyl-5-difluoromethylphenyl Tables 15301 to 15350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-3-methylphenyl Tables 15351 to 15400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-4-methylphenyl Tables 15401 to 15450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-5-methylphenyl Tables 15451 to 15500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethyl-4-methylphenyl Tables 15501 to 15550 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-3-trifluoromethylphenyl Tables 15551 to 15600 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-4-trifluoromethylphenyl Tables 15601 to 15650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-5-trifluoromethylphenyl Tables 15651 to 15700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-6-trifluoromethylphenyl Tables 15701 to 15750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methyl-4-trifluoromethylphenyl Tables 15751 to 15800 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methyl-5-trifluoromethylphenyl Tables 15801 to 15850 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-3-methylphenyl Tables 15851 to 15900 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-4-methylphenyl
Tables 15901 to 15950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-5-methylphenyl
Tables 15951 to 16000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethyl-4-methylphenyl
Tables 16001 to 16050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-3-methoxyphenyl Tables 16051 to 16100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-4-methoxyphenyl
Tables 16101 to 16150 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-5-methoxyphenyl
Tables 16151 to 16200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-6-methoxyphenyl
Tables 16201 to 16250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methyl-4-methoxyphenyl
Tables 16251 to 16300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methyl-5-methoxyphenyl Tables 16301 to 16350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-3-methylphenyl Tables 16351 to 16400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-4-methylphenyl Tables 16401 to 16450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-5-methylphenyl
Tables 16451 to 16500 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methoxy-4-methylphenyl
Tables 16501 to 16550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-3-difluoromethoxyphenyl
Tables 16551 to 16600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-4-difluoromethoxyphenyl
Tables 16601 to 16650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-5-difluoromethoxyphenyl Tables 16651 to 16700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-6-difluoromethoxyphenyl
Tables 16701 to 16750 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methyl-4-difluoromethoxyphenyl
Tables 16751 to 16800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methyl-5-difluoromethoxyphenyl
Tables 16801 to 16850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-3-methylphenyl Tables 16851 to 16900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-4-methylphenyl Tables 16901 to 16950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-5-methylphenyl Tables 16951 to 17000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethoxy-4-methylphenyl Tables 17001 to 17050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-3-trifluoromethoxyphenyl Tables 17051 to 17100 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-4-trifluoromethoxyphenyl Tables 17101 to 17150 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-5-trifluoromethoxyphenyl Tables 17151 to 17200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methyl-6-trifluoromethoxyphenyl Tables 17201 to 17250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methyl-4-trifluoromethoxyphenyl Tables 17251 to 17300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methyl-5-trifluoromethoxyphenyl Tables 17301 to 17350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-3-methylphenyl Tables 17351 to 17400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-4-methylphenyl Tables 17401 to 17450 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-5-methylphenyl Tables 17451 to 17500 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethoxy-4-methylphenyl Tables 17501 to 17550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-3-trifluoromethylphenyl Tables 17551 to 17600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-4-trifluoromethylphenyl Tables 17601 to 17650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-5-trifluoromethylphenyl Tables 17651 to 17700 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-6-trifluoromethylphenyl Tables 17701 to 17750 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethyl-4-trifluoromethylphenyl Tables 17751 to 17800 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethyl-5-trifluoromethylphenyl Tables 17801 to 17850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-3-difluoromethylphenyl Tables 17851 to 17900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-4-difluoromethylphenyl Tables 17901 to 17950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-5-difluoromethylphenyl Tables 17951 to 18000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethyl-4-difluoromethylphenyl Tables 18001 to 18050 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-3-methoxyphenyl Tables 18051 to 18100 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-4-methoxyphenyl Tables 18101 to 18150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-5-methoxyphenyl Tables 18151 to 18200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-6-methoxyphenyl Tables 18201 to 18250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethyl-4-methoxyphenyl Tables 18251 to 18300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethyl-5-methoxyphenyl Tables 18301 to 18350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-3-difluoromethylphenyl Tables 18351 to 18400 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-4-difluoromethylphenyl Tables 18401 to 18450 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-5-difluoromethylphenyl Tables 18451 to 18500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methoxy-4-difluoromethylphenyl Tables 18501 to 18550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-3-difluoromethoxyphenyl Tables 18551 to 18600
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-4-difluoromethoxyphenyl Tables 18601 to 18650 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-5-difluoromethoxyphenyl Tables 18651 to 18700 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-6-difluoromethoxyphenyl Tables 18701 to 18750 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethyl-4-difluoromethoxyphenyl Tables 18751 to 18800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethyl-5-difluoromethoxyphenyl Tables 18801 to 18850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-3-difluoromethylphenyl Tables 18851 to 18900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-4-difluoromethylphenyl Tables 18901 to 18950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-5-difluoromethylphenyl Tables 18951 to 19000 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethoxy-4-difluoromethylphenyl Tables 19001 to 19050 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-3-trifluoromethoxyphenyl Tables 19051 to 19100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-4-trifluoromethoxyphenyl Tables 19101 to 19150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-5-trifluoromethoxyphenyl Tables 19151 to 19200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethyl-6-trifluoromethoxyphenyl Tables 19201 to 19250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethyl-4-trifluoromethoxyphenyl Tables 19251 to 19300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethyl-5-trifluoromethoxyphenyl Tables 19301 to 19350 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-3-difluoromethylphenyl Tables 19351 to 19400 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-4-difluoromethylphenyl Tables 19401 to 19450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-5-difluoromethylphenyl Tables 19451 to 19500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethoxy-4-difluoromethylphenyl Tables 19501 to 19550
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-3-methoxyphenyl Tables 19551 to 19600 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-4-methoxyphenyl Tables 19601 to 19650 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-5-methoxyphenyl Tables 19651 to 19700 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-6-methoxyphenyl Tables 19701 to 19750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethyl-4-methoxyphenyl Tables 19751 to 19800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethyl-5-methoxyphenyl Tables 19801 to 19850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-3-trifluoromethylphenyl Tables 19851 to 19900
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-4-trifluoromethylphenyl Tables 19901 to 19950 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-5-trifluoromethylphenyl Tables 19951 to 20000 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methoxy-4-trifluoromethylphenyl Tables 20001 to 20050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-3-difluoromethoxyphenyl Tables 20051 to 20100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-4-difluoromethoxyphenyl Tables 20101 to 20150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-5-difluoromethoxyphenyl Tables 20151 to 20200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-6-difluoromethoxyphenyl Tables 20201 to 20250
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethyl-4-difluoromethoxyphenyl Tables 20251 to 20300 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethyl-5-difluoromethoxyphenyl Tables 20301 to 20350 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-3-trifluoromethylphenyl Tables 20351 to 20400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-4-trifluoromethylphenyl Tables 20401 to 20450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-5-trifluoromethylphenyl Tables 20451 to 20500
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethoxy-4-trifluoromethylphenyl Tables 20501 to 20550 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-3-trifluoromethoxyphenyl Tables 20551 to 20600 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-4-trifluoromethoxyphenyl Tables 20601 to 20650 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-5-trifluoromethoxyphenyl Tables 20651 to 20700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethyl-6-trifluoromethoxyphenyl Tables 20701 to 20750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethyl-4-trifluoromethoxyphenyl Tables 20751 to 20800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethyl-5-trifluoromethoxyphenyl Tables 20801 to 20850
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-3-trifluoromethylphenyl Tables 20851 to 20900 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-4-trifluoromethylphenyl Tables 20901 to 20950 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-5-trifluoromethylphenyl Tables 20951 to 21000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethoxy-4-trifluoromethylphenyl Tables 21001 to 21050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-3-difluoromethoxyphenyl Tables 21051 to 21 100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-4-difluoromethoxyphenyl Tables 21 101 to 21 150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-5-difluoromethoxyphenyl Tables 21 151 to 21200
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-6-difluoromethoxyphenyl Tables 21201 to 21250 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methoxy-4-difluoromethoxyphenyl Tables 21251 to 21300 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methoxy-5-difluoromethoxyphenyl Tables 21301 to 21350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-3-methoxyphenyl Tables 21351 to 21400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-4-methoxyphenyl Tables 21401 to 21450
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-5-methoxyphenyl Tables 21451 to 21500 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethoxy-4-methoxyphenyl Tables 21501 to 21550 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-3-trifluoromethoxyphenyl Tables 21551 to 21600 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-4-trifluoromethoxyphenyl Tables 21601 to 21650
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-5-trifluoromethoxyphenyl Tables 21651 to 21700
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-methoxy-6-trifluoromethoxyphenyl Tables 21701 to 21750
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methoxy-4-trifluoromethoxyphenyl Tables 21751 to 21800
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-methoxy-5-trifluoromethoxyphenyl Tables 21801 to 21850 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-3-methoxyphenyl Tables 21851 to 21900 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-4-methoxyphenyl Tables 21901 to 21950
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-5-methoxyphenyl Tables 21951 to 22000
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethoxy-4-methoxyphenyl Tables 22001 to 22050
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-3-trifluoromethoxyphenyl Tables 22051 to 22100
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-4-trifluoromethoxyphenyl Tables 22101 to 22150
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-5-trifluoromethoxyphenyl Tables 22151 to 22200 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-difluoromethoxy-6-trifluoromethoxyphenyl Tables 22201 to 22250 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethoxy-4-trifluoromethoxyphenyl Tables 22251 to 22300
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-difluoromethoxy-5-trifluoromethoxyphenyl Tables 22301 to 22350
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-3-difluoromethoxyphenyl Tables 22351 to 22400
Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-4-difluoromethoxyphenyl Tables 22401 to 22450 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 2-trifluoromethoxy-5-difluoromethoxyphenyl Tables 22451 to 22500 Compounds of the formula I.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A, R5 is as defined in any of tables 1 to 50 and R32 is 3-trifluoromethoxy-4-difluoromethoxyphenyl Tables 22501 to 44600 Compounds of the formula I.B3 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A and the combination of R5 and R32 is as defined in any of tables 401 to 22500
Tables 44601 to 66700 Compounds of the formula I.B4 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A and the combination of R5 and R32 is as defined in any of tables 401 to 22500
Tables 66701 to 67100
Compounds of the formula I.B5 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A and the combination of R5 and R31 is as defined in any of tables 1 to 400
Tables 67101 to 89200
Compounds of the formula I.B6 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A and the combination of R5 and R32 is as defined in any of tables 401 to 22500
Tables 89201 to 11 1300
Compounds of the formula I.B7 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A and the combination of R5 and R32 is as defined in any of tables 401 to 22500 Tables 1 1131 to 133400
Compounds of the formula I.B8 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A and the combination of R5 and R32 is as defined in any of tables 401 to 22500
Table 133401 Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is H
Table 133402
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is methyl
Table 133403
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is ethyl
Table 133404
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is propyl Table 133405
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is isopropyl Table 133406
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is n-butyl
Table 133407 Compounds of the formula II.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is sec-butyl
Table 133408
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is isobutyl
Table 133409
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is tert-butyl
Table 133410
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is phenyl Table 13341 1
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is 4-methylphenyl
Table 133412 Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is benzyl
Table 133413
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is methylcarbonyl
Table 133414 Compounds of the formula II.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is ethylcarbonyl
Table 133415 Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is propylcarbonyl
Table 133416
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is isopropylcarbonyl
Table 133417
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is phenylcarbonyl
Table 133418
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is methoxycarbonyl Table 133419
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is ethoxycarbonyl
Table 133420 Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is propoxycarbonyl
Table 133421
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is isopropoxycarbonyl
Table 133422
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is phenoxycarbonyl
Table 133423
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is methylaminocarbonyl Table 133424
Compounds of the formula II.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is ethylaminocarbonyl Table 133425
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is propylaminocarbonyl
Table 133426 Compounds of the formula II.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is isopropylaminocarbonyl
Table 133427
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is phenylaminocarbonyl
Table 133428
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is methylsulfonyl
Table 133429
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is ethylsulfonyl Table 133430
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is propylsulfonyl
Table 133431 Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is isopropylsulfonyl
Table 133432
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is phenylsulfonyl
Table 133433 Compounds of the formula II.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is methoxysulfonyl Table 133434 Compounds of the formula II.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is ethoxysulfonyl Table 133435 Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is propoxysulfonyl Table 133436
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is isopropoxysulfonyl Table 133437
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is phenoxysulfonyl Table 133438
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R31 is methyl and R5a is CN Tables 133439 to 133476 Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is as defined in any of tables 133401 to 133438 and R31 is ethyl Tables 133477 to 133514 Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is as defined in any of tables 133401 to 133438 and R31 is propyl Tables 133515 to 133552
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is as de- fined in any of tables 133401 to 133438 and R31 is isopropyl Tables 133553 to 133590
Compounds of the formula II. B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is as defined in any of tables 133401 to 133438 and R31 is n-butyl Tables 133591 to 133628
Compounds ofthe formula II.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row ofTable A above, R5a is as defined in any oftables 133401 to 133438 and R31 is sec-butyl Tables 133629 to 133666
Compounds ofthe formula II.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row ofTable A above, R5a is as defined in any of tables 133401 to 133438 and R31 is isobutyl Tables 133667 to 133704 Compounds ofthe formula II.B1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row ofTable A above, R5a is as defined in any of tables 133401 to 133438 and R31 is tert-butyl
Tables 133705 to 150500 Compounds ofthe formula II.B2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row ofTable A above, R5a is as defined in any of tables 133401 to 133438 and R32 is as defined in any of tables 401, 451, 501,551,601,651,701,751,801,851,901,951, 1001, 1051, 1101, 1151, 1201, 1251, 1301, 1351, 1401, 1451, 1501, 1551, 1601, 1651, 1701, 1751, 1801, 1851, 1901, 1951, 2001 , 2051,2101, 2151, 2201 , 2251 , 2301, 2351 , 2401, 2451 , 2501 , 2551, 2601 , 2651, 2701 , 2751, 2801 , 2851, 2901 , 2951 , 3001, 3051 , 3101, 3151 , 3201 , 3251, 3301 , 3351, 3401 , 3451 , 3501, 3551 , 3601 , 3651 , 3701 , 3751, 3801 , 3851 , 3901, 3951 , 4001 , 4051 , 4101 , 4151 , 4201, 4251 , 4301 , 4351 , 4401 , 4451, 4501 , 4551 , 4601, 4651 , 4701 , 4751 , 4801 , 4851 , 4901, 4951 , 5001 , 5051 , 5101 , 5151, 5201 , 5251 , 5301, 5351 , 5401 , 5451 , 5501, 5551, 5601, 5651, 5701, 5751, 5801, 5851, 5901, 5951, 6001, 6051, 6101, 6151, 6201 , 6251 , 6301, 6351 , 6401 , 6451 , 6501 , 6551, 6601 , 6651 , 6701, 6751 , 6801 , 6851 , 6901, 6951, 7001, 7051, 7101, 7151, 7201, 7251, 7301, 7351, 7401, 7451, 7501, 7551, 7601, 7651, 7701, 7751, 7801, 7851, 7901, 7951, 8001, 8051, 8101, 8151, 8201, 8251, 8301 , 8351 , 8401, 8451 , 8501 , 8551 , 8601 , 8651, 8701 , 8751 , 8801, 8851 , 8901 , 8951 , 9001, 9051, 9101, 9151, 9201, 9251, 9301, 9351, 9401, 9451, 9501, 9551, 9601, 9651, 9701, 9751, 9801, 9851, 9901, 9951, 10001, 10051, 10101, 10151, 10201, 10251, 10301, 10351, 10401, 10451, 10501, 10551, 10601, 10651, 10701, 10751, 10801, 10851, 10901, 10951, 11001, 11051, 11101, 11151, 11201, 11251, 11301, 11351, 11401, 11451, 11501, 11551, 11601, 11651, 11701, 11751, 11801, 11851, 11901, 11951, 12001, 12051, 12101, 12151, 12201, 12251, 12301, 12351, 12401, 12451, 12501, 12551, 12601, 12651, 12701, 12751, 12801, 12851, 12901, 12951, 13001, 13051, 13101, 13151, 13201, 13251, 13301, 13351, 13401, 13451, 13501, 13551, 13601, 13651, 13701, 13751, 13801, 13851, 13901, 13951, 14001, 14051, 14101, 14151, 14201, 14251, 14301, 14351, 14401, 14451, 14501, 14551, 14601, 14651, 14701, 14751, 14801, 14851, 14901, 14951, 15001, 15051, 15101, 15151, 15201, 15251, 15301, 15351, 15401, 15451, 15501, 15551, 15601, 15651, 15701, 15751, 15801, 15851, 15901, 15951, 16001, 16051, 16101, 16151, 16201, 16251, 16301, 16351, 16401, 16451, 16501, 16551, 16601, 16651, 16701, 16751, 16801, 16851, 16901, 16951, 17001, 17051, 17101, 17151, 17201, 17251, 17301, 17351, 17401, 17451, 17501, 17551, 17601, 17651, 17701, 17751, 17801, 17851, 17901, 17951, 18001, 18051, 18101, 18151, 18201, 18251, 18301, 18351, 18401, 18451, 18501, 18551, 18601, 18651, 18701, 18751, 18801, 18851, 18901, 18951, 19001, 19051, 19101, 19151, 19201, 19251, 19301, 19351, 19401, 19451, 19501, 19551, 19601, 19651,19701,19751,19801,19851,19901,19951,20001,20051,20101,20151, 20201 , 20251 , 20301 , 20351 , 20401 , 20451 , 20501 , 20551 , 20601 , 20651 , 20701 , 20751 , 20801 , 20851 , 20901 , 20951 , 21001 , 21051 , 21101 , 21151 , 21201 , 21251 , 21301,21351,21401,21451,21501,21551,21601,21651,21701,21751,21801, 21851 , 21901 , 21951 , 22001 , 22051 , 22101 , 22151 , 22201 , 22251 , 22301 , 22351 , 22401 and 22451
Tables 150501 to 167296
Compounds ofthe formula II.B3 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row ofTable A above, R5a is as de- fined in any of tables 133401 to 133438 and R32 is as defined in any oftables 401, 451, 501,551,601,651,701,751,801,851,901,951, 1001, 1051, 1101, 1151, 1201, 1251, 1301, 1351, 1401, 1451, 1501, 1551, 1601, 1651, 1701, 1751, 1801, 1851, 1901, 1951, 2001 , 2051 , 2101, 2151 , 2201 , 2251 , 2301 , 2351, 2401 , 2451 , 2501, 2551 , 2601 , 2651 , 2701 , 2751 , 2801, 2851 , 2901 , 2951 , 3001 , 3051, 3101 , 3151 , 3201, 3251 , 3301 , 3351 , 3401 , 3451, 3501 , 3551, 3601 , 3651 , 3701, 3751 , 3801, 3851 , 3901 , 3951, 4001 , 4051, 4101 , 4151 , 4201, 4251 , 4301 , 4351 , 4401 , 4451, 4501 , 4551 , 4601, 4651 , 4701 , 4751 , 4801 , 4851 , 4901, 4951 , 5001 , 5051 , 5101 , 5151, 5201 , 5251 , 5301, 5351 , 5401 , 5451 , 5501, 5551, 5601, 5651, 5701, 5751, 5801, 5851, 5901, 5951, 6001, 6051, 6101, 6151, 6201 , 6251 , 6301, 6351 , 6401 , 6451 , 6501 , 6551, 6601 , 6651 , 6701, 6751 , 6801 , 6851 , 6901, 6951, 7001, 7051, 7101, 7151, 7201, 7251, 7301, 7351, 7401, 7451, 7501, 7551, 7601, 7651, 7701, 7751, 7801, 7851, 7901, 7951, 8001, 8051, 8101, 8151, 8201, 8251, 8301 , 8351 , 8401, 8451 , 8501 , 8551 , 8601 , 8651, 8701 , 8751 , 8801, 8851 , 8901 , 8951 , 9001, 9051, 9101, 9151, 9201, 9251, 9301, 9351, 9401, 9451, 9501, 9551, 9601, 9651, 9701, 9751, 9801, 9851, 9901, 9951, 10001, 10051, 10101, 10151, 10201, 10251, 10301, 10351, 10401, 10451, 10501, 10551, 10601, 10651, 10701, 10751, 10801, 10851, 10901, 10951, 11001, 11051, 11101, 11151, 11201, 11251, 11301, 11351, 11401, 11451, 11501, 11551, 11601, 11651, 11701, 11751, 11801, 11851, 11901, 11951, 12001, 12051, 12101, 12151, 12201, 12251, 12301, 12351, 12401, 12451, 12501, 12551, 12601, 12651, 12701, 12751, 12801, 12851, 12901, 12951, 13001, 13051, 13101, 13151, 13201, 13251, 13301, 13351, 13401, 13451, 13501, 13551, 13601, 13651, 13701, 13751, 13801, 13851, 13901, 13951, 14001, 14051, 14101, 14151, 14201, 14251, 14301, 14351, 14401, 14451, 14501, 14551, 14601, 14651, 14701, 14751, 14801, 14851, 14901, 14951, 15001, 15051, 15101, 15151, 15201, 15251, 15301, 15351, 15401, 15451, 15501, 15551, 15601, 15651, 15701, 15751, 15801, 15851, 15901, 15951, 16001, 16051, 16101, 16151, 16201, 16251, 16301, 16351, 16401, 16451, 16501, 16551, 16601, 16651, 16701, 16751, 16801, 16851, 16901, 16951, 17001, 17051, 17101, 17151, 17201, 17251, 17301, 17351, 17401, 17451, 17501, 17551, 17601, 17651, 17701, 17751, 17801, 17851, 17901, 17951, 18001, 18051, 18101, 18151, 18201, 18251, 18301, 18351, 18401, 18451, 18501, 18551, 18601, 18651, 18701, 18751, 18801, 18851, 18901, 18951, 19001, 19051, 19101, 19151, 19201, 19251, 19301, 19351, 19401, 19451, 19501, 19551, 19601, 19651,19701,19751,19801,19851,19901,19951,20001,20051,20101,20151, 20201 , 20251 , 20301 , 20351 , 20401 , 20451 , 20501 , 20551 , 20601 , 20651 , 20701 , 20751,20801,20851,20901,20951,21001,21051,21101,21151,21201,21251, 21301,21351,21401,21451,21501,21551,21601,21651,21701,21751,21801, 21851 , 21901 , 21951 , 22001 , 22051 , 22101 , 22151 , 22201 , 22251 , 22301 , 22351 , 22401 and 22451
Tables 167297 to 184092
Compounds of the formula II. B4 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is as defined in any of tables 133401 to 133438 and R32 is as defined in any of tables 401, 451, 501, 551, 601, 651, 701, 751, 801, 851, 901, 951, 1001, 1051, 1101, 1151, 1201, 1251, 1301, 1351, 1401, 1451, 1501, 1551, 1601, 1651, 1701, 1751, 1801, 1851, 1901, 1951, 2001 , 2051 , 2101 , 2151 , 2201 , 2251 , 2301 , 2351 , 2401 , 2451 , 2501 , 2551 , 2601 , 2651 , 2701 , 2751 , 2801 , 2851 , 2901 , 2951 , 3001 , 3051 , 3101 , 3151 , 3201 , 3251 , 3301 , 3351 , 3401 , 3451 , 3501 , 3551 , 3601 , 3651 , 3701 , 3751 , 3801 , 3851 , 3901 , 3951 , 4001 , 4051 , 4101 , 4151 , 4201 , 4251 , 4301 , 4351 , 4401 , 4451 , 4501 , 4551 , 4601 , 4651 , 4701 , 4751 , 4801 , 4851 , 4901 , 4951 , 5001 , 5051 , 5101 , 5151 , 5201 , 5251 , 5301 , 5351 , 5401 , 5451 , 5501, 5551, 5601, 5651, 5701, 5751, 5801, 5851, 5901, 5951, 6001, 6051, 6101, 6151, 6201 , 6251 , 6301 , 6351 , 6401 , 6451 , 6501 , 6551 , 6601 , 6651 , 6701 , 6751 , 6801 , 6851 , 6901, 6951, 7001, 7051, 7101, 7151, 7201, 7251, 7301, 7351, 7401, 7451, 7501, 7551, 7601, 7651, 7701, 7751, 7801, 7851, 7901, 7951, 8001, 8051, 8101, 8151, 8201, 8251, 8301 , 8351 , 8401 , 8451 , 8501 , 8551 , 8601 , 8651 , 8701 , 8751 , 8801 , 8851 , 8901 , 8951 , 9001, 9051, 9101, 9151, 9201, 9251, 9301, 9351, 9401, 9451, 9501, 9551, 9601, 9651, 9701, 9751, 9801, 9851, 9901, 9951, 10001, 10051, 10101, 10151, 10201, 10251, 10301, 10351, 10401, 10451, 10501, 10551, 10601, 10651, 10701, 10751, 10801, 10851, 10901, 10951, 11001, 11051, 11101, 11151, 11201, 11251, 11301, 11351, 11401, 11451, 11501, 11551, 11601, 11651, 11701, 11751, 11801, 11851, 11901, 11951, 12001, 12051, 12101, 12151, 12201, 12251, 12301, 12351, 12401, 12451, 12501, 12551, 12601, 12651, 12701, 12751, 12801, 12851, 12901, 12951, 13001, 13051, 13101, 13151, 13201, 13251, 13301, 13351, 13401, 13451, 13501, 13551, 13601, 13651, 13701, 13751, 13801, 13851, 13901, 13951, 14001, 14051, 14101, 14151, 14201, 14251, 14301, 14351, 14401, 14451, 14501, 14551, 14601, 14651, 14701, 14751, 14801, 14851, 14901, 14951, 15001, 15051, 15101, 15151, 15201, 15251, 15301, 15351, 15401, 15451, 15501, 15551, 15601, 15651, 15701, 15751, 15801, 15851, 15901, 15951, 16001, 16051, 16101, 16151, 16201, 16251, 16301, 16351, 16401, 16451, 16501, 16551, 16601, 16651, 16701, 16751, 16801, 16851, 16901, 16951, 17001, 17051, 17101, 17151, 17201, 17251, 17301, 17351, 17401, 17451, 17501, 17551, 17601, 17651, 17701, 17751, 17801, 17851, 17901, 17951, 18001, 18051, 18101, 18151, 18201, 18251, 18301, 18351, 18401, 18451, 18501, 18551, 18601, 18651, 18701, 18751, 18801, 18851, 18901, 18951, 19001, 19051, 19101, 19151, 19201, 19251, 19301, 19351, 19401, 19451, 19501, 19551, 19601, 19651, 19701, 19751, 19801, 19851, 19901, 19951,20001,20051,20101,20151, 20201 , 20251 , 20301 , 20351 , 20401 , 20451 , 20501 , 20551 , 20601 , 20651 , 20701 , 20751 , 20801 , 20851 , 20901 , 20951 , 21001 , 21051 , 21101 , 21151 , 21201 , 21251 , 21301, 21351, 21401, 21451, 21501, 21551, 21601, 21651, 21701, 21751, 21801, 21851 , 21901 , 21951 , 22001 , 22051 , 22101 , 22151 , 22201 , 22251 , 22301 , 22351 , 22401 and 22451
In the above tables 401 to 22500, the given positions of the substituents on the phenyl ring are to be understood as relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
In another preferred embodiment of the invention (embodiment C), R1 is a group of formula V, where
R2 is aryl which may carry 1 , 2, 3, 4 or 5 substituents R7, or is a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heteroaromatic ring may carry 1 , 2, 3 or 4 substituents R8;
R3 is selected from Ci-Cio-alkyl which may carry 1 or 2 substituents R9, C1-C10- haloalkyl which may carry 1 or 2 substituents R9, Cs-Cs-cycloalkyl, C3-C8- cycloalkyl-d^-alkyl, where the cycloalkyl moiety in the 2 last-mentioned radicals may carry 1, 2, 3 or 4 substituents R10, 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
R4 is hydrogen; and R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R2 is 2,4-dichlorophenyl, R3 is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2,2,2-trifluoroethyl, pentafluoroethyl, trifluoromethoxymethyl, 1 ,1-difluoroethoxymethyl, 1 ,1 ,2,2-tetrafluoroethoxymethyl, cyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-cyclopropylethyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, 4-fluorophenyl, 4-chlorophenyl, 4-fluorophenylmethyl or 4-chlorophenylmethyl and R4 is H; . except for compounds wherein R2 is 4-fluorophenyl, 2-chlorophenyl, 4-chlorophenyl, 2,4,6-trichlorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl or 2- trifluoromethoxyphenyl, R3 is n-propyl and R4 is H; and except for compounds wherein R2 is 4-fluorophenyl, 2-chlorophenyl or 4-chlorophenyl, R3 is 1 ,1 ,2,2-tetrafluoroethoxymethyl and R4 is H.
In the above definitions, aryl is preferably phenyl.
More preferabyl (embodiment C.1 ), R1 is a group of formula V, where
R2 is phenyl which may carry 1 , 2 or 3 substituents R7;
R3 is selected from Ci-Cio-alkyl which may carry 1 or 2 substituents R9, C1-C4- haloalkyl, C3-C8-cycloalkyl and C3-C8-cycloalkyl-Ci-C4-alkyl, where the cycloalkyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3 or 4 substituents R10; R4 is hydrogen; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3; each R9 is independently selected from Ci-C4-alkoxy and Ci-C4-fluoroalkoxy; each R10 is independently selected from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl; and R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R2 is 2,4-dichlorophenyl, R3 is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2,2,2-trifluoroethyl, pentafluoroethyl, trifluoromethoxymethyl, 1 ,1-difluoroethoxymethyl, 1 ,1 ,2,2-tetrafluoroethoxymethyl, cyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-cyclopropylethyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, 4-fluorophenyl, 4-chlorophenyl, 4-fluorophenylmethyl or 4-chlorophenylmethyl and R4 is H; . except for compounds wherein R2 is 4-fluorophenyl, 2-chlorophenyl, 4-chlorophenyl, 2,4,6-trichlorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl or 2- trifluoromethoxyphenyl, R3 is n-propyl and R4 is H; and except for compounds wherein R2 is 4-fluorophenyl, 2-chlorophenyl or 4-chlorophenyl, R3 is 1 ,1 ,2,2-tetrafluoroethoxymethyl and R4 is H.
Even more preferably (embodiment C.1.1), R1 is a group of formula V, where R2 is phenyl which may carry 1 , 2 or 3 substituents R7;
R3 is selected from Ci-Cβ-alkyl, d-Cε-alkyl which carries 1 substituent R9, cyclopro- pyl and cyclopropyl-Ci-C2-alkyl, where the cyclopropyl moiety in the 2 last- mentioned radicals may carry 1 or 2 substituents R10; R4 is hydrogen; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3; R9 is Ci-C4-fluoroalkoxy; each R10 is independently selected from halogen and Ci-C4-alkyl; and R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R2 is 2,4-dichlorophenyl, R3 is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2,2,2-trifluoroethyl, pentafluoroethyl, trifluoromethoxymethyl, 1 ,1-difluoroethoxymethyl, 1 ,1 ,2,2-tetrafluoroethoxymethyl, cyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-cyclopropylethyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, 4-fluorophenyl, 4-chlorophenyl, 4-fluorophenylmethyl or 4-chlorophenylmethyl and R4 is H; . except for compounds wherein R2 is 4-fluorophenyl, 2-chlorophenyl, 4-chlorophenyl, 2,4,6-trichlorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl or 2- trifluoromethoxyphenyl, R3 is n-propyl and R4 is H; and except for compounds wherein R2 is 4-fluorophenyl, 2-chlorophenyl or 4-chlorophenyl, R3 is 1 ,1 ,2,2-tetrafluoroethoxymethyl and R4 is H.
Particularly preferably (embodiment C.1.1.1 ), R1 is a group of formula V, where R2 is phenyl which may carry 1 , 2 or 3 substituents R7;
R3 is selected from Ci-C4-alkyl, Ci-C2-alkyl which carries 1 substituent R9, cyclopropyl and cyclopropyl-Ci-C2-alkyl, where the cyclopropyl moiety in the 2 last- mentioned radicals may carry 1 or 2 substituents R10;
R4 is hydrogen; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3;
R9 is Ci-C2-fluoroalkoxy; each R10 is independently selected from halogen and Ci-C4-alkyl; and R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R2 is 2,4-dichlorophenyl, R3 is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2,2,2-trifluoroethyl, pentafluoroethyl, trifluoromethoxymethyl, 1 ,1-difluoroethoxymethyl, 1 ,1 ,2,2-tetrafluoroethoxymethyl, cyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-cyclopropylethyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, 4-fluorophenyl, 4-chlorophenyl, 4-fluorophenylmethyl or 4-chlorophenylmethyl and R4 is H; . except for compounds wherein R2 is 4-fluorophenyl, 2-chlorophenyl, 4-chlorophenyl, 2,4,6-trichlorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl or 2- trifluoromethoxyphenyl, R3 is n-propyl and R4 is H; and except for compounds wherein R2 is 4-fluorophenyl, 2-chlorophenyl or 4-chlorophenyl, R3 is 1 ,1 ,2,2-tetrafluoroethoxymethyl and R4 is H.
Specifically (embodiment C.1.1.1.1 ), R1 is a group of formula V, where
R2 is phenyl which may carry 1 , 2 or 3 substituents R7;
R3 is selected from Ci-C4-alkyl, methyl which carries 1 substituent R9, cyclopropyl and cyclopropyl-Ci-C2-alkyl, where the cyclopropyl moiety in the 2 last-mentioned radicals may carry 1 or 2 substituents R10; R4 is hydrogen; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3;
R9 is selected from OCF3, OCF2CH3, OCF2CHF2 and OCF2CF3; each R10 is independently selected from halogen and Ci-C4-alkyl; and
R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R2 is 2,4-dichlorophenyl, R3 is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2,2,2-trifluoroethyl, pentafluoroethyl, trifluoromethoxymethyl, 1 ,1-difluoroethoxymethyl, 1 ,1 ,2,2-tetrafluoroethoxymethyl, cyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-cyclopropylethyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, 4-fluorophenyl, 4-chlorophenyl, 4-fluorophenylmethyl or
4-chlorophenylmethyl and R4 is H; . except for compounds wherein R2 is 4-fluorophenyl, 2-chlorophenyl, 4-chlorophenyl, 2,4,6-trichlorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl or 2- trifluoromethoxyphenyl, R3 is n-propyl and R4 is H; and except for compounds wherein R2 is 4-fluorophenyl, 2-chlorophenyl or 4-chlorophenyl,
R3 is 1 ,1 ,2,2-tetrafluoroethoxymethyl and R4 is H. If R2 is phenyl which carries 1 substituent R7, this is preferably bound in 2- or 4- position, more preferably in 2-position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
If R3 is phenyl which carries 1 substituent R11, this is preferably bound in 2- or 4- position, more preferably in 2-position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule. If R3 is phenyl-Ci-C4-alkyl, where the phenyl moiety carries 1 substituent R11, this is preferably bound in 2- or 4-position, more preferably in 2-position, relative to the 1 -position of the attachment point of the phenyl ring to the Ci-C4-alkyl group.
If R2 is phenyl which carries 2 substituents R7, these are preferably bound in 2,4- position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
If R3 is phenyl which carries 2 substituents R11, these are preferably bound in 2,4- position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule. If R3 is phenyl-Ci-C4-alkyl, where the phenyl moiety carries 2 substituents R11, these are preferably bound in 2,4-position, relative to the 1-position of the attachment point of the phenyl ring to the Ci-C4-alkyl group.
Examples for preferred compounds I and Il of embodiment C are compounds of formulae I.C1 , I.C2 and II.C1 , where the variables R71, R72, R73, R74 and R75 are hydrogen or have one of the general or, in particular, one of the preferred meanings given above for R7, where the variables R5 and R5a have one of the general or, in particular, one of the preferred meanings given above, where the variable R3 has one of the preferred meanings given above for R3 in context with embodiment C. Examples of preferred compounds are the individual compounds compiled in the tables 1 to 1068 below. More- over, 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 imgf000169_0001
Table 1
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5 is H and R3 is methyl
Table 2
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5 is H and R3 is ethyl
Table 3
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5 is H and R3 is propyl Table 4
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5 is H and R3 is isopropyl
Table 5 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5 is H and R3 is n-butyl
Table 6
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5 is H and R3 is sec-butyl
Table 7
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5 is H and R3 is isobutyl Table 8
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5 is H and R3 is tert-butyl Table 9
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5 is H and R3 is cyclopropyl Table 10
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5 is H and R3 is i-chlorocyclopropyl Table 11
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5 is H and R3 is 1-cyclopropylethyl Table 12 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5 is H and R3 is CH2-O-CF2CHF2 Tables 13 to 24 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is methyl Tables 25 to 36
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 1 to 12 and R5 is ethyl Tables 37 to 48
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is propyl Tables 49 to 60
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is isopropyl Tables 61 to 72
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is n-butyl Tables 73 to 84
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is sec-butyl Tables 85 to 96 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is isobutyl Tables 97 to 108 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is tert-butyl Tables 109 to 120
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 1 to 12 and R5 is phenyl Tables 121 to 132
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is 4-methylphenyl Tables 133 to 144
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is benzyl Tables 145 to 156 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is Li+ Tables 157 to 168 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is Na+ Tables 169 to 180 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is K+ Tables 181 to 192
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is YiMg2+ Tables 193 to 204
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 1 to 12 and R5 is Y2Cu2+ Tables 205 to 216
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is YzZn2+ Tables 229 to 240
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is YiFe2+ Tables 217 to 228 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is VzNi2+ Tables 241 to 252 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is NH(CH3)S+ Tables 253 to 264
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 1 to 12 and R5 is NH(C2H5)S+ Tables 265 to 276
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is NH(CH2CH2CH2)S+ Tables 277 to 288
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is NH(CH(CH3)2)s+ Tables 289 to 300 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is NH(CH2CH2CH2CH2)S+ Tables 301 to 312 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is methylcarbonyl Tables 313 to 324 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is ethylcarbonyl Tables 325 to 336
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 1 to 12 and R5 is propylcarbonyl Tables 337 to 348
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is isopropylcarbonyl Tables 349 to 360
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is methoxycarbonyl Tables 361 to 372 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is ethoxycarbonyl Tables 373 to 384 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is propoxycarbonyl Tables 385 to 396
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 1 to 12 and R5 is isopropoxycarbonyl Tables 397 to 408
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is phenoxycarbonyl Tables 409 to 420
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is methylaminocarbonyl Tables 421 to 432
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is ethylaminocarbonyl Tables 433 to 444 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is propylaminocarbonyl Tables 445 to 456 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is isopropylaminocarbonyl Tables 457 to 468
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 1 to 12 and R5 is phenylaminocarbonyl Tables 469 to 480
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is methylsulfonyl Tables 481 to 492
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is ethylsulfonyl Tables 493 to 504 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is propylsulfonyl Tables 505 to 516 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is isopropylsulfonyl Tables 517 to 528 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is phenylsulfonyl Tables 529 to 540 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is methoxysulfonyl Tables 541 to 552 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is ethoxysulfonyl Tables 553 to 564
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 1 to 12 and R5 is propoxysulfonyl Tables 565 to 576
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is isopropoxysulfonyl Tables 577 to 588
Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is phenoxysulfonyl Tables 589 to 600 Compounds of the formula I.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 1 to 12 and R5 is CN Tables 601 to 612 Compounds of the formula I.C2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R3 is as defined in any of tables 1 to 12 Table 613
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is H and R3 is methyl Table 614
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is H and R3 is ethyl Table 615
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is H and
R3 is propyl Table 616
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is H and
R3 is isopropyl
Table 617 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is H and
R3 is n-butyl
Table 618
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is H and
R3 is sec-butyl
Table 619
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is H and R3 is isobutyl
Table 620
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is H and
R3 is tert-butyl Table 621
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is H and
R3 is cyclopropyl
Table 622 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is H and
R3 is i-chlorocyclopropyl
Table 623
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is H and
R3 is 1-cyclopropylethyl
Table 624
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R5a is H and R3 is CH2-O-CF2CH F2 Tables 625 to 636
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is methyl Tables 637 to 648
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 613 to 624 and R5a is ethyl Tables 649 to 660
Compounds of the formula II.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is propyl Tables 661 to 672
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is isopropyl Tables 673 to 684 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is n-butyl Tables 685 to 696 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is sec-butyl Tables 697 to 708
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 613 to 624 and R5a is isobutyl Tables 709 to 720
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is tert-butyl Tables 721 to 732
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is phenyl Tables 733 to 744
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is 4-methylphenyl Tables 745 to 756
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is benzyl Tables 757 to 768 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is methylcarbonyl Tables 769 to 780 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is ethylcarbonyl Tables 781 to 792
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 613 to 624 and R5a is propylcarbonyl Tables 793 to 804
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is isopropylcarbonyl Tables 805 to 816
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is phenylcarbonyl Tables 817 to 828 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is methoxycarbonyl Tables 829 to 840 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is ethoxycarbonyl Tables 841 to 852 Compounds of the formula II. C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is propoxycarbonyl Tables 853 to 864 Compounds of the formula II.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is isopropoxycarbonyl Tables 865 to 876 Compounds of the formula II.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is phenoxycarbonyl Tables 877 to 888
Compounds of the formula II.C1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 613 to 624 and R5a is methylaminocarbonyl Tables 889 to 900
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is ethylaminocarbonyl Tables 901 to 912
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is propylaminocarbonyl Tables 913 to 924 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is isopropylaminocarbonyl Tables 925 to 936 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is phenylaminocarbonyl Tables 937 to 948
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 613 to 624 and R5a is methylsulfonyl Tables 949 to 960
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is ethylsulfonyl Tables 961 to 972
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is propylsulfonyl Tables 973 to 984
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is isopropylsulfonyl Tables 985 to 996 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is phenylsulfonyl Tables 997 to 1008 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is methoxysulfonyl Tables 1009 to 1020
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as de- fined in any of tables 613 to 624 and R5a is ethoxysulfonyl Tables 1021 to 1032
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is propoxysulfonyl Tables 1033 to 1044
Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is isopropoxysulfonyl Tables 1045 to 1056 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is phenoxysulfonyl Tables 1057 to 1068 Compounds of the formula 11.01 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above, R3 is as defined in any of tables 613 to 624 and R5a is CN In another preferred embodiment of the invention (embodiment D), R1 is a group of formula V, where
R2 is phenyl which may carry 1 , 2, 3, 4 or 5 substituents R7; R3 is selected from Ci-Cio-alkyl which may carry 1 substituent R9; R4 is OH;
R9 is Si(R20)3; and
R5/R5a, R20 and m have one of the above given general or, preferably, one of the above-given preferred meanings; except for compounds wherein R2 is 2,4-dichlorophenyl, R3 is n-Butyl, R4 is OH and R5 is H, methyl or CN, preferably except for compounds wherein R2 is 2,4-dichlorophenyl, R3 is n-Butyl and R4 is OH.
In a more preferred embodiment of the invention (embodiment D.1 ), R1 is a group of formula V, where R2 is phenyl which may carry 1 , 2 or 3 substituents R7; R3 is d-Cβ-alkyl; R4 is OH; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3; and
R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R2 is 2,4-dichlorophenyl, R3 is n-Butyl, R4 is OH and R5 is H, methyl or CN, preferably except for compounds wherein R2 is 2,4-dichlorophenyl, R3 is n-Butyl and R4 is OH.
Even more preferably (embodiment D.1.1 ), R1 is a group of formula V, where
R2 is phenyl which may carry 1 , 2 or 3 substituents R7;
R3 is Ci-C4-alkyl, specifically n-butyl; R4 is OH; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3; and
R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R2 is 2,4-dichlorophenyl, R3 is n-Butyl, R4 is OH and R5 is H, methyl or CN, preferably except for compounds wherein R2 is 2,4-dichlorophenyl,
R3 is n-Butyl and R4 is OH. In an alternatively more preferred embodiment of the invention (embodiment D.2), R1 is a group of formula V, where
R2 is phenyl which may carry 1 , 2 or 3 substituents R7; R3 is Ci-C2-alkyl which carries 1 substituent R9; R4 is OH; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3,
OCH3, OCHF2 and OCF3; R9 is Si(R20)3; and R5/R5a, R20 and m have one of the above given general or, preferably, one of the above-given preferred meanings.
Even more preferably (embodiment D.2.1 ), R1 is a group of formula V, where
R2 is phenyl which may carry 1 , 2 or 3 substituents R7; R3 is CH2-Si(R20)3;
R4 is OH; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3; R20 is Ci-C4-alkyl, preferably methyl; and
R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings.
If R2 is phenyl which carries 1 substituent R7, this is preferably bound in 2- or 4- position, more preferably in 2-position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
If R2 is phenyl which carries 2 substituents R7, these are preferably bound in 2,4- position, relative to the 1 -position of the attachment point of the phenyl ring to the re- mainder 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 R71, R72, R73, R74 and R75 are hy- drogen or have one of the general or, in particular, one of the preferred meanings given above for R7, and where the variables R5 and R5a have one of the general or, in particular, one of the preferred meanings given above. Examples of preferred compounds are the individual compounds compiled in the tables 1 to 178 below. Moreover, the meanings mentioned below for the individual variables in the tables are per se, independ- ently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
Figure imgf000183_0001
Table 1 Compounds of the formula I. D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is H
Table 2
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is methyl
Table 3
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is ethyl
Table 4 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is propyl
Table 5
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- p ropy I Table 6
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is n- butyl Table 7
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is sec- butyl Table 8
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- butyl Table 9 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is tert- butyl Table 10 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is phenyl Table 11
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is 4- methylphenyl Table 12
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is benzyl Table 13
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is Li+ Table 14
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is Na+
Table 15 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is K+
Table 16
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is Y2Mg2+
Table 17
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
1/_Cu2+ Table 18
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
1Z-Zn2+
Table 19 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
Y2Fe2+
Table 20
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is !4Ni2+
Table 21
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
NH(CHs)3 + Table 22
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
NH(C2Hs)3 +
Table 23 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
Figure imgf000185_0001
Table 24 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
Figure imgf000186_0001
Table 25 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
Figure imgf000186_0002
Table 26
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is me- thylcarbonyl
Table 27
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is ethyl- carbonyl
Table 28
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is pro- pylcarbonyl Table 29
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- propylcarbonyl
Table 30 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is methoxycarbonyl
Table 31
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is eth- oxycarbonyl
Table 32
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is pro- poxycarbonyl
Table 33
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- propoxycarbonyl Table 34
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is phenoxycarbonyl Table 35
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is me- thylaminocarbonyl
Table 36 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is ethylaminocarbonyl
Table 37
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is pro- pylaminocarbonyl
Table 38
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- propylaminocarbonyl
Table 39
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is phenylaminocarbonyl Table 40
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is me- thylsulfonyl
Table 41 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is ethyl- sulfonyl
Table 42
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is pro- pylsulfonyl
Table 43 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- propylsulfonyl
Table 44 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is phenylsulfonyl
Table 45
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is methoxysulfonyl
Table 46
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is eth- oxysulfonyl
Table 47
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is pro- poxysulfonyl Table 48
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- propoxysulfonyl
Table 49 Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is phenoxysulfonyl
Table 50
Compounds of the formula I.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is CN
Table 51
Compounds of the formula I.D2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above
Tables 52 to 101 Compounds of the formula I.D3 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is as defined in any of tables 1 to 50
Table 102 Compounds of the formula I.D4 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above
Table 103
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is H
Table 104
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is methyl Table 105
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is ethyl
Table 106
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is propyl
Table 107
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- propyl
Table 108
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is n- butyl Table 109
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is sec- butyl
Table 110 Compounds of the formula II. D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- butyl
Table 11 1
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is tert- butyl
Table 112
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is phenyl
Table 113
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is 4- methylphenyl
Table 114
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is ben- zyl
Table 115
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is me- thylcarbonyl Table 116
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is ethylcarbonyl
Table 117 Compounds of the formula II. D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is pro- pylcarbonyl
Table 118
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- propylcarbonyl
Table 119
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is phenylcarbonyl
Table 120
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is methoxycarbonyl Table 121
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is eth- oxycarbonyl
Table 122 Compounds of the formula II. D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is pro- poxycarbonyl
Table 123 Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- propoxycarbonyl
Table 124
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is phenoxycarbonyl
Table 125
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is me- thylaminocarbonyl
Table 126
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is ethylaminocarbonyl Table 127
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is pro- pylaminocarbonyl
Table 128 Compounds of the formula II. D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- propylaminocarbonyl
Table 129
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is phenylaminocarbonyl
Table 130
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is me- thylsulfonyl
Table 131
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is ethylsulfonyl Table 132
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is pro- pylsulfonyl Table 133
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- propylsulfonyl
Table 134 Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is phenylsulfonyl
Table 135
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is methoxysulfonyl
Table 136
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is eth- oxysulfonyl
Table 137
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is pro- poxysulfonyl Table 138
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- propoxysulfonyl
Table 139 Compounds of the formula II. D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is phenoxysulfonyl
Table 140
Compounds of the formula II.D1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is CN
Tables 141 to 178
Compounds of the formula II.D2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is as defined in any of tables 103 to 140 In another preferred embodiment of the invention (embodiment E), R1 is a group of formula Vl, where A is selected from -(CH2J2-, -CH2-CH(CH3)-, -CH2-CH(C2H5)-,
-CH2-CH(CH2CH2CH3)-, -CH2-CH(CH2CH2CH2CH3)-, -CH2-CHF-, -CH(CHs)-CH(CH3)-, -(CH2)S-, -CH2-CH2-CH(CH3)-, -CH2-CH(CHs)-CH2- and -CH2-C(CHs)2-CH2-, and is preferably -CH2-CH(CH2CH2CHs)-; R2 is phenyl which may carry 1 , 2, 4 or 5 substituents R7; and R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings; except for compounds wherein R2 is phenyl, 4-fluorophenyl, 2,4-difluorophenyl, A- chlorophenyl, 2,4-dichlorophenyl, 2,4,6-trichlorophenyl, 4-trifluoromethylphenyl, 2- difluoromethoxyphenyl or 4-trifluoromethoxyphenyl.
More preferably, (embodiment E.1 ), R1 is a group of formula Vl, where
A is -CH2-CH(CH2CH2CH3)- ;
R2 is phenyl which may carry 1 , 2 or 3 substituents R7; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3,
OCHF2 and OCF3, and more preferably from F and Cl; and R5/R5a and m have one of the above given general or, preferably, one of the above- given preferred meanings, except for compounds wherein R2 is phenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,4- dichlorophenyl, 2,4,6-trichlorophenyl, 4-trifluoromethylphenyl, 2-difluoromethoxyphenyl or 4-trifluoromethoxyphenyl, preferably except for compounds wherein R2 is phenyl, 4-fluorophenyl, 2,4- difluorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,4,6-trichlorophenyl, A- trifluoromethylphenyl, 2-difluoromethoxyphenyl or 4-trifluoromethoxyphenyl.
If R2 is phenyl which carries 1 substituent R7, this is preferably bound in 2- or A- position, more preferably in 2-position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
If R2 is phenyl which carries 2 substituents R7, these are preferably bound in 2,4- position, relative to the 1 -position of the attachment point of the phenyl ring to the remainder of the molecule.
Particular compounds of this embodiment E are compounds I and II, wherein - R5 or R5a are H, m is 0, A is is -CH2-CH(CH2CH2CH3)- and R2 is 2,3-difluorophenyl (compound E1 );
- R5 or R5a are H, m is 0, A is is -CH2-CH(CH2CH2CH3)- and R2 is 2-fluoro-4- chlorophenyl (compound E2); - R5 or R5a are H, m is 0, A is is -CH2-CH(CH2CH2CH3)- and R2 is 2-chloro-4- fluorophenyl (compound E3);
- R5 or R5a are H, m is 0, A is is -CH2-CH(CH2CH2CH3)- and R2 is 3,4-difluorophenyl (compound E4).
Particular compounds of this embodiment E are also compounds I and II, wherein
- R5 or R5a are H, m is 0, A is is -CH2-CH(CH2CH2CH3)- and R2 is 4-chlorophenyl (compound E5);
- R5 or R5a are H, m is 0, A is is -CH2-CH(CH2CH2CH3)- and R2 is 2,4-difluorophenyl (compound E6).
Examples for preferred compounds I and Il of embodiment E are compounds of formulae I.E1 , I.E2 and II. E1 , where the variables R71, R72, R73, R74 and R75 are hydrogen or have one of the general or, in particular, one of the preferred meanings given above for R7, and where the variables R5 and R5a have one of the general or, in particular, one of the preferred meanings given above. Examples of preferred compounds are the individual compounds compiled in the tables 1 to 89 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 imgf000194_0001
Table 1
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is H Table 2
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is methyl Table 3
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is ethyl
Table 4 Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is propyl
Table 5
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- p ropy I
Table 6
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is n- butyl
Table 7
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is sec- butyl Table 8
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- butyl
Table 9 Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is tert- butyl
Table 10
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is phenyl
Table 11
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is 4- methylphenyl
Table 12
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is ben- zyl Table 13
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is Li+
Table 14 Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is Na+
Table 15
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is K+ Table 16
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
1/2Mg2+
Table 17 Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
1Z-Cu2+
Table 18
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
1Z-Zn2+
Table 19
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
Table 20
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is !4Ni2+
Table 21 Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
NH(CHs)3 +
Table 22
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
NH(C2Hs)3 +
Table 23 Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
Figure imgf000197_0001
Table 24 Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
Figure imgf000197_0002
Table 25
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is
Figure imgf000197_0003
Table 26
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is me- thylcarbonyl
Table 27
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is ethyl- carbonyl Table 28
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is pro- pylcarbonyl
Table 29 Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- propylcarbonyl
Table 30
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is methoxycarbonyl
Table 31
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is eth- oxycarbonyl
Table 32
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is pro- poxycarbonyl Table 33
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- propoxycarbonyl Table 34
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is phenoxycarbonyl
Table 35 Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is me- thylaminocarbonyl
Table 36
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is ethylaminocarbonyl
Table 37
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is pro- pylaminocarbonyl
Table 38
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- propylaminocarbonyl Table 39
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is phenylaminocarbonyl
Table 40 Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is me- thylsulfonyl
Table 41
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is ethyl- sulfonyl
Table 42 Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is pro- pylsulfonyl
Table 43 Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- propylsulfonyl
Table 44
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is phenylsulfonyl
Table 45
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is methoxysulfonyl
Table 46
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is eth- oxysulfonyl Table 47
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is pro- poxysulfonyl
Table 48 Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is iso- propoxysulfonyl
Table 49
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is phenoxysulfonyl
Table 50
Compounds of the formula I.E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5 is CN Table 51
Compounds of the formula I.E2 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above Table 52
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is H
Table 53 Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is methyl
Table 54
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is ethyl
Table 55
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is propyl Table 56
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- p ropy I
Table 57 Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is n- butyl
Table 58
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is sec- butyl
Table 59
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- butyl
Table 60
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is tert- butyl Table 61
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is phenyl Table 62
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is 4- methylphenyl Table 63
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is benzyl
Table 64 Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is me- thylcarbonyl
Table 65
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is ethylcarbonyl
Table 66
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is pro- pylcarbonyl
Table 67
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- propylcarbonyl Table 68
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is phenylcarbonyl
Table 69 Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is methoxycarbonyl
Table 70
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is eth- oxycarbonyl
Table 71 Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is pro- poxycarbonyl
Table 72 Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- propoxycarbonyl
Table 73
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is phenoxycarbonyl
Table 74
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is me- thylaminocarbonyl
Table 75
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is ethylaminocarbonyl Table 76
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is pro- pylaminocarbonyl
Table 77 Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- propylaminocarbonyl
Table 78
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is phenylaminocarbonyl
Table 79
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is me- thylsulfonyl
Table 80
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is ethylsulfonyl Table 81
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is pro- pylsulfonyl Table 82
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- propylsulfonyl
Table 83 Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is phenylsulfonyl
Table 84
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is methoxysulfonyl
Table 85
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is eth- oxysulfonyl
Table 86
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is pro- poxysulfonyl Table 87
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is iso- propoxysulfonyl
Table 88 Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is phenoxysulfonyl
Table 89
Compounds of the formula II. E1 in which the combination of R71, R72, R73, R74 and R75 for a compound corresponds in each case to one row of Table A above and R5a is CN
Among the above embodiments A, B, C, D and E, preference is given to embodiment
E. 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 14 and in the syntheses descriptions below. The variables are as defined above for formulae I and II.
Compounds of formula I, wherein R5 is H and m is 0 (or compounds II, wherein R5a is H), can be prepared by sulfurizing the corresponding triazole derivative IV 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 tetrame- thylethylene 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, tetrahydro- furan or dioxane, dimethoxyethane, liquid ammonia, dimethylsulfoxide or dimethylfor- mamide. 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 IV 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 hydrolyzed, 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 compound I.
Scheme 1
Figure imgf000204_0001
IV I
(R5/R5a = H; m = 0)
The triazole compound IV, wherein R1 is a group V wherein R4 is OH, can be prepared in analogy to known methods, such as described, for example, in EP-A-15756, EP-A- 537957 or DE-A-3042302, as outlined in scheme 2. For instance, the oxirane compound 1 and [1 ,2,4]-1 H-triazole can be reacted 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. so- dium carbonate, potassium carbonate, caesium carbonate). The 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.
Scheme 2
Figure imgf000205_0001
(R4 = OH)
The oxirane 1 in turn can be prepared in analogy to known methods, such as described, for example, in EP-A-0267778, Org. Syn. 49, 78 (1968) or J. Am. Chem. Soc. 1975, 1353, as outlined in scheme 3 below. For instance, the ketone 2 may be reacted with a sulfonium ylide or an oxosulfonium ylide, such as dimethyloxosulfonium me- thylide or dimethylsulfonium methylide in a solvent. Alternatively, the oxirane 1 can be prepared in an epoxidation reaction in analogy to the method described in Tetrahedron Lett. 23, 5283 (1982) or in EP-A-0655443 by subjecting 2 to the reaction with a trimethylsulfonium salt, such as trimethylsulfonium bromide, trimethylsulfonium iodide or methyltrimethylsulfonium sulfate, in the presence of a metal oxide, such as alkaline metal oxides (e.g. sodium oxide, potassium oxide), alkaline earth metal oxides (e.g. magnesium oxide, calcium oxide, barium oxide) or zinc oxide, and optionally a base, such as 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) in a two-phase solid/liquid system comprising an organic solvent, such as toluene, N- methypyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran), acetonitrile or N, N- dimethylformamide. Alternatively, the oxirane 1 can be prepared in analogy to the method described in Tetrahedron 1985, 1259 by epoxidation of 2 with a trimethylsulfonium salt, such as trimethylsulfonium bromide, trimethylsulfonium iodide or methyltrimethylsulfonium sulfate, or a trimethylsulfoxonium salt, such as trimethylsulfoxonium bromide, trimethylsulfoxonium iodide or methyltrimethylsulfoxonium sulfate and potassium sulfate/aluminium oxide.
Scheme 3
Figure imgf000206_0001
The ketone 2 can be obtained from the halide 4" by a Grignard reaction with the aldehyde 5\ or from the halide 4" by a Grignard reaction with the aldehyde 5", as outlined in scheme 4 below. Oxidation of the obtained alcohol 3 via known methods, such as oxidation with the Swern reagent, hypervalent iodine compounds (IBX, Martin's reagent), chromine compounds (e.g. pyridinium dichromate, pyridinium chlorochromate, dipyridinium chromine trioxide), sodium hypochlorite and the like, yields the ketone 2.
Scheme 4
Figure imgf000206_0002
(Hal = halogen)
Alternatively, the ketone 2 can be prepared by a Friedel-Crafts acylation of R2-H with the acylchloride R3-C(=O)-CI in the presence of a Lewis acid, such as AICb or FeCb, under reaction conditions customary for this reaction type.
As an alternative to the process described in scheme 3, the oxirane 1 can be prepared in analogy to the method described in Org. Syn. 40, 66, 1966, J. Org. Chem. 28, 1 128, 1963 and Org. Syn. Coll. Vol. 4, 552, 1963 as outlined in scheme 5 below by first subjecting the ketone 2 to a Wittig reaction, thus yielding the corresponding olefinic compound 6, and then subjecting this to an epoxidation reaction. The Wittig reaction can be carried out under standard conditions, such as the use of methyltriphenylphosphonium bromide or iodide in the presence of an alkali metal base, such as n-butyllithium, sec- butyllithium or tert-butyllithium. Epoxidation can also be carried out with standard reagents, such as peracetic acid, perbenzoic acid meta-chloroperbenzoic acid, perphthalic acid and the like. Olefination (i.e. transformation of the C=O into a C=CHb group) of 2 can alternatively be achieved by the use of Tebbe's reagent ((C5Hs)2TiCH2CIAI(CHs)2).
Scheme 5
olefination epoxidation
Figure imgf000207_0002
Figure imgf000207_0001
Figure imgf000207_0003
As an alternative to the process described in scheme 1 , compounds I, wherein R5 is H and m is 0 (or compounds II, wherein R5a is H) and wherein R1 is a group V wherein R4 is OH, can also be prepared in analogy to the method described in WO 99/18088 as outlined in scheme 6 below. Epoxide opening of 1 with hydrazine, optionally in the presence of an acid (e.g. hydrochloric acid, hydrobromic acid, acetic acid, sulfuric acid or p-toluenesulfonic acid) or a base (e.g. triethylamine, diisopropylethylamine, sodium carbonate or potassium carbonate) in a suitable solvent, such as an alcohol (e.g. methanol, ethanol, isopropanol, tert-butanol), N-methylpyrrolidinone, an ether (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane), acetonitrile, N,N-dimethyl- formamide or dimethylsulfoxide, yields 7. This is then converted into the semicarbazide 8 by reaction with a thiocyanate, such as sodium thiocyanate, potassium thiocyanate or ammonium thiocyanate (i.e. M+ = e.g. Na+, K+, NH4 +), in a suitable solvent, such as an alcohol (e.g. methanol, ethanol, isopropanol, tert-butanol), N-methylpyrrolidinone, an ether (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane), acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, toluene or xylene. The semicarbazide is then converted into l/ll via reaction with a formic acid alkyl ester (e.g. formic acid methyl ester, formic acid ethyl ester) in a solvent. Suitable solvents are, for example, alcohols (e.g. methanol, ethanol, isopropanol, tert-butanol), N-methylpyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane), acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, toluene or xylene. Alternatively, 7 can be reacted with hydrogen thiocyanate and formaldehyde in a solvent. Suitable solvents are, for example, alcohols (e.g. methanol, ethanol, isopropanol, tert-butanol), N-methyl- pyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane), acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, toluene or xylene. The resulting triazolidinthione 9 is then oxidized using, for example, FeCb in an aqueous acid (e.g. hydrochloric acid) or oxygen in the presence of an alkali metal hydroxide (e.g. sodium hydroxide, potassium hydroxide) and elemental sulfur to l/ll. In a yet fur- ther alternative, 7 is reacted with a dialkyl ketone (e.g. acetone, diethylketone, methyl ethyl ketone) and a thiocyanate (e.g. sodium thiocyanate, potassium thiocyanate, ammonium thiocyanate) in a solvent to give the triazolidinthione 10. Suitable solvents are, for example, alcohols (e.g. methanol, ethanol, isopropanol, tert-butanol), N- methylpyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2- dimethoxyethane), acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, toluene or xylene. The triazolidinthione 10 is then converted into l/ll by reaction with formic acid in the presence of an acid (e.g. hydrochloric acid, hydrobromic acid, acetic acid, sulfuric acid, p-toluenesulfonic acid) or a metal oxide (e.g. amorphous Tiθ2).
Scheme 6
Figure imgf000208_0001
Figure imgf000208_0002
Oxidation
Figure imgf000208_0004
Figure imgf000208_0003
(R5/R 5a = H, m = O, R1 = group V,
Figure imgf000208_0005
wherein R4 = OH)
The halides 41 and 4", the aldehydes 51 and 5" and the compounds R2-H and R3-C(=O)-CI used in the above reactions are either commercially available or can be produced by standard methods known to the skilled person.
The triazole compound IV, wherein R1 is a group V wherein R4 is CN, can be prepared in analogy to known methods, such as described, for example, in EP-A-145294 or DE- A-3721786, as outlined in scheme 7. For instance, the bromide 11 and [1 ,2,4]-1 H- triazole can be reacted 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 reaction is suitably carried out in a solvent. Suitable solvents are, for example, toluene, the xylenes, dimethylsulfoxide, or N, N- dimethylformamide. The reaction temperature is not very critical and can range, for example, from 0 to 1500C and is preferably in the range from 25 to 1000C.
Scheme 7
Figure imgf000209_0001
(R4 = CN)
The bromide 11 can in turn be prepared by bromomethylation of 12 with methylene- bromide 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 alcoholate (e.g. sodium methoxide, potassium methoxide or potassium tert-butanolate), as outlined in scheme 8. The reaction temperature is not very critical and can range, for example, from 0 to 150°C and is preferably in the range from 25 to 1000C.
Scheme 8
Figure imgf000209_0002
base 12 11
Compounds 12, wherein R3 is an aliphatic or cycloaliphatic group, can be prepared by phase transfer alkylation of the benzylcyanide 13 with the compound 14, wherein X is a good leaving group, such as Cl, Br, I, tosylae or triflate, in the presence of a base, such as an alkali metal hydroxide (e.g. sodium hydroxide, potassium hydroxide), or an alkali metal alcoholate (e.g. sodium methoxide, potassium methoxide or potassium tert- butanolate), and a suitable phase transfer catalyst, such as tetrabutylammnium bromide, as outlined in scheme 9.
Scheme 9
Figure imgf000210_0001
14 13 12
Compounds 13 and 14 used in the above reactions are either commercially available or can be produced by standard methods known to the skilled person.
The triazole compound IV, wherein R1 is a group V wherein R4 is H, can be prepared in analogy to known methods, such as described, for example, in EP-A-145294 or DE-A- 2735827, as outlined in scheme 10. For instance, compound 15, wherein X is a good leaving group, such as Cl, Br, I, tosylate or triflate, and [1 ,2,4]-1 H-triazole can be re- acted 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 reaction is suitably carried out in a solvent. Suitable solvents are, for example, toluene, the xylenes, dimethylsulfoxide, or N,N-dimethylformamide. The reaction temperature is not very critical and can range, for example, from 0 to 1500C and is preferably in the range from 25 to 1000C.
Scheme 10
Figure imgf000210_0002
(R4 = H)
The triazole compound IV, wherein R1 is a group Vl, can be prepared in analogy to known methods, such as described, for example, in DE-A-255156 or EP-A-0065485, as outlined in scheme 1 1. For instance, the compound 16, wherein X 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 the [1 ,2,4]- 1 H-triazole compound 17, 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, potassium hy- droxide), an alkali metal carbonate (e.g. sodium carbonate, potassium carbonate, caesium carbonate) or a suitable amine (e.g. triethylamine, triethylenediamine, piperidine, pyridine, 4-dimethylaminopyτidine, 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 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 1 1
Figure imgf000211_0001
(R1 = a group Vl)
Compound 16 in turn can be prepared in analogy to known methods, such as described, for example, in DE-A-255156 or EP-A-0065485 or in Synthesis, 1974, I, 23, as outlined in scheme 12 below. For instance, the ketone 18 may be reacted with a diol HO-A-OH for several hours preferably in the presence of an azeotrope-forming com- pound, such as benzene, toluene, xylene, chloroform or tetrachloromethane, 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 re- flux. Subsequent halogenation of the resulting ketale 19 yields ketale 16, wherein X is a halogen atom, which, if desired, can be converted into a compound 16, wherein X is a leaving group X other than halogen.
Scheme 12
Figure imgf000212_0001
18 19 16
As an alternative to the process described in scheme 11 , compound IV can be prepared in analogy to the method described in EP-A-0065485 as outlined in scheme 13 below by a ketalization reaction of the ketone 20 with a diol HO-A-OH. The ketalization reaction can be carried out under reaction conditions described for scheme 12.
Scheme 13
Figure imgf000212_0002
(R1 = a group Vl)
The ketone 20 in turn can be prepared in analogy to the method described in EP-A- 0065485 as outlined in scheme 14 below by reacting the compound 21 , wherein X 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 triazole compound 17 under reaction conditions described for the reaction in scheme 1 1. Compound 21 , in turn, can be obtained from the halogenation of the ketone 18.
Scheme 14
Figure imgf000212_0003
Ketone 18 used in the above reactions is either commercially available or can be produced by standard methods known to the skilled person, for instance by a Friedel- Crafts acylation of R2-H with acetylchloride in the presence of a Lewis acid, such as AICb or FeCb, under reaction conditions customary for this reaction type. Compounds of formula I, wherein R5 is different from hydrogen and m is 0, can be prepared from compounds I (wherein R5 = H and m = 0).
Compounds of formula I, wherein m is 0 and R5 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 R5 is H, with a compound R5-LG, where R5 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, 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 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 R5 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 IV with a disulfide R5-S-S-R5 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 R5 is -C(=O)R13 or -C(=S)R13, may be prepared in analogy to the method described in DE-A-19617461 by reacting a compound I, wherein m is 0 and R5 is H, with a compound R13-C(=O)-W, R13-C(=S)-W, R13'- N=C=O or R13'-N=C=S, wherein R13 has one of the above meanings, R13' is C1-C10- 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 hydrox- ide), 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 exam- pie, 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 R5 is -SO2R13, may be prepared in analogy to the method described in DE-A-19620590 by reacting a compound I, wherein m is 0 and R5 is H, with a compound R13-Sθ2-W, wherein R13 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 car- bonates (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 R5 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 R5 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 R5 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 R5 is a group of formula III, may be pre- pared in analogy to the method described in WO 97/43269 by reacting a compound I, wherein m is O and R5 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, 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 R5 is -P(=Q)R14R15, may be prepared in analogy to the method described in WO 99/05149.
Compounds of formula II, wherein R5a is hydrogen (or compounds of formula I, wherein m is 0 and R5 is hydrogen), can be prepared in analogy to the method described in WO 99/18087 by reacting a triazolidinthione 9 with an oxidizing agent, optionally in the presence of a catalyst. Suitable oxidizing agents are, for example, oxygen, sulfur and potassium superoxide. Especially in case oxygen is used as oxidizing agent, it is ad- vantageous to carry out the oxidation reaction in the presence of a catalyst. A suitable catalyst is, for example, a mixture of powdery sulfur and KOH. The reaction is generally carried out in a suitable solvent. Suitable solvents are, for example, aliphatic hydrocarbons (e.g. pentane, hexane), cycloaliphatic hydrocarbons (e.g. cyclohexane), aromatic hydrocarbons (e.g. bemzene, toluene, the xylenes), ethers (e.g. diethylether, methyl- tert-butylether), and esters (e.g. ethylecetate, propylacetate, n-butylacetate).
The oxidation of the triazolidinthione 9 may also be carried out with ferric chloride (FeCb) in an acidic aqueous solution in analogy to the method described in WO 01/46158. The reaction is generally carried out in a suitable solvent. Suitable solvents are, for example, ethanol, ethylacetate and mixtures of ethanol with toluene.
The oxidation of the triazolidinthione 9 may also be carried out with formic acid, option- ally in the presence of a catalyst, in analogy to the method described in WO 99/18086 or WO 99/18088. Suitable catalysts are, for example, acids, like hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, and metal oxides, like amorphous titanium dioxide. The reaction is generally carried out in a suitable solvent. Suitable solvents are weakly polar solvents like, for example, alcohols such as propanol, butanol and pentanol, es- ters, like ethyl acetate, butyl acetate and isobutyl formate, ethers, like 1 ,2- dimethoxyethane, methyl-tert-butyl ether and methyl-tert-amylether, and formic acid used in excess.
Compounds of formula II, wherein R5a is different from hydrogen, can be prepared by reacting the NR5a group, wherein R5a is H, in analogy to the above-described conversion of compounds I, wherein R5 is H, into compounds, wherein R5 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 pre- pared from compounds IV by first deprotonating the triazolyl ring and then reacting with a sulfonyl chloride R5Sθ2CI. Compounds I, wherein m is 3, can be prepared from compounds IV by first deprotonating the triazolyl ring and then reacting with sulfuric acid chloride or a sulfuric ester chloride of formula R5OSθ2CI, wherein R5 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 IV
Λ— N
// W
N
> N
R' (IV)
wherein R1 has one of the general or, in particular, one of the preferred meanings given above for compounds I and II.
Compounds IV are on the one side valuable intermediates in the preparation of compounds 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 com- pound 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 compositions 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; insec- ticidal 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 pa- pain 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 recep- tors); 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 Cry1 Ab 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 Monsanto 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 Solanum 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 person 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. solani or A. alternata), tomatoes (e. g. A. solani or A. alternata) 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 cereals, 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 or- namentals; 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 liriodendrϊ. Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum (damping off) on soy- beans; 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. halstediiou 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 on hop; Pseudopezicula tracheiphila (red fire disease or , rotbrenner' , anamorph: Phialo- phora) 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 incamata (grey snow mold) on barley or wheat; Uro- cystis spp., e. g. U. occulta (stem smut) on rye; Uromyces 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., Ceratocysf/s 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 Mucorspp., 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 impro- ving 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 tol- erance 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, materials 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 damage 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, ketones 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 formal- dehyde, 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. Ex- amples 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 polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols and cellulose ethers (Tylose®, Shin-Etsu, Japan).
Powders, materials for spreading and dusts can be prepared by mixing or conco- mitantly 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 sub- stance 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 inven- tion 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 suspension 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 applied 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%, preferably 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 employed 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,
011 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 invention. 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 comprising 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-pyτidin-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-acety^-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-pyπmidin- 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 compound 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 embodi- ments, 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 obtained. 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 com- pounds 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) (compo- nent 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) (com- ponent 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 B-1 to B-346 of Table B.
A further embodiment relates to the compositions B-1 to B-346 listed in Table B, where a row of Table B 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 B: Composition comprising one indiviualized compound I or Il and one further active substance from groups A) to I)
Figure imgf000242_0001
Figure imgf000243_0001
Figure imgf000244_0001
Figure imgf000245_0001
Figure imgf000246_0001
Figure imgf000247_0001
Figure imgf000248_0001
Figure imgf000249_0001
Figure imgf000250_0001
Figure imgf000251_0001
Figure imgf000253_0001
Figure imgf000254_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 com- pounds I and/or Il respectively.
The compounds I, Il and IV and pharmaceutically acceptable salts thereof are also suitable for treating diseases in men and animals, especially as antimycotics, for treat- ing 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 IV 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 IV, 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 IV 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 IV or of pharmaceutically ac- ceptable 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 IV or of pharmaceutically acceptable salts thereof for preparing a medicament for the treatment or prophylaxis of virus infections.
The compounds of formulae I, Il and IV 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 1, 11 and IV 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, oesophagus, stomach, ovaries, pancreas, liver and brain or CNS.
The compounds of formulae 1, 11 and IV 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 compound 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, excipients, 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 intraperitoneal^. Solutions 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 microorganisms. 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
Proton and carbon NMR spectra were obtained on a Bruker AC 300 spectrometer at 300 MHz. Proton spectra were referenced to tetramethylsilane as an internal standard and the carbon spectra were referenced to CDCb (purchased from Aldrich or Cambridge Isotope Laboratories, unless otherwise specified). Melting points were obtained on a Mel-Temp Il apparatus and are uncorrected. ESI Mass spectra were obtained on a Shimadzu LCMS-2010 EV Mass Spectrometer. HPLC analyses were obtained using an Alltech Alltima C18 Rocket Column utilizing PDA detection at 254 nm (unless otherwise specified) on a Shimadzu Prominence HPLC system. The following time program was utilized (flow rate of 2.5 mL per minute):
Figure imgf000257_0001
Figure imgf000258_0001
1. Preparation of 1 -{[2-(2,4-Difluorophenyl)-4-propyl-1 ,3-dioxolan-2-yl]methyl}-1 H- 1 ,2,4-triazole-5(4/-/)-thione (compound E6)
1.1 2-Bromo-1-(2,4-difluorophenyl)ethanone
To a stirred solution of 1-(2,4-difluorophenyl)ethanone (7.1 g, 45.5 mmol) in MeOH (200 ml_), Br2 (7.3 g, 45.5 mmol) was added dropwise at 0 0C. The mixture was then stirred for 8 h at room temperature. The reaction mixture was diluted with EtOAc (1 L) and washed with brine (2x200 ml_). The organic layer was separated, dried with sodium sulfate, and concentrated in vacuum to afford crude 2-bromoehtanone 2 (1O g, 93%) as red oil.
1.2 2-(Bromomethyl)-2-(2,4-difluorophenyl)-4-propyl-1 ,3-dioxolane
To a solution of 2-bromo-1-(2,4-difluorophenyl)ethanone (3.8 g, 16.2 mmol) and pen- tane-1 ,2-diol (21.0 mmol) in toluene (50 ml_), was added PTSA (279 mg, 1.62 mmol). The solution was stirred and heated at reflux with a Dean-Stark trap for 5 h, collecting water to facilitate the ketal formation. The reaction mixture was diluted with EtOAc (ethylacetate; 100 ml.) and washed with brine (2x50 ml_). The organic layer was separated, dried with sodium sulfate, and concentrated in vacuum. The residue was purified by column chromatography (silica gel, eluents: hexanes/EtOAc 4:1 ) to afford the title ketal compound (2.3 g, 44%) as clear oil.
1.3 1 -{[2-(2,4-Difluorophenyl)-4-propyl-1 ,3-dioxolan-2-yl]methyl}- 7H-1 ,2,4-triazole
To a stirred mixture of 1 ,2,4-triazole (193 mg, 2.8 mmol) and CS2CO3 (1.43 g, 4.4 mmol) in DMF (20 ml_), a solution of the ketal obtained in step 1.2 (1.3 g, 4.0 mmol) in DMF (10 ml.) was added dropwise at 0 0C. The reaction mixture was heated at 100 0C and stirred for 24 h. Ice-water (200 ml.) was added, and the product was extracted with EtOAc (2x50 ml_). The combined organic layers were dried with sodium sulfate and concentrated in vacuum. The residue was purified by column chromatography (silica gel, eluents: hexanes/EtOAc 3:2) to afford the title compound (150 mg, 17%) as clear oil.
1.4 1 -{[2-(2,4-Difluorophenyl)-4-propyl-1 ,3-dioxolan-2-yl]methyl}-1 H- 1 ,2,4-triazole- 5(4H)-thione To a stirred solution of triazole ketal obtained in step 1.3 (170 mg, 0.55 mmol) in DMF (10 ml), Ss (176 mg, 5.5 mmol) was added. The mixture was heated at reflux and stirring for 3 days. The reaction mixture was quenched with brine (50 ml.) and extracted with EtOAc (50 ml_). The organic layer was additionally washed with brine (50 ml_), separated, dried with sodium sulfate and concentrated in vacuum. The residue was then purified by column chromatography (silica gel, eluents: EtOAc/hexanes 1 :9 to 2:3) to afford the titled triazole thione as white solid (70 mg, 38%).
m.p. = 135-136 0C.
The following compounds were prepared in an analogous manner.
2. Preparation of 1 -{[2-(4-chlorophenyl)-4-propyl-1 ,3-dioxolan-2-yl]methyl}- 7H-1 ,2,4- triazole-5(4H)-thione (compound E5)
In this case, the ethanone (2-bromo-1-(4-chlorophenyl)ethanone) was commercially available.
m.p. = 133-134 0C
3. Preparation of 1 -{[2-(4-chloro-2-fluorophenyl)-4-propyl-1 ,3-dioxolan-2-yl)methyl)- 7H-1 ,2,4-triazole-5(4H)-thione (compound E2)
m.p. = 115-116 0C
4. Preparation of 1-{[2-(2-chloro-4-fluorophenyl)-4-propyl-1 ,3-dioxolan-2-yl]methyl}- 7H-1 ,2,4-triazole-5(4H)-thione (compound E3)
m.p. = 107-108 0C
5. Preparation of 1 -{[2-(3,4-difluorophenyl)-4-propyl-1 ,3-dioxolan-2-yl]methyl}- 7H- 1 ,2,4-triazole-5(4H)-thione (compound E4)
m.p. = 145-146 0C
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 absorption photometer, the microtiter plates were measured at 405 nm on day 7 after the in- oculation. 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 vol- ume 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 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 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 culti- vated 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 be- low. 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 triticiou 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 mildew of wheat (Blumeria graminis tritici). The plants were then returned into the green- house 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. Triazole compounds of the formulae I and Il
Figure imgf000263_0001
(I) (H)
wherein
R1 is group of formula V or a group of formula Vl
Figure imgf000263_0002
(V) (Vl) wherein
# is the attachment point to the remainder of the molecule;
A is a linear d-Cs-alkylene bridge which may be substituted by 1 , 2, 3 or 4 substituents R6;
R2 is aryl which may carry 1 , 2, 3, 4 or 5 substituents R7, or is a 5- or 6- membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heteroaromatic ring may carry 1 , 2, 3 or 4 substituents R8;
R3 is selected from Ci-Cio-alkyl which may carry 1 or 2 substituents R9, C1-C10- haloalkyl which may carry 1 or 2 substituents R9, Cs-Cs-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 R10, 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 R11;
R4 is hydrogen, OH or CN; R5 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, Cs-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 R12, 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 R12; or, in case m is 0, may also be selected from -C(=O)R13, -C(=S)R13, -S(O)2R13, -CN, -P(=Q)R14R15, M and a group of the formula III
Figure imgf000264_0001
wherein
R1 is as defined for formulae I and II; and
# is the attachment point to the remainder of the molecule;
R5a 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 R12, 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 R12, -C(=O)R13, -C(=S)R13, -S(O)2R13, -CN, -P(=Q)R14R15 and M;
each R6 is independently selected from halogen, OH, SH, NR16R17, 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 R18; or
two radicals R6 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 un- saturated 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 R12;
each R7 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, CrC4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR16R17;
each R8 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, CrC4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR16R17;
each R9 is independently selected from nitro, CN, OH, SH, Si(R20)3, NR16R17, Cr
C4-alkoxy, Ci-C4-haloalkoxy, Cs-Cβ-cycloalkyl, Cs-Cβ-halocycloalkyl and C3- Cβ-cycloaloxy;
each R10 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, CrC4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR16R17;
each R11 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, CrC4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR16R17;
each R12 is independently selected from halogen, nitro, CN, Ci-C4-alkyl, CrC4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR16R17;
R13 is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, Ci-Cio-alkoxy, Cr Cio-haloalkoxy, Ci-Cio-aminoalkyl, 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 R12, 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 R12, and NR16R17;
R14 and R15, 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 NR16R17;
each R16 is independently selected from hydrogen and d-Cβ-alkyl; each R17 is independently selected from hydrogen, C-i-Cs-alkyl, phenyl, and phenyl-Ci-C4-alkyl;
or R16 and R17 together form a linear C4- or Cs-alkylene bridge or a group
-CH2CH2OCH2CH2- or -CH2CH2NR19CH2CH2-;
each R18 is independently selected from nitro, CN, OH, SH, COR13, NR16R17, C3- Cβ-cycloalkyl, Cs-Cβ-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6- cycloaloxy, phenyl and phenoxy;
each R19 is independently selected from hydrogen and Ci-C4-alkyl;
each R20 is independently selected from Ci-Cβ-alkyl, C-i-Cβ-haloalkyl, phenyl, phenyl-Ci-C4-alkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
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 NR16R17;
m is 0, 1 , 2 or 3; and
and the agriculturally acceptable salts thereof.
2. The compounds of formulae I and Il as claimed in claim 1 , where R1 is a group of formula V, where
R2 is phenyl which may carry 1 , 2, 3, 4 or 5 substituents R7;
R3 is phenyl which may carry 1 , 2, 3, 4 or 5 substituents R11; and
R4 is OH.
3. The compounds of formulae I and Il as claimed in claim 2, where R1 is a group of formula V, where
R2 is phenyl which may carry 1 , 2 or 3 substituents R7;
R3 is phenyl which may carry 1 , 2 or 3 substituents R11; R4 is OH; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3; and each R11 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
Ci-C4-alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3.
4. The compounds of formulae I and Il as claimed in claim 1 , where R1 is a group of formula V, where
R2 is aryl which may carry 1 , 2, 3, 4 or 5 substituents R7, or is a 5- or 6- membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heteroaromatic ring may carry 1 , 2, 3 or 4 substituents R8; R3 is selected from Ci-Cio-alkyl, Ci-Cio-haloalkyl, 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 R11; and R4 is CN.
5. The compounds of formulae I and Il as claimed in claim 4, where R1 is a group of formula V, where
R2 is aryl, preferably phenyl, which may carry 1 , 2 or 3 substituents R7; R3 is selected from Ci-Cβ-alkyl, Ci-C4-haloalkyl, phenyl and phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2 or 3 substituents R11, and is preferably Ci-Cβ-alkyl or phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2 or 3 substituents R11; R4 is CN; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2,
CF3, OCH3, OCHF2 and OCF3; and each R11 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3.
6. The compounds of formulae I and Il as claimed in claim 1 , where R1 is a group of formula V, where R2 is aryl which may carry 1 , 2, 3, 4 or 5 substituents R7, or is a 5- or 6- membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heteroaromatic ring may carry 1 , 2, 3 or 4 substituents R8; R3 is selected from Ci-Cio-alkyl which may carry 1 or 2 substituents R9, C1-C10- haloalkyl which may carry 1 or 2 substituents R9, C3-C8-cycloalkyl, C3-Cs- cycloalkyl-d^-alkyl, where the cycloalkyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3 or 4 substituents R10, 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 R11; and R4 is hydrogen.
7. The compounds of formulae I and Il as claimed in claim 6, where R1 is a group of formula V, where
R2 is phenyl which may carry 1 , 2 or 3 substituents R7;
R3 is selected from Ci-Cio-alkyl which may carry 1 or 2 substituents R9, C1-C4- haloalkyl, Cs-Cs-cycloalkyl and C3-Cs-cycloalkyl-Ci-C4-alkyl, where the cycloalkyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3 or 4 substituents R10; R4 is hydrogen; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2,
CF3, OCH3, OCHF2 and OCF3; each R9 is independently selected from Ci-C4-alkoxy and Ci-C4-fluoroalkoxy; and each R10 is independently selected from halogen, Ci-C4-alkyl and C1-C4- haloalkyl.
8. The compounds of formulae I and Il as claimed in claim 7, where R1 is a group of formula V, where
R2 is phenyl which may carry 1 , 2 or 3 substituents R7;
R3 is selected from Ci-Cβ-alkyl, Ci-Cβ-alkyl which carries 1 substituent R9, cyclopropyl and cyclopropyl-Ci-C2-alkyl, where the cyclopropyl moiety in the 2 last-mentioned radicals may carry 1 or 2 substituents R10;
R4 is hydrogen; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3;
R9 is Ci-C4-fluoroalkoxy; and each R10 is independently selected from halogen and Ci-C4-alkyl.
9. The compounds of formulae I and Il as claimed in claim 1 , where R1 is a group of formula V, where
R2 is phenyl which may carry 1 , 2, 3, 4 or 5 substituents R7; R3 is selected from Ci-Cio-alkyl which may carry 1 substituent R9; R4 is OH; and
R9 is Si(R20)3.
10. The compounds of formulae I and Il as claimed in claim 9, where R1 is a group of formula V, where R2 is phenyl which may carry 1 , 2 or 3 substituents R7;
R3 is selected from Ci-C6-alkyl and CH2-Si(R20)3;
R4 is OH; each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3; and
R20 is Ci-C4-alkyl.
1 1. The compounds of formulae I and Il as claimed in claim 1 , where R1 is a group of formula Vl.
12. The compounds of formulae I and Il as claimed in claim 11 , where A is selected from -(CH2J2-, -CH2-CH(CH3)-, -CH2-CH(C2H5)-,
-CH2-CH(CH2CH2CH3)-, -CH2-CH(CH2CH2CH2CH3)-, -CH2-CHF-, -CH(CHs)-CH(CH3)-, -(CHz)3-, -CH2-CH2-CH(CH3)-, -CH2-CH(CHs)-CH2- and -CH2-C(CHs)2-CH2-, and is preferably -CH2-CH(CH2CH2CHs)-; and
R2 is phenyl which may carry 1 , 2, 4 or 5 substituents R7;
except for compounds wherein R2 is phenyl, 4-fluorophenyl, 2,4-difluorophenyl, 4- chlorophenyl, 2,4-dichlorophenyl, 2,4,6-trichlorophenyl, 4-trifluoromethylphenyl, 2-difluoromethoxyphenyl or 4-trifluoromethoxyphenyl.
13. The compounds of formulae I and Il as claimed in claim 12, where A is -CH2-CH(CH2CH2CH3)- ;
R2 is phenyl which may carry 1 , 2 or 3 substituents R7; and each R7 is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-
C4-alkoxy and Ci-C4-haloalkoxy, and preferably from F, Cl, Br, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3; except for compounds wherein R2 is phenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,4-dichlorophenyl, 2,4,6-trichlorophenyl, 4-trifluoromethylphenyl, 2- difluoromethoxyphenyl or 4-trifluoromethoxyphenyl.
14. The compounds of formulae I and Il as claimed in any of the preceding claims, where R13 is selected from Ci-C4-alkyl, Ci-C2-haloalkyl, Ci-C4-alkoxy, C1-C2- haloalkoxy, phenyl, phenoxy and NR16R17, where R16 is hydrogen and R17 is selected from hydrogen, Ci-C4-alkyl and phenyl or the two of R16 and R17 are C1-C4- alkyl.
15. The compounds of formulae I and Il as claimed in any of the preceding claims, where R5 is selected from hydrogen, Ci-C4-alkyl, -C(=O)R13, -S(O)2R13, -CN, M and a group of the formula III and preferably from hydrogen, CN, -C(=O)CH3, -C(=O)OCH3 and methyl.
16. The compounds of formulae I and Il as claimed in any of the preceding claims, where R5a is selected from hydrogen, Ci-C4-alkyl and -C(=O)R13.
17. The compounds of formulae I and Il as claimed in any of the preceding claims, where m is 0.
18. Compounds of formula IV
Figure imgf000270_0001
where R1 is as defined in any of claims 1 to 13.
19. An agricultural composition comprising at least one compound of formula I, Il and/or IV as defined in any of claims 1 to 18 or an agriculturally acceptable salt thereof and a liquid or solid carrier.
20. The use of a compound of formula I, Il and/or IV as defined in any of claims 1 to 16 for controlling harmful fungi.
21. A method for controlling harmful fungi, wherein the fungi, their habitat or the ma- terials 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 IV, where compounds 1, 11 and IV are as defined in any of claims 1 to 18.
22. Seed, comprising at least compound of formula I, Il and/or IV, where compounds I, Il and IV are as defined in any of claims 1 to 18, in an amount of from 0.1 g to 10 kg per 100 kg of seeds.
23. A pharmaceutical composition comprising at least one compound of formula I, Il and/or IV as defined in any of claims 1 to 18 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable carrier.
24. The use of a compound of formula I, Il or IV as defined in any of claims 1 to 18 or a pharmaceutically acceptable salt thereof for preparing a medicament for the treatment of cancer or virus infections or for preparing an antimycotic medicament.
25. 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 1 , 11 and/or IV as defined in any of claims 1 to 18, with at least one pharmaceutically acceptable salt thereof or with a phar- maceutical composition as defined in claim 23.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013047308A1 (en) * 2011-09-27 2013-04-04 株式会社クレハ Azole derivative, agricultural/horticultural chemical, industrial material protecting agent, method for controlling plant disease, and seed
EP2746255A1 (en) * 2012-12-19 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds

Citations (113)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3060084A (en) 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
US3299566A (en) 1964-06-01 1967-01-24 Olin Mathieson Water soluble film containing agricultural chemicals
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
US3920442A (en) 1972-09-18 1975-11-18 Du Pont Water-dispersible pesticide aggregates
DE2551560A1 (en) 1974-11-18 1976-05-20 Janssen Pharmaceutica Nv 1- (BETA-ARYL) -AETHYL-1H-1,2,4-TRIAZOLKETALS AND THEIR SALES, METHOD FOR THEIR PRODUCTION AND FUNGICIDALS AND PLANT REGULATORY AGENTS
DE2735827A1 (en) 1977-08-09 1979-02-22 Wolff Hans Dietrich Nut-cracker with double spring action - has aluminium wedge ring and holding surface remaining in touch with holder lever when not in use
US4144050A (en) 1969-02-05 1979-03-13 Hoechst Aktiengesellschaft Micro granules for pesticides and process for their manufacture
US4172714A (en) 1976-12-20 1979-10-30 E. I. Du Pont De Nemours And Company Dry compactible, swellable herbicidal compositions and pellets produced therefrom
IL50898A (en) * 1972-11-20 1980-05-30 Ciba Geigy Ag Thiophosphoric and phosphoric acid 3-(1-(2-methoxy-1-methyl)--5-(lower alkylthio)-h-1,2,4-triazol-3-yl)ester,their manufacture and their use as pesticides
EP0015756A1 (en) 1979-03-07 1980-09-17 Imperial Chemical Industries Plc Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them
DE3042302A1 (en) 1979-11-13 1981-08-27 Sandoz-Patent-GmbH, 7850 Lörrach ORGANIC COMPOUNDS, THEIR PRODUCTION AND USE
EP0036153A1 (en) * 1980-03-15 1981-09-23 BASF Aktiengesellschaft 1,1-Diphenyl-2-(1,2,4-triazol-1-yl)-ethan-1-oles as antimycotic agents
GB2095558A (en) 1981-03-30 1982-10-06 Avon Packers Ltd Formulation of agricultural chemicals
EP0065485A2 (en) 1981-05-12 1982-11-24 Ciba-Geigy Ag Arylphenyl ether derivatives as microbicides, process for their preparation and their application
EP0141317A2 (en) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines and fungicides containing them
EP0145294A2 (en) 1983-11-10 1985-06-19 Rohm And Haas Company Substituted triazoles, processes for making them, their use as fungicides and fungicidal compositions containing them
EP0152031A2 (en) 1984-02-03 1985-08-21 Shionogi & Co., Ltd. Azolyl cycloalkanol derivatives and agricultural fungicides
EP0196039A2 (en) * 1985-03-29 1986-10-01 BASF Aktiengesellschaft Use of 1-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-ethan-1-ol for the preparation of medicaments for viral diseases.
EP0226917A1 (en) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Acrylic acid esters and fungicides containing these compounds
EP0242246A1 (en) 1986-03-11 1987-10-21 Plant Genetic Systems N.V. Plant cells resistant to glutamine synthetase inhibitors, made by genetic engineering
EP0243970A1 (en) 1986-05-02 1987-11-04 Stauffer Chemical Company Fungicidal pyridyl imidates
DE3721786A1 (en) 1986-07-02 1988-01-07 Rohm & Haas FUNGICIDAL COMPOUND, METHOD FOR THEIR PRODUCTION AND MEANS CONTAINING THEM
EP0256503A2 (en) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Pyridinecarboxamide derivatives and their use as fungicide
EP0267778A2 (en) 1986-11-10 1988-05-18 Kureha Kagaku Kogyo Kabushiki Kaisha Azole derivatives useful in controlling plant diseases and regulating plant growth
EP0374753A2 (en) 1988-12-19 1990-06-27 American Cyanamid Company Insecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines
EP0392225A2 (en) 1989-03-24 1990-10-17 Ciba-Geigy Ag Disease-resistant transgenic plants
EP0427529A1 (en) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Larvicidal lectins and plant insect resistance based thereon
EP0428941A1 (en) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Hexahydrotriazine compounds and insecticides
WO1991013546A1 (en) 1990-03-12 1991-09-19 E.I. Du Pont De Nemours And Company Water-dispersible or water-soluble pesticide granules from heat-activated binders
EP0451878A1 (en) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modifying plants by genetic engineering to combat or control insects
WO1992000377A1 (en) 1990-06-25 1992-01-09 Monsanto Company Glyphosate tolerant plants
US5180587A (en) 1988-06-28 1993-01-19 E. I. Du Pont De Nemours And Company Tablet formulations of pesticides
EP0532022A1 (en) 1991-09-13 1993-03-17 Ube Industries, Ltd. Acrylate compound, preparation process thereof and fungicide using the same
WO1993007278A1 (en) 1991-10-04 1993-04-15 Ciba-Geigy Ag Synthetic dna sequence having enhanced insecticidal activity in maize
EP0537957A1 (en) 1991-10-09 1993-04-21 Sankyo Company Limited Fungicidal silicon-containing compounds, their preparation and their agrochemical and medicinal uses
US5208030A (en) 1989-08-30 1993-05-04 Imperial Chemical Industries Plc Active ingredient dosage device
US5232701A (en) 1990-10-11 1993-08-03 Sumitomo Chemical Company, Limited Boron carbonate and solid acid pesticidal composition
EP0655443A2 (en) 1993-11-11 1995-05-31 Kureha Chemical Industry Co., Ltd. Process for the preparation of azolylmethylcycloalkanol derivatives
WO1995034656A1 (en) 1994-06-10 1995-12-21 Ciba-Geigy Ag Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests
EP0707445A1 (en) 1993-07-03 1996-04-24 Basf Ag Stable, ready-to-use, multi-phase aqueous pesticide formulations and methods of preparing them
DE19528046A1 (en) 1994-11-21 1996-05-23 Bayer Ag New sulphur substd tri:azole derivs
US5559024A (en) 1988-03-23 1996-09-24 Rhone-Poulenc Agrochimie Chimeric nitrilase-encoding gene for herbicidal resistance
DE19520098A1 (en) 1995-06-01 1996-12-05 Bayer Ag Triazolylmethyl-cyclopentanols
WO1996041804A1 (en) * 1995-06-13 1996-12-27 Bayer Aktiengesellschaft Microbicidal (mercapto-triazolyl methyl)-dioxacycloalkanes
DE19528300A1 (en) 1995-08-02 1997-02-06 Bayer Ag 2-phenylethyl-mercapto-triazole
DE19529089A1 (en) 1995-08-08 1997-02-13 Bayer Ag Mercapto-triazolyl nitriles
WO1997041107A1 (en) * 1996-04-30 1997-11-06 Bayer Aktiengesellschaft Triazolyl mercaptides and their use as microbicides
DE19617461A1 (en) 1996-05-02 1997-11-06 Bayer Ag Acylmercapto triazolyl derivatives
WO1997041218A1 (en) 1996-04-29 1997-11-06 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Herbicide resistant rice
WO1997043269A1 (en) 1996-05-15 1997-11-20 Bayer Aktiengesellschaft Triazolyl disulphides
DE19620407A1 (en) 1996-05-21 1997-11-27 Bayer Ag Thiocyano-triazolyl derivatives
WO1997044332A1 (en) * 1996-05-22 1997-11-27 Bayer Aktiengesellschaft Sulphonyl-mercapto-triazolyl derivatives and their use as microbicides
WO1998002526A1 (en) 1996-07-17 1998-01-22 Michigan State University Imidazolinone herbicide resistant sugar beet plants
WO1998002527A1 (en) 1996-07-17 1998-01-22 Michigan State University Imidazolinone herbicide resistant sugar beet plants
DE19650197A1 (en) 1996-12-04 1998-06-10 Bayer Ag 3-thiocarbamoylpyrazole derivatives
WO1998046608A1 (en) 1997-04-14 1998-10-22 American Cyanamid Company Fungicidal trifluoromethylalkylamino-triazolopyrimidines
WO1999005149A1 (en) 1997-07-25 1999-02-04 Bayer Aktiengesellschaft Triazoline-thion-phosphoric acid derivatives
WO1999014187A1 (en) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Benzamidoxim derivatives, intermediate products and methods for preparing and using them as fungicides
WO1999018086A1 (en) 1997-10-08 1999-04-15 Bayer Aktiengesellschaft Method for producing triazolinethione derivatives
WO1999018088A1 (en) 1997-10-08 1999-04-15 Bayer Aktiengesellschaft Method for producing triazolinthion derivatives
WO1999018087A1 (en) 1997-10-08 1999-04-15 Bayer Aktiengesellschaft Method for producing triazolinthion derivatives
WO1999024413A2 (en) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Isothiazole carboxylic acid amides and the application thereof in order to protect plants
WO1999027783A1 (en) 1997-12-04 1999-06-10 Dow Agrosciences Llc Fungicidal compositions and methods, and compounds and methods for the preparation thereof
WO2000026390A2 (en) 1998-10-29 2000-05-11 American Cyanamid Company Genes and vectors for conferring herbicide resistance in plants
WO2000029404A1 (en) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives and agricultura/horticultural bactericides
WO2000046148A1 (en) 1999-02-02 2000-08-10 Sintokogio, Ltd. Silica gel carrying titanium oxide photocatalyst in high concentration and method for preparation thereof
EP1028125A1 (en) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptide compounds having fungicidal activity and their agronomic use
EP1035122A1 (en) 1999-03-11 2000-09-13 Rohm And Haas Company Heterocyclic subsituted isoxazolidines and their use as fungicides
WO2000065913A1 (en) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Sulfonamide derivatives
US6222100B1 (en) 1984-03-06 2001-04-24 Mgi Pharma, Inc. Herbicide resistance in plants
DE10021412A1 (en) 1999-12-13 2001-06-21 Bayer Ag Fungicidal active ingredient combinations
WO2001046158A1 (en) 1999-12-21 2001-06-28 Bayer Aktiengesellschaft Method for production of a triazolinethione derivative
WO2001054501A2 (en) 2000-01-25 2001-08-02 Syngenta Participations Ag Herbicidal composition
EP1122244A1 (en) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Uracil compounds and their use
WO2001056358A2 (en) 2000-01-28 2001-08-09 Rohm And Haas Company Enhanced propertied pesticides
WO2001082685A1 (en) 2000-04-28 2001-11-08 Basf Aktiengesellschaft Use of the maize x112 mutant ahas 2 gene and imidazolinone herbicides for selection of transgenic monocots, maize, rice and wheat plants resistant to the imidazolinone herbicides
WO2002015701A2 (en) 2000-08-25 2002-02-28 Syngenta Participations Ag Bacillus thuringiensis crystal protein hybrids
WO2002022583A2 (en) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl amides and imides for use as fungicides
EP1201648A1 (en) 1999-08-05 2002-05-02 Kumiai Chemical Industry Co., Ltd. Carbamate derivatives and agricultural/horticultural bactericides
WO2002040431A2 (en) 2000-11-17 2002-05-23 Dow Agrosciences Llc Compounds having fungicidal activity and processes to make and use same
JP2002316902A (en) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd Plant blight-preventing agent composition
WO2003010149A1 (en) 2001-07-25 2003-02-06 Bayer Cropscience Ag Pyrazolylcarboxanilides as fungicides
WO2003011853A1 (en) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates and their use as herbicides
WO2003014103A1 (en) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Iodobenzopyran-4-one derivatives having fungicidal activity
WO2003014356A1 (en) 2001-08-09 2003-02-20 University Of Saskatchewan Wheat plants having increased resistance to imidazolinone herbicides
WO2003013225A2 (en) 2001-08-09 2003-02-20 Northwest Plant Breeding Company Wheat plants having increased resistance to imidazolinone herbicides
WO2003014357A1 (en) 2001-08-09 2003-02-20 University Of Saskatchewan Wheat plants having increased resistance to imidazolinone herbicides
WO2003016286A1 (en) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited 3-phenoxy-4-pyridazinol derivative and herbicide composition containing the same
WO2003018810A2 (en) 2001-08-31 2003-03-06 Syngenta Participations Ag Modified cry3a toxins and nucleic acid sequences coding therefor
WO2003052073A2 (en) 2001-12-17 2003-06-26 Syngenta Participations Ag Novel corn event
WO2003053145A1 (en) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Bactericidal composition
WO2003061388A1 (en) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Fused heterocyclic sulfonylurea compound, herbicide containing the same, and method of controlling weed with the same
WO2003066609A1 (en) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Disubstituted thiazolyl carboxanilides and their use as microbicides
WO2003074491A1 (en) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyl-carboxanilides and their use as fungicides
WO2004016073A2 (en) 2002-07-10 2004-02-26 The Department Of Agriculture, Western Australia Wheat plants having increased resistance to imidazolinone herbicides
WO2004049804A2 (en) 2002-11-29 2004-06-17 Syngenta Participations Ag Fungicidal combinations for crop potection
WO2004083193A1 (en) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Amide compound and bactericide composition containing the same
WO2004106529A2 (en) 2003-05-28 2004-12-09 Basf Aktiengesellschaft Wheat plants having increased tolerance to imidazolinone herbicides
WO2005020673A1 (en) 2003-08-29 2005-03-10 Instituto Nacional De Technologia Agropecuaria Rice plants having increased tolerance to imidazolinone herbicides
WO2005063721A1 (en) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Herbicidal pyrimidines
WO2005087773A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005087772A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005120234A2 (en) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Fungicidal mixtures of amidinylphenyl compounds
WO2005123690A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-difluoromethyl-pyrazol-4-carbonic acid-(ortho-phenyl)-anilides, and use thereof as a fungicide
WO2005123689A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl)-anilides and to use thereof as fungicide
WO2006015866A1 (en) 2004-08-12 2006-02-16 Syngenta Participations Ag Method for protecting useful plants or plant propagation material
WO2006087325A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said substances
WO2006087343A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi
DE102005009458A1 (en) 2005-03-02 2006-09-07 Bayer Cropscience Ag pyrazolylcarboxanilides
WO2007082098A2 (en) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides
WO2007090624A2 (en) 2006-02-09 2007-08-16 Syngenta Participations Ag A method of protecting a plant propagation material, a plant, and/or plant organs
WO2008151437A1 (en) * 2007-06-14 2008-12-18 Osta Biotechnologies Heme-oxygenase inhibitors and use of the same in the treatment of cancer and diseases of the central nervous system

Patent Citations (121)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3060084A (en) 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
US3299566A (en) 1964-06-01 1967-01-24 Olin Mathieson Water soluble film containing agricultural chemicals
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
US4144050A (en) 1969-02-05 1979-03-13 Hoechst Aktiengesellschaft Micro granules for pesticides and process for their manufacture
US3920442A (en) 1972-09-18 1975-11-18 Du Pont Water-dispersible pesticide aggregates
IL50898A (en) * 1972-11-20 1980-05-30 Ciba Geigy Ag Thiophosphoric and phosphoric acid 3-(1-(2-methoxy-1-methyl)--5-(lower alkylthio)-h-1,2,4-triazol-3-yl)ester,their manufacture and their use as pesticides
DE2551560A1 (en) 1974-11-18 1976-05-20 Janssen Pharmaceutica Nv 1- (BETA-ARYL) -AETHYL-1H-1,2,4-TRIAZOLKETALS AND THEIR SALES, METHOD FOR THEIR PRODUCTION AND FUNGICIDALS AND PLANT REGULATORY AGENTS
US4172714A (en) 1976-12-20 1979-10-30 E. I. Du Pont De Nemours And Company Dry compactible, swellable herbicidal compositions and pellets produced therefrom
DE2735827A1 (en) 1977-08-09 1979-02-22 Wolff Hans Dietrich Nut-cracker with double spring action - has aluminium wedge ring and holding surface remaining in touch with holder lever when not in use
EP0015756A1 (en) 1979-03-07 1980-09-17 Imperial Chemical Industries Plc Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them
DE3042302A1 (en) 1979-11-13 1981-08-27 Sandoz-Patent-GmbH, 7850 Lörrach ORGANIC COMPOUNDS, THEIR PRODUCTION AND USE
EP0036153A1 (en) * 1980-03-15 1981-09-23 BASF Aktiengesellschaft 1,1-Diphenyl-2-(1,2,4-triazol-1-yl)-ethan-1-oles as antimycotic agents
GB2095558A (en) 1981-03-30 1982-10-06 Avon Packers Ltd Formulation of agricultural chemicals
EP0065485A2 (en) 1981-05-12 1982-11-24 Ciba-Geigy Ag Arylphenyl ether derivatives as microbicides, process for their preparation and their application
EP0141317A2 (en) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines and fungicides containing them
EP0145294A2 (en) 1983-11-10 1985-06-19 Rohm And Haas Company Substituted triazoles, processes for making them, their use as fungicides and fungicidal compositions containing them
EP0152031A2 (en) 1984-02-03 1985-08-21 Shionogi & Co., Ltd. Azolyl cycloalkanol derivatives and agricultural fungicides
US6222100B1 (en) 1984-03-06 2001-04-24 Mgi Pharma, Inc. Herbicide resistance in plants
EP0451878A1 (en) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modifying plants by genetic engineering to combat or control insects
EP0196039A2 (en) * 1985-03-29 1986-10-01 BASF Aktiengesellschaft Use of 1-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-ethan-1-ol for the preparation of medicaments for viral diseases.
EP0226917A1 (en) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Acrylic acid esters and fungicides containing these compounds
EP0242246A1 (en) 1986-03-11 1987-10-21 Plant Genetic Systems N.V. Plant cells resistant to glutamine synthetase inhibitors, made by genetic engineering
EP0242236A1 (en) 1986-03-11 1987-10-21 Plant Genetic Systems N.V. Plant cells resistant to glutamine synthetase inhibitors, made by genetic engineering
EP0243970A1 (en) 1986-05-02 1987-11-04 Stauffer Chemical Company Fungicidal pyridyl imidates
DE3721786A1 (en) 1986-07-02 1988-01-07 Rohm & Haas FUNGICIDAL COMPOUND, METHOD FOR THEIR PRODUCTION AND MEANS CONTAINING THEM
EP0256503A2 (en) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Pyridinecarboxamide derivatives and their use as fungicide
EP0267778A2 (en) 1986-11-10 1988-05-18 Kureha Kagaku Kogyo Kabushiki Kaisha Azole derivatives useful in controlling plant diseases and regulating plant growth
US5559024A (en) 1988-03-23 1996-09-24 Rhone-Poulenc Agrochimie Chimeric nitrilase-encoding gene for herbicidal resistance
US5180587A (en) 1988-06-28 1993-01-19 E. I. Du Pont De Nemours And Company Tablet formulations of pesticides
EP0374753A2 (en) 1988-12-19 1990-06-27 American Cyanamid Company Insecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines
EP0392225A2 (en) 1989-03-24 1990-10-17 Ciba-Geigy Ag Disease-resistant transgenic plants
US5208030A (en) 1989-08-30 1993-05-04 Imperial Chemical Industries Plc Active ingredient dosage device
EP0427529A1 (en) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Larvicidal lectins and plant insect resistance based thereon
EP0428941A1 (en) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Hexahydrotriazine compounds and insecticides
WO1991013546A1 (en) 1990-03-12 1991-09-19 E.I. Du Pont De Nemours And Company Water-dispersible or water-soluble pesticide granules from heat-activated binders
WO1992000377A1 (en) 1990-06-25 1992-01-09 Monsanto Company Glyphosate tolerant plants
US5232701A (en) 1990-10-11 1993-08-03 Sumitomo Chemical Company, Limited Boron carbonate and solid acid pesticidal composition
EP0532022A1 (en) 1991-09-13 1993-03-17 Ube Industries, Ltd. Acrylate compound, preparation process thereof and fungicide using the same
WO1993007278A1 (en) 1991-10-04 1993-04-15 Ciba-Geigy Ag Synthetic dna sequence having enhanced insecticidal activity in maize
EP0537957A1 (en) 1991-10-09 1993-04-21 Sankyo Company Limited Fungicidal silicon-containing compounds, their preparation and their agrochemical and medicinal uses
EP0707445A1 (en) 1993-07-03 1996-04-24 Basf Ag Stable, ready-to-use, multi-phase aqueous pesticide formulations and methods of preparing them
EP0655443A2 (en) 1993-11-11 1995-05-31 Kureha Chemical Industry Co., Ltd. Process for the preparation of azolylmethylcycloalkanol derivatives
WO1995034656A1 (en) 1994-06-10 1995-12-21 Ciba-Geigy Ag Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests
DE19528046A1 (en) 1994-11-21 1996-05-23 Bayer Ag New sulphur substd tri:azole derivs
WO1996016048A1 (en) 1994-11-21 1996-05-30 Bayer Aktiengesellschaft Microbicidal triazolyl derivatives
DE19520098A1 (en) 1995-06-01 1996-12-05 Bayer Ag Triazolylmethyl-cyclopentanols
WO1996041804A1 (en) * 1995-06-13 1996-12-27 Bayer Aktiengesellschaft Microbicidal (mercapto-triazolyl methyl)-dioxacycloalkanes
DE19528300A1 (en) 1995-08-02 1997-02-06 Bayer Ag 2-phenylethyl-mercapto-triazole
WO1997005119A1 (en) * 1995-08-02 1997-02-13 Bayer Aktiengesellschaft Microbicidal 2-phenylethyl-mercapto-triazoles
WO1997006152A1 (en) 1995-08-08 1997-02-20 Bayer Aktiengesellschaft Microbicidal mercapto-triazolyl-nitriles
DE19529089A1 (en) 1995-08-08 1997-02-13 Bayer Ag Mercapto-triazolyl nitriles
WO1997041218A1 (en) 1996-04-29 1997-11-06 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Herbicide resistant rice
WO1997041107A1 (en) * 1996-04-30 1997-11-06 Bayer Aktiengesellschaft Triazolyl mercaptides and their use as microbicides
DE19617282A1 (en) 1996-04-30 1997-11-06 Bayer Ag Triazolyl mercaptide
DE19617461A1 (en) 1996-05-02 1997-11-06 Bayer Ag Acylmercapto triazolyl derivatives
WO1997042178A1 (en) * 1996-05-02 1997-11-13 Bayer Aktiengesellschaft Acyl mercapto-triazolyl derivatives and the use thereof as microbicides
WO1997043269A1 (en) 1996-05-15 1997-11-20 Bayer Aktiengesellschaft Triazolyl disulphides
DE19620407A1 (en) 1996-05-21 1997-11-27 Bayer Ag Thiocyano-triazolyl derivatives
WO1997044331A1 (en) * 1996-05-21 1997-11-27 Bayer Aktiengesellschaft Thiocyano-triazolyl derivatives and their use as microbicides
DE19620590A1 (en) 1996-05-22 1997-11-27 Bayer Ag Sulfonyl-mercapto-triazolyl derivatives
WO1997044332A1 (en) * 1996-05-22 1997-11-27 Bayer Aktiengesellschaft Sulphonyl-mercapto-triazolyl derivatives and their use as microbicides
WO1998002527A1 (en) 1996-07-17 1998-01-22 Michigan State University Imidazolinone herbicide resistant sugar beet plants
WO1998002526A1 (en) 1996-07-17 1998-01-22 Michigan State University Imidazolinone herbicide resistant sugar beet plants
DE19650197A1 (en) 1996-12-04 1998-06-10 Bayer Ag 3-thiocarbamoylpyrazole derivatives
WO1998046608A1 (en) 1997-04-14 1998-10-22 American Cyanamid Company Fungicidal trifluoromethylalkylamino-triazolopyrimidines
WO1999005149A1 (en) 1997-07-25 1999-02-04 Bayer Aktiengesellschaft Triazoline-thion-phosphoric acid derivatives
WO1999014187A1 (en) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Benzamidoxim derivatives, intermediate products and methods for preparing and using them as fungicides
WO1999018086A1 (en) 1997-10-08 1999-04-15 Bayer Aktiengesellschaft Method for producing triazolinethione derivatives
WO1999018087A1 (en) 1997-10-08 1999-04-15 Bayer Aktiengesellschaft Method for producing triazolinthion derivatives
WO1999018088A1 (en) 1997-10-08 1999-04-15 Bayer Aktiengesellschaft Method for producing triazolinthion derivatives
WO1999024413A2 (en) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Isothiazole carboxylic acid amides and the application thereof in order to protect plants
WO1999027783A1 (en) 1997-12-04 1999-06-10 Dow Agrosciences Llc Fungicidal compositions and methods, and compounds and methods for the preparation thereof
WO2000026390A2 (en) 1998-10-29 2000-05-11 American Cyanamid Company Genes and vectors for conferring herbicide resistance in plants
WO2000029404A1 (en) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives and agricultura/horticultural bactericides
EP1028125A1 (en) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptide compounds having fungicidal activity and their agronomic use
WO2000046148A1 (en) 1999-02-02 2000-08-10 Sintokogio, Ltd. Silica gel carrying titanium oxide photocatalyst in high concentration and method for preparation thereof
EP1035122A1 (en) 1999-03-11 2000-09-13 Rohm And Haas Company Heterocyclic subsituted isoxazolidines and their use as fungicides
WO2000065913A1 (en) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Sulfonamide derivatives
EP1201648A1 (en) 1999-08-05 2002-05-02 Kumiai Chemical Industry Co., Ltd. Carbamate derivatives and agricultural/horticultural bactericides
DE10021412A1 (en) 1999-12-13 2001-06-21 Bayer Ag Fungicidal active ingredient combinations
WO2001046158A1 (en) 1999-12-21 2001-06-28 Bayer Aktiengesellschaft Method for production of a triazolinethione derivative
WO2001054501A2 (en) 2000-01-25 2001-08-02 Syngenta Participations Ag Herbicidal composition
WO2001056358A2 (en) 2000-01-28 2001-08-09 Rohm And Haas Company Enhanced propertied pesticides
EP1122244A1 (en) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Uracil compounds and their use
WO2001082685A1 (en) 2000-04-28 2001-11-08 Basf Aktiengesellschaft Use of the maize x112 mutant ahas 2 gene and imidazolinone herbicides for selection of transgenic monocots, maize, rice and wheat plants resistant to the imidazolinone herbicides
WO2002015701A2 (en) 2000-08-25 2002-02-28 Syngenta Participations Ag Bacillus thuringiensis crystal protein hybrids
WO2002022583A2 (en) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl amides and imides for use as fungicides
WO2002040431A2 (en) 2000-11-17 2002-05-23 Dow Agrosciences Llc Compounds having fungicidal activity and processes to make and use same
JP2002316902A (en) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd Plant blight-preventing agent composition
WO2003010149A1 (en) 2001-07-25 2003-02-06 Bayer Cropscience Ag Pyrazolylcarboxanilides as fungicides
WO2003011853A1 (en) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates and their use as herbicides
WO2003014103A1 (en) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Iodobenzopyran-4-one derivatives having fungicidal activity
WO2003014356A1 (en) 2001-08-09 2003-02-20 University Of Saskatchewan Wheat plants having increased resistance to imidazolinone herbicides
WO2003013225A2 (en) 2001-08-09 2003-02-20 Northwest Plant Breeding Company Wheat plants having increased resistance to imidazolinone herbicides
WO2003014357A1 (en) 2001-08-09 2003-02-20 University Of Saskatchewan Wheat plants having increased resistance to imidazolinone herbicides
WO2003016286A1 (en) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited 3-phenoxy-4-pyridazinol derivative and herbicide composition containing the same
WO2003018810A2 (en) 2001-08-31 2003-03-06 Syngenta Participations Ag Modified cry3a toxins and nucleic acid sequences coding therefor
WO2003052073A2 (en) 2001-12-17 2003-06-26 Syngenta Participations Ag Novel corn event
WO2003053145A1 (en) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Bactericidal composition
WO2003061388A1 (en) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Fused heterocyclic sulfonylurea compound, herbicide containing the same, and method of controlling weed with the same
WO2003066609A1 (en) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Disubstituted thiazolyl carboxanilides and their use as microbicides
WO2003074491A1 (en) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyl-carboxanilides and their use as fungicides
WO2004016073A2 (en) 2002-07-10 2004-02-26 The Department Of Agriculture, Western Australia Wheat plants having increased resistance to imidazolinone herbicides
WO2004049804A2 (en) 2002-11-29 2004-06-17 Syngenta Participations Ag Fungicidal combinations for crop potection
WO2004083193A1 (en) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Amide compound and bactericide composition containing the same
WO2004106529A2 (en) 2003-05-28 2004-12-09 Basf Aktiengesellschaft Wheat plants having increased tolerance to imidazolinone herbicides
WO2005020673A1 (en) 2003-08-29 2005-03-10 Instituto Nacional De Technologia Agropecuaria Rice plants having increased tolerance to imidazolinone herbicides
WO2005063721A1 (en) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Herbicidal pyrimidines
WO2005087773A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005087772A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005120234A2 (en) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Fungicidal mixtures of amidinylphenyl compounds
WO2005123690A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-difluoromethyl-pyrazol-4-carbonic acid-(ortho-phenyl)-anilides, and use thereof as a fungicide
WO2005123689A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl)-anilides and to use thereof as fungicide
WO2006015866A1 (en) 2004-08-12 2006-02-16 Syngenta Participations Ag Method for protecting useful plants or plant propagation material
WO2006087325A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said substances
WO2006087343A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi
DE102005009458A1 (en) 2005-03-02 2006-09-07 Bayer Cropscience Ag pyrazolylcarboxanilides
WO2007082098A2 (en) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides
WO2007090624A2 (en) 2006-02-09 2007-08-16 Syngenta Participations Ag A method of protecting a plant propagation material, a plant, and/or plant organs
WO2008151437A1 (en) * 2007-06-14 2008-12-18 Osta Biotechnologies Heme-oxygenase inhibitors and use of the same in the treatment of cancer and diseases of the central nervous system

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
BROWNING: "Agglomeration", CHEMICAL ENGINEERING, 4 December 1967 (1967-12-04), pages 147 - 48
CAN. J. PLANT SCI., vol. 48, no. 6, 1968, pages 587 - 94
HETEROCYCLES, vol. 23, no. 7, 1985, pages 1645 - 1649
J. AM. CHEM. SOC., 1975, pages 1353
J. ORG. CHEM., vol. 28, 1963, pages 1128
ORG. SYN. COLL., vol. 4, 1963, pages 552
ORG. SYN., vol. 40, 1966, pages 66
ORG. SYN., vol. 49, 1968, pages 78
TETRAHEDRON LETT., vol. 23, 1982, pages 5283
TETRAHEDRON, 1985, pages 1259

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013047308A1 (en) * 2011-09-27 2013-04-04 株式会社クレハ Azole derivative, agricultural/horticultural chemical, industrial material protecting agent, method for controlling plant disease, and seed
EP2746255A1 (en) * 2012-12-19 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds

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