WO2011006886A2 - Composés azole portant un substituant soufré xiv - Google Patents

Composés azole portant un substituant soufré xiv Download PDF

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WO2011006886A2
WO2011006886A2 PCT/EP2010/060046 EP2010060046W WO2011006886A2 WO 2011006886 A2 WO2011006886 A2 WO 2011006886A2 EP 2010060046 W EP2010060046 W EP 2010060046W WO 2011006886 A2 WO2011006886 A2 WO 2011006886A2
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formula
compounds
combination
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case
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PCT/EP2010/060046
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WO2011006886A3 (fr
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Jochen Dietz
Thomas Grote
Egon Haden
Bernd Müller
Jan Klaas Lohmann
Jens Renner
Sarah Ulmschneider
Alice GLÄTTLI
Marianna Vrettou-Schultes
Wassilios Grammenos
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/84—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Definitions

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

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Abstract

La présente invention a pour objet de nouveaux composés azole des formules I et II telles que définies ci-dessous qui portent un substituant soufré, des compositions agricoles les contenant, leur utilisation en tant que fongicides et des composés intermédiaires utilisés dans leur procédé de production.
PCT/EP2010/060046 2009-07-14 2010-07-13 Composés azole portant un substituant soufré xiv WO2011006886A2 (fr)

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BR112012001001A BR112012001001A2 (pt) 2009-07-14 2010-07-13 compositos azol das formulas i e ii, compostos das formulas i e i, compostos de formula ix, composição agricola, uso de um composto farmaceutica, metodo para tratar infecções de câncer ou virus para combater fungos zoopatigênicos ou humanopatogenicos

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