WO2014095381A1 - Composés imidazolyl et triazolyl fongicides - Google Patents

Composés imidazolyl et triazolyl fongicides Download PDF

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WO2014095381A1
WO2014095381A1 PCT/EP2013/075616 EP2013075616W WO2014095381A1 WO 2014095381 A1 WO2014095381 A1 WO 2014095381A1 EP 2013075616 W EP2013075616 W EP 2013075616W WO 2014095381 A1 WO2014095381 A1 WO 2014095381A1
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compounds
alkyl
corresponds
para
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Wassilios Grammenos
Ian Robert CRAIG
Nadege Boudet
Bernd Müller
Jochen Dietz
Erica May Wilson LAUTERWASSER
Jan Klaas Lohmann
Thomas Grote
Egon Haden
Ana Escribano Cuesta
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Basf Se
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    • 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
    • C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • 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
    • C07D233/68—Halogen atoms
    • 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
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/10—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members

Definitions

  • the present invention relates to fungicidal imidazolyl and triazolyl compounds, agrochemical compositions comprising them, to their use and to methods for combating phytopathogenic fungi.
  • the present invention also relates to seeds treated with at least one such compound.
  • the invention relates to processes for preparing compounds of formula I as well as to specific intermediates that are obtained during the reaction sequence.
  • US 4664696 A relates to a-phenyl- or benzyl-a-cyclopropylalkylene-1 H-imidazole- and 1 ,2,4-triazole-1 -ethanols and their use against fungi.
  • DE 3337937 A1 describes similar triazole fungicides, their use in agriculture and on humans as well as compositions comprising them.
  • WO 96/16048 A1 relates to microbicidal triazolyl-derivatives, their preparation and to their use for protection of plants and materials.
  • the fungicidal activity of known fungicidal compounds is unsatisfactory. Based on this, it was an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic fungi. This objective is achieved by the use of substituted imidazolyl and triazolyl compounds of formula I having good fungicidal activity against phytopathogenic fungi.
  • the compounds according to the present invention differ from those described in the abovementioned publications in that the divalent methylene group adjacent to the triazole or imidazole ring carries at least one further substituent.
  • A is N or CH
  • R D is hydrogen, CN, d-C 6 -alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl,
  • C2-C6-haloalkenyl, C2-C6-alkynyl or C2-C6-haloalkynyl; is halogen, CN, N0 2 , OH, SH, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, Ci-C 6 - alkylsulfinyl, Ci-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkynyl, C 3 -C8-cycloalkyl, Cs-Cs-cycloalkoxy, C 3 -C 8 -cycloalkyl-Ci-C 4 -alkyl, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 - alkyl) 2 , NH(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalky
  • substituents R 1a wherein is halogen, CN, N0 2 , OH, SH, NH 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alk- oxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C 3 -C8-cycloalkyl or Ci-C 4 -alkoxy-Ci-C 4 -alkyl;
  • R 11 and R 22 are independently selected from the group consisting of
  • R 1 and R 2 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six- or seven-membered carbocycle or a saturated or partially unsaturated three-, four-, five-, six- or seven-membered heterocycle, wherein the heterocycle includes beside carbon atoms one, two, three or four heteroatoms independently selected from the group consisting of N, O and S, and wherein the carbo- and heterocycle are unsubstituted or carry one, two, three or
  • R 12 is halogen, CN, N0 2 , OH, SH, NH 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl,
  • R 2a is halogen, CN, N0 2 , OH, SH, NH 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl,
  • X is OR 3 or CN;
  • R 3 alkylphenyl, phenyl, phenyl-Ci-C 4 -alkyl, phenyl-C 2 -C 4 -alkenyl or phenyl- C 2 -C 4 -alkynyl; wherein the aliphatic, alicyclic and aromatic moieties of R 3 are unsubstituted or substituted by one, two, three or four or up to the maximum possible number of independently selected substituents R 3a ; wherein R 3a is halogen, CN, N0 2 , OH, C C 4 -alkyl, C C 4 -halogenalkyl, C 3 -C 8 - cycloalkyl, Ci-C 4 -alkoxy or Ci-C 4 -halogenalkoxy;
  • R 4 is independently selected from the group consisting of halogen, CN, N0 2 , OH, SH, d-Ce-alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, Ci-C 6 -alkylsulfinyl, Ci-C 6 - alkylsulfonyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, C 3 -C8-cycloalkyl, C 3 -C8-cycloalkyloxy,
  • R YN , R Y , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 and R Y8 are independently selected from the group consisting of hydrogen, halogen, CN, nitro, OH, Ci-C 4 -alkyl,
  • R La is halogen, CN, N0 2 , OH, SH, NH 2 , Ci-Ce-alkyl, Ci-C 6 -haloalkyl,
  • R 51 is halogen, CN, N0 2 , OH, SH, NH 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl,
  • Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8- cycloalkyl and Ci-C4-alkoxy-Ci-C4-alkyl; or R 5 and R 6 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six- or seven-membered carbocycle or a saturated or partially unsaturated three-, four-, five-, six- or seven-membered heterocycle, wherein the heterocycle includes beside carbon atoms one, two, three or four heteroatoms independently selected from the group consisting of N, O and S, and wherein the carbo- and heterocycle are unsubstituted or carry one, two, three or four independently selected substituents R 56 , wherein one or two CH2 groups of the carbo- or heterocycle may be replaced by one or two groups independently selected from the group of C( 0
  • R 56 is halogen, CN, N0 2 , OH, SH, NH 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl,
  • R 52 and R 53 are independently selected from the group consisting of
  • R" is hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or Ci-C -alkoxy-Ci-C -alkyl;
  • R 7 is hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy or C1-C6- haloalkoxy; and the N-oxides and the agriculturally acceptable salts of the compounds
  • the present invention also provides a use of compounds I and/or their agriculturally useful salts for controlling phytopathogenic fungi and to methods for combating phytopathogenic fungi.
  • the invention further provides compositions comprising these compounds I and/or their agriculturally acceptable salts.
  • the present invention also relates to seeds treated with at least one such compound.
  • the invention relates to processes for preparing compounds of formula I and to intermediates such as compounds of formulae IV, V and VI.
  • Compounds I 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.
  • Compounds I can be present in different crystal modifications whose biological activity may differ. They also form part of the subject matter of the present invention.
  • the compounds of formula I can be present in atropisomers arising from restricted rotation about a single bond of asymmetric groups. They also form part of the subject matter of the present invention.
  • the embodiments of the intermediates correspond to the embodiments of the compounds of formula I.
  • the term "compounds I" refers to compounds of formula I.
  • C n -C m indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
  • halogen refers to fluorine, chlorine, bromine and iodine.
  • Ci-C6-alkyl refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, and 1 ,1 -dimethylethyl.
  • Ci-C6-haloalkyl refers to a straight-chained or branched alkyl group having 1 to 6 carbon atoms (as defined above), wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example 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-tri- fluoroethyl, 2-chloro-2 -fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl
  • Ci-C6-alkoxy refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms (as defined above) which is bonded via an oxygen, at any position in the alkyl group, for example methoxy, ethoxy, n-propoxy, 1 -methylethoxy, butoxy, 1 -meth- yhpropoxy, 2-methylpropoxy or 1 ,1 -dimethylethoxy.
  • Ci-C6-hydroxyalkyl refers to a straight-chained or branched alkyl group having 1 to 6 carbon atoms (as defined above), wherein one hydrogen atom in these groups may be replaced by one hydroxy group, for example hydroxym ethyl,
  • Ci-C6-haloalkoxy refers to a Ci-C6-alkoxy group as defined above, wherein some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, for example, OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCHC , OCCI 3 , chlorofluoro- methoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloro- ethoxy, 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, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,
  • Ci-C4-alkoxy-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy group (as defined above).
  • Ci-C4-alkoxy-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C6-alkoxy group (as defined above).
  • Ci-C6-alkylthio refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above) bonded via a sulfur atom.
  • Ci-C6-haloalkylthio refers to straight-chain or branched haloalkyl group having 1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, at any position in the haloalkyl group.
  • C2-C6-alkenyl refers to a straight-chain or branched unsaturated
  • hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position such as ethenyl, 1 -propenyl, 2-propenyl (allyl), 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2- propenyl.
  • C2-C6-alkynyl refers to a straight-chain or branched unsaturated
  • hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond such as ethynyl, 1 -propynyl, 2-propynyl (propargyl), 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl.
  • Cs-Cs-cycloalkyl refers to monocyclic saturated hydrocarbon radicals having 3 to 8 carbon ring members, such as cyclopropyl (C3H5), cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
  • C3-C8-cycloalkyl-Ci-C4-alkyl refers to a cycloalkyl radical having 3 to 8 carbon atoms (as defined above), which is bonded via a Ci-C4-alkyl group (as defined above).
  • Cs-Cs-cycloalkyl-Cs-Cs-cycloalkyl refers to a cycloalkyl radical having 3 to 8 carbon atoms (as defined above), which is substituted by a further cycloalkyl radical having 3 to 8 carbon atoms.
  • Cs-Cs-cycloalkoxy refers to a cycloalkyl radical having 3 to 8 carbon atoms (as defined above), which is bonded via an oxygen.
  • the number of valence of carbon is 4, that of nitrogen is 3.
  • saturated or partially unsaturated 3-, 4- 5-, 6- or 7-membered carbocycle is to be understood as meaning both saturated or partially unsaturated carbocycles having 3, 4, 5, 6 or 7 ring members.
  • Examples include cyclopropyl, cyclopentyl, cyclopentenyl, cyclopentadienyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, cycloheptyl, cycloheptenyl, cycloheptadienyl, and the like.
  • saturated or partially unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocycle, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms independently selected from the group of N, O and S is to be understood as meaning both saturated and partially unsaturated heterocycles, for example: a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of N, O and S as ring members such as oxirane, aziridine, thiirane, oxetane, azetidine, thiethane, [1 ,2]dioxetane, [1 ,2]dithietane, [1 ,2]diazetidine; and
  • a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of N, O and S as ring members such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3- tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 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- imidazolid
  • a 7-membered saturated or partially unsaturated heterocycle such as 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-,-4-,-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-tetra
  • 5-membered heteroaryl refers to aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example, a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5- yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4- yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-3-yl,
  • a 6-membered heteroaryl such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
  • inventive compounds I can be prepared by various routes in analogy to known processes described in the prior art, and, advantageously, by the synthesis shown in the following schemes and in the experimental part of this application.
  • the alcohol IV may then be transformed by way of introduction of a leaving group LG, which is replaceable by a nucleophile, as shown in Scheme 2, for example by halogenation (LG meaning, for example, chlorine, bromine or iodine) or sulfonation (LG meaning, for example, methylsulfonate or tosylsulfonate) to provide compounds of formula V.
  • LG halogenation
  • the leaving group can then be replaced by an azole or imidazole residue upon treatment with triazole or imidazole in the presence of a base to yield compounds of the formula I wherein D is hydrogen.
  • compounds of the formula I can be prepared by transforming compound II into an epoxide of the formula VI with a suitable epoxidation method as outlined in Scheme 3 and described in WO 2010142779 A1 ; Organic Letters 2010, 12(4), 844- 846; Synthesis 2008, (9), 1404-1414; EP 29542 A2).
  • Compounds VI can be reacted with triazole or imidazole in the presence of a base, which ultimately leads to compounds of the formula I wherein D is hydrogen.
  • hexamethyldisilazide lithium 2,2,6,6-tertramethylpiperidide or zink 2,2,6,6- tertramethylpiperidide, at low temperature in a suitable solvent such as Et.20, MTBE or THF, followed by addition of a suitable electrophile, for example Ss, CH3-S-S-CH3, , ICI, C2F 4 Br2, to obtain correspondingly substituted azole compounds as has been described in Tetrahedron Letters 201 1 , 52(36), 4590-4594; WO 2006/102194 A1 , Journal of Organic Chemistry 2009, 74(21 ), 8309-8313; WO 201 1/1 13820 A1 ; WO 2012/025506 A1 , WO 9616048 A1 or in Synthesis 1999, 1 , 100-106.
  • a suitable solvent such as Et.20, MTBE or THF
  • a suitable electrophile for example Ss, CH3-S-S-CH3, , ICI, C
  • Compounds I wherein D is SCN can be obtained by treating a compound I wherei D is SH with cyanogen halide such as Br-CN or CI-CN and a base (organic or inorganic base such as K2CO3, NaOH, KOH or NEt.3, DBU) in a suitable solvent such as acetone, MeCN or THF in analogy to methods reported in: WO 2009/077497 A2 or in Chemical & Pharmaceutical Bulletin 1964, 12(2), 182-191 .
  • cyanogen halide such as Br-CN or CI-CN
  • a base organic or inorganic base such as K2CO3, NaOH, KOH or NEt.3, DBU
  • suitable solvent such as acetone, MeCN or THF
  • Compounds I wherein D is SH can be functionalized at the sulfur atom using standard procedures, for example with an alkylation agent such as metyl iodide in the presence of a base (organic or inorganic base such as K2CO3, NaOH, KOH or NEt.3, DBU) in a suitable solvent such as acetone, MeCN or THF.
  • an alkylation agent such as metyl iodide
  • a base organic or inorganic base such as K2CO3, NaOH, KOH or NEt.3, DBU
  • suitable solvent such as acetone, MeCN or THF.
  • Compounds of the formula I wherein X is OR 3 can be obtained from the reaction of compound I wherein X is OH in the presence of an electrophile (e.g. Mel, ethyl bromide, cyclopropyl bromide, 1 ,4-dibromobutane, propargyl bromide, methyl chloroformate, allyl bromide, acetylene, cyclohexene, cyclopentene, phenol) and a base (e.g. NaH, KH, f-BuOK, NaH, KOH, Et 3 N, LDA, imidazole, K 2 C0 3 , Cs 2 C0 3 ) and in an inert organic solvent preferably (e.g.
  • an electrophile e.g. Mel, ethyl bromide, cyclopropyl bromide, 1 ,4-dibromobutane, propargyl bromide, methyl chloroformate,
  • nitriles can also be obtained from compounds I wherein X is OH in presence of a reagent, for example cyanuric trichloride, NaCN, tetrabutylammonium cyanide and/or an additive (for example N-tosylimidazole, Bu 4 NI, Bu 4 NCI, Bu 4 NBr, TMSCI, DDQ, PPh 3 ) in an inert organic solvent (for example THF, DME, Et20, DMF, NMP, DMSO, toluene, acetonitrile).
  • a reagent for example cyanuric trichloride, NaCN, tetrabutylammonium cyanide and/or an additive (for example N-tosylimidazole, Bu 4 NI, Bu 4 NCI, Bu 4 NBr, TMSCI, DDQ, PPh 3 ) in an inert organic solvent (for example THF, DME, Et20, DMF, N
  • Compounds II can be prepared from carboxyclic acid chlorides and Grignard reagents as shown in Scheme 4. Reaction of a suitably substituted halobenzene compound A, wherein Hal stands for halogen, for example chlorine, bromine or iodine, with trans- metallation reagents such as isopropylmagnesium halides and subsequent reaction with a carboxyclic acid chloride, preferably under anhydrous conditions, and optionally in the presence of a catalyst such as CuCI, AICI 3 , LiCI and mixtures thereof, provides acetophenones of the formula II.
  • Hal stands for halogen, for example chlorine, bromine or iodine
  • the N-oxides may be prepared from the compounds I according to conventional oxidation methods, e. g. by treating compounds I with an organic peracid such as metachloroperbenzoic acid (cf. WO 03/64572 or J. Med. Chem. (1995), 38(1 1 ), 1892-1903,); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. (1981 ), 18 (7), 1305-1308) or oxone (cf. J. Am. Chem. Soc. (2001 ), 123 (25), 5962-5973).
  • the oxidation may lead to pure mono-N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.
  • reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and, if appropriate, chromatic purification of the crude products.
  • the intermediates and end products are obtained in the form of colorless or slightly viscous oils which can be freed from volatile components or purified under reduced pressure and at moderately elevated temperatures. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.
  • Agriculturally useful salts of the compounds I encompass 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.
  • Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, 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, tetrabutylammonium, 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,
  • Ci-C4-alkanoic acids preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound I with an acid of the
  • anion preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the invention relates to intermediates of formula IV. In a further aspect the invention relates to intermediates of formula V. In still another aspect the invention relates to intermediates of formula VI.
  • the meaning of the substituents of the compounds used according to the invention is further defined. Thereby, in each case the substituents are meant to have the given meanings and preferred meaning on their own or in any combination with the meanings or preferred meanings of any other substituent.
  • the groups mentioned herein in tables A and B, as well as in tables 1 to 1288, for a combination of substituents are furthermore, independently of the combination in which they are mentioned, particularly preferred embodiments of the substituent or of the combination of substituents in question.
  • a according to the invention is N or CH. According to one embodiment A is N.
  • A is CH.
  • R D is hydrogen, halogen or SR D , wherein R D is hydrogen, CN, d-Ce-alkyl, d-Ce-haloalkyl, C2-Ce-alkenyl, C2-Ce-haloalkenyl, C2-C6- alkynyl or C2-C6-haloalkynyl.
  • D is hydrogen.
  • D is halogen, in particular iodine.
  • D is SR D .
  • R D is H.
  • R D is CN.
  • R D is
  • R 2 is hydrogen, halogen, CN, NO2, OH, SH , Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C2-C6-alkenyl, C2-Ce-alkynyl, C 3 -C8-cycloalkyl, C 3 -C8-cycloalkyloxy, C 3 -C8-cycloalkyl-Ci-C 4 -alkyl, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , N H(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 ,
  • Ci-C6-haloalkoxy Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl or d-d-alkoxy- Ci-C 4 -alkyl.
  • R 2 is hydrogen, halogen, CN, N0 2 , OH, SH, Ci-C6-alkyl, Ci-C6-hydroxyalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, d-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 - alkynyl, C 2 -C6-haloalkenyl, d-drhaloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkyloxy, C 3 -Cs-cycloalkyl-Ci-C4-alkyl, NH 2 , NH(Ci-C 4 -alkyl) or N(Ci-C 4 -alkyl,
  • R 2 is halogen, CN, N0 2 , OH, NH 2 , N(CH 3 ) 2 , Ci-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, d-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-C4-alkoxy-Ci-C 4 -alkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl or Cs-Cs-cycloalkyl.
  • R 2 is halogen, CN , N0 2 , OH, SH, Ci-Ce- alkyl, Ci-C6-hydroxyalkyl, Ci-drhaloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C4-alkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkyloxy, C3-C8- cycloalkyl-Ci-C 4 -alkyl, NH 2 , NH(Ci-C 4 -alkyl) or N(Ci-C 4 -alkyl) 2 .
  • R 2 is halogen, CN, N0 2 , OH, NH 2 , N(CH 3 ) 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy,
  • R 2 is hydrogen, halogen, CN, OH, NH2, N(CHs)2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6- alkynyl or Cs-Cs-cycloalkyl.
  • R 2 is halogen, CN, OH, NH2, N(CHs)2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl or Cs-Cs- cycloalkyl.
  • R 2 is hydrogen, halogen, CN, OH, NH2, N(CHs)2, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl and Cs-Cs-cycloalkyl.
  • R 2 is halogen, CN, OH, NH2, N(CHs)2, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl and Cs-Cs-cycloalkyl.
  • R 2 is Cs-Cs-cycloalkyl, phenyl or 5- or 6-membered heteroaryl, wherein the alicyclic and aromatic moieties of R 2 are unsubstituted or substituted by one, two, three or four or up to the maximum possible number of independently selected substituents R 2a .
  • R 2 is Cs-Cs-cycloalkyl, in particular cyclopropyl.
  • R 2 is phenyl or 5- or 6- membered heteroaryl, wherein the aromatic moieties of R 2 is unsubstituted or substituted by one, two, three or four or up to the maximum possible number of independently selected substituents R 2a .
  • R 2 is C2-C6-alkenyl, in particular 2-propenyl, or C2-C6- alkynyl, in particular 2-propynyl and 2-butynyl.
  • R 2 is Ci-C6-haloalkyl, in particular CF3 or CHF2, or Ci-C6-haloalkoxy, in particular OCF3 or OCHF2.
  • R 2 is halogen, in particular chlorine or bromine.
  • R 2 is Ci-C6-alkyl, in particular Ci-C 4 -alkyl, more particularly methyl, ethyl and 1 -methylethyl.
  • R 2 is Ci-C6-alkoxy, in particular methoxy, ethoxy or 1 -methylethoxy.
  • R 2 is C2-C6-alkenyl, in particular 2-propenyl, or C2-C6- alkynyl, in particular 2-propynyl and 2-butynyl.
  • R 2 is Ci-C6-haloalkyl, in particular CF3 or CHF2, or Ci-C6-haloalkoxy, in particular OCF3 or OCHF2.
  • R 2 is hydrogen.
  • R 1 is halogen, CN, N0 2 , OH, SH, Ci-C6-alkyl, C1-C6- hydroxyalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, C 2 -C6-haloalkenyl, C 2 -C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyloxy, C3-C8-cycloalkyl-Ci-C 4 -alkyl, NH 2 , NH(Ci-C 4 -alkyl) or N(Ci-C 4 -alkyl,
  • R 1 is halogen, CN, N0 2 , OH, NH 2 , N(CH 3 ) 2 , Ci-C 6 -alkyl, Ci-C 6 - haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C 4 - alkoxy-Ci-C 4 -alkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl or Cs-Cs-cycloalkyl and R 2 is as defined or preferably defined above.
  • R 1 is halogen, CN, OH, NH 2 , N(CHs) 2 , d-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 2 -C 6 -alk- enyl, C 2 -C6-alkynyl or Cs-Cs-cycloalkyl and R 2 is independently as defined or preferably defined above.
  • R 1 is halogen, CN, OH, NH 2 , N(CHs) 2 , Ci-C6-alkyl, Ci-C6-alkoxy, C 2 -C6-alkenyl, C 2 -C6-alkynyl and Cs-Cs-cycloalkyl and R 2 is
  • R 1 is halogen, CN, N0 2 , OH, NH 2 , N(CHs) 2 , Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C 2 -C6-alkenyl C 2 -C6-alkynyl or Cs-Cs-cycloalkyl, and wherein R 2 is hydrogen or a radical as defined for R 1 .
  • R 1 is CN and R 2 is as defined or preferably defined above.
  • R 1 is CN and R 2 is CN.
  • R 1 is CN and R 2 is hydrogen.
  • R 1 is OH, SH or NH 2 and R 2 is as defined or preferably defined above.
  • R 2 is hydrogen and R 1 is OH, SH or NH 2 .
  • R 2 is hydrogen and R 1 is OH, SH or NH 2 .
  • R 1 is C 2 -C6-alkenyl, in particular 2-propenyl, or C 2 -C6- alkynyl, in particular 2-propynyl and 2-butynyl and R 2 is as defined or preferably defined above.
  • R 2 is hydrogen and R 1 is C 2 -C6-alkenyl, in particular 2-propenyl, or C 2 -C6-alkynyl, in particular 2-propynyl and 2-butynyl.
  • R 1 is Ci-C6-haloalkyl, in particular CF3 or CHF 2 , or Ci-C6-haloalkoxy and R 2 is as defined or preferably defined above.
  • R 2 is hydrogen and R 1 is Ci-C6-haloalkyl, in particular CF3 or CHF 2 , or Ci-C6-haloalkoxy, in particular OCF3 or OCHF 2 .
  • R 1 is Cs-Cs-cycloalkyl, phenyl or 5- or 6-membered heteroaryl, wherein the alicyclic and aromatic moieties of R 1 are unsubstituted or substituted by one, two, three or four or up to the maximum possible number of independently selected substituents R 1a and R 2 is as defined or preferably defined above.
  • R 2 is hydrogen and R 1 is Cs-Cs-cycloalkyl, phenyl or 5- or 6-membered heteroaryl, wherein the alicyclic and aromatic moieties of R 1 are unsubstituted or substituted by one, two, three or four or up to the maximum possible number of independently selected substituents R 1a .
  • R 1 is phenyl or 5- or 6-membered heteroaryl, wherein the aromatic moieties of R 1 are unsubstituted or substituted by one, two, three or four or up to the maximum possible number of independently selected substituents R 1a and R 2 is independently as defined or preferably defined above.
  • R 2 is hydrogen and R 1 is phenyl or 5- or 6-membered heteroaryl, wherein the aromatic moieties of R 1 are unsubstituted or substituted by one, two, three or four or up to the maximum possible number of independently selected substituents R 1a .
  • R 1 is Cs-Cs-cycloalkyl, in particular cyclopropyl and R 2 is as defined or preferably defined above.
  • R 2 is hydrogen and R 1 is Cs-Cs-cycloalkyl, in particular cyclopropyl.
  • R 1 and R 2 together with the carbon atom to which they are bound form a vinyl group
  • C * CR 11 R 22 , wherein R 11 and R 22 are as defined or preferably defined below; or R 1 and R 2 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six- or seven-membered carbocycle or a saturated or partially unsaturated three-, four-, five-, six- or seven-membered heterocycle, wherein the heterocycle includes beside carbon atoms one, two, three or four heteroatoms independently selected from the group consisting of N, O and S, and wherein the carbo- and heterocycle are unsubstituted or carry one, two, three or four independently selected substituents R 12 as defined and preferably defined below, and wherein one or two Chb groups of the carbo- or heterocycle may be replaced by one or two groups
  • R 1 and R 2 together with the carbon atom to which they are bound form a vinyl group
  • R 11 and R 22 are independently selected from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, NH2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio and Ci-C4-alkoxy- Ci-C4-alkyl.
  • R 1 and R 2 are independently selected from the group consisting of hydrogen, halogen and Ci-C6-alkyl.
  • R 11 and R 22 are hydrogen
  • R 1 and R 2 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six- or seven-membered carbocycle which is unsubstituted or carries one, two, three or four independently selected substituents R 12 as defined and preferably defined below.
  • R 1 and R 2 together with the carbon atom to which they are bound form a saturated carbocycle, in particular selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl, wherein the carbocycle in each case is unsubstituted or carries one, two, three or four
  • R 1 and R 2 together with the carbon atom to which they are bound form a partially unsaturated carbocycle, in particular selected from the group consisting of cyclopentenyl, cyclopentadienyl and cyclohexenyl and wherein the carbocycle is unsubstituted or carries one, two, three or four independently selected substituents R 12 as defined and preferably defined below.
  • R 1 and R 2 together with the carbon atom to which they are bound form a cyclopropyl ring which is unsubstituted or carries one, two, three or four independently selected substituents R 12 as defined and preferably defined below.
  • R 1 and R 2 together with the carbon atom to which they are bound form a cyclobutyl ring which is unsubstituted or carries one, two, three or four independently selected substituents R 12 as defined and preferably defined below.
  • R 1 and R 2 together with the carbon atom to which they are bound form a cyclopentyl ring which is unsubstituted or carries one, two, three or four independently selected substituents R 12 as defined and preferably defined below.
  • R 1 and R 2 together with the carbon atom to which they are bound form a cyclohexyl ring which is unsubstituted or carries one, two, three or four independently selected substituents R 12 as defined and preferably defined below.
  • R 1 and R 2 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six- or seven-membered heterocycle, in particular a three-, four- or five- membered heterocycle, wherein the heterocycle includes beside carbon atoms one, two, three or four, in particular one or two, heteroatoms independently selected from the group consisting of N, O and S, and wherein the heterocycle is unsubstituted or carries one, two, three or four independently selected substituents R 12 as defined and preferably defined below.
  • R 1 and R 2 form a heterocycle selected from the group consisting of oxirane, aziridine, thiirane, oxetane, azetidine, thiethane, 2- tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl and 3-tetrahydrothienyl, wherein the heterocycle is unsubstituted or carries one, two, three or four
  • R 1 and R 2 together with the carbon atom to which they are bound form an oxirane which is unsubstituted or carries one, two, three or four independently selected substituents R 12 as defined and preferably defined below.
  • R 1 and R 2 together with the carbon atom to which they are bound form an oxetane which is unsubstituted or carries one, two, three or four independently selected substituents R 12 as defined and preferably defined below.
  • R 12 according to the invention is in each case independently selected from the group consisting of halogen, CN , N0 2 , OH , SH , N H 2 , Ci-C 6 -alkyl, d-C 6 -haloalkyl,
  • R 12 is halogen, CN , NO2, OH , SH , N H2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio or C 1 -C 4 -a I koxy-C 1 -C 4 -a I ky I .
  • R 12 is halogen, CN , Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy.
  • R 12 is halogen, CN or Ci-C6-alkyl.
  • R 12 is halogen, in particular fluorine.
  • R 12 is chlorine.
  • R 12 is Ci-C6-alkyl, in particular Ci-C 4 -alkyl, even more preferably methyl.
  • X according to the invention is OR 3 or CN .
  • X is CN .
  • R 3 is hydrogen
  • R 3 is hydrogen Ci-C6-alkyl, Ci-C6-hydroxyalkyl, Ci-C6-haloalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
  • R 3 is hydrogen, Ci-C6-alkyl, C1-C6- hydroxyalkyl, Ci-C6-haloalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C 4 -alkyl, Ci-Ce-alkylsulfonyl, phenyl or wherein the aliphatic, alicyclic and aromatic groups of R 3 in each case either do not carry any further substituents or in each case may further carry one, two, three or up to the maximum possible number independently selected substituents R 3a as defined and preferably defined below.
  • R 3 is Ci-C6-alkylsulfonyl, in particular
  • R 3 is Ci-C6-alkyl, preferably Ci-C4-alkyl, in particular methyl or ethyl.
  • R 3 is C2-C6-alkenyl, in particular
  • R 3 is C2-C6-alkynyl, in particular 2-propynyl or 2-butynyl.
  • R 3 is phenyl, which is unsubstituted or carries one, two, three or up to the maximum possible number of independently selected substituents R 3a as defined and preferably defined below.
  • R 3 is phenyl-Ci-C4-alkyl, in particular benzyl, wherein the aromatic moiety is unsubstituted or carries one, two, three or up to the maximum possible number of independently selected substituents R 3a as defined and preferably defined below.
  • R 3 is Ci-C4-alkoxy-Ci-C6-alkyl, in particular methoxymethyl.
  • R 3a is independently selected from a group consisting of halogen, CN, N0 2 , OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, C 3 -C 8 -cycloalkyl, Ci-C 4 -alkoxy and Ci-C4-halogenalkoxy.
  • R 3a is independently selected from the group consisting of halogen, in particular F and CI, Ci-C4-alkoxy, in particular methoxy, and Ci-C4-alkyl, in particular methyl and ethyl.
  • R 4 is independently selected from the group consisting of halogen, CN, NO2, OH, SH, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C4-alkoxy-Ci-C4-alkyl,
  • R 4 is independently selected from the group consisting of halogen, CN, NO2, OH, d-Ce-alkyl, d-Ce-haloalkyl, d-Ce-alkoxy, d-Ce-haloalkoxy, d-dralkenyl, d-Gs-alkynyl, d-drhaloalkenyl and d-drhaloalkynyl.
  • R 4 is independently selected from the group consisting of halogen and d-C6-haloalkyl.
  • R 4 is independently selected from the group consisting of 2-F, 3-F, 4-F, 2-CI, 3-CI, 4-CI, 4-Br, 4-1, 4-CH 3 , 4-OCH 3 , 2-CF 3 , 3-CF 3 , 4- CF 3 , 2-CH F2, 3-CH F2, 4-CH F2, 2,4-F 2 , 2,3-F 2 , 2,5-F 2 , 2,6-F 2 , 3,4-F 2 , 3,5-F 2 , 2,4-CI 2 , 2,3- Cl 2 , 2,5-CI 2 , 2,6-CI 2 , 3,4-CI 2 , 3,5-CI 2 , 2,4-(CH 3 ) 2 , 2,4-(CF 3 ) 2 , 2,4-(CHF 2 ) 2 , 2-F-4-CI, 2-F- 4-CF 3 , 2-F-4-CH F2, 2-CI-4-F, 2-CI-4-CF 3 , 2-CI-4-CHF 2 , 2-CF 3 -4-F, 2-CF 3 -4-F, 2-CF 3
  • R 4 is independently selected from the group consisting of halogen, in particular fluorine and chlorine. In a particularly preferred aspect of the invention R 4 is fluorine. In another particularly preferred aspect R 4 is chlorine.
  • R 4 is independently selected from the group consisting of d-C6-haloalkyl, in particular CF 3 or CH F2. In yet another preferred aspect of the invention R 4 is CN.
  • n is 0, 1 , 2, 3 or 4. In a preferred embodiment n is 1 , 2, 3 or 4. In another preferred embodiment n is 0, 1 , 2 or 3. In another preferred embodiment n is 1 , 2 or 3. In a preferred aspect n is 0, 1 or 2. In still another preferred aspect n is 1 or 2. In a further preferred embodiment n is 1 . In yet another preferred embodiment the invention relates to compounds I wherein n is 2.
  • n is 1 , 2, 3 or 4, in particular 1 , 2 or 3, wherein in each case one radical R 4 is located in ortho-position of the phenyl ring.
  • n is 1 , 2, 3 or 4, in particular 1 , 2 or 3, wherein in each case one radical R 4 is located in para-position of the phenyl ring.
  • n is 1 , 2, 3 or 4, in particular 1 , 2 or 3, or particularly 1 or 2, wherein in each case one R 4 is located in ortho- and one R 4 is located in para-position of the phenyl ring.
  • n is 1 and this R 4 is located in ortho- position of the phenyl ring.
  • n is 1 and this R 4 is located in para-position of the phenyl ring.
  • R 5 and R 6 are independently selected from the group consisting of hydrogen, halogen, CN, N0 2 , OH, SH , Ci-Ce-alkyl, d-Ce-hydroxyalkyl, d-Ce-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-d-alkoxy- Ci-d-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Cs-Cs- cycloalkyl, C3-Cs-cycloalkyloxy and C3-C8-cycloalkyl-Ci-C4-alkyl.
  • R 5 and R 6 are independently selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, d-dralkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl and C3-Cs-cycloa I kyl-Ci -C4-a I kyl .
  • R 5 and R 6 are independently selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Cs-Cs-cycloalkyl.
  • R 5 and R 6 are Ci-C4-alkyl, in particular methyl.
  • R 5 is hydrogen and R 6 is halogen, CN, Ci-dr alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl and Cs-Cs-cycloalkyl-Ci-d-alkyl.
  • R 5 is hydrogen and R 6 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Cs-Cs-cycloalkyl.
  • R 5 is hydrogen and R 6 is Ci-C6-alkyl, in particular methyl.
  • R 5 and R 6 are hydrogen.
  • R 5 and R 6 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six- or seven- membered, in particular three-, four- or five-membered, carbocycle or a saturated or partially unsaturated three-, four-, five-, six- or seven-membered, in particular three-, four- or five-membered heterocycle, wherein the heterocycle includes beside carbon atoms one, two, three or four heteroatoms independently selected from the group consisting of N, O and S, and wherein the carbo- and heterocycle are unsubstituted or carry one, two, three or four, in particular one or two, independently selected substituents R 51 as defined or preferaby defined below; and wherein one or two Chb groups of the carbo- or heterocycle may be replaced by one
  • R 5 and R 6 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six- or seven-membered, in particular three-, four- or five-membered, carbocycle which is unsubstituted or carries one, two, three or four independently selected substituents R 51 as defined or preferaby defined below.
  • R 5 and R 6 together with the carbon atom to which they are bound form a carbocycle selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl and wherein the carbocycle is unsubstituted or carries one, two, three or four independently selected substituents R 51 as defined or preferaby defined below.
  • R 5 and R 6 together with the carbon atom to which they are bound form a carbocycle selected from the group consisting cyclopentenyl, cyclopentadienyl and cyclohexenyl and wherein the carbocycle is unsubstituted or carries one, two, three or four independently selected substituents R 51 as defined or preferaby defined below.
  • R 5 and R 6 together with the carbon atom to which they are bound form a cyclopropyl ring which is unsubstituted or carries one, two, three or four independently selected substituents R 51 as defined or preferaby defined below.
  • R 5 and R 6 together with the carbon atom to which they are bound form a cyclobutyl ring which is unsubstituted or carries one, two, three or four independently selected substituents R 51 as defined or preferaby defined below.
  • R 5 and R 6 together with the carbon atom to which they are bound form a cyclopentyl ring which is unsubstituted or carries one, two, three or four independently selected substituents R 51 as defined or preferaby defined below.
  • R 5 and R 6 together with the carbon atom to which they are bound form a cyclohexyl ring which is unsubstituted or carries one, two, three or four independently selected substituents R 51 as defined or preferaby defined below.
  • R 5 and R 6 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six- or seven-membered heterocycle, wherein the heterocycle includes beside carbon atoms one, two, three or four heteroatoms independently selected from the group consisting of N, O and S, and wherein the heterocycle is unsubstituted or carries one, two, three or four independently selected substituents R 51 as defined or preferaby defined below.
  • R 5 and R 5 together with the carbon atom to which they are bound form a three-, four-, five-, six- or seven-membered
  • heterocycle wherein the heterocycle includes beside carbon atoms one, two, three or four heteroatoms independently selected from the group consisting of N, O and S, and wherein the carbo- and heterocycle are unsubstituted or carry one, two, three or four substituents R 51 as defined or preferaby defined below.
  • R 5 and R 5 together with the carbon atom to which they are bound form a heterocycle selected from the group consisting of oxirane, aziridine, thiirane, oxetane, azetidine, thiethane, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl and 3- tetrahydrothienyl, wherein the heterocycle is unsubstituted or carries one, two, three or four independently selected substituents R 51 as defined or preferaby defined below.
  • R 5 and R 6 together with the carbon atom to which they are bound form an oxirane which is unsubstituted or carries one, two, three or four independently selected substituents R 51 .
  • R 5 and R 6 together with the carbon atom to which they are bound form an oxetane which is unsubstituted or carries one, two, three or four independently selected substituents R 51 as defined or preferaby defined below.
  • R 51 according to the invention in each case is independently selected from the group consisting of halogen, CN, N0 2 , OH, SH, NH 2 , Ci-C 6 -alkyl, d-C 6 -haloalkyl,
  • R 51 in each case preferably is halogen, CN, NO2, OH, SH, NH2, d-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, Ci-C 6 -alkylthio, Ci-C 6 - haloalkylthio or Ci-C4-alkoxy-Ci-C4-alkyl.
  • R 51 in each case is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy.
  • R 51 is halogen, CN or Ci-C6-alkyl.
  • R 51 in each case is halogen, in particular fluorine.
  • R 51 in each case is chlorine.
  • R 51 in each case is Ci-C6-alkyl, in particular methyl.
  • R 7 accding to the invention is hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy.
  • R 7 is hydrogen, halogen, CN or Ci-C6-alkyl.
  • R 7 is hydrogen.
  • R 7 is halogen, in particular fluorine or chlorine.
  • Y is a direct bond, -O- or -CH2-.
  • R YN , R Y , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 and R Y8 according to the invention are
  • R YN , R Y , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 and R Y8 are independently selected from the group consisting of hydrogen and halogen, in particular fluorine or chlorine.
  • R YN , R Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 and R Y8 are independently selected from the group consisting of hydrogen and Ci-C 4 -alkyl, in particular methyl or ethyl.
  • R YN , R Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 and R Y8 are independently selected from the group consisting of hydrogen and Ci-C4-alkoxy, in particular methoxy and ethoxy.
  • R YN , R Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 and R Y8 are independently selected from hydrogen or CN.
  • R YN , R Y , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 and R Y8 are independently selected from hydrogen or OH.
  • Z according to the invention is phenyl or a five- or six-membered heteroaryl, wherein the aromatic moiety is unsubstituted or carries one, two, three or four independently selected radicals R L as defined or preferably defined below.
  • Z is phenyl or a five- or six-membered heteroaryl selected from the group consisting of pyrimidin-2-yl, pyrimidin-3-yl, pyrimidin-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol- 4-yl, isothiazol-5-yl, pyrazin-2-yl, pyridazin-3-yl, 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl; and wherein the phenyl or heteroaryl carry one, two, three or four independently selected radicals R L as defined or preferably defined below.
  • Z is phenyl which is unsubstituted or carries one, two, three or four independently selected radicals R L as defined or preferably defined below.
  • Z is a five- or six-membered heteroaryl which is unsubstituted or carries one, two, three or four independently selected radicals R L as defined or preferably defined below.
  • Z is a six-membered heteroaryl which is
  • Z is selected from the group consisting of pyrimidin-2-yl, pyrimidin-3-yl, pyrimidin-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiazol-2-yl, pyrazin-2-yl, pyridazin-3-yl, 1 ,3,5-triazin-2-yl, and 1 ,2,4-triazin- 3-yl; preferably Z is pyrimidin-2-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl and thiazol-2-yl, which are unsubstituted or carry one, two, three or four independently selected radicals R L as defined or preferably defined below.
  • Z is substituted by exactly one radical R L as defined or preferably defined below.
  • Z is substituted by two independently selected radicals R L as defined or preferably defined below.
  • Z is substituted by three independently selected radicals R L as defined or preferably defined below.
  • Z is substituted by four independently selected radicals R L as defined or preferably defined below.
  • R L is independently selected from the group consisting of halogen, CN , N0 2 , OH , SH , d-Ce-alkyl, d-Ce-hydroxyalkyl, Ci-Ce- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-drhaloalkylthio, C1-C6- alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, Ci-C 4 - alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy, C 2 -C6-alkenyl, C 2 -C6-alkynyl,
  • R L is independently selected from the group consisting of halogen, CN , OH , Ci-C6-alkyl, Ci-drhaloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.
  • R L is independently selected from the group consisting of halogen, in particular fluorine or chlorine.
  • R L is independently selected from the group consisting of Ci-C6-haloalkyl, in particular CF 3 or CH F 2 .
  • R L is CN .
  • R L is independently selected from the group consisting of 2-F, 3-F, 4-F, 2-CI, 3-CI, 4-CI, 2-CF 3 , 3-CF 3 , 4-CF 3 , 2,4-F 2 , 2,4-CI 2 , 2,6-CI 2 , 2-CN, 3-CN, 4- CN, 2-F-4-CN and 2-CI-4-CN.
  • m is 0 or 1. In a preferred embodiment m is 1 . In another preferred embodiment m is 0.
  • the group Z-Y- is attached to the phenyl ring in para-position with respect to the triazole bearing residue.
  • the group Z-Y- is attached to the phenyl ring in metha-position with respect to the triazole bearing moiety.
  • R 1 , R 2 , D, X, Y and the position of Y with regards to the triazole bearing residue in each case are one of the following combinations of lines A-1 to A-2688 in table A.
  • A-136 CH 2 SH OH -0- para
  • A-160 CH 2 S-allyl OH -0- para
  • A-184 CH 2 SCN OH -0- para
  • A-256 CH 2 S-allyl methoxy -0- para
  • A-328 CH 2 SH ethoxy -0- para
  • A-472 CH 2 SCN O-allyl -0- para
  • A-496 CH 2 H O-propargyl -0- para
  • A-520 CH 2 SH O-propargyl -0- para
  • A-544 CH 2 S-allyl O-propargyl -0- para
  • A-616 CH 2 SH O-benzyl -0- para
  • A-832 CH 2 S-allyl OH -0- meta
  • A-856 CH 2 SCN OH -0- meta
  • A-880 CH 2 H methoxy -0- meta
  • A-904 CH 2 SH methoxy -0- meta
  • A-976 CH 2 H ethoxy -0- meta
  • A-1048 CH 2 SCN ethoxy -0- meta
  • A-1288 CH 2 SH O-benzyl -0- meta
  • A-1312 CH 2 S-allyl O-benzyl -0- meta
  • A-1360 CH 2 H CN direct bond para
  • A-1384 CH 2 SH CN direct bond para
  • A-1552 CH 2 H methoxy direct bond para
  • A-1576 CH 2 SH methoxy direct bond para
  • A-1600 CH 2 S-allyl methoxy direct bond para
  • A-1624 CH 2 SCN methoxy direct bond para
  • A-1696 CH 2 S-allyl ethoxy direct bond para
  • A-1768 CH 2 SH O-allyl direct bond para
  • A-2008 CH 2 SCN O-benzyl direct bond para
  • A-2032 CH 2 H CN direct bond meta

Abstract

La présente invention concerne des composés imidazolyl et triazolyl fongicides (I), des compositions agrochimiques les comprenant, leur utilisation et des procédés permettant de combattre des champignons phytopathogènes. La présente invention concerne également des graines traitées par au moins un desdits composés. L'invention concerne en outre des procédés pour la préparation des composés de formule I ainsi que des intermédiaires spécifiques qui sont obtenus pendant la séquence de réaction.
PCT/EP2013/075616 2012-12-19 2013-12-05 Composés imidazolyl et triazolyl fongicides WO2014095381A1 (fr)

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EP2924027A1 (fr) * 2014-03-28 2015-09-30 Basf Se Composés fongicides de [1,2,4]triazole substitué et d'imidazole substitué
CN107188829A (zh) * 2017-05-17 2017-09-22 中节能万润股份有限公司 一种以全氟代亚苯基为核心的oled光电材料及其应用
US9815798B2 (en) 2014-03-26 2017-11-14 Basf Se Substituted [1,2,4]triazole and imidazole compounds as fungicides
US10053432B2 (en) 2013-12-12 2018-08-21 Basf Se Substituted [1,2,4]triazole and imidazole compounds
US10112913B2 (en) 2014-05-13 2018-10-30 Basf Se Substituted [1,2,4]triazole and imidazole compounds as fungicides
US10450279B2 (en) 2014-06-06 2019-10-22 Basf Se Substituted [1,2,4]triazole compounds

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