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WO2008037607A1 - Composés hétérocycliques à teneur en groupe carbonyle et leur utilisation pour lutter contre des champignons phytopathogènes - Google Patents

Composés hétérocycliques à teneur en groupe carbonyle et leur utilisation pour lutter contre des champignons phytopathogènes Download PDF

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Publication number
WO2008037607A1
WO2008037607A1 PCT/EP2007/059720 EP2007059720W WO2008037607A1 WO 2008037607 A1 WO2008037607 A1 WO 2008037607A1 EP 2007059720 W EP2007059720 W EP 2007059720W WO 2008037607 A1 WO2008037607 A1 WO 2008037607A1
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compounds
formulas
combination
row
alkyl
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PCT/EP2007/059720
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German (de)
English (en)
Inventor
Jochen Dietz
Thomas Grote
Wassilios Grammenos
Bernd Müller
Jan Klaas Lohmann
Jens Renner
Sarah Ulmschneider
Frank Schieweck
Marianna Vrettou
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Basf Se
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Publication of WO2008037607A1 publication Critical patent/WO2008037607A1/fr

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    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • a bond represented by is a single bond or a double bond wherein either the bond between X and C-8 or the bond between C-8 and Y is a single bond and the other one is a double bond and in which the variables have the following meanings:
  • X is CR 1 R 2 or NR 3 when between the carbon atom at ring position 8 and X is a single bond, or CR 1 when between the carbon atom in ring position 8 and X is a double bond; where R 1 , R 2 and R 3 are
  • R 1 is hydrogen, halogen, hydroxy, cyano, Ci-Ci2-alkyl, Ci-Ci2 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -alkyl kinyl, C 3 - C 8 haloalkynyl, C 8 - alkoxy, Ci-C8-haloalkoxy, C3-C8 cycloalkyl, C3-C8-halocycloalkyl, C3-C 8 - cycloalkenyl, C 3 -C 8 halocycloalkenyl, C - C 8 -alkylthio, C 1 -C 8 -alkylsulfinyl, d-
  • R 2 is hydrogen, halogen, cyano, Ci-Ci 2 -alkyl, C 2 -haloalkyl, C 2 -C 8 -
  • R a is halogen, cyano, nitro, hydroxy, carboxyl, amino, d-Cs-alkyl, Ci-C 8 - haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, Cs-C 8 -
  • R a where the aliphatic, alicyclic and aromatic groups in R a its part one, two or three identical or different groups R b may carry:
  • R b is halogen, cyano, nitro, hydroxy, carboxyl, mercapto, amino, formyl, aminocarbonyl, aminothiocarbonyl, C 1 -C 8 -alkyl, C 1 -C 5 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 4 -C 10 -alkadienyl, C 2 -C 8 -
  • R 4 is hydrogen, halogen, cyano, Ci -C 8 -alkyl, C 8 haloalkyl, C 8 -
  • R 5 is hydrogen, Ci-C 8 -alkyl, C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 - haloalkenyl, C 2 -C 8 -alkyl kinyl, C3-C8 haloalkynyl , C3-C8 cycloalkyl, C3-C 8 - halocycloalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl;
  • n O, 1 or 2;
  • a 1 is hydrogen, hydroxy, Ci-C 8 -alkyl, C-8 alkoxy, Ci-C8-halo-alkoxy, Ci-C8-haloalkyl, amino, Ci-C8-alkylamino or di-CrC 8 alkylamino means One of said at A 1 groups or NR 8 R 9 A 2, C2-C8-alkenyl, C 2 - Cs haloalkenyl, C2-C8-alkynyl, C3-C8 haloalkynyl, C 2 -C 8 - alkenyloxy, C2 C8 haloalkenyloxy, C2-C8-alkynyloxy, C3-C8 haloalkynyloxy, C3-C8 cycloalkyl, C3-C8-halocycloalkyl, C3-C8-halocycloalkyl, C3-C8-halocycloalkyl, C3-C8-halocyclo
  • Cycloalkoxy, C3-C 8 or C -Halogencycloalkoxy means 8 alkylthio
  • W contains at least one substituent L ortho to the point of attachment of W to the backbone of formula I, when W is phenyl, R 3 is hydrogen
  • a hydrogen atom is replaced by a substituent L as defined above, and Z is oxygen;
  • W contains at least one substituent L when W is furyl, R 3 is hydrogen
  • a hydrogen atom is replaced by a substituent L as defined in claim 1, and Z is oxygen;
  • W contains at least one substituent L, when W is phenyl, R 3 is hydrogen or C 1 -C 12 -alkyl,
  • W contains at least two substituents L, at least one of which is ortho to the point of attachment of W to the skeleton of formula I, when W is phenyl, R 1 and R 5 are hydrogen,
  • W contains at least one substituent L, when W is phenyl, R 1 is C 1 -C 12 -alkyl or phenyl, R 5 is hydrogen,
  • W contains at least one substituent L when R 1 is phenyl, R 5 is hydrogen,
  • condition b) already occurs when R 3 is hydrogen, R 4 is not hydrogen,
  • condition c) already occurs when W is a heteroaromatic, R 3 is hydrogen, R 4 is C 3 -C 8 -cycloalkyl,
  • R 4 is generally not equal to hydrogen.
  • condition f) already occurs when W is a heteroaromatic, R 1 and R 5 are hydrogen,
  • condition g) already occurs when W is phenyl, R 1 is not hydrogen, R 5 is hydrogen, stands for and Z means oxygen.
  • condition h) already occurs when R 1 is not hydrogen, R 5 is hydrogen,
  • the present invention relates to such compounds thereof, wherein R 4 is not hydrogen. Further preferably, the present invention relates to such compounds thereof, wherein R 1 is not hydrogen. Also preferably, the present invention relates to such compounds thereof, wherein R 3 is not hydrogen. Also preferably, the present invention relates to such compounds thereof, wherein R 5 is not hydrogen. Further preferably, the present invention relates to such compounds thereof, wherein W contains at least one substituent L. Further preferably, the present invention relates to such compounds thereof, wherein W contains at least one substituent L in ortho position to the point of attachment of W with the backbone of formula I. Further preferably, the present invention relates to wherein the five-membered heteroaromatic ring
  • the present invention relates to processes and intermediates for the preparation of the compounds according to the invention and agents comprising compounds of the formula I.
  • the object of the present invention is to provide compounds with at least comparable action, preferably improved action and / or broadened spectrum of action.
  • the compounds defined above and the use of the compounds of the formula I have been found for the control of harmful fungi. Furthermore, methods and intermediates for their preparation, agents containing them have been disclosed and methods for controlling harmful fungi using the compounds I found.
  • the compounds of the formula I can have one or more centers of chirality and are then present as enantiomer or diastereomer mixtures.
  • the invention relates to both the pure enantiomers or diastereomers or rotamers and mixtures thereof.
  • Suitable compounds of formula I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • the compounds of the invention may be present in various crystal modifications, which are also the subject of the present invention.
  • suitable agriculturally acceptable salts are, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the fungicidal action of the compounds according to the invention.
  • the ions of the alkali metals preferably sodium or potassium, the alkaline earth metals, preferably calcium, magnesium or barium, the transition metals, preferably manganese, copper, zinc or iron, or the ammonium ion, the desired one to four (Ci-C4 ) -Alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri- (C 1 -C 4) -alkylsulfonium and sulfoxonium ions, preferably tri (Ci -C4) -alkylsulfoxonium, into consideration.
  • the alkali metals preferably sodium or potassium
  • the alkaline earth metals preferably calcium, magnesium or barium
  • the transition metals preferably manganes
  • Anions of advantageously usable acid addition salts are, for example, chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of (C 1 -C 4) -alkanoic acids, preferably formate , Acetate, propionate and butyrate. They can be obtained by reaction of the compounds of the formula I according to the invention with an acid of the corresponding anion, preferably
  • Hydrochloric acid hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • A is carbon
  • B is nitrogen
  • R 3 is Ci-Ci2-alkyl, in particular Ci-Ce-Al kyl, preferably Ci-C6-alkyl and especially methyl, ethyl, n-propyl or i-propyl, beispielswei Compounds Ib-1
  • Compounds Ib-1, wherein Z is oxygen can be obtained by condensation of ⁇ -keto esters of the formula II wherein W and R 4 are as defined herein and R 'is C 1 -C 4 alkyl, especially methyl or ethyl, with the corresponding amino-substituted five-membered hetero-compounds wherein
  • N-N H are reacted to compound lb-1 (see also Reiter, J; Pong ⁇ , L; Somorai, T .;
  • the five-membered heteroaromatic is exemplified as imidazole, wherein one or two hydrogen atoms may be replaced by same or different substituents L (represented by “(L) n ", where "n” may also be “0"), such as suitable reduction conditions are, for example, palladium on carbon with hydrogen (1 atm) and an alcoholic solvent (eg ethanol).
  • suitable reduction conditions are, for example, palladium on carbon with hydrogen (1 atm) and an alcoholic solvent (eg ethanol).
  • a base such as, for example, Mg (OEt) 2, LiNhb, LiHMDS, KO 1 Bu and the like, as described, for example, in Wiles, C .; Watts, P .; Haswell, S .; Pombo-Villar, E., Tetrahedron Lett. 2002, 43, 2945.
  • a base such as, for example, Mg (OEt) 2, LiNhb, LiHMDS, KO 1 Bu and the like, as described, for example, in Wiles, C .; Watts, P .; Haswell, S .; Pombo-Villar, E., Tetrahedron Lett. 2002, 43, 2945.
  • a base such as, for example, Mg (OEt) 2, LiNhb, LiHMDS, KO 1 Bu and the like, as described, for example, in Wiles, C .; Watts, P .; Haswell, S .; Pombo-Villar, E., Tetrahedron Lett. 2002,
  • one or two hydrogen atoms may be replaced by identical or different substituents L. (See also Abdulla, R., Tetrahedron Letters 1976, 7, 521).
  • N-amino heterocycles for example imidazoles of the formula IIIa, where "(L) n " has the abovementioned meaning, with ⁇ -keto esters of the formula II (see above) (see also Brueckner, R., Lattauer, J., Viallefont, P., Liebigs Annalen der Chemie 1979, 5, 639).
  • the synthesis of the N-amino heterocycles used is described, for example, in Beyer, H .; Hetzheim, A .; Honeck, H .; Ling, D .; PyI, T., Chemische Berichte 1968, 101, 3151.
  • Heterocycles having an N-amino function are also commercially available or can be prepared by standard methods. Inventive compounds of the formula Id
  • the variables have the meanings or preferred meanings given herein.
  • ized triazole S-33 can be carried out by reacting the corresponding -S- (C 1 -C 4) -alkyl derivative, in particular the -S-methyl derivative, as shown by way of example below, of the formula VII
  • V l " is reacted with hydrazine with an optionally substituted orthoester, followed by a cyclization takes place (see also WO 2003/044021).
  • Chloropyrimidines of the formula VIII are known to the person skilled in the art or are described in, for example, WO 2005/047279 and WO 2002/058695.
  • the reaction mixtures are worked up in the usual way, e.g. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products.
  • the intermediate and end products are z.T. in the form of colorless or slightly brownish, viscous oils which are freed from volatile constituents under reduced pressure and at moderately elevated temperature. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6, 8 or 12 carbon atoms, for example C 1 -C 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1 Methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- Dimethylbutyl, 1-ethylbutyl, 2-e
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2, 4, 6, 8 or 12 carbon atoms (as mentioned above), wherein in these groups partially or completely replaces the hydrogen atoms by halogen atoms as mentioned above in particular C 1 -C 2 -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloro
  • Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 6 or 8 carbon atoms and one or two double bonds in any position, e.g. C2-C6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1 Methyl 2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3 Methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl 3-butenyl, 1, 1-dimethyl-2-propen
  • Haloalkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 8 carbon atoms and one or two double bonds in any position (as mentioned above), wherein in these groups, the hydrogen atoms partially or completely replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine could be;
  • Alkynyl straight-chain or branched hydrocarbon groups having 2 to 4, 6 or 8 carbon atoms and one or two triple bonds in any position, for example C 2 -C 6 alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl , 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2 Methyl 3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5 Hexynyl, 1-methyl-2-pentyny
  • Cycloalkyl mono- or bicyclic saturated hydrocarbon groups having 3 to 6 or 8 carbon ring members, e.g. Cs-Cs-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
  • heterocyclyl in particular: five- or six-membered saturated or partially unsaturated heterocycle (hereinafter also heterocyclyl) containing one, two, three or four heteroatoms from the group oxygen, nitrogen and sulfur as ring members: for example monocyclic saturated or partially unsaturated heterocycles, containing in addition Carbon ring members one to three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, eg 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-pyrazolid
  • - seven-membered saturated or partially unsaturated heterocycle containing one, two, three or four heteroatoms from the group oxygen, nitrogen and sulfur as ring members e.g. mono- and bicyclic heterocycles having 7 ring members, containing in addition to carbon ring members one to three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example tetra- and Hexahydroazepinyl as
  • hexahydrooxepinyl such as 2,3,4,5-tetrahydro [1 H] oxepin-2, -3, -4, -5, -6 or -7-yl, 2,3,4, 7-tetrahydro [1 H] oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro [1 H] oxepin 2-, -3-, -A-, -5-, -6- or -7-yl, hexahydroazepine-1, -2-, -3- or -4-yl, tetra- and hexahydro-1, 3 diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-o
  • Alkylene divalent unbranched chains of preferably 1 to 6, in particular 3 to 5 CH 2 groups, for example 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 ;
  • Oxyalkylene divalent unbranched chains of preferably 2 to 4 CH 2 groups, wherein a valence is bonded to the skeleton via an oxygen atom, for example OCH 2 CH 2 , OCH 2 CH 2 CH 2 and OCH 2 CH 2 CH 2 CH 2 ;
  • Oxyalkylenoxy divalent unbranched chains of preferably 1 to 3 CH 2 groups, both valences being bonded to the skeleton via an oxygen atom, for example OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O;
  • Aryl aromatic hydrocarbon cycles, in particular having 6 to 14, preferably 6 to 10 carbon atoms.
  • Preferred according to the invention are phenyl (C ⁇ Hs) and naphthyl (Ci 0 H 7 -).
  • X in the compounds of the formula I is CR 1 R 2 or NR 3 if between the carbon atom at ring position 8 and X is a single bond, or CR 1 , if between the carbon atom in ring position 8 and X is a double bond.
  • Y is CR 4 or N when there is a double bond between the carbon at ring position 8 and Y, or NR 5 when there is a single bond between the carbon in ring position 8 and Y.
  • the present invention relates to compounds of the formula Ia
  • the present invention relates to compounds of formula Ib
  • the present invention relates to compounds of the formula Ic
  • the present invention relates to compounds of formula Id
  • the present invention relates to compounds of the formula Ie
  • R 1 in the compounds according to the invention or used according to the invention does not mean hydrogen according to one embodiment.
  • R 1 C T-Ci2 alkyl, Ci-Ci2 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 -alkyl kinyl, Ci-Ci2 hydroxyalkyl, d- C 4 is alkoxyalkyl, C 3 - C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, phenyl, naphthyl, a five- or six-membered saturated, partially unsaturated or an aromatic heterocycle containing Two, three or four heteroatoms from the group O, N and S.
  • R 1 may carry one, two, three or four identical or different groups R a , wherein R a as defined elsewhere herein.
  • R 1 Ci -Ce-Al kyl, d-Cs-haloalkyl, C 3 -C 6 represents - cycloalkyl-Ci-C4-alkyl, benzyl, halophenyl-Ci-C4-alkyl, Ci-C 4 - alkylphenyl-C 4 - alkyl, Ci-C4-alkoxyphenyl-Ci-C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 8 - cycloalkyl.
  • R 1 is methyl, ethyl, propyl, isobutyl, n-butyl, t-butyl, CH 2 CH (CHs) 2 , CH (CH 3 ) CH 2 (CH 3 ), n-pentyl, CH ( CH 3 ) (CH 2 ) 2 CH 3 , CH 2 CH (CH 3 ) CH 2 CH 3 , CH 2 CH 2 CH (CHs) 2 , CH (CH 3 ) CH (CHS) 2 , CH 2 C (CHS) 3 , C (CHs) 2 CH 2 CH 3 , CH (CH 2 CHs) 2 , CH 2 (CHz) 4 CH 3 , CH (CH 3 ) (CH 2 ) s CH 3 , CH 2 CH (CH 3 ) (CH 2 ) 2 CHs, CH 2 CH 2 CH (CHS) CH 2 CHS, CH 2 (CH 2 ) 2 CH (CH 3 ) 2 , CH 2 CH (CHS) CH 2 CHS, CH 2 (CH 2 ) 2 CH (CH
  • R 1 is Ci-Ci 2 -alkyl, wherein the alkyl group is preferably branched, phenyl, or 5- or six-membered heteroaryl, containing one, two, or three hetero atoms from the group O, N and S, said R 1 may be substituted by one, two or three halogen, hydroxy and / or C 1 -C 4 -alkoxy.
  • R 2 in the compounds according to the invention or used according to the invention does not mean hydrogen according to one embodiment.
  • R 2 is hydrogen, wherein according to a specific embodiment, R 1 is not hydrogen at the same time.
  • neither R 1 nor R 2 is hydrogen.
  • R 2 is Ci-Ci 2 -alkyl, preferably C 1 -C 6 -alkyl or by one, two, three or four identical or different groups R a , as defined herein, substituted C 1 -C 12 -alkyl or C 1 -C 6 -alkyl.
  • R 3 in the compounds according to the invention or used according to the invention is not hydrogen.
  • R 3 has the meanings as defined for R 1 herein.
  • R 3 particularly preferably stands for C 1 -C 12 -alkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, phenyl or halophenyl.
  • R 3 is methyl, ethyl, propyl, isobutyl, n-butyl, CH 2 CH (CHs) 2 , CH (CH 3 ) CH 2 (CH 3 ), n -pentyl, CH (CH 3 ) (CH 2 () 2 CH 3, CH 2 CH CH 3) CH 2 CH 3, CH 2 CH 2 CH (CHs) 2, CH (CH 3) CH (CHs) 2, CH 2 C (CHs) 3, C (CHs) 2 CH 2 CH 3 , CH (CH 2 CHs) 2 , CH 2 (CH 2 ) 4 CH 3 , CH (CH 3 ) (CH 2 ) 3 CH 3 , CH 2 CH (CH 3 ) (CH 2 ) 2 CHs , CH 2 CH 2 CH (CH 3 ) CH 2 CHS, CH 2 (CH 2 ) 2 CH (CH 3 ) 2 , C (CHs) 2 (CH 2 ) 2 CH 3 , CH 2 C (CHs) 2 CH 2 CH 3 , CH 2 CH 2 C (CH (CHs
  • R 4 in the compounds according to the invention or used according to the invention does not mean hydrogen according to one embodiment.
  • R 4 is halogen, cyano, Ci-C 6 alkyl, Ci-C 6 haloalkyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, Cs-C 6 cycloalkyl or C 3 -C 6 halocycloalkyl ,
  • R 5 in the compounds according to the invention or used according to the invention does not mean hydrogen according to one embodiment.
  • Z in the compounds of the formula I is oxygen
  • Z in the compounds of the formula I (or in one of the formulas Ia to Ie) is sulfur.
  • R 7 is C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl or C 1 -C 4 -alkoxy.
  • W is in each case unsubstituted or substituted by one, two, three, four or five substituents L, as defined herein, unless otherwise stated:
  • W is six-, seven-, eight-, nine- or ten-membered aryl, such as e.g. Phenyl or naphthyl.
  • W is unsubstituted or substituted phenyl.
  • the phenyl group When the phenyl group is substituted, it preferably has one, two, three or four substituents L, which may be the same or different.
  • L is halogen, cyano, nitro, hydroxy, cyanato (OCN), (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -
  • Haloalkyl (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -Cs) -alkynyl, (C 2 -C 8 ) -haloalkynyl, (C 4 -C 10) -alkadienyl, (C4-Cio) -Halogenalkadienyl, (Ci-Cs) alkoxy, (Ci-Cs) haloalkoxy, (C 2 -C 8) alkenyloxy, (C 2 -C 8) haloalkenyloxy, (C 2 -C 8) - alkynyloxy, (C 2 -C 8) haloalkynyloxy, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) cycloalkyl-halo, (C3
  • n O, 1 or 2;
  • a 1 is hydrogen, hydroxy, (C 1 -C 5) -alkyl, (C 1 -C 8 ) -haloalkyl, amino, (C 1 -C 8 ) -
  • a 2 is one of the groups mentioned at A 1 or (C 2 -Cs) -alkenyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -Cs) -alkynyl, (C 2 -C 8 ) - haloalkynyl, (Ci-Cs) -alkoxy, (Ci-C 8) - haloalkoxy, (C 2 -C 8) alkenyloxy, (C 2 -C 8) haloalkenyloxy, (C 2 -C 8) - alkynyloxy, ( C 2 -C 8) haloalkynyloxy, (C3-C8) cycloalkoxy, (C 3 -C 8) cycloalkoxy-halo group;
  • R 5 , R 6 independently of one another are hydrogen, (C 1 -C 5 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -Cs ) Alkynyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -halocycloalkyl, (C 3 -C 8 ) -cycloalkenyl or (C 3 -C 8 ) - halocycloalkenyl, where the aliphatic groups of the radical definitions of L can in turn carry one to four identical or different groups R L :
  • R L is halogen, cyano, (C 1 -C 8 ) -alkoxy, (C 2 -C 8 ) -alkenyloxy, (C 2 -C 8 ) -alkynyloxy, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -Cycloalkenyl, (C 3 -C 8 ) -cycloalkyloxy, (C 3 -C 8 ) -cycloalkenyloxy,
  • L is in each case selected from halogen, cyano, nitro, (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 4 ) -cycloalkoxy, -COO (C 1 -C 4 ), -CONH 2 or -CSNH 2 ; more preferably L is methyl, ethyl, isopropyl, cyclopropyl, fluoro, chloro, bromo, -COOCH 3 and CN.
  • W has one, two or three identical or different substituents L selected from halogen, cyano, nitro, amino, (C 1 -C 6) alkylamino, di (C 1 -C 6) alkylamino , (Ci-Ce) alkyl, (Ci-C 6) -haloalkyl, (Ci-Ce) alkoxy, (Ci-C 6) -haloalkoxy, NH (CO) - (Ci-C 6) alkyl, C (S) A 2 and C (O) A 2 , wherein A 2 has the abovementioned meanings and preferably (C 1 -C 4 ) -alkoxy, NH 2 , (C 1 -C 4 ) -alkylamino or di- (C 1 -C 4 -alkyl) 4 ) -alkylamino.
  • substituents L selected from halogen, cyano, nitro, amino, (C 1 -C 6) alky
  • each L is selected from fluorine, chlorine, bromine, cyano, nitro, (d- C4) alkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy and (Ci-C 4) Alkylcarbonyl, particularly preferably fluorine, chlorine, (C 1 -C 2 ) -alkyl, such as methyl or ethyl, (C 1 -C 2 ) -fluoroalkyl, such as trifluoroalkyl, (C 1 -C 2 ) -alkoxy, such as methoxy and (C 1 -C 2 ) Alkoxycarbonyl such as methoxycarbonyl.
  • W is phenyl which has at least one substituent L.
  • W is phenyl which has at least two substituents L.
  • at least one substituent L is in each case ortho to the point of attachment of W to the skeleton of the formula I. It may be particularly preferable if the ortho-position L is fluorine, chlorine, (Ci-C 2 ) - Alkyl such as methyl or ethyl, (Ci-C 2 ) - fluoroalkyl such as trifluoroalkyl or (Ci-C 2 ) alkoxy such as methoxy.
  • W stands for a substituted phenyl group A
  • L 1 is fluorine, chlorine, CH 3 or CF 3 ;
  • L 2 , L 4 are independently hydrogen, fluorine or methoxy;
  • L 3 is hydrogen, fluorine, chlorine, CN, CH 3 , OCH 3 , NH 2 , NHCH 3 , N (CH 2 ) 2 , C (O) NH 2 ,
  • L 5 is hydrogen, fluorine, chlorine or CH 3 .
  • W stands for one of the following substituents: 2-fluoro-6-chlorophenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 2-fluoro-6-methylphenyl, 2,4, 6-trifluorophenyl, 2,6-difluoro-4-methoxyphenyl, 2-chloro-4-methoxyphenyl, pentafluorophenyl, 2-methyl-4-fluorophenyl, 2-trifluoromethylphenyl, 2-methoxy-6-fluorophenyl, 2-chlorophenyl, 2-fluorophenyl, 2,4-difluorophenyl, 2-fluoro-4-chlorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5-fluorophenyl, 2,3-difluorophenyl, 2,5-difluorophenyl, 2,3, 4-trifluorophenyl, 2-methyl
  • W is phenyl which is unsubstituted or substituted with one, two or three substituents L independently selected from fluoro, chloro, bromo, cyano, nitro, formyl, methyl, ethyl, n -propyl, i -propyl, n Butyl, i-butyl, s-butyl, t-butyl, allyl, propargyl, methoxy, ethoxy, n-propoxy, i-propoxy, methylthio, ethylthio, n-propylthio, i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl , Ethylsulfonyl, allyloxy, propargyloxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluoroch
  • W contains at least one substituent L selected from 1,3-linked 1,3-propanediyl, methylenedioxy (-O-CH 2 -O-) and 1,2-ethylenedioxy (-O-CH 2 -CH 2 -O-), which radicals may in turn carry one or more identical or different substituents which are independently selected from fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl and trifluoromethyl.
  • substituent L selected from 1,3-linked 1,3-propanediyl, methylenedioxy (-O-CH 2 -O-) and 1,2-ethylenedioxy (-O-CH 2 -CH 2 -O-), which radicals may in turn carry one or more identical or different substituents which are independently selected from fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl and trifluoromethyl.
  • W is phenyl which contains one, two or three substituents in 2, 4 and / or 6-position, which are independently selected from the L mentioned herein as preferred, in particular independently selected from fluorine and chlorine ,
  • W is 2,4-disubstituted, 2,4-disubstituted, phenyl, 2-substituted phenyl or 2,4,6-trisubstituted phenyl with substituents L which are selected independently the group fluorine, chlorine, bromine, Cyano, nitro, OH, mercapto, methyl, ethyl, methoxy, methylthio, hydroxyiminomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, carboxy and carboxymethyl.
  • substituents L which are selected independently the group fluorine, chlorine, bromine, Cyano, nitro, OH, mercapto, methyl, ethyl, methoxy, methylthio, hydroxyiminomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, carboxy and carboxymethyl.
  • W is 2-trifluoromethylphenyl, 2-chloro-5-nitrophenyl or 2-chloro-4-methoxyphenyl.
  • W is a five-, six-, seven-, eight-, nine- or ten-membered aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S.
  • W stands wherein an unsubstituted or substituted five- or six-membered aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S.
  • the heteroaromatic may each (also in the following described embodiments) via a ring carbon atom or via a ring nitrogen atom be bound to the skeleton of the formula I.
  • Each L is independently selected from the meanings given above for L unless otherwise specified.
  • W contains at least one ring nitrogen atom. It may be preferred that the binding site of W to the skeleton of the formula I is in the ortho position to the at least one nitrogen atom.
  • W is an unsubstituted or substituted 5-membered heteroaromatic radical containing one, two, three or four heteroatoms from the group oxygen, nitrogen and sulfur, where W is unsubstituted or substituted by one, two, three or four identical or different substituents L.
  • the five-membered heteroaromatic radical is nitrogen-containing.
  • the optionally substituted five-membered heteroaryl radical may each be bonded to the skeleton of the formula I via a ring carbon atom or via a ring nitrogen atom.
  • the heteroaryl (W) has at least one substituent which is in the ortho position to the point of attachment to the skeleton to which W is bonded. It may be particularly preferred if the ortho-permanent L is fluorine, chlorine, (C 1 -C 2) -alkyl, such as methyl or ethyl, (C 1 -C 2) -fluoroalkyl, such as trifluoroalkyl or (C 1 -C 2) -alkoxy, such as methoxy ,
  • L when L is bonded to a ring nitrogen of W, it is particularly preferred that L in each case independently be
  • L is particularly preferably (C 1 -C 6) -alkyl or (C 1 -C 6) -haloalkyl, more preferably (C 1 -C 4) -alkyl or (C 1 -C 4) -haloalkyl, in particular methyl or ethyl, particularly preferably methyl ,
  • L is independently:
  • a 1 is amino, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (Ci-C 6) alkylamino or di- (CrC 6) - alkylamino group;
  • n O, 1 or 2;
  • a 2 is one of the groups mentioned at A 1 or (C 2 -Cs) -alkenyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -haloalkynyl, (Ci-Ce) alkoxy, (Ci-C 6) -haloalkoxy, (C 2 - C 8) alkenyloxy, (C 2 -C 8) haloalkenyloxy, (C 2 -C 8) -alkynyloxy, (C 2 -C 8 ) -haloalkynyloxy, (C 3 -C 8) -cycloalkoxy or (C 3 -C 8) -halocycloxy;
  • R 5 , R 6 are independently hydrogen or (Ci-Ce) alkyl, (Ci-C6) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -Cs) -alkynyl, (C 2 -C 8) -haloalkynyl, (C 3 -C 8 -) - cycloalkyl, (C 3 -C 8 -) - halocycloalkyl, (C 3 -C 8) cycloalkenyl or (C 3 -C 8) halocycloalkenyl mean.
  • L when it is bonded to a ring nitrogen of W, in each case particularly preferably (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, -COO (C 1 -C 4 ), -CONH 2 or -CSNH 2 , in particular methyl, ethyl, isopropyl, cyclopropyl or -COOCH 3.
  • W may contain one to four, or one to three, or one or two identical or different substituents L, preferably identical substituents L. More preferably, W contains one or two substituents L, more preferably one or two identical substituents L. Furthermore, W preferably has two identical substituents L.
  • W is thiazolyl, imidazolyl, pyrazolyl, 1, 2,4-triazolyl or 1,2,3-triazolyl and especially pyrazol-1-yl, where the abovementioned radicals are unsubstituted or 1, Have 2 or 3 substituents L.
  • W is in particular one of the radicals Het-1 to Het-31 given below:
  • L 1 , L 2 , and L 3 independently of one another represent hydrogen or have one of the meanings given for L.
  • the radicals L 1 , L 2 and L 3 are independently selected from hydrogen, halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, especially C 1 -C 2 -fluoroalkyl, C 1 -C 4 -alkoxy and
  • L 1 , L 2 and L 3 are independently selected from hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl.
  • Het-1 are 3,5-dimethylpyrazol-1-yl, 3,5-diisopropylpyrazol-1-yl, 3-methyl-5-isopropyl-pyrazol-1-yl, 3-isopropyl-5-methyl-pyrazole 1-yl, 3-ethyl-5-methyl-pyrazol-1-yl, 3,4,5-trimethyl-pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-methyl-pyrazole-1 yl, 3-methyl-4-chloro-pyrazol-1-yl, 3-trifluoromethylpyrazol-1-yl, 3-trifluoromethyl-5-methoxypyrazol-1-yl, 3-trifluoromethyl-5-methyl-pyrazole 1-yl, 3-methyl-5-methoxypyrazol-1-yl, 3,5-dichloro-4-methyl-pyrazol-1-yl, 3,5-dimethyl-4-chloro-pyrazol-1-yl, 3, 5-Ditrifluoromethyl-pyrazo
  • Het-2 are 1, 3-dimethylpyrazol-5-yl and 1-methyl-3-trifluoromethylpyrazol-5-yl.
  • Het-3 are 1, 5-dimethylpyrazol-3-yl and 1-methyl-5-methoxypy ⁇ azol-3-yl.
  • Het-4 examples include 1, 3-dimethylpyrazol-4-yl, 1, 5-dimethylpyrazol-4-yl, 1, 3,5-trimethylpyrazol-4-yl, 1-methyl-3-trifluoromethylpyrazol-4-yl and 1-methyl-5-trifluoromethylpyrazol-4-yl.
  • Het-5 are 1-methylpyrrol-2-yl, 1, 4-dimethylpyrrol-2-yl, 1-methyl-5-chloropyrrol-2-yl and 1-methyl-3,5- dichloropyrrole-2-yl.
  • Het-6 are 1, 4-dimethylpyrazol-3-yl and 1-methylpyrazol-3-yl.
  • Het-7 examples include thiazol-4-yl, 2-methylthiazol-4-yl, 2-methyl-5-bromothiazol-4-yl, 2-methyl-5-chlorothiazol-4-yl and 2,5-dichloro-thiazol-4-yl.
  • Het-8 is thiazol-2-yl.
  • Het-9 is thiazol-5-yl.
  • Het-10 examples include 3-methyl-isothiazol-4-yl and 3-methyl-5-chloro-isothiazol-4-yl.
  • Het-1 1 is isothiazol-3-yl.
  • het-12 is isothiazol-5-yl.
  • het-13 examples include isoxazol-4-yl, 3,5-dimethylisoxazol-4-yl, 3-methylisoxazole and 3-chloro-isoxazol-4-yl,
  • Het-14 is isoxazol-3-yl.
  • Het-15 is isoxazol-5-yl.
  • Het-16 examples include oxazol-4-yl, 2-methyl-oxazol-4-yl and 2,5-dimethyloxazol-4-yl,
  • Het-17 is oxazol-2-yl.
  • het-18 is oxazol-5-yl.
  • Het-19 examples include 4,5-dichloro-imidazol-1-yl and 4,5-dimethyl-imidazol-1-yl.
  • Het-20 is 1-methyl-imidazol-4-yl.
  • Het-21 is 1-methylimidazol-2-yl.
  • Het-22 is 1-methylimidazol-5-yl.
  • Examples of het-23 include 3-chloro-1, 2,4-triazol-1-yl, 3-fluoro-1, 2,4-triazol-1-yl, 3-bromo-1, 2,4-triazole 1 -yl, 3-trifluoromethyl-1, 2,4-triazol-1-yl, 3,5-dimethyl-1,2,4-triazol-1-yl, 3,5-dichloro-1, 2,4- triazol-1-yl, 3,5-dibromo-1, 2,4-triazol-1-yl, 3,5-difluoro-1, 2,4-triazol-1-yl and 3,5-ditrifluoromethyl-1, 2,4-triazol-1-yl.
  • Het-24 examples include 4,5-dimethyl-1,2,3-triazol-1-yl, 4,5-dichloro-1,2,3-triazol-1-yl, 4,5-dibromo-1, 2,3-triazol-1-yl, 4,5-difluoro-1,2,3-triazol-1-yl, 4,5-ditrifluoromethyl-1,2,3-triazol-1-yl, 5-methyl 1, 2,3-triazol-1-yl, 5-chloro-1, 2,3-triazol-1-yl, 5-fluoro-1, 2,3-triazol-1-yl, 5-bromo-1, 2,3-triazol-1-yl, 5-trifluoromethyl-1,2,3-triazol-1-yl.
  • Het-25 is 1,2,3-triazol-2-yl.
  • Het-26 is 1-methyl-1,2,4-triazol-5-yl.
  • Het-27 is 1-methyl-1,2,3-triazol-5-yl.
  • Het-28 is 2-methyl-1,2,3-triazol-4-yl.
  • Het-29 is 1-methyl-1,2,4-triazol-3-yl.
  • Het-30 is 1-methyl-1,2,3-triazol-4-yl.
  • Het-31 is 2-methyl-1,2,3-triazol-5-yl.
  • W is thienyl which is unsubstituted or has 1, 2 or 3 substituents L. Accordingly, W represents one of the following residues Het-32 or Het-33, in which # denotes the attachment site and L 1 , L 2 , and L 3 independently of one another have the meanings previously given for the formulas Het-1 to Het-31.
  • Het-32 2-thienyl, 5-methylthiophene-2-yl, 5-chlorothiophene-2-yl, 5-bromothiophene-2-yl, 3,5-dichlorothiophene-2-yl, 3,4,5- Trichlorothiophen-2-yl and 5-bromothiophen-2-yl.
  • Het-33 3-thienyl, 2-methylthiophen-3-yl, 2,5-dichlorothiophene-3-yl, 2,4,5-trichloro-thiophen-3-yl and 2,5-dibromothiophene-3 yl.
  • a further embodiment of the invention relates to compounds of the formula I in which W is 1, 2,3-triazolyl or 1,2,4-triazolyl, where W may have two identical or different substituents L.
  • Preferred embodiments of these W are 3,5-dimethyl-1, 2,4-triazol-1-yl, 3,5-dichloro-1, 2,4-triazol-1-yl, 3,5-dibromo-1, 2,4-triazol-1-yl, 3,5-difluoro-1, 2,4-triazol-1-yl, 3,5-di- (trifluoromethyl) -1, 2,4-triazol-1-yl, 3-methyl-1, 2,4-triazol-1-yl, 3-chloro-1, 2,4-triazol-1-yl, 3-fluoro-1, 2,4-triazol-1-yl, 3 bromo-1, 2,4-triazol-1-yl, 3-trifluoromethyl-1, 2,4-triazol-1-yl, 4,5-dimethyl-1,2,3-triazol-1-yl, 4, 5-dichloro-1,2,3-triazol-1-yl, 4,5-dibromo-1,2,3-triazol-1-yl
  • W is a five-membered nitrogen-containing heteroaromatic ring selected from pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl and isothiazolyl, where W is unsubstituted or substituted by one, two, three or four same or various substituents L.
  • W here is unsubstituted or substituted pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl or isothiazolyl.
  • W is optionally substituted pyrrolyl, preferably via a ring carbon bonded to the skeleton of the formula I pyrrolyl, ie 2-, or 3-pyrrolyl, more preferably 2-pyrrolyl.
  • the pyrrolyl radical has one, two, three or four substituents L.
  • W is optionally substituted pyrazolyl, such as 1-, 3-, 4- or 5-pyrazolyl. Particularly preferred is W-pyrazolyl or 4-pyrazolyl, more preferably 1-pyrazolyl.
  • the pyrazolyl radical preferably has one, two or three substituents L.
  • W is optionally substituted imidazolyl, ie 1-, 2-, or 4-imidazolyl, more preferably 1- or 2-imidazolyl.
  • the imidazolyl radical has one, two or three substituents L.
  • # means in each case the point of attachment of the respective W to the skeleton of the compounds of the formula I or with the precursors thereof.
  • a substitution pattern is selected from A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29 and A-30. specifically selected from A-22, A-23, A-24, A-25 and A-27, A-28, and A-29.
  • W is oxazolyl
  • a substitution pattern selected from A-36 and A-37 is particularly preferable.
  • W is isoxazolyl
  • a substitution pattern selected from A-39, A-40 and A-41 is particularly preferable.
  • W are: 1-methylpyrrol-2-yl, 1, 4-dimethylpyrrol-2-yl, 1-methyl-5-chloropyrrol-2-yl, 1-methyl-3,5-dichloropyrrol-2-yl, 3-methyl-5-isopropylpyrazol-1-yl, 3,5-dimethylpyrazol-1-yl, 3-isopropyl-5-methylpyrazol-1-yl, 3-ethyl-5-methylpyrazol-1-yl, 3 Methyl 5-methoxypyrazol-1-yl, 3,4,5-trimethylpyrazol-1-yl, 3,5-dimethyl-4-chloropyrazol-1-yl, 3-chloropyrazol-1-yl, 3,4-dichloro 5-trichloromethylpyrazol-1-yl, 3-methylpyrazol-1-yl, 3,5-dichloro-4-methylpyrazol-1-yl, 3-methyl-4-chloropyrazol-1-yl, 1, 3-dimethylpyrazole-5
  • W is a five-membered teroaryl group containing two nitrogen atoms as ring members, which is selected from 1, 2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2 , 5-thiadiazolyl, 1, 2,4-oxadiazolyl, 1, 3,4-oxadiazolyl and 1, 2,5-oxadiazolyl, wherein W may be unsubstituted or substituted with one or two L, wherein L is as defined above, or is preferably defined.
  • W is a 6-membered heteroaromatic radical having 1, 2 or 3 nitrogen atoms as ring members and which is unsubstituted or 1, 2, 3 or 4, preferably 1, 2 or 3 substituents L carries.
  • W is preferably pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl, (1, 2,4-triazinyl or 1, 3,5-triazinyl), in particular pyridinyl, pyrimidinyl or pyrazinyl.
  • compounds of general formula I wherein W is pyridinyl, optionally having 1, 2, 3 or 4 substituents L, are preferred.
  • W is pyridinyl, optionally having 1, 2, 3 or 4 substituents L.
  • W is 2-pyridinyl which has 1 or 2 substituents L.
  • those compounds are particularly preferred in which one of the substituents L is located in the 5-position of the pyridinyl ring.
  • most preferred are compounds I wherein one of the substituents L is located in the 3-position of the pyridinyl ring.
  • L has in particular the meanings given as preferred.
  • Also preferred among the compounds of this embodiment are compounds of general formula I wherein W is 3-pyridinyl, optionally having 1 or 2 substituents L. Among them, preferred are those having a substituent L in the 2-position and / or a substituent L in the 4-position of the pyridine ring.
  • Also preferred among the compounds of this embodiment are compounds of general formula I wherein W is 4-pyridinyl, optionally having 1 or 2 substituents L. Among them, preferred are compounds having a substituent L in the 3-position and / or a substituent L in the 5-position of the pyridine ring.
  • a further preferred embodiment of the invention relates to compounds of the general formula I in which W is 2-pyrazinyl, which optionally has 1, 2 or 3 substituents L.
  • a further preferred embodiment of the invention relates to compounds of the general formula I in which W is 4-pyridazinyl which optionally has 1, 2 or 3 substituents L.
  • a further preferred embodiment of the invention relates to compounds of general formula I, wherein W is 1, 3,5-triazinyl, which optionally has 1 or 2 substituents L.
  • heterocyclic radicals W of this embodiment are the radicals Het-34 to Het-39 given below:
  • L 1 , L 2 , L 3 and L 4 independently of one another are hydrogen or have one of the meanings given for L.
  • the radicals L 1 , L 2 , L 3 and L 4 are independently selected from among hydrogen, halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, especially C 1 -C 2 -fluoroalkyl, C 1 -C 4 -Aikoxy and C 1 -C 4 -alkoxycarbonyl.
  • L 1 , L 2 , L 3 and L 4 are independently selected from hydrogen, nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl.
  • Het-34 examples are 2-pyridyl, 3-fluoro-pyridin-2-yl, 3-chloro-pyridin-2-yl, 3-bromo-2-pyridin-2-yl, 3-trifluoromethyl-pyridine-2-yl yl, 3-methylpyridin-2-yl, 3-ethyl-pyridin-2-yl 3,5-difluoropyridin-2-yl, 3,5-dichloro-pyridin-2-yl, 3,5-dibromo -pyridin-2-yl, 3-fluoro-5-trifluoromethyl-pyridin-2-yl, 3,5-dimethyl-pyridin-2-yl, 5-nitro-pyridin-2-yl, 5-cyano-pyridine-2 -yl, 5-methoxycarbonylpyridin-2-yl, 5-trifluoromethylpyridin-2-yl, 5-methylpyridin-2-yl, 4-methylpyridin-2-yl, and 6-methylpyridine 2-yl
  • Het-35 examples are 3-pyridyl, 2-chloro-pyridin-3-yl, 2-bromo-pyridin-2-yl, 2-methyl-pyridin-3-yl, 2,4-dichloro-pyridine-3 yl, 2,4-dibromopyridin-3-yl, 2,4-dimethyl-pyridin-3-yl, 2,4,6-trichloropyridin-3-yl, 2,4,6-tribromopyridin-3-yl, 2,4,6-trimethylpyridin-3-yl and 2,4-dichloro-6-methylpyridin-3-yl.
  • Het-36 examples include 4-pyridyl, 3-chloro-pyridin-4-yl, 3-bromo-pyridin-4-yl, 3-methyl-pyridin-4-yl, 3,5-dichloro-pyridine-4 yl, 3,5-dibromo-pyridin-4-yl and 3,5-dimethyl-pyridin-4-yl
  • Het-37 examples include 5-chloropyrimidin-4-yl, 5-fluoropyrimidin-4-yl, 5-fluoro-6-chloropyrimidin-4-yl, 2-methyl-6-trifluoromethyl-pyrimidin-4-yl, 2, 5-Dimethyl-6-trifluoromethyl-pyrimidin-4-yl, 5-methyl-6-trifluoromethyl-pyrimidin-4-yl, 6-trifluoromethyl-pyrimidin-4-yl, 2-methyl-5-fluoro-pyrimidine-4 yl, 2-methyl-5-chloro-pyrimidin-4-yl, 5-chloro-6-methyl-pyrimidin-4-yl, 5-chloro-6-ethyl-pyrimidin-4-yl, 5-chloro-6 isopropyl-pyrimidin-4-yl, 5-bromo-6-methyl-pyrimidin-4-yl, 5-fluoro-6-methyl-pyrimidin-4-yl, 5-fluoro-6-fluoromethyl-pyrimidin-4-y
  • het-38 examples include 4-methyl-pyrimidin-5-yl, 4,6-dimethyl-pyrimidin-5-yl, 2,4,6-trimethyl-pyrimidin-5-yl and 4-trifluoromethyl-6-methyl-pyrimidine 5-yl.
  • Het-39 examples include 4,6-dimethylpyrimidin-2-yl, 4,5,6-trimethylpyrimidin-2-yl, 4,6-ditrifluoromethyl-pyrimidin-2-yl and 4,6-dimethyl-5-chloro pyrimidin-2-yl.
  • the group stands in which # 1 is the
  • X and # 2 represents lenstoffatom point of linkage is the linkage point to the adjacent coal, in the compounds I preferably a five-membered heteroaromatic ring containing one, two or three nitrogen atoms, or one or two nitrogen atoms and one oxygen or sulfur atom, or contains an oxygen or a sulfur atom.
  • the heteroaromatic ring is unsubstituted or substituted with one, two or three same or different substituents L as it is is defined elsewhere herein. In one embodiment, the heteroaromatic is unsubstituted.
  • group G stands (hereinafter called group G) for one of the following five-membered heteroaromatic rings S-1 to S-40, each of which is unsubstituted or wherein one, two or three hydrogen atoms are replaced by the same or different substituents L as defined elsewhere herein can:
  • the heteroaromatic is in each case unsubstituted.
  • the other substituents in the compounds of formula I are each defined as described elsewhere herein.
  • the group G is S-1.
  • the group G is S-2.
  • the group G is S-3.
  • the group G is S-4.
  • the group G is S-5.
  • the five-membered heteroaromatic rings S-1, S-2, S-3, S-4 and S-5 are each unsubstituted or one, two or three hydrogen atoms are represented by the same or different substituents L as herein elsewhere defined, replaced.
  • the group G is S-6.
  • the group G is S-7.
  • the group G is S-8.
  • the group G is S-9.
  • the group G is S-10.
  • the group G S-1 is 1.
  • the five-membered heteroaromatic rings S-6, S-7, S-8, S-9, S-10 and S-1 1 are each unsubstituted or one or two hydrogen atoms are represented by the same or different substituents L , as defined elsewhere herein.
  • the group G is S-12.
  • the group G is S-13.
  • the group G is S-14.
  • the group G is S-15.
  • the group G is S-16.
  • the group G is S-17.
  • the group G is S-18.
  • the group G is S-19.
  • the group G is S-20.
  • the five-membered heteroaromatic rings are S-12, S-13, S-14, S-15, S-16, S-17, S-18, S-19 and S-20, respectively unsubstituted or one or two hydrogen atoms are replaced by the same or different substituents L as defined elsewhere herein.
  • the group G is S-21.
  • the group G is S-22.
  • the group G is S-23. According to yet another specific embodiment of the invention, the group G is S-24.
  • the group G is S-25.
  • the group G is S-26.
  • the group G is S-27.
  • the group G is S-28.
  • the five-membered heteroaromatic rings S-21, S-22, S-23, S-24, S-25, S-26, S-27 and S-28 are each unsubstituted or a hydrogen atom is L, as defined elsewhere herein.
  • the group G is S-29.
  • the group G is S-30.
  • the group G is S-31.
  • the group G is S-32.
  • the group G is S-33.
  • the group G is S-34.
  • the group G is S-35.
  • the five-membered heteroaromatic rings S-29, S-30, S-31, S-32, S-33, S-34 and S-35 are each unsubstituted or a hydrogen atom by L , as defined elsewhere herein.
  • the group G is S-36.
  • the group G is S-37.
  • the group G is S-38.
  • the group G is S-39.
  • the group G is the five-membered heteroaromatic ring S-40.
  • R 5 and R 6 are independently of one another preferably hydrogen or C 1 -C 4 -alkyl.
  • R 7 is preferably hydrogen or C 1 -C 6 -alkyl.
  • R 8 and R 9 independently of one another preferably represent hydrogen or C 1 -C 6 -alkyl.
  • a 1 is preferably hydrogen, C 1 -C 6 -alkyl or amino.
  • the index n is preferably 0, 1 or 2.
  • a 2 preferably stands for -C 4 -alkoxy, Nhb, Ci-C 4 - alkylamino alkylamino or di-Ci-C. 4
  • L 1 , R 3 and R 4 for a compound corresponds in each case to one row of Table B.
  • R 3 and R 4 for a compound corresponds in each case to one row of Table B.
  • R 3 and R 4 for a compound corresponds in each case to one row of Table B.
  • R 3 and R 4 for a compound corresponds in each case to one row of Table B.
  • Table 80 Compounds of the formulas 1-1.1, 1-1.2, 1-1.3, 1-1.4, 1-2.1, I-2.2, I-2.3, I-2.4, 1-3.1, I-3.2,
  • Table 81 Compounds of the formulas 1-1.1, 1-1.2, 1-1.3, 1-1.4, 1-2.1, I-2.2, I-2.3, I-2.4, 1-3.1, I-3.2,
  • Table 82 Compounds of the formulas 1-1.1, 1-1.2, 1-1.3, 1-1.4, 1-2.1, I-2.2, I-2.3, I-2.4, 1-3.1, I-3.2,
  • Table 83 Compounds of the formulas 1-1.1, 1-1.2, 1-1.3, 1-1.4, 1-2.1, I-2.2, I-2.3, I-2.4, 1-3.1, I-3.2,
  • Table 84 Compounds of the formulas 1-1.1, 1-1.2, 1-1.3, 1-1.4, 1-2.1, I-2.2, I-2.3, I-2.4, 1-3.1, I-3.2,
  • L 1 and R 3 for a compound corresponds in each case to one row of Table C.
  • R 3 for a compound corresponds in each case to one row of Table C.
  • Table 150 Compounds of the formulas 1-14.1, 1-14.2, 1-14.3, 1-14.4, 1-15.1, 1-15.2, 1-15.3, 1-15.4,
  • L 1 and R 3 for a compound corresponds in each case to one row of Table C.
  • Table 162 Compounds of the formulas 1-14.1, 1-14.2, 1-14.3, 1-14.4, 1-15.1, 1-15.2, 1-15.3, 1-15.4,
  • Table 170 Compounds of the formulas 1-14.1, 1-14.2, 1-14.3, 1-14.4, 1-15.1, 1-15.2, 1-15.3, 1-15.4,
  • Table 210 Compounds of the formulas 1-19.1, 1-19.2, 1-19.3, 1-19.4, 1-19.5, 1-19.6, 1-19.7, 1-19.8,
  • R 4 for a compound of one row of Table B corresponds to Table 222
  • R 1 and R 4 for a compound corresponds in each case to one row of Table B.
  • L 1 , R 1 and R 4 for a compound corresponds in each case to one row of Table B.
  • Table 234 Compounds of the formulas 1-19.1, 1-19.2, 1-19.3, 1-19.4, 1-19.5, 1-19.6, 1-19.7, 1-19.8,
  • L 1 , R 1 and R 4 for a compound corresponds in each case to one row of Table B.
  • L 1 , R 1 and R 4 for a compound corresponds in each case to one row of Table B.
  • Table 252 Compounds of the formulas 1-19.1, 1-19.2, 1-19.3, 1-19.4, 1-19.5, 1-19.6, 1-19.7, 1-19.8,
  • R 1 and R 4 for a compound corresponds in each case to one row of Table B.
  • L 1 , R 1 and R 4 for a compound corresponds in each case to one row of Table B.
  • L 1 , R 1 and R 4 for a compound corresponds in each case to one row of Table B.
  • Table 282 Compounds of the formulas 1-19.1, 1-19.2, 1-19.3, 1-19.4, 1-19.5, 1-19.6, 1-19.7, 1-19.8,
  • L 1 and R 1 for a compound corresponds in each case to one row of Table C.
  • R 1 for a compound corresponds in each case to one row of Table C.
  • L 1 and R 1 for a compound corresponds in each case to one row of Table C.

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Abstract

La présente invention concerne des composés de la formule (I) et leur utilisation pour lutter contre des champignons phytopathogènes, les variables et les substituants ayant les significations telles qu'elles sont décrites dans les revendications et la description.
PCT/EP2007/059720 2006-09-25 2007-09-14 Composés hétérocycliques à teneur en groupe carbonyle et leur utilisation pour lutter contre des champignons phytopathogènes WO2008037607A1 (fr)

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