Substituted thiophenecarboxamides and derivatives thereof

Abstract

The present invention relates to substituted thiophenecarboxamide derivatives, to the use thereof for controlling phytopathogenic microorganisms and to compositions comprising same.

Description

[0001] This application is a divisional application of the Chinese invention patent application with application number 202080095827.9, filed on December 17, 2020, and invention name “Substituted thiophenecarboxamides and their derivatives”. Technical Field

[0002] The present invention relates to substituted thiophenecarboxamide derivatives, their use for controlling phytopathogenic microorganisms and compositions containing them. Background Art

[0003] Although many microbicides have been developed so far, there is still a need to develop new microbicidal compounds to address the increasing environmental and economic requirements imposed on modern crop protection agents and compositions. This includes, for example, improving the spectrum of action, safety, selectivity, application rate, formation of residues and good preparation capabilities. It may also be necessary to have new compounds to prevent the emergence of drug resistance.

[0004] The present invention provides novel compounds that are superior to known compounds and compositions in at least some of these respects.

[0005] EP 0 450 355 discloses thiophenecarboxamide derivatives which can be used for protecting plants from attack by plant-destroying microorganisms.

[0006] GB 1241589 discloses thiophene derivatives for agricultural use, including their use as plant fungicides. Summary of the invention

[0007] The present invention relates to compounds of formula (I) as described herein as well as isomers, polymorphs, salts, N-oxides and solvates thereof.

[0008] The present invention relates to a composition comprising at least one compound of formula (I) or as defined herein and at least one agriculturally suitable carrier.

[0009] The present invention relates to processes for the preparation of compounds of formula (I) and intermediates thereof as described herein.

[0010] The present invention relates to a method for controlling phytopathogenic microorganisms, which method comprises the step of applying at least one compound of formula (I) as defined herein or a composition as defined herein to plants, plant parts, seeds, fruits or soil in which the plants grow.

[0011] definition

[0012] The term "alkyl" as used herein in the context of alkyl or alkylsulfonyl, alkylsulfinyl, alkylthio, alkylamino, for example, is to be understood as preferably meaning branched and unbranched alkyl groups, meaning for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl and decyl and isomers thereof.

[0013] As used herein, the term "alkenyl" is to be understood as preferably meaning branched and unbranched alkenyl groups, for example vinyl, prop-1-yl, prop-2-yl, but-1-en-1-yl, but-1-en-2-yl, but-2-en-1-yl, but-2-en-2-yl, but-1-en-3-yl, 2-methyl-prop-2-en-1-yl or 2-methyl-prop-1-en-1-yl groups.

[0014] As used herein, the term "alkynyl" is to be understood as preferably meaning branched and unbranched alkynyl groups, such as ethynyl, prop-1-yn-1-yl, but-1-yn-1-yl, but-2-yn-1-yl or but-3-yn-1-yl groups.

[0015] As used herein, the term "halogen" or "Hal" shall be understood to mean fluorine, chlorine, bromine or iodine.

[0016] The term "halo" or "halogeno" (eg, haloalkyl, "C1-C6-haloalkyl" or "C1-C8-haloalkyl") means that one or more halogen substituents which may be the same or different are optionally present.

[0017] As used herein, the term "haloalkyl" is understood to preferably mean branched and unbranched alkyl as defined above, wherein one or more hydrogen substituents are replaced by halogen in the same or different manner. Particularly preferably, the haloalkyl is, for example, chloromethyl, fluoropropyl, fluoromethyl, difluoromethyl, trichloromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, bromobutyl, trifluoromethyl, iodoethyl, and isomers thereof.

[0018] As used herein, the term "haloalkenyl" is understood to denote preferably branched and unbranched alkenyl groups as defined above, wherein one or more hydrogen substituents are replaced in the same or different manner by halogen.

[0019] As used herein, the term "haloalkynyl" is to be understood as preferably denotes branched and unbranched alkynyl groups as defined above, wherein one or more hydrogen substituents are replaced in the same or different manner by halogen.

[0020] As used herein, the term "alkoxy" refers to a group of the formula (alkyl)-O-, wherein the term "alkyl" is as defined herein. Examples of C1-C8-alkoxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, n-hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy.

[0021] As used herein, the term "haloalkoxy" refers to an alkoxy group as defined above, wherein one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different. Examples of C1-C8-haloalkoxy include, but are not limited to, chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 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, pentafluoroethoxy and 1,1,1-trifluoropropane-2-oxy.

[0022] As used herein, the term "alkylsulfanyl" refers to a saturated, straight-chain or branched group of the formula (alkyl)-S-, wherein the term "alkyl" is as defined herein. Examples of C1-C8-alkylsulfanyl include, but are not limited to, methylthio, ethylthio, propylthio, isopropylthio, butylthio, sec-butylthio, isobutylthio, tert-butylthio, pentylthio, isopentylthio, hexylthio.

[0023] As used herein, the term "haloalkylsulfanyl" refers to an alkylsulfanyl group as defined above wherein one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0024] As used herein, the term "alkylsulfinyl" refers to a saturated, straight-chain or branched group of the formula (alkyl)-S(=O)-, wherein the term "alkyl" is as defined herein. Examples of C1-C8-alkylsulfinyl include, but are not limited to, saturated straight-chain or branched alkylsulfinyl groups having 1-8, preferably 1-6, and more preferably 1-4 carbon atoms, such as, but not limited to, methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2 ... The invention also includes but is not limited to: 1-methylbutylsulfinyl, 1-hexylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.

[0025] As used herein, the term "haloalkylsulfinyl" refers to an alkylsulfinyl group as defined above wherein one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0026] As used herein, the term "alkylsulfonyl" refers to a saturated straight or branched chain group of the formula (alkyl)-S(=O)2-, wherein the term "alkyl" is as defined herein. Examples of C1-C8-alkylsulfonyl include, but are not limited to, methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl.

[0027] As used herein, the term "haloalkylsulfonyl" refers to a C1-C8-alkylsulfonyl group as defined above, wherein one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0028] As used herein, the term "alkylcarbonyl" refers to a saturated, straight-chain or branched group of the formula (alkyl)-C(=O)-, wherein the term "alkyl" is as defined herein.

[0029] As used herein, the term "haloalkylcarbonyl" refers to an alkylcarbonyl group as defined above wherein one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0030] As used herein, the term "alkoxycarbonyl" refers to a saturated straight or branched chain group of the formula (alkoxy)-C(=O)-, wherein the term "alkoxy" is as defined herein.

[0031] As used herein, the term "haloalkoxycarbonyl" refers to an alkoxycarbonyl group as defined above wherein one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0032] As used herein, the term "cycloalkyl" refers to a non-aromatic monocyclic carbon-containing ring having 3 to 8 carbon atoms. Examples of saturated cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl.

[0033] As used herein, the term "heterocyclyl" refers to a four-, five- or six-membered saturated or partially unsaturated heterocyclic ring containing one to four heteroatoms independently selected from oxygen, nitrogen and sulfur. If the ring contains more than one oxygen atom, they are not directly adjacent.

[0034] As used herein, the term "aryl" refers to an aromatic, hydrocarbon ring system containing 6 to 15 carbon atoms, or 6 to 12 carbon atoms, preferably 6 to 10 carbon atoms. The ring system can be a monocyclic or fused polycyclic (e.g., bicyclic or tricyclic) aromatic ring system. Examples of aryl include, but are not limited to, phenyl, azulenyl, naphthyl, and fluorenyl. It should also be understood that when the aryl is substituted with one or more substituents, the substituents may be located at any position on the aromatic ring. In particular, in the case where the aryl is a phenyl group, the substituents may occupy one or two ortho positions, one or two meta positions, or para positions, or any combination of these positions. This definition also applies to aryl groups that are part of a composite substituent (e.g., aryloxy).

[0035] As used herein, the term "aralkyl" refers to a C1-C6-alkyl group substituted with an aryl group as defined herein. Examples of aralkyl groups include benzyl (-CH2-C6H5).

[0036] As used herein, the term "aromatic 5- to 14-membered heterocycle" or "heteroaryl" refers to an aromatic ring system containing 1 to 4 heteroatoms independently selected from oxygen, nitrogen and sulfur. Aromatic heterocycles include aromatic 5- or 6-membered monocyclic heterocycles and 6- to 14-membered polycyclic (e.g., bicyclic or tricyclic) aromatic heterocycles. The 5- to 14-membered aromatic heterocycle can be attached to the parent molecular moiety via any carbon atom or nitrogen atom contained within the heterocycle.

[0037] As used herein, the term "C1-C6", for example in the context of the definition of "C1-C6-alkyl" or "C1-C6-alkoxy", is to be understood as meaning a group having a finite number of carbon atoms from 1 to 6, i.e. 1, 2, 3, 4, 5 or 6 carbon atoms.

[0038] As used herein, the term "C1-C8", for example in the context of the definition of "C1-C8-alkyl" or "C1-C8-alkoxy", is to be understood as meaning a group having a finite number of carbon atoms from 1 to 8, i.e. 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms.

[0039] As used herein, the term "oxo" refers to an oxygen atom bound to a carbon atom or a sulfur atom through a double bond.

[0040] As used herein, the term "leaving group" is understood to mean a group that is displaced from a compound in a substitution or elimination reaction, such as a halogen atom, a trifluoromethanesulfonate ("triflate") group, an alkoxy group, a mesylate, a p-toluenesulfonate, and the like. DETAILED DESCRIPTION

[0041] The present invention relates to compounds of formula (I):

[0042]

[0043] in

[0044] R 1 , R 2 and R 3 Each is chlorine;

[0045] R 4 and R 5are independently selected from hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, -OC(=O)-C1-C6-alkyl, C3-C6-carbocycle, 4-, 5- or 6-membered non-aromatic heterocyclic group, -C(=O)-NH2, -C(=O)-NH(C1-C6-alkyl), -C(=O)-N(C1-C6-alkyl)2, -C(=O)-OH, -C(=O)-O-C1-C6-alkyl, aryl, 5- to 9-membered heteroaryl, -C1-C6-alkyl-C1-C6-alkoxy, -C1-C6-alkyl-C1-C6-haloalkyl, -C1-C6-alkyl-C3 -C6-carbocycle, -C1-C6-alkyl-4, 5 or 6-membered non-aromatic heterocyclic group, -C1-C6-alkyl-aryl, -C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl-5 to 9-membered heteroaryl, -C1-C6-alkyl-S-C1-C6-alkyl, -C1-C6-alkyl-SC(═O)-C1-C6-alkyl, -C1-C6-alkyl-O-(C═O)-C1-C6-alkyl, -C1-C6-alkyl-C(═O)-NH2, -C1-C6-alkyl-C(═O)-NH(C1-C6-alkyl), -C1-C6-alkyl-C(═O)-N(C1-C6-alkyl)2, -C1-C6-alkyl-C(═O)- =O)-OH, -C1-C6-alkyl-C(=O)-O-C1-C6-alkyl, -C1-C6-alkyl-NH-C(=NH)-NH2, -S-C1-C6-alkyl, -SC(=O)-C1-C6-alkyl, -SC(=O)-O-C1-C6-alkyl, -SC(=S)-O-C1-C6-alkyl, -SC(=O)-S-C1-C6-alkyl, -SC(=O)-NH2, -SC(=O)-NH(C1-C6-alkyl), -SC(=O)-NH(C1-C6-alkyl)2, -SC(=S)-NH2, -SC(=S)-NH(C1-C6-alkyl), -SC(=S) -NH(C1-C6-alkyl)2, -C1-C6-alkyl-SC(=O)-O-C1-C6-alkyl, -C1-C6-alkyl-SC(=O)-S-C1-C6-alkyl, -C1-C6-alkyl-SC(=O)-NH2, -C1-C6-alkyl-SC(=O)-NH(C1-C6-alkyl), -C1-C6-alkyl-SC(=O)-NH(C1-C6-alkyl)2, -C1-C6-alkyl-SC(=S)-NH2, -C1-C6-alkyl-SC(=S)-NH(C1-C6-alkyl), -C1-C6-alkyl-SC(=S)-NH(C1-C6-alkyl)2, wherein the cyclic R 4 , R5 The group may be one or more R x Substituent substitution, where R 4 and R 5 At least one is hydrogen, C1-C6-alkyl or C3-C6-carbocycle, or R 4 and R 5 Together with the carbon atoms to which they are attached, they form a C3-C6-carbocyclic ring or a 3- to 6-membered heterocyclic ring, wherein the C3-C6-carbocyclic ring and the 3- to 6-membered heterocyclic ring may be replaced by one or more R x Substituent substitution, where R x Independently selected from the following groups: halogen, nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-λ 6 -sulfanyl, formyl, carbamoyl, carbamate, C1-C8-alkyl, C3-C7-cycloalkyl, C1-C8-haloalkyl having 1 to 5 halogen atoms, C3-C7-halocycloalkyl having 1 to 5 halogen atoms, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkylamino, di-C1-C8-alkylamino, C1-C8-alkoxy, C1-C8-haloalkoxy having 1 to 5 halogen atoms, C1-C8-alkylsulfanyl, C1-C8-haloalkylsulfanyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyl, C1-C8-haloalkylcarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbamoyl, di-C1-C8-alkylcarbamoyl, C1-C8-alkoxycarbonyl, C1-C8-alkylsulfanyl having 1 to 5 halogen atoms C1-C8-haloalkoxycarbonyl, C1-C8-alkylcarbonyloxy, C1-C8-haloalkylcarbonyloxy having 1 to 5 halogen atoms, C1-C8-alkylcarbonylamino, C1-C8-haloalkylcarbonylamino having 1 to 5 halogen atoms, C1-C8-alkylsulfanyl, C1-C8-haloalkylsulfanyl having 1 to 5 halogen atoms, C1-C8-alkylsulfinyl, C1-C8-haloalkylsulfinyl having 1 to 5 halogen atoms, C1-C8-alkylsulfonyl, C1-C8-haloalkylsulfonyl having 1 to 5 halogen atoms; C1-C8-alkylsulfonylamino, C1-C8-haloalkylsulfonyl having 1 to 5 halogen atoms; sulfamoyl; C1-C8-alkylsulfamoyl and di-C1-C8-alkylsulfamoyl;

[0046] R 6 and R 7 are independently selected from hydrogen, C1-C6-alkyl, C3-C6-carbocycle; or R 6 and R 7 Together with the carbon atoms to which they are attached, they form a C3-C6-carbocyclic ring or a 3- to 6-membered heterocyclic ring;

[0047] n is 0 or 1;

[0048] W is oxygen or sulfur;

[0049] Y is NR 8 , R 8 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, hydroxy, C1-C6-alkoxy or C3-C6-carbocycle;

[0050] Z is selected from -C(=O)-OR a , -C(=O)-SR a 、-C(=O)-NR b R c , -C(=S)-NR b R c or

[0051] -C(=O)-NH-CR d R e -C(=O)-OR a , where R a is selected from hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, aryl, aralkyl, 4-, 5- or 6-membered non-aromatic heterocyclyl, -C1-C6-alkyl-Si(C1-C6-alkyl)3, -C1-C6-alkyl-C3-C8-cycloalkyl, 5- to 9-membered heteroaryl and -C1-C6-alkyl-5- to 9-membered heteroaryl, or R a Together with R4 and the atoms to which they are attached, they can form a 4- to 7-membered heterocyclic ring, wherein R b and R c R is independently selected from hydrogen, C1-C6-alkyl, hydroxy, C1-C6-alkoxy, cyano, C1-C6-cyanoalkyl, or b Can be used with R 4 Together with the atoms to which they are attached, they form a 4- to 7-membered heterocyclic ring, R d and R eindependently selected from hydrogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, -OC(=O)-C1-C6-alkyl, C3-C6-carbocycle, -C(=O)-NH2, -C(=O)-NH(C1-C6-alkyl), -C(=O)-N(C1-C6-alkyl)2, -C(=O)OH, -C(=O)-O-C1-C6-alkyl, aryl, 5- to 9-membered heteroaryl, -C1-C6-alkyl-C1-C6-alkoxy, -C1-C6-alkyl-C3-C6-carbocycle, -C1-C6-alkyl-aryl, -C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl -5 to 9 membered heteroaryl, -C1-C6-alkyl-S-C1-C6-alkyl, -C1-C6-alkyl-SC(═O)-C1-C6-alkyl, -C1-C6-alkyl-O-(C═O)-C1-C6-alkyl, -C1-C6-alkyl-C(═O)-NH2, -C1-C6-alkyl-C(═O)-NH(C1-C6-alkyl), -C1-C6-alkyl-C(═O)-N(C1-C6-alkyl)2, -C1-C6-alkyl-C(═O)-OH, -C1-C6-alkyl-C(═O)-O-C1-C6-alkyl, -C1-C6-alkyl-NH-C(═NH)-NH2, wherein R d and R e At least one is hydrogen, C1-C6-alkyl or C3-C6 carbocycle, or R d and R e Together with the carbon atom to which they are attached, they form a carbonyl group, a C3-C6-carbocycle or a 3- to 6-membered heterocycle;

[0052] The condition is to exclude 3,4,5-trichloro-N-(2-cyanoethyl)-N-cyclohexylthiophene-2-carboxamide [24504-23-2], 3,4,5-trichloro-N,N-bis(2-cyanoethyl)thiophene-2-carboxamide in the compound of formula (I)

[0053] [24467-28-5] and 3,4,5-trichloro-N-(2-cyanoethyl)-N-methylthiophene-2-carboxamide [24417-82-1],

[0054] Where W is oxygen, Y is NR 8 , R 8 is hydrogen or C1-C6-alkyl, n=0, R 4 is selected from hydrogen, C1-C6-alkyl, C1-C6-alkyl-aryl, C1-C6-alkylhydroxyaryl, a cyclopropyl group, R 5 is hydrogen or R 4 and R 5 Together with the carbon atom to which they are attached, they form a cyclopropyl group, then Z is selected from C(=O)-SRa 、-C(=O)-NR b R c 、-C(=S)-NR b R c ,

[0055] -C(=O)-NH-CR d R e -C(=O)-OR a .

[0056] A preferred embodiment, wherein R 4 and R 5 are independently selected from hydrogen, C1-C6-alkyl, C1-C6-hydroxyalkyl, C3-C6-carbocycle, aryl, -C1-C6-alkyl-C1-C6-alkoxy, -C1-C6-alkyl-C3-C6-carbocycle, C1-C6-alkyl-O-(C=O)-C1-C6-alkyl, -C1-C6-alkyl-C(=O)-OH; C1-C6-alkyl-aryl, -C1-C6-alkyl-S-C1-C6-alkyl, wherein R 4 and R 5 At least one of them is hydrogen, C1-C6-alkyl or C3-C6-carbocycle, n is 0, and W is oxygen, and if Y is NR 8 , where R 8 is selected from hydrogen, C1-C6-alkyl, then Z is selected from -C(=0)-SR a 、-C(=S)-NR b R c or -C(=O)-NH-CR d R e -C(=O)-OR a .

[0057] Also preferred is an embodiment in which R 4 and R 5 R is independently selected from hydrogen, C1-C6-alkyl, C1-C6-hydroxyalkyl, C3-C6-carbocycle, C(=O)-OH, C(=O)-O-C1-C6-alkyl, -C1-C6-alkyl-C1-C6-alkoxy, -C1-C6-alkyl-C1-C6-haloalkyl, -C1-C6-alkyl-C3-C6-carbocycle, -C1-C6-alkyl-aryl, -C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl-S-C1-C6-alkyl-, -C1-C6-alkyl-C(=O)NH2, -C1-C6-alkyl-C(=O)-OH, -C1-C6-alkyl-C(=O)-O-C1-C6-alkyl; or R 4 and R 5Together with the carbon atom to which they are attached they form a C3-C6-carbocycle.

[0058] Yet another embodiment is preferred wherein W is oxygen.

[0059] Other preferred embodiments wherein Y is NR 8 And R 8 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, hydroxy, C1-C6-alkoxy or C3-C6-carbocycle, and wherein Y is more preferably NR 8 , R 8 It's hydrogen.

[0060] According to another preferred embodiment, Z is selected from cyano, -C(=O)SR a , -C(=S)-NR b R c or -C(=O)-NH-CR d R e -C(=O)-OR a , and more preferably Z is selected from -C(=O)-OR a 、C(=O)-NR b R c .

[0061] Another preferred embodiment, wherein

[0062] Where R 4 and R 5 independently of one another are selected from hydrogen, C1-C6-alkyl, C1-C6-hydroxyalkyl, C3-C6-carbocycle, C(═O)—OH, —C(═O)—O—C1-C6-alkyl, —C1-C6-alkyl-C1-C6-alkoxy,

[0063] -C1-C6-alkyl-C1-C6-haloalkyl, -C1-C6-alkyl-C3-C6-carbocycle, C1-C6-alkyl-aryl, -C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl-S-C1-C6-alkyl-, -C1-C6-alkyl-C(=O)-NH2, -C1-C6-alkyl-C(=O)-OH, -C1-C6-alkyl

[0064] -C(=O)-O-C1-C6-alkyl; or R 4 and R 5 Together with the carbon atoms to which they are attached, they form

[0065] C3-C6-Carbocycle;

[0066] R 6 and R 7 is hydrogen or R 6and R 7 Together with the carbon atom to which they are attached, they form a C3-carbocycle;

[0067] W is oxygen;

[0068] Y is NR 8 , R 8 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, hydroxy

[0069] C1-C6-alkoxy or C3-C6-carbocycle;

[0070] n is 0 or 1;

[0071] Z is selected from -C(=O)-SR a 、-C(=S)-NR b R c or -C(=O)-NH-CR d R e C(=O)-OR a ,

[0072] And more preferably Z is selected from -C(=O)-OR a 、C(=O)-NR b R c .

[0073] Another preferred embodiment, wherein

[0074] Where R 4 and R 5 R is independently selected from hydrogen, C1-C6-alkyl, C1-C6-hydroxyalkyl, C3-C6-carbocycle, C(=O)-OH, -C(=O)-O-C1-C6-alkyl, -C1-C6-alkyl-C1-C6-alkoxy, -C1-C6-alkyl-C1-C6-haloalkyl, -C1-C6-alkyl-C3-C6-carbocycle, C1-C6-alkyl-aryl, -C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl-S-C1-C6-alkyl-, -C1-C6-alkyl-C(=O)-NH2, -C1-C6-alkyl-C(=O)-OH, -C1-C6-alkyl-C(=O)-O-C1-C6-alkyl; or R 4 and R 5 Together with the carbon atom to which they are attached they form a C3-C6-carbocycle.

[0075] R 6 and R 7 is hydrogen or R 6 and R 7 Together with the carbon atom to which they are attached, they form a C3-carbocycle;

[0076] W is oxygen;

[0077] Y is NR 8 , R 8 It is hydrogen;

[0078] n is 0 or 1;

[0079] Z is selected from -C(=O)-SR a , -C(=S)-NR b R c or -C(=O)-NH-CR d R e C(=O)-OR a More preferably, Z is selected from -C(=O)-OR a 、C(=O)-NR b R c .

[0080] Another preferred embodiment, wherein

[0081] Where R 4 and R 5 R is independently selected from hydrogen, C1-C6-alkyl, C1-C6-hydroxyalkyl, C3-C6-carbocycle, C(=O)-OH, -C(=O)-O-C1-C6-alkyl, -C1-C6-alkyl-C1-C6-alkoxy, -C1-C6-alkyl-C1-C6-haloalkyl, -C1-C6-alkyl-C3-C6-carbocycle, C1-C6-alkyl-aryl, -C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl-S-C1-C6-alkyl-, -C1-C6-alkyl-C(=O)-NH2, -C1-C6-alkyl-C(=O)-OH, -C1-C6-alkyl-C(=O)-O-C1-C6-alkyl; or R 4 and R 5 Together with the carbon atom to which they are attached they form a C3-C6-carbocycle;

[0082] W is oxygen;

[0083] Y is NR 8 , R 8 It is hydrogen;

[0084] n is 0 or 1;

[0085] Z is selected from -C(=O)-SR a , -C(=S)-NR b R c or -C(=O)-NH-CR d R e C(=O)-OR a , and more preferably Z is selected from -C(=O)-ORa 、C(=O)-NR b R c .

[0086] Another preferred embodiment, wherein

[0087] Where R 4 and R 5 R is independently selected from hydrogen, C1-C6-alkyl, C1-C6-hydroxyalkyl, C3-C6-carbocycle, C(=O)-OH, -C(=O)-O-C1-C6-alkyl, -C1-C6-alkyl-C1-C6-alkoxy, -C1-C6-alkyl-C1-C6-haloalkyl, -C1-C6-alkyl-C3-C6-carbocycle, C1-C6-alkyl-aryl, -C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl-S-C1-C6-alkyl-, -C1-C6-alkyl-C(=O)-NH2, -C1-C6-alkyl-C(=O)-OH, -C1-C6-alkyl-C(=O)-O-C1-C6-alkyl; or R 4 and R 5 Together with the carbon atom to which they are attached they form a C3-C6-carbocycle;

[0088] W is oxygen;

[0089] Y is NR 8 , R 8 It is hydrogen;

[0090] n is 0;

[0091] Z is selected from -C(=O)-OR a 、C(=O)-NR b R c .

[0092] In another embodiment, R 4 and R 5are independently selected from halogen, cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkyl, -OC(=O)-C1-C6-alkyl, 4-, 5- or 6-membered non-aromatic heterocyclic radical, -C(=O)-NH2, -C(=O)-NH(C1-C6-alkyl), -C(=O)-N(C1-C6-alkyl)2, -C(=O)-OH, -C(=O)-O-C1-C6-alkyl, 5- to 9-membered heteroaryl, -C1-C6-alkyl-C1-C6-haloalkyl, C1-C6-alkyl-4-, 5- or 6-membered non-aromatic heterocyclic radical, -C1- C6-alkyl-hydroxyaryl, -C1-C6-alkyl-5 to 9-membered heteroaryl, -C1-C6-alkyl-SC(=O)-C1-C6-alkyl, -C1-C6-alkyl-C(=O)-NH2, -C1-C6-alkyl-C(=O)NH(C1-C6-alkyl), -C1-C6-alkyl-C(=O)-N(C1-C6-alkyl)2, -C1-C6-alkyl-C(=O)-O-C1-C6-alkyl, -C1-C6-alkylNH-C(=NH)-NH2, -S-C1-C6-alkyl, -SC(=O) -C1-C6-alkyl, -SC(=O)-O-C1-C6-alkyl, -SC(=S)-O-C1-C6-alkyl, -SC(=O)-S-C1-C6-alkyl, -SC(=O)-NH2, -SC(=O)-NH(C1-C6-alkyl), -SC(=O)-NH(C1-C6-alkyl)2, SC(=S)-NH2, -SC(=S)-NH(C1-C6-alkyl), -SC(=S)-NH(C1-C6-alkyl)2, -C1-C6-alkyl-SC(=O)-O-C1-C6 -alkyl, -C1-C6-alkyl-SC(=O)-S-C1-C6-alkyl, -C1-C6-alkyl-SC(=O)-NH2, -C1-C6-alkyl-SC(=O)-NH(C1-C6-alkyl), -C1-C6-alkyl-SC(=O)-NH(C1-C6-alkyl)2, -C1-C6-alkyl-SC(=S)-NH2, -C1-C6-alkyl-SC(=S)-NH(C1-C6-alkyl), -C1-C6-alkyl-SC(=S)-NH(C1-C6-alkyl)2, wherein the cyclic R 4 , R 5 The group may be one or more R x Substituent substitution, where R 4 and R 5 At least one is hydrogen, C1-C6-alkyl or C3-C6-carbocycle. 4 and R 5are independently selected from hydrogen, C1-C6-alkyl, C1-C6-hydroxyalkyl, C3-C6-carbocycle, aryl, -C1-C6-alkyl-C1-C6-alkoxy, -C1-C6-alkyl-C3-C6-carbocycle, C1-C6-alkyl-O-(C=O)-C1-C6-alkyl, -C1-C6-alkyl-C(=O)-OH; C1-C6-alkyl-aryl, -C1-C6-alkyl-S-C1-C6-alkyl, wherein the acyclic R 4 , R 5 The group may be one or more R w Substituent substitution, wherein the cyclic R 4 , R 5 The group may be one or more R x Substituent substitution, where R 4 and R 5 at least one is hydrogen, C1-C6-alkyl or C3-C6-carbocycle; or R 4 and R 5 Together with the carbon atoms to which they are attached, they form a C3-C6-carbocyclic ring or a 3- to 6-membered heterocyclic ring, wherein the C3-C6-carbocyclic ring and the 3- to 6-membered heterocyclic ring may be replaced by one or more R x In another embodiment, R 4 is hydrogen, C1-C6-alkyl, C1-C6-hydroxyalkyl, C3-C6-carbocycle, C(=O)-OH, -C(=O)-O-C1-C6-alkyl, -C1-C6-alkyl-C1-C6-alkoxy, -C1-C6-alkyl-C1-C6-haloalkyl, -C1-C6-alkyl-C3-C6-carbocycle, -C1-C6-alkyl-aryl, -C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl-S-C1-C6-alkyl, -C1-C6-alkyl-C(=O)-NH2, -C1-C6-alkyl-C(=O)-OH, -C1-C6-alkyl-C(=O)-O-C1-C6-alkyl, R 5 is hydrogen, C1-C6-alkyl or C3-C6-carbocycle; or R 4 and R 5 Together with the carbon atom to which they are attached, they form a C3-C6-carbocycle. 4 is hydrogen, C1-C6-alkyl, C3-C6-carbocycle, -C1-C6-alkyl-C1-C6-haloalkyl, -C1-C6-alkyl-C3-C6-carbocycle, -C1-C6-alkyl-aryl, C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl-S-C1-C6-alkyl-, R 5 is hydrogen or C1-C6-alkyl; or R 4 and R 5Together with the carbon atom to which they are attached, they form a C3-C6-carbocycle. 4 is hydrogen, C1-C6-alkyl, C3-C6-carbocycle, -C1-C6-alkyl-C1-C6-haloalkyl, -C1-C6-alkyl-C3-C6-carbocycle, -C1-C6-alkyl-aryl, -C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl-S-C1-C6-alkyl-, R 5 is hydrogen or C1-C6-alkyl. In another embodiment, R 4 and R 5 Together with the carbon atoms to which they are attached, they form a C3-C6-carbocyclic ring or a 3- to 6-membered heterocyclic ring. 4 and R 5 Together with the carbon atom to which they are attached, they form a C3-C6-carbocycle. 4 and R 5 Together with the carbon atom to which they are attached they form a cyclopropyl or cyclobutyl group.

[0093] In another embodiment, n is 0. In another embodiment, n is 1.

[0094] In another embodiment, W is oxygen. In another embodiment, W is sulfur.

[0095] In another embodiment, Y is NR 8 , R 8 In another embodiment, Y is NR 8 , R 8 It is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, hydroxy, C1-C6-alkoxy or C3-C6-carbocycle.

[0096] In another embodiment, Z is selected from -C(=O)-SR a 、-C(=S)-NR b R c or

[0097] -C(=O)-NH-CR d R e C(=O)-OR a In another embodiment, Z is -C(=O)-SR a or -C(=S)-NR b R c In another embodiment, Z is -C(=O)-SR a In another embodiment, Z is -C(=S)-NR b R c .

[0098] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 The above definitions of W, Y, Z and n can be combined in various ways to provide sub-groups of compounds according to the invention.

[0099] Compounds resulting from combinations that violate the laws of nature are not included herein, and therefore a person skilled in the art will exclude them based on his / her expertise. For example, ring structures with three or more adjacent oxygen atoms are excluded.

[0100] Depending on the nature of the substituents, compounds of formula (I) or (II) may exist in the form of different stereoisomers. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Therefore, the present invention includes pure stereoisomers and any mixtures of these isomers. When a compound can exist in two or more tautomeric forms at equilibrium, the compound mentioned by a tautomeric description is considered to include all tautomeric forms.

[0101] Depending on the number of double bonds in the compound, any compound of the invention may also exist in one or more geometric isomers. Geometric isomers of the nature of substituents around double bonds or rings may exist in cis (=Z-) or trans (=E-) form. Therefore, the present invention also relates to all geometric isomers in all proportions and all possible mixtures.

[0102] The compound of formula (I) or (II) may suitably be in free form, salt form, N-oxide form or solvate form (eg hydrate).

[0103] Depending on the nature of the substituents, the compounds of the formula (I) or (II) can be present in the form of free compounds and / or salts thereof (eg agrochemically active salts).

[0104] Agrochemically active salts include acid addition salts of inorganic and organic acids and salts of common bases. Examples of inorganic acids are hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid, and acid salts such as sodium hydrogen sulfate and potassium hydrogen sulfate. Useful organic acids include, for example, formic acid, carbonic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, as well as glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono- or di-unsaturated fatty acids having 6 to 20 carbon atoms, alkyl sulfate monoesters, alkyl sulfonic acids (sulfonic acids having linear or branched alkyl groups having 1 to 20 carbon atoms), aryl sulfonic acids or aryl disulfonic acids (aryl groups with one or two sulfonic acid groups, such as phenyl and naphthyl), alkyl phosphonic acids (phosphonic acids having linear or branched alkyl groups having 1 to 20 carbon atoms), aryl phosphonic acids or aryl diphosphonic acids (aryl groups, such as phenyl and naphthyl groups, which have one or two phosphonic acid groups), wherein the alkyl and aryl groups may have other substituents, for example p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.

[0105] A solvate of a compound of formula (I) or (II) or a salt thereof is a stoichiometric composition of the compound and a solvent.

[0106] The compounds of formula (I) or (II) may exist in a variety of crystalline and / or non-crystalline forms. Crystalline forms include non-solvated crystalline forms, solvates and hydrates.

[0107] The present invention relates to any compound of formula (I) disclosed in the table and their use in crop protection (ie for controlling phytopathogenic fungi and / or bacteria on plants or plant parts).

[0108] Another aspect of the present invention relates to a composition comprising at least one compound of formula (I) according to the invention and at least one agriculturally suitable adjuvant.

[0109] Another aspect of the present invention relates to a method for controlling bacterial and / or fungal diseases in plants, comprising the step of applying at least one compound of formula (I) according to the invention or a composition according to the invention to plants, plant parts, seeds, fruits or the soil in which the plants grow.

[0110] Another aspect of the present invention relates to the use of the compounds according to the invention or the compositions according to the invention for controlling bacterial and / or fungal diseases on plants or plant parts. Preferably, they are used for controlling fungal diseases on plants or plant parts.

[0111] Another aspect of the present invention relates to the use of compounds of formula (I) for controlling bacterial diseases on plants or plant parts:

[0112]

[0113] in

[0114] R 1 , R 2 and R 3 Each is chlorine;

[0115] R 4 and R 5are independently selected from hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, -OC(=O)-C1-C6-alkyl, C3-C6-carbocycle, 4-, 5- or 6-membered non-aromatic heterocyclic group, -C(=O)-NH2, -C(=O)-NH(C1-C6-alkyl), -C(=O)-N(C1-C6-alkyl)2, -C(=O)-OH, -C(=O)-O-C1-C6-alkyl, aryl, 5- to 9-membered heteroaryl, -C1-C6-alkyl-C1-C6-alkoxy, -C1-C6-alkyl-C1-C6-haloalkyl, -C1-C6-alkyl-C3 -C6-carbocycle, -C1-C6-alkyl-4, 5 or 6-membered non-aromatic heterocyclic group, -C1-C6-alkyl-aryl, -C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl-5 to 9-membered heteroaryl, -C1-C6-alkyl-S-C1-C6-alkyl, -C1-C6-alkyl-SC(═O)-C1-C6-alkyl, -C1-C6-alkyl-O-(C═O)-C1-C6-alkyl, -C1-C6-alkyl-C(═O)-NH2, -C1-C6-alkyl-C(═O)-NH(C1-C6-alkyl), -C1-C6-alkyl-C(═O)-N(C1-C6-alkyl)2, -C1-C6-alkyl-C(═O)- =O)-OH, -C1-C6-alkyl-C(=O)-O-C1-C6-alkyl, -C1-C6-alkyl-NH-C(=NH)-NH2, -S-C1-C6-alkyl, -SC(=O)-C1-C6-alkyl, -SC(=O)-O-C1-C6-alkyl, -SC(=S)-O-C1-C6-alkyl, -SC(=O)-S-C1-C6-alkyl, -SC(=O)-NH2, -SC(=O)-NH(C1-C6-alkyl), -SC(=O)-NH(C1-C6-alkyl)2, -SC(=S)-NH2, -SC(=S)-NH(C1-C6-alkyl), -SC(=S) -NH(C1-C6-alkyl)2, -C1-C6-alkyl-SC(=O)-O-C1-C6-alkyl, -C1-C6-alkyl-SC(=O)-S-C1-C6-alkyl, -C1-C6-alkyl-SC(=O)-NH2, -C1-C6-alkyl-SC(=O)-NH(C1-C6-alkyl), -C1-C6-alkyl-SC(=O)-NH(C1-C6-alkyl)2, -C1-C6-alkyl-SC(=S)-NH2, -C1-C6-alkyl-SC(=S)-NH(C1-C6-alkyl), -C1-C6-alkyl-SC(=S)-NH(C1-C6-alkyl)2, wherein the cyclic R 4 , R5 The group may be one or more R x Substituent substitution, where R 4 and R 5 At least one is hydrogen, C1-C6-alkyl or C3-C6-carbocycle, or R 4 and R 5 Together with the carbon atoms to which they are attached, they form a C3-C6-carbocyclic ring or a 3- to 6-membered heterocyclic ring, wherein the C3-C6-carbocyclic ring and the 3- to 6-membered heterocyclic ring may be replaced by one or more R x Substituent substitution, where R x Independently selected from the following groups: halogen, nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-λ 6 -sulfanyl, formyl, carbamoyl, carbamate, C1-C8-alkyl, C3-C7-cycloalkyl, C1-C8-haloalkyl having 1 to 5 halogen atoms, C3-C7-halocycloalkyl having 1 to 5 halogen atoms, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkylamino, di-C1-C8-alkylamino, C1-C8-alkoxy, C1-C8-haloalkoxy having 1 to 5 halogen atoms, C1-C8-alkylsulfanyl, C1-C8-haloalkylsulfanyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyl, C1-C8-haloalkylcarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbamoyl, di-C1-C8-alkylcarbamoyl, C1-C8-alkoxycarbonyl, C1-C8-alkylsulfanyl having 1 to 5 halogen atoms C1-C8-haloalkoxycarbonyl, C1-C8-alkylcarbonyloxy, C1-C8-haloalkylcarbonyloxy having 1 to 5 halogen atoms, C1-C8-alkylcarbonylamino, C1-C8-haloalkylcarbonylamino having 1 to 5 halogen atoms, C1-C8-alkylsulfanyl, C1-C8-haloalkylsulfanyl having 1 to 5 halogen atoms, C1-C8-alkylsulfinyl, C1-C8-haloalkylsulfinyl having 1 to 5 halogen atoms, C1-C8-alkylsulfonyl, C1-C8-haloalkylsulfonyl having 1 to 5 halogen atoms; C1-C8-alkylsulfonylamino, C1-C8-haloalkylsulfonyl having 1 to 5 halogen atoms; sulfamoyl; C1-C8-alkylsulfamoyl and di-C1-C8-alkylsulfamoyl;

[0116] R 6 and R 7 are independently selected from hydrogen, C1-C6-alkyl, C3-C6-carbocycle; or R 6 and R 7 Together with the carbon atoms to which they are attached, they form a C3-C6-carbocyclic ring or a 3- to 6-membered heterocyclic ring;

[0117] n is 0 or 1;

[0118] W is oxygen or sulfur;

[0119] Y is NR 8 , R 8 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, hydroxy, C1-C6-alkoxy or C3-C6-carbocycle;

[0120] Z is selected from cyano, -C(=O)-OR a , -C(=O)-SR a 、-C(=O)-NR b R c , -C(=S)-NR b R c

[0121] or -C(=O)-NH-CR d R e -C(=O)-OR a , where R a is selected from hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, aryl, aralkyl, 4-, 5- or 6-membered non-aromatic heterocyclyl, -C1-C6-alkyl-Si(C1-C6-alkyl)3, -C1-C6-alkyl-C3-C8-cycloalkyl, 5- to 9-membered heteroaryl and -C1-C6-alkyl-5- to 9-membered heteroaryl, or R a Can be used with R 4 Together with the atoms to which they are attached, they form a 4- to 7-membered heterocyclic ring, R b and R c R is independently selected from hydrogen, C1-C6-alkyl, hydroxy, C1-C6-alkoxy, cyano, C1-C6-cyanoalkyl, or b Together with R4 and the atoms to which they are attached, they can form a 4- to 7-membered heterocyclic ring, wherein R d and R eindependently selected from hydrogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, -OC(=O)-C1-C6-alkyl, C3-C6-carbocycle, -C(=O)-NH2, -C(=O)-NH(C1-C6-alkyl), -C(=O)-N(C1-C6-alkyl)2, -C(=O)OH, -C(=O)-O-C1-C6-alkyl, aryl, 5- to 9-membered heteroaryl, -C1-C6-alkyl-C1-C6-alkoxy, -C1-C6-alkyl-C3-C6-carbocycle, -C1-C6-alkyl-aryl, -C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl -5 to 9 membered heteroaryl, -C1-C6-alkyl-S-C1-C6-alkyl, -C1-C6-alkyl-SC(═O)-C1-C6-alkyl, -C1-C6-alkyl-O-(C═O)-C1-C6-alkyl, -C1-C6-alkyl-C(═O)-NH2, -C1-C6-alkyl-C(═O)-NH(C1-C6-alkyl), -C1-C6-alkyl-C(═O)-N(C1-C6-alkyl)2, -C1-C6-alkyl-C(═O)-OH, -C1-C6-alkyl-C(═O)-O-C1-C6-alkyl, -C1-C6-alkyl-NH-C(═NH)-NH2, wherein R d and R e At least one is hydrogen, C1-C6-alkyl or C3-C6 carbocycle, or R d and R e Together with the carbon atom to which they are attached, they form a carbonyl group, a C3-C6-carbocycle or a 3- to 6-membered heterocycle;

[0122] The condition is to exclude 3,4,5-trichloro-N-(2-cyanoethyl)-N-cyclohexylthiophene-2-carboxamide [2450423-2], 3,4,5-trichloro-N,N-bis(2-cyanoethyl)thiophene-2-carboxamide [24467-28-5] and 3,4,5-trichloro-N-(2-cyanoethyl)-N-methylthiophene-2-carboxamide [24417-82-1] in the compound of formula (l),

[0123] Where W is oxygen, Y is NR 8 , R 8 is hydrogen or C1-C6-alkyl, n=0, R 4 is selected from hydrogen, C1-C6-alkyl, C1-C6-alkyl-aryl, C1-C6-alkylhydroxyaryl, cyclopropyl radical, R 5 is hydrogen or R 4 and R 5 Together with the carbon atom to which they are attached, they form a cyclopropyl group, then Z is selected from cyano, C(=O)-SR a 、-C(=O)-NRb R c , -C(=S)-NR b R c ,

[0124] -C(=O)-NH-CR d R e -C(=O)-OR a .

[0125] A further aspect of the present invention relates to the use of a compound according to the invention or a composition according to the invention for controlling nematodes on plants or plant parts.

[0126] A further aspect of the present invention relates to the use of a compound according to the invention or a composition according to the invention for controlling viruses on plants or plant parts.

[0127] Preferably, the compounds or compositions according to the invention are used to combat diseases caused by powdery mildew pathogens, for example Podosphaera species (e.g. Podosphaera leucotricha), Sphaerotheca species (e.g. Sphaerotheca fuliginea); diseases caused by rust pathogens, for example Uromyces species (e.g. Uromyces appendiculatus); diseases caused by oomycete pathogens, for example Peronospora species (e.g. Peronospora parasitica), Phytophthora species (e.g. Phytophthora infestans), Plasmopara species (e.g. Plasmopara spp. viticola), Pseudoperonospora species (e.g. Pseudoperonospora humuli or Pseudoperonospora cubensis), Pythium species (e.g. Pythium ultimum); by, for example, Alternaria species (e.g. Alternaria solani), Cercospora, Cercospora species (e.g. Cercospora beticola), Colletotrichum species (e.g. Colletotrichum lindemuthanium), leaf spot and leaf blight caused by Venturia species (e.g. Venturia inaequalis); diseases caused by bacterial pathogens, such as Xanthomonas species (e.g. Xanthomonas campestris pv. Campestris), Pseudomonas species (e.g. Pseudomonas syringae pv.Tomato), Erwinia species (e.g., Erwinia amylovora), Liberibacter species (e.g., Liberibacter Candidatus), Ralstonia species (e.g., Ralstonia solanacearum).

[0128] According to another aspect of the invention, the compounds or compositions of the invention are used as plant defense activators.Plant defense inducers according to the invention are compounds or compositions which stimulate the plant's own defense system.

[0129] Preparation method of compound of formula (I)

[0130] The present invention relates to a process for preparing compounds of formula (I). Compounds of formula (I) can be prepared by various routes analogous to known methods (see references therein), as well as by one or more of the following synthetic routes described below and in the experimental part.

[0131] General synthetic route for compounds of formula (I)

[0132] Unless otherwise stated, in the following text, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , W, Y, Z and n have the same meanings as given above for the compounds of formula (I).

[0133] Method A1

[0134] Compounds of formula (Ia) as defined herein may be prepared by process A1 comprising the step of reacting a compound of formula (II) or one of its salts with a compound of formula (III) or one of its salts, as shown by the following reaction scheme:

[0135]

[0136] Among them U 1 is halogen, hydroxy or a C1-C6-alkoxy group.

[0137] When U 1When represents a hydroxyl group, process A1 is advantageously carried out in the presence of a condensing agent. Suitable condensing agents may be selected from the following non-limiting list of acid halide forming agents, such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus trichloride oxide, oxalyl chloride or thionyl chloride; acid anhydride forming agents, such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; carbodiimides, such as N,N'-dicyclohexylcarbodiimide (DCC), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC) or other commonly used condensing agents, such as phosphorus pentoxide, polyphosphoric acid, bis(2-oxy-3-oxazolidinyl)phosphine chloride, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridine, 3-oxyhexafluorophosphate (HATU), 2-(1-H-benzotriazol-1-yl)-1-nitropropene. -1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU), (1-cyano-2-ethoxy-2-oxyethyleneaminooxy)dimethylamine-morpholine-hexafluorophosphate, N,N'-carbonyl-diimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / tetrachloromethane, 4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholine chloride hydrate, bis(2-oxo-3-oxazolidinyl)phosphinyl chloride (BOP-CI), bromotripyrrolidinylphosphonium hexafluorophosphate (PyBroP), 2-chloro-1,3-dimethylimidazolinium chloride (DMC), propanephosphonic anhydride (T3P), and 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT).

[0138] When U 1 When represents a halogen, method A1 is advantageously carried out in the presence of an acid binder. Suitable acid binders for implementing method A1 are in each case all inorganic and organic bases commonly used for such reactions. Preferred are alkali metal carbonates, such as cesium carbonate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate and tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, N-methylpiperidine, N,N-dimethylpyridine-4-amine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU), or aromatic bases, such as pyridine.

[0139] When U 1 In the case of C1 -C6 -alkoxy groups, process A1 can be carried out with an excess of the amine component, optionally in the presence of a Lewis acid (eg trimethylaluminum).

[0140] Process A1 can be carried out, if appropriate, in the presence of a base and, if appropriate, in the presence of a solvent, preferably under anhydrous conditions.

[0141] Suitable solvents for carrying out process A1 are not particularly limited. They may be customary inert organic solvents, provided that they do not dissolve the compounds to be reacted therewith or show any particular interaction. Preference is given to using optionally halogenated, aliphatic, alicyclic or aromatic hydrocarbons, for example petroleum ether, pentane, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene, decalin, ISOPAR TM E or ISOPAR TM G, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or trichloroethane; ethers, for example diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, for example acetonitrile, propionitrile, n-butyronitrile or isobutyronitrile or benzonitrile; amides, for example N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; ureas, for example 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone); esters, for example methyl acetate or ethyl acetate, sulfoxides, for example dimethyl sulfoxide, or sulfones, for example sulfolane; and mixtures thereof.

[0142] Method A1 can be carried out in an inert atmosphere (such as argon or nitrogen atmosphere). When implementing method A1, 1 mole or an excess of the compound of formula (III) and 1 to 5 moles of base can be used per mole of the compound of formula (II). Other ratios of reaction components can also be used. Post-treatment is carried out by known methods.

[0143] Compounds of formula (III) are commercially available or can be prepared by well-known methods (J. Med. Chem. 2018, 61, 8670-8692; Tetrahedron, 44 (1), 195-202; 1988, W02009070485; W02019086142; Chem. Res. Toxicol. 1990, 3, 118-124; JP49035334; JP49000223; Journal of Organic Chemistry (1989), 54 (12), 2940-2949).

[0144] Among them U 1 The compound of formula (IIa) representing a hydroxyl group is commercially available and can be prepared from 1 The compound of formula (IIb) representing a C1-C6-alkoxy group is prepared by well-known methods such as basic hydrolysis, or can be prepared by known methods (Beilstein J. Org. Chem. 2007, 3, No. 23).

[0145] Among them U 1 Compounds of formula (IIc) representing halogen are commercially available or can be prepared by well-known methods from 1 Preparation of compounds of formula (IIa) representing a hydroxyl group.

[0146] Among them U 1 Compounds of formula (IIb) representing C1-C6-alkoxy groups can be prepared by well-known methods from which U 1 Preparation of compounds of formula (IIa) representing a hydroxyl group.

[0147] Method B1

[0148] The compound of formula (Ib) can be prepared by method B1 from the compound of formula (Ia) by a sulfurization reaction, as shown in the following reaction scheme:

[0149]

[0150] Process B1 according to the invention is carried out in the presence of a sulphurizing agent.

[0151] Suitable sulfiding agents for carrying out the process B1 according to the invention may be sulfur (S), sulfuric acid (H2S), sodium sulfide (Na2S), sodium hydrosulfide (NaHS), boron trisulfide (B2S3), bis(diethylaluminum) sulfide ((AIEt2)2S), ammonium sulfide ((NH4)25), phosphorus pentasulfide (P2S5), Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiodiphosphine-2,4-disulfide) or polymer-supported sulfiding agents, as described, for example, in Journal of the Chemical Society, Perkin 1 (2001), 358, optionally in the presence of a catalytic or stoichiometric or excess amount of a base (e.g. an inorganic and organic base). Preference is given to using alkali metal carbonates, for example sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate; heterocyclic aromatic bases, for example pyridine, picoline, lutidine, collidine; and tertiary amines, for example trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylpyridin-4-amine or N-methyl-piperidine.

[0152] Suitable solvents for carrying out the process B1 according to the invention may be customary inert organic solvents. Preference is given to using optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, for example petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, for example diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane; nitriles, for example acetonitrile, propionitrile, n-butyronitrile or isobutyronitrile or benzonitrile, sulfur-containing solvents, for example sulfolane or carbon disulfide.

[0153] When carrying out process B1 according to the invention, it is possible to use 1 mol or an excess of sulfur equivalents of the sulfurizing agent and 1 to 3 mol of the base per mole of the amide reactant (Ia).

[0154] Other ratios of the reaction components can also be used. Work-up is carried out by known methods.

[0155] Method C1

[0156] The compound of formula (I) as defined herein can be prepared by method C1 from a compound of formula (IV) or one of its salts by chlorination reaction as shown in the following reaction scheme:

[0157]

[0158] Among them U 4 , U 5 and U 6 are independently hydrogen or chlorine, provided that U 4 , U 5 or U 6 At least one is hydrogen.

[0159] Method C1 can be carried out according to known methods (Angewandte Chemie, International Edition, 52 (16), 4440-4444; 2013; ACS Catalysis, 6 (11), 7839-7843; 2016; Journal of the American Chemical Society, 2017, 139, 888; Angewandte Chemie, International Edition, 2014, 53, 7928; Journal of the American Chemical Society, 2018, 140, 2789; W02008156879; W02012114285;

[0160] W02008109786; W02007098356).

[0161] Process C1 is carried out in the presence of a chlorinating agent and, if appropriate, a solvent.

[0162] Suitable chlorinating agents for carrying out the method C1 are not particularly limited as long as they can be used for chlorination. Examples of the chlorinating agent include N-chlorosuccinimide, sulfuryl chloride, hexachloroethane and 1,3-dichloro-5,5-dimethyl-2,4-imidazolidinedione.

[0163] Suitable solvents for implementing method C1 are not particularly limited. They can be commonly used inert organic solvents, as long as it does not dissolve the compound reacted with it or show any specific interaction. Suitable solvents can be, for example, solvents disclosed in connection with method A1. In order to implement method C1, it is also advantageous to use an organic acid (such as acetic acid or trifluoroacetic acid) as a solvent or cosolvent. In order to implement method C1, it is also advantageous to use a Lewis acid (such as zinc (II) chloride) as a catalyst. In order to implement method C1, it is also advantageous to use a transition metal catalyst (such as a palladium catalyst). In order to implement method C1, it is also advantageous to use a suitable organometallic reagent (such as n-butyl lithium). In order to implement method C1, according to known methods (WO2020079205), it is also advantageous to use a suitable base before halogenation, such as n-butyl lithium, lithium diisopropylamine, tetramethyl piperidine lithium, bis (trimethylsilyl) amine lithium, methyl lithium or chloro-(2,2,6,6-tetramethyl-1-piperidyl) magnesium, etc., preferably under anhydrous conditions. Optionally, lithium chloride may be used in a preformed combination with these reagents.

[0164] Method D1

[0165] The compounds of formula (I) as defined herein can be prepared by process D1 comprising the steps of diazotizing a compound of formula (V) or one of its salts followed by aromatic substitution to provide a compound of formula (I), as shown in the following reaction scheme:

[0166]

[0167] Among them U 7 , U 8 and U 9 are independently amino groups or chlorine, provided that U 7 , U 8 or U 9 At least one of them is an amino group.

[0168] Method D1 can be carried out according to a known method (The Chemistry of diazonium and diazogroups; Saul Patai; Wiley-Interscience; 1978; 288-280 and 645-657; Account of Chemical Research (2018), 51, 496 and references cited therein).

[0169] The compound of formula (V) as defined herein or one of its salts can be prepared by a process comprising a step of reducing the nitro group according to well-known methods (Science of Synthesis: Catalytic

[0170] Reduction in Organic Synthesis 2;JG de Vries, 2018, chapter 2.7: Reduction of Nitro Compounds to Amines, Azo Compounds, Hydroxylamines, and Oximes, and Reduction of N-Oxides to Amines, and references cited therein) or deprotecting the protected amino group according to well-known methods.

[0171] Examples of amino-protecting groups include a benzyl group, a 4-methoxybenzyl group, an allyl group, an unsubstituted or substituted C1-C6-alkylsulfonyl group, a trifluoromethylsulfonyl group, an unsubstituted or substituted benzenesulfonyl group, an unsubstituted or substituted C1-C6-alkoxycarbonyl group, an unsubstituted or substituted benzyloxycarbonyl group, an allyloxycarbonyl group, an acetyl group or a trifluoroacetyl group.

[0172] The deprotection method can be carried out according to known methods for removing protecting groups (Greene's Protective Groups in Organic Synthesis; Peter GMWuts; Wiley; Fifth Edition; 2014; 895-1194). For example, tert-butyloxycarbonyl and benzyloxycarbonyl protecting groups can be removed in an acidic medium (e.g., with hydrochloric acid or trifluoroacetic acid). The benzyl protecting group can be removed with hydrogen in the presence of a catalyst (e.g., palladium on activated carbon). The trifluoroacetyl group can be removed in an alkaline medium (e.g., potassium carbonate or lithium hydroxide).

[0173] A compound of formula (Ic) wherein Z is -C(=O)-OR a , where R aselected from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, aryl, aralkyl, 4-, 5- or 6-membered non-aromatic heterocyclic group, -C1-C6-alkyl-Si(C1-C6-alkyl)3, -C1-C6-alkyl-C3-C8-cycloalkyl, 5- to 9-membered heteroaryl and -C1-C6-alkyl-5 to 9-membered heteroaryl, can be prepared from compounds of formula (ld) by well-known coupling methods under the conditions described in method A1, wherein Z in formula (ld) is -C(=O)-OR a , where R a is hydrogen and the corresponding alcohol or one of its salts.

[0174] A compound of formula (Id) wherein Z is -C(=O)-OR a , where R a is hydrogen, wherein Z is -C(=O)-OR a The compound of formula (Ic) wherein R a is selected from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, aryl, aralkyl, 4, 5 or 6-membered non-aromatic heterocyclic group, -C1-C6-alkyl-Si(C1-C6-alkyl)3, -C1-C6-alkyl-C3-C8-cycloalkyl, 5 to 9-membered heteroaryl and -C1-C6-alkyl-5 to 9-membered heteroaryl. Examples of hydrolysis agents include lithium hydroxide, potassium hydroxide, sodium hydroxide, trimethyltin hydroxide. The hydrolysis can be carried out as described in WO2008157844; WO2006002099; WO20050256107; Angewandte Chemie, International Edition (2005), 44 (9), 1378-1382.

[0175] Where Z is -C(=O)-SR a 、-C(=O)-NR b R c 、-C(=O)-NH-CR d R e -C(=O)-OR a The compound of formula (Ie) may be a compound wherein Z is -C(=O)-OR a Compounds of formula (Ic) are prepared by well-known coupling methods under the conditions described in Method A1, wherein R a is hydrogen and one of the corresponding thiol, amine or its salt.

[0176] Compositions and preparations

[0177] The present invention also relates to a composition, in particular a composition for controlling unwanted microorganisms, comprising one or more compounds of formula (I). The composition is preferably a fungicidal composition.

[0178] The compositions generally comprise one or more compounds of formula (I) and one or more acceptable carriers, especially one or more agriculturally acceptable carriers.

[0179] Carriers are generally inert solid or liquid, natural or synthetic, organic or inorganic substances. Carriers generally improve the application of compounds, for example, to plants, plant parts or seeds. Examples of suitable solid carriers include, but are not limited to, ammonium salts, natural rock powders, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, and synthetic rock powders, such as finely divided silicon dioxide, aluminum oxide and silicates. Examples of useful solid carriers commonly used in the preparation of granules include, but are not limited to, crushed and decomposed natural rocks, such as calcite, marble, pumice, sepiolite and dolomite, synthetic particles of inorganic and organic flours and particles of organic materials, such as paper, sawdust, coconut shells, corn cobs and tobacco rods. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents and combinations thereof. Examples of suitable solvents include polar and nonpolar organic chemical liquids, such as aromatic and nonaromatic hydrocarbons (e.g. cyclohexane, alkanes, alkylbenzenes, xylenes, toluene alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride or methylene chloride), alcohols and polyols (which may also be optionally substituted, etherified and / or esterified, such as butanol or ethylene glycol), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (e.g. dimethylformamide), lactams (e.g. N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (e.g. dimethyl sulfoxide). The carrier may also be a liquefied gaseous extender, i.e. a liquid which is gaseous at standard temperature and standard pressure, such as an aerosol propellant, such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide. The amount of carrier is generally 1-99.99%, preferably 5-99.9%, more preferably 10-99.5%, most preferably 20-99% by weight of the composition.

[0180] The composition may further comprise one or more acceptable adjuvants commonly used in formulating compositions (eg agrochemical compositions), such as one or more surfactants.

[0181] Surfactant can be ionic (cationic or anionic) or nonionic surfactant, such as ionic or nonionic emulsifier, foaming agent, dispersant, wetting agent and any mixture thereof. Examples of suitable surfactants include but are not limited to polyacrylate, lignin sulfonate, phenol sulfonate or naphthalene sulfonate, polycondensates (polyoxyethylene fatty esters, polyoxyethylene fatty alcohol ethers, such as alkyl aryl polyglycol ethers) of ethylene and / or propylene oxide and fatty alcohol, fatty acid or fatty amine, substituted phenol (preferably alkylphenol or arylphenol), sulfosuccinate salts, taurine derivatives (preferably taurine alkyl esters), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty esters of polyols and derivatives containing sulfate, sulfonate, phosphate (such as alkyl sulfonate, alkyl sulfate, aryl sulfonate) and protein hydrolyzate compounds, lignosulfite waste liquor and methylcellulose. When the compound of formula (I) and / or carrier are insoluble in water and the application is prepared with water, surfactant is usually used. Then, the amount of surfactant is usually 5-40% of the composition weight.

[0182] Other examples of adjuvants conventionally used in formulating agrochemical compositions include water-proofing agents, desiccants, binders (adhesives, tackifiers, fixatives, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalin and lecithin and synthetic phospholipids, polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and cellulose), thickeners, stabilizers (such as cold stabilizers, preservatives, antioxidants, light stabilizers or other stabilizers that improve chemical and / or physical stability), dyes or pigments (such as Inorganic pigments, such as iron oxide, titanium oxide and Prussian blue; organic dyes, such as alizarin, azo and metal phthalocyanine dyes), defoamers (such as silicone defoamers and magnesium stearate), preservatives (such as dichlorophenol and benzyl alcohol hemiformal), auxiliary thickeners (cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clay and finely divided silica), adhesives, gibberellins and processing aids, mineral oils and vegetable oils, fragrances, waxes, nutrients (including trace nutrients, such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts), protective colloids, thixotropic substances, penetrants, chelating agents and complexing agents.

[0183] The selection of auxiliary agent is relevant to the expected mode of application and / or physical property of the compound of formula (I). In addition, the use form specific characteristics (technical, physical and / or biological characteristics) of the composition or prepared therefrom can be conferred by selecting auxiliary agent. The selection of auxiliary agent can allow the composition to be customized according to specific needs.

[0184] The composition may be in any conventional form, such as solutions (e.g. aqueous solutions), emulsions, wettable powders, water-based and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural or synthetic products impregnated with the compounds of the invention, fertilizers and microcapsules in polymeric materials. The compounds of formula (I) may be present in suspended, emulsified or dissolved form.

[0185] The composition can be provided to the end user as a ready-to-use formulation, i.e. the composition can be applied directly to plants or seeds by suitable devices such as spraying or dusting devices. Alternatively, the composition can be provided to the end user in the form of a concentrate, which must be diluted before use, preferably with water.

[0186] Such compositions may be prepared in customary manner, for example by mixing a compound of formula (I) with one or more suitable auxiliaries, for example disclosed above.

[0187] The composition typically contains 0.01 to 99%, 0.05 to 98%, preferably 0.1 to 95%, more preferably 0.5 to 90%, most preferably 1 to 80% by weight of the compound of formula (I).

[0188] The compound and the composition comprising it can be mixed with other active ingredients, such as fungicides, bactericides, miticides, nematicides, insecticides, herbicides, fertilizers, growth regulators, safeners or chemical semiochemicals. This can broaden the spectrum of activity or prevent the development of drug resistance. Examples of known fungicides, insecticides, miticides, nematicides and bactericides are disclosed in Pesticide Manual, 17th Edition.

[0189] The active ingredients designated herein by their common names are known and described in the Pesticide Manual (16th Ed. British Crop Protection Council) or can be found on websites such as www.alanwood.net / pesticides.

[0190] Compound (A) or compound (B) may exist in tautomeric forms, such that reference to such compounds above and below is to be understood as also including, where applicable, the corresponding tautomeric forms, even if these are not specifically mentioned in each case.

[0191] Examples of fungicides that can be mixed with the compounds of formula (I) and the compositions of the invention are:

[0192] 1) Inhibitors of ergosterol synthesis, for example (1.001) cyproconazole, (1.002) diclobutrazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulphate), (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazole, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) 1.024) tridemorph, (1.025) triticonazole, (1.026) (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1-H-1,2.4-triazole-1-methylene) cyclopentanol, (1.027) (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1- (1-H-1,2.4-triazol-1-methylene)cyclopentanol, (1.028) (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.029) (2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,

[0193] (1.030) (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.031) (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.032) (2S)-2-(1-chlorocyclopropyl)-4-[(1S) -2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.033) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,

[0194] (1.035) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.038) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3- 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxy-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxy-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate,

[0195] (1.042) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,

[0196] (1.044) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.045) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,

[0197] (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,

[0198] (1.048) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,

[0199] (1.051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) chlorfenapyr (mef entrifluconazole), (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluoro-phenyl)oxirane-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-2,4-dihydro-3H-1,2 ,4-triazole-3-thione, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.060) 5-(allylthio)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylthio)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)epoxy-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylthio)-1-{[rel(2R,3S )-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazole, (1.063) N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]thio}phenyl)-N-ethyl-N-iminocarboxamide, (1.064) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]thio}phenyl)-N-ethyl-N-iminocarboxamide, (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]thio}phenyl)-N-ethyl-N-iminocarboxamide, (1.066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]thio}phenyl)-N-ethyl-N-iminocarboxamide, (1.067) N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)phenyl]thio}phenyl)-N-ethyl-N-iminocarboxamide, (1.068) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)thio]phenoxy}phenyl)-N-ethyl-N-iminocarboxamide, (1.069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropoxy)thio]phenoxy}phenyl)-N-ethyl-N-iminocarboxamide, (1. 070) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)thio]phenoxy}phenyl)-N-ethyl-N-iminocarboxamide, (1.071) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine hydrochloride, (1.072) N'-(4-{[3-(difluoromethoxy)phenyl]sulfonyl}-2,5-dimethylphenyl)-N-ethyl-N-iminocarboxamide, (1.073) N'-(4-{3-[(difluoromethyl)thio]phenoxy}-2,5-xylyl)-N-ethyl-N-iminocarboxamide, (1.074) N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2- N-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-iminocarboxamide, (1.077) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-iminocarboxamide, (1.078) N'-{5-bromo-6-[(cis-4-isopropyl)-1-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-iminocarboxamide, N-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-iminocarboxamide, (1.079) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-iminocarboxamide, (1.080) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylformamidine hydrochloride, (1.081) ipfentrifluconazole, (1.082) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.083) 1-[1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.084) 1-[1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.085) 1-[1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.086) 1-[1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.087) 1-[1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.088) 1-[1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.089) 1-[1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.0083) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.084) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.085).

[0200] 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, (1.086)

[0201] 4-[[6-[rac-(2R)-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thione-4H-1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile, (1.087) N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methyliminocarboxamide, (1.088) N'-{5-bromo-2-methyl-6-[(1-propoxyprop-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-iminocarboxamide, (1.089) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate.

[0202] 2) Inhibitors of respiratory chain complex I or II, such as (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr, (2.009) isofetamid, (2.010) pyrazolone pyrazam (trans epimers 1R, 4S, 9S), (2.011) isopyrazam (trans epimers 1S, 4R, 9R), (2.012) isopyrazam (trans epimers 1RS, 4SR, 9SR), (2.013) isopyrazam (mixture of cis epimers 1RS, 4SR, 9RS and trans epimers 1RS, 4SR, 9SR), (2.014) isopyrazam (cis epimers 1R, 4S, 9R), (2.015 ) isopyrazam (cis-diameric enantiomers 1S, 4R, 9S), (2.016) isopyrazam (cis-diameric racemates 1RS, 4SR, 9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl)- ... -yl)-1H-pyrazole-4-carboxamide, (2.023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.028) inpyrfluxam, (2.029) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) fluindapyr, (2.031) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)-pyridin-2-yl]oxy}phenyl)ethyl]quinolin-4-amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole- 4-carboxamide, (2.036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) isoflucypram, (2.039) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methylenenaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methylenenaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide )-1,2,3,4-tetrahydro-1,4-methylenenaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxyprop-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042) N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl 1H-pyrazole-4-carboxamide, (2.048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.049) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro -1-methyl-1H-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-( (2.056) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.057) pyrapropoyne, (2.058) N-[rac-(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)-nicotinamide, (2.059) N-[(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.060) fluorophenyl ether amide (flubeneteram). .

[0203] 3) Inhibitors at complex III of the respiratory chain, such as (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enestroburin, (3.009) famoxa done), (3.010) fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018) pyramet ostrobin), (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpentan-3-amide, (3.023) (2R)-2-{2-[ (2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) fenpicoxamid, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcycloethyl)-3-carboxamide-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpentan-3-amide, (3.029)029) methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.030) metyltetraprole, (3.031) florylpicoxamid. .

[0204] 4) Inhibitors of mitosis and cell division, for example (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) pyridachlometyl, (4.010) pyridachlometyl, (4.011) pyridachlometyl, (4.012) pyridachlometyl, (4.013) pyridachlometyl, (4.014) pyridachlometyl, (4.015) pyridachlometyl, (4.016) pyridachlometyl, (4.017) pyridachlometyl, (4.018) pyridachlometyl, (4.019) pyridachlometyl, (4.020) pyridachlometyl, (4.021) pyridachlometyl, (4.022) pyridachlometyl, (4.023) pyridachlometyl, (4.024) pyridachlometyl, (4.025) pyridachlometyl, (4.026) pyridachlometyl, (4.027) pyridachlometyl, (4.028) pyridachlometyl, (4.029) pyridachlometyl, (4.030) pyridachlometyl, (4.031) pyridachlometyl, (4.032) pyridachlometyl, (4.033) pyridachlometyl, (4.034) pyridachlometyl, ( 010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.015) 4-(2-Bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.016) 4-(2-Bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.017) 4-(2-Bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.018) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-diphenyl-1H-pyrazol-5-amine, (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5 -amine, (4.020) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1-1H-pyrazol-5-amine, (4.022) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.025) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.026) fluopimomide.

[0205] 5) Compounds capable of multi-site action, such as (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, oxychloride), (5.009) copper (2+) sulphate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinc, (5.017) oxine-copper, (5.018) propineb, (5.019) sulfur and sulfur preparations including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram, (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

[0206] 6) Compounds capable of inducing host defense, such as (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, and (6.004) tiadinil.

[0207] 7) Inhibitors of amino acid and / or protein biosynthesis, for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

[0208] 8) Inhibitors of ATP production, for example (8.001) silthiofam.

[0209] 9) Inhibitors of cell wall synthesis, for example: (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamide, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

[0210] 10) Inhibitors of lipid and membrane synthesis, for example: (10.001) prothiocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

[0211] 11) Melanin biosynthesis inhibitors, for example (11.001) tricyclazole, (11.002) tolprocarb.

[0212] 12) Nucleic acid synthesis inhibitors, for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[0213] 13) Signal transduction inhibitors, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) fludioxonil, (13.005) quinoxyfen, (13.006) vinclozolin.

[0214] 14) Compounds capable of acting as uncouplers, for example (14.001) fluazinam and (14.002) meptyldinocap.

[0215] 15) Other fungicides selected from: (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone, (15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid, (15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014) fosetyl-sodium, (15.015) methyl isothiocyanate isothiocyanate), (15.016) metrafenone, (15.017) mildiomycin, (15.018) natamycin, (15.019) nickeldimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) oxathiapiprolin, (15.023) oxyfenthiin, (15.024) pentachlorophenol and its salts, (15.025) phosphorous acid and its salts itssalts), (15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone), (15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]vinyl ketone, (15.032) 1-(4-{4-[(5S)-5-(2,6-difluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]vinone, (15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034) dipymetitrone, (15.035) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl)- 1-yl] ene ketone, (15.036) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl] ene ketone, (15.037) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl] ene ketone, (15.038) 2-[6-(3-fluoro- 4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.039) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.040) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.041) ipflufenoquin , (15.042) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}isopropanol, (15.043) fluoxapiprolin, (15.044) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate, (15.045) 2-phenylphenol and its salts, (15.046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.047) quinofumelin, (15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomer: 4-amino-5-fluoropyrimidin-2(1H)-alkanone), (15.049) 4-oxo-4-[(2-phenylethyl)amino]butyric acid, (15.050) 5-amino-1,3,4-thiadiazole-2-thiol, (15.051) 5-chloro-N'-phenyl-N'-(propan-2 -alkyn-1-yloxy)thiophene-2-sulfonylhydrazide, (15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]-pyrimidin-4-amine, (15.053) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzodiazepine 、(15.055) but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.056) (2Z)-3-amino-2-cyano-3-phenylacrylate ethyl ester, (15.057) phenazine-1-carboxylic acid, (15.058) 3,4,5-trihydroxybenzoic acid propyl ester, (15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061) tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.062).

[0216] 5-Fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-alkanone, (15.063)aminopyrifen, (15.064) (N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyliminocarboxamide), (15.065) (N'-(2-chloro-5-methyl- 4-phenoxyphenyl)-N-ethyl-N-methyliminocarboxamide), (15.066) (2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}isopropanol), (15.067) (5-bromo-1-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline), (15.068) (3-(4,4-difluoro-5, 5-dimethyl-4,5-dihydrothiophene[2,3-c]pyridin-7-yl)quinoline), (15.069) (1-(4,5-dimethyl-1H-benzoimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline), (15.070) 8-fluoro-3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15.071) 8 -Fluoro-3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15.072) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-8-fluoroquinoline, (15.073) (N-methyl-N-phenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide), (15.074)

[0217] {4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamic acid methyl ester, (15.075)

[0218] (N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}cyclopropaneamide), (15.076) N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.077) N-[(E)-methoxyimino-methyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.078) N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.079)

[0219] N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclopropanamide, (15.080) N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.081) 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, (15.082) N-propenyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]acetamide, (15.083)

[0220] N-[(E)-N-methoxy-C-methyl-carbonimido]-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.084) N-[(Z)-N-methoxy-C-methyl-carbonimido]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.085) N-propenyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.086) 4,4-dimethyl-1-[[4-[5-(difluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrol-2-one, (15.087 )N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzylthioamide, (15.088)5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrol-2-one, (15.089)N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoropropionamide, (15.090)1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.091)1,1-diethyl-3-[[4-[ 5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.092) N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.093) N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanamide, (15.094) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.095) N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl] methyl]cyclopropanamide, (15.096) N,2-dimethoxy-N-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.097) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]propanamide, (15.098) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.099) 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.100) 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.101).

[0221] 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.102) 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazol-3-one, (15.103) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazol-3-one, (15.104) 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.105) 1-[[3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclohexylimine-2-one, (15.106) 4,4-dimethyl-2-[[4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazol-3-one, (15.107) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazol-3-one oxazol-3-one, (15.108) 1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazole-4-carboxylic acid ethyl ester, (15.109) N,N-dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-1,2,4-triazol-3-amine, (15.110) N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butanamide, (15.111) N-(1-methylcyclopropyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.112) N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.113) 1-(5,6-dimethylpyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.114) 1-(6-(difluoromethyl)-5-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.115)

[0222] 1-(5-(Fluoromethyl)-6-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.116) 1-(6-(difluoromethyl)-5-methoxy-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.117) 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl dimethylcarbamate, (15.118) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}propionamide, (15.119 )3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.120)9-fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.121)3-[2-(1-{[3,5-di(dioxepin-6-yl) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.122) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-9-fluoro-1,5-difluoro-2,4-benzodioxepin-6-yl methanesulfonate, (15.123) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.124) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.125) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.126) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.127) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)- Methyl-3,4-dihydroisoquinoline, (15.124) 8-fluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline-3-carboxamide, (15.125) 8-fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl]quinoline-3-carboxamide, (15.126) N-(2,4-dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide and (15.127) N-[(2S)-2,4-dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide.

[0223] All named mixing partners of classes (1) to (15) can, if their functional groups are capable, optionally form salts with suitable bases or acids.

[0224] Another aspect of the present invention relates to one or more of the following combinations of compounds:

[0225] (I.001)+(1.001)、(I.001)+(1.002)、(I.001)+(1.003)、(I.001)+(1.004)、(I.001)+(1.005)、(I.001)+(1.006)、(I.001)+(1.007)、(I.001)+(1.008)、(I.001)+(1.009)、(I.001)+(1.010)、(I.001)+(1.011)、(I.001)+(1.012)、(I.001)+(1.013)、(I.001)+(1.014)、(I.001)+(1.015)、(I.001)+(1.016)、(I.001)+(1.017)、(I.001)+(1.018)、(I.001)+(1.019)、(I.001)+(1.020)、(I.001)+(1.021)、(I.001)+(1.022)、(I.001)+(1.023)、(I.001)+(1.024)、(I.001)+(1.025)、(I.001)+(1.026)、(I.001)+(1.027)、(I.001)+(1.028)、(I.001)+(1.029)、(I.001)+(1.030)、(I.001)+(1.031)、(I.001)+(1.032)、(I.001)+(1.033)、(I.001)+(1.034)、(I.001)+(1.035)、(I.001)+(1.036)、(I.001)+(1.037)、(I.001)+(1.038)、(I.001)+(1.039)、(I.001)+(1.040)、(I.001)+(1.041)、(I.001)+(1.042)、(I.001)+(1.043)、(I.001)+(1.044)、(I.001)+(1.045)、(I.001)+(1.046)、(I.001)+(1.047)、(I.001)+(1.048)、(I.001)+(1.049)、(I.001)+(1.050)、(I.001)+(1.051)、(I.001)+(1.052)、(I.001)+(1.053)、(I.001)+(1.054)、(I.001)+(1.055)、(I.001)+(1.056)、(I.001)+(1.057)、(I.001)+(1.058)、(I.001)+(1.059)、(I.001)+(1.060)、(I.001)+(1.061)、(I.001)+(1.062)、(I.001)+(1.063)、(I.001)+(1.064)、(I.001)+(1.065)、(I.001)+(1.066)、(I.001)+(1.067)、(I.001)+(1.068)、(I.001)+(1.069)、(I.001)+(1.070)、(I.001)+(1.071)、(I.001)+(1.072)、(I.001)+(1.073)、(I.001)+(1.074)、(I.001)+(1.075)、(I.001)+(1.076)、(I.001)+(1.077)、(I.001)+(1.078)、(I.001)+(1.079)、(I.001)+(1.080)、(I.001)+(1.081)、(I.001)+(1.082)、(I.001)+(1.083)、(I.001)+(1.084)、(I.001)+(1.085)、(I.001)+(1.086)、(I.001)+(1.087)、(I.001)+(1.088)、(I.001)+(1.089)、(I.001)+(2.001)、(I.001)+(2.002)、(I.001)+(2.003)、(I.001)+(2.004)、(I.001)+(2.005)、(I.001)+(2.006)、(I.001)+(2.007)、(I.001)+(2.008)、(I.001)+(2.009)、(I.001)+(2.010)、(I.001)+(2.011)、(I.001)+(2.012)、(I.001)+(2.013)、(I.001)+(2.014)、(I.001)+(2.015)、(I.001)+(2.016)、(I.001)+(2.017)、(I.001)+(2.018)、(I.001)+(2.019)、(I.001)+(2.020)、(I.001)+(2.021)、(I.001)+(2.022)、(I.001)+(2.023)、(I.001)+(2.024)、(I.001)+(2.025)、(I.001)+(2.026)、(I.001)+(2.027)、(I.001)+(2.028)、(I.001)+(2.029)、(I.001)+(2.030)、(I.001)+(2.031)、(I.001)+(2.032)、(I.001)+(2.033)、(I.001)+(2.034)、(I.001)+(2.035)、(I.001)+(2.036)、(I.001)+(2.037)、(I.001)+(2.038)、(I.001)+(2.039)、(I.001)+(2.040)、(I.001)+(2.041)、(I.001)+(2.042)、(I.001)+(2.043)、(I.001)+(2.044)、(I.001)+(2.045)、(I.001)+(2.046)、(I.001)+(2.047)、(I.001)+(2.048)、(I.001)+(2.049)、(I.001)+(2.050)、(I.001)+(2.051)、(I.001)+(2.052)、(I.001)+(2.053)、(I.001)+(2.054)、(I.001)+(2.055)、(I.001)+(2.056)、(I.001)+(2.057)、(I.001)+(2.058)、(I.001)+(2.059)、(I.001)+(2.060)、(I.001)+(3.001)、(I.001)+(3.002)、(I.001)+(3.003)、(I.001)+(3.004)、(I.001)+(3.005)、(I.001)+(3.006)、(I.001)+(3.007)、(I.001)+(3.008)、(I.001)+(3.009)、(I.001)+(3.010)、(I.001)+(3.011)、(I.001)+(3.012)、(I.001)+(3.013)、(I.001)+(3.014)、(I.001)+(3.015)、(I.001)+(3.016)、(I.001)+(3.017)、(I.001)+(3.018)、(I.001)+(3.019)、(I.001)+(3.020)、(I.001)+(3.021)、(I.001)+(3.022)、(I.001)+(3.023)、(I.001)+(3.024)、(I.001)+(3.025)、(I.001)+(3.026)、(I.001)+(3.027)、(I.001)+(3.028)、(I.001)+(3.029)、(I.001)+(3.030)、(I.001)+(3.031)、(I.001)+(4.001)、(I.001)+(4.002)、(I.001)+(4.003)、(I.001)+(4.004)、(I.001)+(4.005)、(I.001)+(4.006)、(I.001)+(4.007)、(I.001)+(4.008)、(I.001)+(4.009)、(I.001)+(4.010)、(I.001)+(4.011)、(I.001)+(4.012)、(I.001)+(4.013)、(I.001)+(4.014)、(I.001)+(4.015)、(I.001)+(4.016)、(I.001)+(4.017)、(I.001)+(4.018)、(I.001)+(4.019)、(I.001)+(4.020)、(I.001)+(4.021)、(I.001)+(4.022)、(I.001)+(4.023)、(I.001)+(4.024)、(I.001)+(4.025)、(I.001)+(4.026)、(I.001)+(5.001)、(I.001)+(5.002)、(I.001)+(5.003)、(I.001)+(5.004)、(I.001)+(5.005)、(I.001)+(5.006)、(I.001)+(5.007)、(I.001)+(5.008)、(I.001)+(5.009)、(I.001)+(5.010)、(I.001)+(5.011)、(I.001)+(5.012)、(I.001)+(5.013)、(I.001)+(5.014)、(I.001)+(5.015)、(I.001)+(5.016)、(I.001)+(5.017)、(I.001)+(5.018)、(I.001)+(5.019)、(I.001)+(5.020)、(I.001)+(5.021)、(I.001)+(5.022)、(I.001)+(5.023)、(I.001)+(6.001)、(I.001)+(6.002)、(I.001)+(6.003)、(I.001)+(6.004)、(I.001)+(7.001)、(I.001)+(7.002)、(I.001)+(7.003)、(I.001)+(7.004)、(I.001)+(7.005)、(I.001)+(7.006)、(I.001)+(8.001)、(I.001)+(9.001)、(I.001)+(9.002)、(I.001)+(9.003)、(I.001)+(9.004)、(I.001)+(9.005)、(I.001)+(9.006)、(I.001)+(9.007)、(I.001)+(9.008)、(I.001)+(9.009)、(I.001)+(10.001)、(I.001)+(10.002)、(I.001)+(10.003)、(I.001)+(11.001)、(I.001)+(11.002)、(I.001)+(12.001)、(I.001)+(12.002)、(I.001)+(12.003)、(I.001)+(12.004)、(I.001)+(13.001)、(I.001)+(13.002)、(I.001)+(13.003)、(I.001)+(13.004)、(I.001)+(13.005)、(I.001)+(13.006)、(I.001)+(14.001)、(I.001)+(14.002)、(I.001)+(15.001)、(I.001)+(15.002)、(I.001)+(15.003)、(I.001)+(15.004)、(I.001)+(15.005)、(I.001)+(15.006)、(I.001)+(15.007)、(I.001)+(15.008)、(I.001)+(15.009)、(I.001)+(15.010)、(I.001)+(15.011)、(I.001)+(15.012)、(I.001)+(15.013)、(I.001)+(15.014)、(I.001)+(15.015)、(I.001)+(15.016)、(I.001)+(15.017)、(I.001)+(15.018)、(I.001)+(15.019)、(I.001)+(15.020)、(I.001)+(15.021)、(I.001)+(15.022)、(I.001)+(15.023)、(I.001)+(15.024)、(I.001)+(15.025)、(I.001)+(15.026)、(I.001)+(15.027)、(I.001)+(15.028)、(I.001)+(15.029)、(I.001)+(15.030)、(I.001)+(15.031)、(I.001)+(15.032)、(I.001)+(15.033)、(I.001)+(15.034)、(I.001)+(15.035)、(I.001)+(15.036)、(I.001)+(15.037)、(I.001)+(15.038)、(I.001)+(15.039)、(I.001)+(15.040)、(I.001)+(15.041)、(I.001)+(15.042)、(I.001)+(15.043)、(I.001)+(15.044)、(I.001)+(15.045)、(I.001)+(15.046)、(I.001)+(15.047)、(I.001)+(15.048)、(I.001)+(15.049)、(I.001)+(15.050)、(I.001)+(15.051)、(I.001)+(15.052)、(I.001)+(15.053)、(I.001)+(15.054)、(I.001)+(15.055)、(I.001)+(15.056)、(I.001)+(15.057)、(I.001)+(15.058)、(I.001)+(15.059)、(I.001)+(15.060)、(I.001)+(15.061)、(I.001)+(15.062)、(I.001)+(15.063)、(I.001)+(15.064)、(I.001)+(15.065)、(I.001)+15.066)、(I.001)+(15.067)、(I.001)+(15.068)、(I.001)+(15.069)、(I.001)+(15.070)、(I.001)+(15.071)、(I.001)+(15.072)、(I.001)+(15.073)、(I.001)+(15.074)、(I.001)+(15.075)、(I.001)+(15.076)、(I.001)+(15.077)、(I.001)+(15.078)、(I.001)+(15.079)、(I.001)+(15.080)、(I.001)+(15.081)、(I.001)+(15.082)、(I.001)+(15.083)、(I.001)+(15.084)、(I.001)+(15.085)、(I.001)+(15.086)、(I.001)+(15.087)、(I.001)+(15.088)、(I.001)+(15.089)、(I.001)+(15.090)、(I.001)+(15.091)、(I.001)+(15.092)、(I.001)+(15.093)、(I.001)+(15.094)、(I.001)+(15.095)、(I.001)+(15.096)、(I.001)+(15.097)、(I.001)+(15.098)、(I.001)+(15.099)、(I.001)+(15.100)、(I.001)+(15.101), (I.001)+(15.102), (I.001)+(15.103), (I.001)+(15.104), (I.001)+(15.105), (I.001)+(15.106), (I.001)+(15.107), (I.0 01)+(15.108), (I.001)+(15.109), (I.001)+(15.110), (I.001)+(15.111), (I.001)+(15.112), (I.001)+(15.113), (I.001)+(15.11 4), (I.001)+(15.115), (I.001)+(15.116), (I.001)+(15.117), (I.001)+(15.118), (I.001)+(15.119), (I.001)+(15.120), (I.001) +(15.121), (I.001)+(15.122), (I.001)+(15.123), (I.001)+(15.124), (I.001)+(15.125), (I.001)+(15.126), (I.001)+(15.127). .

[0226] In these combinations, the first component is a compound of formula (1) as defined in Tables 1a and 1b (e.g. I.001) and the second component is a fungicide from Groups 1 to 15 as defined herein. For example, the combination (I.001) + (1.001) corresponds to a combination comprising compound I.001 in Tables 1a and 1b and cyproconazole (1.001).

[0227] In some other embodiments, the compound combinations correspond to the above combinations, wherein compound (I.001) is replaced by any one of the compounds listed in Tables Ia and Ib.

[0228] The compound of formula (1) and the fungicide selected from groups (1) to (15) may be present in a weight ratio of 100:1 to 1:100 (compound of formula (1) : fungicide selected from groups (1) to (15)), or in the range of 50:1 to 1:50, or in the range of 20:1 to 1:20. Other examples of weight ratio ranges include 95: 1 to 1:95, 90: 1 to 1:90, 85: 1 to 1:85, 80: 1 to 1:80, 75: 1 to 1:75, 70: 1 to 1:70, 65: 1 to 1:65, 60: 1 to 1:60, 55: 1 to 1:55, 45: 1 to 1:45, 40: 1 to 1:40, 35: 1 to 1:35, 30: 1 to 1:30, 25: 1 to 1:25, 15: 1 to 1:15, 10: 1 to 1:10, 5: 1 to 1:5, 4: 1 to 1:4, 3: 1 to 1:3, and 2: 1 to 1:2.

[0229] Another fungicide selected from Groups 1 to 15 as defined herein may be added to the combination of compounds.

[0230] The compounds of formula (1) and compositions comprising the same may be combined with one or more biological control agents.

[0231] Examples of biological control agents that can be combined with the compounds of formula (1) and compositions comprising the same are:

[0232] (A) an antibacterial agent selected from the group consisting of:

[0233] (A1) bacteria, for example (A1.1) Bacillus subtilis, in particular strain QST713 / AQ713 (SERENADE OPTI or SERENADE ASO available from Bayer CropScience LP, USA, with accession number NRRL B-21661, described in U.S. Pat. No. 6,060,051); (A1.2) Bacillus amyloliquefaciens, in particular strain D747 (Double Nickel available from Certis, USA TM , with accession number FERM BP-8234, disclosed in U.S. Pat. No. 7,094,592); (A1.3) Bacillus pumilus, in particular strain BU F-33 (with NRRL accession number 50185); (A1.4) Bacillus subtilis var. amyloliquefaciens strain FZB24 (available from Novozymes, USA (A1.5) Paenibacillus sp. strain having accession number NRRL B-50972 or accession number NRRL B-67129, described in International Patent Publication No. WO 2016 / 154297; and

[0234] (A2) fungi, for example (A2.1) budding spores of Aureobasidium pullulans, in particular the blastospores of strain DSM 14940; (A2.2) blastospores of Aureobasidium pullulans strain DSM 14941; (A2.3) budding spores of Aureobasidium pullulans, in particular a mixture of blastospores of strains DSM 14940 and DSM 14941;

[0235] (B) a fungicide selected from the group consisting of:

[0236] (B1) bacteria, for example (B1.1) Bacillus subtilis, in particular strain QST713 / AQ713 (SERENADE OPTI or SERENADE ASO available from Bayer CropScience LP, USA, with accession number NRRL B-21661, described in U.S. Pat. No. 6,060,051); (B1.2) Bacillus pumilus, in particular strain QST2808 (available from Bayer CropScience LP, USA, with accession number NRRL B-21661, described in U.S. Pat. No. 6,060,051); Accession No. NRRL B-30087, described in U.S. Pat. No. 6,245,551); (B1.3) Bacillus pumilus, in particular strain GB34 (available from Bayer AG, DE as YIELD ); (B1.4) Bacillus pumilus, in particular strain BU F-33 (with accession number NRRL 50185); (B1.5) Bacillus amyloliquefaciens, in particular strain D747 (available from Double Nickel, Certis, USA TM , with accession number FERM BP-8234, disclosed in U.S. Pat. No. 7,094,592); (B1.6) Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan, China WP, registered as a biofungicide in Taiwan, China with registration numbers 4764, 5454, 5096 and 5277); (B1.7) Bacillus amyloliquefaciens var. subtilis strain MBI600 (available from SUBTILEX of BASF SE); (B1.8) Bacillus subtilis strain GB03 (available from ); (B1.9) Bacillus subtilis var. amyloliquefaciens strain FZB24 (fungicide available from Novozymes Biologicals Inc., Salem, Virginia or Syngenta Crop Protection, LLC, Greensboro, North Carolina or ECO (EPA registration number 70127-5); (B1.10) Bacillus mycoides, isolate J (available from BMJ TGAI or WG from Certis USA); (B1.11) Bacillus licheniformis, specifically strain SB3086 (available from EcoGuard from Novozymes TM Biofungicide and Green Releaf); (B1.12) Paenibacillus sp. strain having accession number NRRL B-50972 or accession number NRRL B-67129, described in International Patent Publication No. WO 2016 / 154297.

[0237] In some embodiments, the biological control agent is a strain of Bacillus subtilis or Bacillus amyloliquefaciens that produces a toyogenin or phosphatidin-type compound, an iturin-type compound, and / or a surfactin-type compound. For background, see the following review article: Ongena, M., et al.,

[0238] "Bacillus Lipopeptides: Versatile Weapons for Plant Disease Biocontrol," Trends in Microbiology, Vol 16, No. 3, March 2008, pp. 115-125. Bacillus strains capable of producing lipopeptides include Bacillus subtilis QST713 (SERENADEOPTI or SERENADE ASO available from Bayer CropScience LP, USA, with accession number NRRL B-21661, described in U.S. Pat. No. 6,060,051), Bacillus amyloliquefaciens strain D747 (Double Nickel available from Certis, USA TM , with accession number FERM BP-8234, disclosed in U.S. Pat. No. 7,094,592), Bacillus subtilis MBI600 (available from Becker Underwood, U.S. EPA Reg. No. 71840-8); Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan, China WP, registered as a biofungicide in Taiwan under the registration numbers 4764, 5454, 5096 and 5277; Bacillus amyloliquefaciens, in particular strain FZB42 (available from ABiTEP, DE ); and Bacillus subtilis var. amyloliquefaciens strain FZB24 (fungicides available from Novozymes Biologicals Inc., Salem, Virginia or Syngenta Crop Protection, LLC, Greensboro, North Carolina or ECO (EPA Registration No. 70127-5); and

[0239] (B2) Fungi, for example: (B2.1) Coniothyrium minitans, in particular strain CON / M / 91-8 (accession number DSM-9660; e.g., Bayer ); (B2.2) Metschnikowia fructicola, in particular strain NRRL Y-30752 (e.g. ); (B2.3) Microsphaeropsis ochracea (e.g. Prophyta ); (B2.5) Trichoderma sp. including Trichoderma atroviride strain SC1, described in International Application No. PCT / IT2008 / 000196); (B2.6) Trichoderma harzianum rifai strain KRL-AG2 (also known as strain T-22, / ATCC 208479, such as PlantShield T-22G from BioWorks, USA, and TurfShield); (B2.14) Gliocladium roseum strain 321U from WF Stoneman Company LL; (B2.35) Talaromyces flavus strain V117b; (B2.36) Trichoderma asperellum strain ICC 012 from lsagro; (B2.37) Trichoderma asperellum strain SKT-1 (e.g., from Kumiai Chemical Industry ); (B2.38) Trichoderma atroviride, strain CNCM 1-1237 (e.g. Agrauxine, FR ); (B2.39) dark green Trichoderma strain number V08 / 002387; (B2.40) dark green Trichoderma, strain NMI number V08 / 002388; (B2.41) dark green Trichoderma, strain NMI number V08 / 002389; (B2.42) dark green Trichoderma, strain NMI number V08 / 002390; (B2.43) dark green Trichoderma, strain LC52 (e.g. Tenet from Agrimm Technologies Limited); (B2.44) dark green Trichoderma, strain ATCC 20476 (IMI206040); (B2.45) dark green Trichoderma, strain T11 (IM1352941 / CECT20498); (B2.46) Trichoderma harzianum; (B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum T39 (e.g., Makhteshim, USA ); (B2.49) Trichoderma harzianum, in particular strain KD (e.g. Trichoplus from Biological Control Products, SA (available from Becker Underwood)); (B2.50) Trichoderma harzianum, strain ITEM 908 (e.g. Trianum-P from Koppert); (B2.51) Trichoderma harzianum, strain TH35 (e.g. Root-Pro from Mycontrol); (B2.52) Trichoderma virens (also known as Gliocladium virens), in particular strain GL-21 (e.g. SoilGard 12G from Certis, USA); (B2.53) Trichoderma virens, strain TV1 (e.g. Trianum-P from Koppert); (B2.54) Ampelomyces quisqualis, in particular strain AQ 10 (e.g. AQ 100); (B2.56) budding mold, in particular spores of strain DSM 14940; (B2.57) budding mold, in particular spores of strain DSM 14941; (B2.58) budding mold, in particular spores of strains DSM 14940 and DSM 14941 (e.g. bio-ferm, CH ); (B2.64) Cladosporium cladosporioides, strain H39 (from Stichting Dienst Landbouwkundig Onderzoek); (B2.69) Gliocladium catenulatum Synonym: Clonostachys rosea f. catenulate strain J1446 (e.g. from AgBio Inc. and for example Kemira Agro Oy ); (B2.70) conidia of Lecanicillium lecanii (formerly known as Verticillium lecanii) strain KV01 (e.g. Koppert / Arysta ); (B2.71) Penicillium vermiculatum; (B2.72) Pichia anomala, strain WRL-076 (NRRL Y-30842); (B2.75) Trichoderma aureum, strain SKT-1 (FERM P-16510); (B2.76) Trichoderma aureum, strain SKT-2 (FERM P-16511); (B2.77) Trichoderma aureum, strain SKT-3 (FERM P-17021); (B2.78) Trichoderma magamsii (formerly known as T. viride), strain ICC080 (IMI CC 392151 CABI, such as AGROBIOSOL DE MEXICO, SADE CV's BioDerma); (B2.79) Trichoderma harzianum, strain DB 103 (such as Dagutat (B2.80) Trichoderma polysporum, strain IMI 206039 (e.g. Binab TF WP from BINAB Bio-Innovation AB, Sweden); (B2.81) Trichoderma stromaticum (e.g. Tricovab from Ceplac, Brazil); (B2.83) Ulocladium oudemansii, in particular strain HRU3 (e.g. Botry-Zen Ltd, NZ ); (B2.84) Verticillium albo-atrum (formerly known as V. dahlia), strain WCS850 (CBS276.92; for example, Dutch Trig from Tree Care Innovations); (B2.86) Verticillium chlamydosporium; (B2.87) a mixture of Trichoderma spinulosa strain ICC 012 and Trichoderma gemsii strain ICC 080 (products such as B10-TAM from Bayer CropScience LP, USA TM ).

[0240] Other examples of biological control agents that can be combined with the compounds of formula (1) and compositions comprising the same are:

[0241] The bacteria are selected from the group consisting of Bacillus cereus, in particular Bacillus licheniformis strain CNCM 1-1562 and Bacillus firmus strain 1-1582 (accession number CNCM 1-1582), Bacillus subtilis strain OST 30002 (accession number NRRL B-50421), Bacillus thuringiensis, in particular Bacillus thuringiensis serotype H-14 strain AM65-52 (accession number ATCC 1276), Bacillus thuringiensis serotype Ayuzawa, in particular strain ABTS-1857 (SD-1372), Bacillus thuringiensis serotype Kustak strain HD-1, Bacillus thuringiensis serotype NB 176 (SD-5428), Pasteuria spp. spp.) (Rotylenchulus reniformisnematode)-PR3 (Accession No. ATCC SD-5834), Streptomyces microflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), and Streptomyces galbus strain AQ6047 (Accession No. NRRL 30232);

[0242] The fungi and yeasts are selected from Beauveria bassiana, in particular strain ATCC 74040, Lecanicillium spp., in particular strain HRO LEC 12, Metarhizium anisopliae, in particular strain F52 (DSM 3884 or ATCC 90448), Paecilomyces fumosoroseus (now: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (accession number ATCC 20874), and Paecilomyces lilacinus, in particular Paecilomyces lilacinus strain 251 (AGAL 89 / 030550);

[0243] The virus is selected from the group consisting of Adoxophyes orana granulovirus (GV), Cydiapomonella granulovirus (GV), Helicoverpa armigera nuclear polyhedrosis virus (NPV), Spodoptera exigua mNPV, Spodoptera frugiperda mNPV, and Spodoptera littoralis NPV.

[0244] Bacteria and fungi that can be added to plants or plant parts or plant organs as "inoculants" can, due to their special properties, promote plant growth and plant health. Examples are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly Pseudomonas cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp.), Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., particularly Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., and Streptomyces spp.

[0245] Plant extracts and products formed by microorganisms, including proteins and secondary metabolites, can be used as biological control agents, such as Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, " insecticides", rotenone, ryania / ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, extracts from the Brassicaceae family, especially canola or mustard powder.

[0246] Examples of insecticides, acaricides and nematicides which can be mixed with the compounds of formula (I) and compositions comprising them, respectively, are:

[0247] (1) Acetylcholinesterase (AChE) inhibitors, such as carbamates selected from the group consisting of: alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, fenamiprid formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or organophosphates such as acephate ), azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos vos / DDVP), dicrotophos, dimethoate, dimethylvinphos, disulphoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos,isopropyl O-(methoxyaminothiophosphoryl)salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamide amidon), phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, and vamidothion.

[0248] (2) GABA-gated chloride channel blockers, such as cyclopentadiene-organochlorines selected from chlordane and endosulfan; or phenylpyrazoles (fiproles) selected from ethiprole and fipronil.

[0249] (3) Sodium channel modulators, such as pyrethroids, for example, acrinathrin, allethrin, d-cis-trans allethrin, d-transallethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, isomer), bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, 1R-trans isomer

[0250] cyphenothrin [(1R)-trans-isomers]), deltamethrin, empenthrin [(EZ)-(1R)-isomers], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kafenthrin dethrin), momfluorothrin, permethrin, phenothrin [(1R)-trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, and transfluthrin, or DDT or methoxychlor.

[0251] (4) Competitive modulators of nicotinic acetylcholine receptors (nAChR), for example, neonicotinoids, for example, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.

[0252] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators (site I), such as spinosyns, for example spinetoram and spinosad.

[0253] (6) Glutamate-gated chloride channel (GluCl) allosteric modulators, such as avermectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin and milbemycin.

[0254] (7) Juvenile hormone analogs, for example juvenile hormone analogs, such as hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxifen.

[0255] (8) Various nonspecific (multi-site) inhibitors, for example halogenated hydrocarbons, such as methyl bromide and other halogenated hydrocarbons, or chloropicrine or sulphuryl fluoride or borax or tartar emetic or methyl isocyanate activators, such as diazomet and metam.

[0256] (9) String modifiers, such as pymetrozine and flonicamid.

[0257] (10) Mite growth inhibitors, for example clofentezine, hexythiazox and diflovidazin or etoxazole.

[0258] (11) Microbial disruptors of insect gut membranes, such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and Bt plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Ab1 / 35Ab1.

[0259] (12) Mitochondrial ATP synthase inhibitors, for example ATP disruptors, for example diafenthiuron or organotin compounds, for example azocyclotin, cyhexatin and fenbutatinoxide or propargite or tetradifon.

[0260] (13) Oxidative phosphorylation uncouplers that act by disrupting the proton gradient, such as chlorfenapyr, dinitrocresol (DNOC), and sulfluramid.

[0261] (14) Nicotinic acetylcholine receptor channel blockers, for example, bensultap, cartap hydrochloride, thiocylam and thiosultap-sodium.

[0262] (15) Type O chitin biosynthesis inhibitors, for example bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0263] (16) Type 1 chitin biosynthesis inhibitors, such as buprofezin.

[0264] (17) Molting disruptors (particularly Diptera, e.g. insects of the order Diptera), for example cyromazine.

[0265] (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0266] (19) Octopamine receptor agonists, such as amitraz.

[0267] (20) Mitochondrial complex III electron transfer inhibitors, such as hydramethylnone, acequinocyl or fluacrypyrim.

[0268] (21) Mitochondrial complex I electron transfer inhibitors, for example METI acaricides, for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad and rotenone (Derris).

[0269] (22) Voltage-dependent sodium channel blockers, such as indoxacarb or metaflumizone.

[0270] (23) Acetyl-CoA carboxylase inhibitors, for example tetronic and tetramicacid derivatives, for example spirodiclofen, spiromesifen and spirotetramate.

[0271] (24) Mitochondrial complex IV electron transfer inhibitors, for example phosphides, such as aluminum phosphide, calcium phosphide, phosphine and zinc phosphide, or cyanides, such as calcium cyanide, potassium cyanide and sodium cyanide.

[0272] (25) Mitochondrial complex II electron transfer inhibitors, for example, beta-ketonitrile derivatives, such as cyenopyrafen and cyflumetofen, and carboxanilides, such as pyflubumide.

[0273] (28) Ryanodine receptor modulators, for example diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide.

[0274] Other active compounds, such as Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Chinomethionat, Chloroprallethrin, Cryolite, Cyclaniliprole, Cycloxa prid), Cyhalodiamide, Dicloromezotiaz, Dicofol, Epsilon-Metofluthrin, Epsilon-Momfluthrin, Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram (Fluopyram), Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Trifluthrin Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tigolaner, Tioxazafen, Thiofluoximate, Triflumezopyrim, and Iodomethane,Other Bacillus firmus (1-1582, BioNeem, Votivo) preparations, and the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethane)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO 2006 / 043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-yn-1-yl]-5-fluorospiro[indole-3,4'-piperidinyl]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO 2003 / 106457) (CAS 637360-23-7), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-yn-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO 2006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010 / 052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethane carbonate (known from EP 2647626) (CAS 1440516-42-6), 4-(but-2-yn-1-oxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO 2004 / 099160) (CAS 792914-58-0), PF1364 (known from JP 2010 / 018586) (CAS 1204776-60-2), N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (known from WO 2012 / 029672) (CAS 1363400-41-2), (3E)-3-[1-[(6-chloro-3-pyridinyl)methyl]-2-pyridylidene]-1,1,1-trifluoro-propan-2-one (known from WO 2013 / 144213) (CAS 1461743-15-6), N-[3-(benzyloxycarbonyl)-4-chlorophenyl]-1-methyl 3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (known from CN 103232431) (CAS 1449220-44-3),4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxo-3-thietanyl)-benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxo-3-thietanyl)-benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxo-3-thietanyl)-benzamide (known from WO 2013 / 050317 A1) (CAS 1332628-83-7), N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide, (+)-N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide and (-)-N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide (known from WO 2013 / 162715 A2, WO 2013 / 162716 A2, US Patent Application No. 2014 / 0213448 A1) (CAS 1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)formyl]phenyl]-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, known from CN 103109816A) (CAS 1232543-85-9); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO 2012 / 034403A1) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (known from WO 2011 / 085575A1) (CAS 1233882-22-8),4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)-pyrimidine (known from CN 101337940A) (CAS 1108184-52-6); (2E)- and 2(Z)-2-[2-(4-benzonitrile)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide (known from CN 101715774A) (CAS 1232543-85-9); 3-(2,2-dichlorovinyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropanecarboxylate (known from CN 103524422 A) (CAS 1542271-46-4); (4aS)-7-chloro-2,5-dihydro-2-[[(carbomethoxy)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]-indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2,4-di-O-methyl-, 1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-pyranose (known from U.S. Patent Application Publication No. 2014 / 0275503A1) (CAS 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-thioazapurine-bicyclool[3.2.1]octane (CAS 1253850-56-4), (8-trans)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-thiopurine-bicyclool and [3.2.1] octane (CAS 933798-27-7), (8-cis)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-thiopurine-bicyclool and [3.2.1] octane (known from WO 2007 / 040280 A1, WO 2007 / 040282 A1) (CAS 934001-66-8),N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]-propionamide (known from WO 2015 / 058021 A1, WO 2015 / 058028 A1) (CAS 1477919-27-9) and N-[4-(methoxyamino)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (known from CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-dioxane-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (known from WO 2013 / 115391 A1) (CAS 1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010 / 066780 A1, WO 2011 / 151146 A1) (CAS 1229023-34-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (known from WO 2014 / 187846 A1) (CAS 1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxy-1,8-diazaspiro[4.5]dec-3-en-4-yl-carbonic acid ethyl ester (known from WO 2010 / 066780A1, WO2011151146 A1) (CAS 1229023-00-0), N-[1-[(6-chloro-3-pyridyl)methyl]-2(1H)-pyridylidene]-2,2,2-trifluoro-acetamide (known from DE 3639877 A1, WO 2012029672 A1) (CAS 1363400-41-2), [N(E)]-N-[1-[(6-chloro-3-pyridyl)methyl]-2(1H)-pyridylidene]-2,2,2-trifluoro-acetamide (known from WO 2016005276A1) (CAS 1689566-03-7), [N(Z)]-N-[1-[(6-chloro-3-pyridyl)methyl]-2(1H)-pyridylidene]-2,2,2-trifluoro-acetamide (CAS 1702305-40-5), 3-endo-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridyl]oxy]-9-azabicyclo[3.3.1]nonane (known from WO 2011 / 105506 A1, WO 2016 / 1 33011 A1) (CAS 1332838-17-1).

[0275] Examples of safeners that can be mixed with the compounds of formula (I) and compositions comprising them are, for example, benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl chloride)amino]phenyl}thio)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-1-oxo-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

[0276] Examples of herbicides that can be mixed with the compounds of formula (I) and compositions comprising the same are:

[0277] Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulfamate sulfamate), anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenpyridine ap), bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor,butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium dium), chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl n-ethyl), cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butoxy, -butyl, -dimethylamine, -diolamin, -ethyl, -2-ethylhexyl, -isobutyl, -isooctyl, -isopropyl-amine, -potassium, -triisopropanolamine, and -triethanolamine (2,4-D, 2,4-D-butotyl, -butyl,-dimethylammonium, -diolamin, -ethyl, -2-ethylhexyl, -isobutyl, -isooctyl, -isopropyl-ammonium, -potassium, -triisopropanolammonium, and -trolamine), 2,4-DB, 2,4-DB-butyl, -dimethyl-ammonium, -isooctyl, -potassium, and -sodium (2,4-DB, 2,4-DB-butyl, -dimethyl-ammonium, -isooctyl, -potassium, and -sodium assium and -sodium), daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one), 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop,

[0278] (dichlorprop), dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, isopentyl

[0279] dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, diinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron methyl (ethametsulfuron-methyl), ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, for example, N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5-oxy-4,5-dihydro-1H-tetrazol-1-yl]phenyl}ethylsulfonamide, F-7967, for example, 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione), fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, bispyribacylsulfone florasulam), fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flufenpyramide,

[0280] flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, dimethylamine and methyl (flurenol-butyl,

[0281] -dimethylammonium and -methyl), fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium odium), foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium, -trimethylsulfonate (glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium), H-9201, for example, O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylthiophosphoramidate, haloxifen, haloxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl xyethyl), haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, for example, 1-(dimethoxyphosphoryl)ethyl-(2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium,

[0282] (imazapic-ammonium), imazapyr, imazapic-ammonium

[0283] (imazapyr-isopropylammonium), imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octane esters, potassium and sodium salts (ioxynil-octanoate, -potassium and -sodium), ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, for example, 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole), ketospirazone, x), lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium, and -sodium, MCPB, MCPB-methyl, -ethyl, and -sodium, mecoprop, 2-methyl-4-chloropropionic acid- mecoprop-sodium and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione,Methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, metiozolin, methylisothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron etoxuron), metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, for example, N-(3-chloro-4-isopropylphenyl)-2-methylpentylamine, NGGC-011, napropamide, NC-310, for example, [5-(benzyloxy)-1-methyl-1H-pyrazol-4-yl](2,4-dichlorophenyl)methanone, neburon, nicosulfuron, nonanoic acid acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram,picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, fenpropiamine (propham), propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazol ynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyribenzoxim riminobac), pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P,Quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron methyl ometuron-methyl), sulfosulfuron, SYN-523, SYP-249, such as 1-ethoxy-3-methyl-1-oxybut-3-en-2-yl, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl ester), SYP-300, such as 1-[7-fluoro-3-oxy-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione), 2,3,6-TBA, trichloroacetic acid TCA (trichloroacetic acid acid), TCA sodium salt, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron,trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, for example, 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:

[0284]

[0285] Examples of plant growth regulators are:

[0286] Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolid, catechine, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium salt, disodium salt, and mono(N,N-dimethylalkylamine)

[0287] (endothal-dipotassium, -disodium, and

[0288] -mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, butyl fluorenol, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, methyl jasmonate, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid acid), 2-naphthyloxyacetic acid, nitrophenolate-mixture, paclobutrazol, N-(2-phenylethyl)-β-alanine, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0289] Methods and uses

[0290] The compounds of formula (1) and compositions comprising them have potent microbicidal activity. They can be used to control unwanted microorganisms, such as unwanted fungi and bacteria. They can be particularly useful for crop protection (they control microorganisms that cause plant diseases) or for protecting materials (such as industrial materials, timber, stored goods), as described in detail below. More specifically, the compounds of formula (1) and compositions comprising them can be used to protect seeds, germinated seeds, sprouted seedlings, plants, plant parts, fruits, harvests and / or soils where plants grow from harmful microorganisms.

[0291] As used herein, control includes protective, curative and eradicative treatment of unwanted microorganisms. The unwanted microorganisms can be pathogenic bacteria, pathogenic viruses, pathogenic oomycetes or pathogenic fungi, more specifically, plant pathogenic bacteria, plant pathogenic viruses, plant pathogenic oomycetes or plant pathogenic fungi. As described in detail below, these plant pathogenic microorganisms are the causative agents of a broad spectrum of plant diseases.

[0292] More specifically, the compounds of formula (I) and compositions comprising the same can be used as fungicides. For the purposes of this specification, the term "fungicide" refers to compounds or compositions that can be used in crop protection to control unwanted fungi (e.g. Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes) and / or for controlling oomycetes, more preferably for controlling basidiomycetes (causing rust).

[0293] The invention also relates to a method for controlling unwanted microorganisms, such as phytopathogenic fungi, oomycetes and bacteria, which comprises applying at least one compound of formula (I) or at least one composition comprising the same to the microorganisms and / or their habitat (plants, plant parts, seeds, fruits or soil in which the plants grow).

[0294] Typically, when the compounds and compositions of the invention are used in a method of treatment or protection against plant pathogenic fungi and / or plant pathogenic oomycetes, an effective and plant-compatible amount is applied to the plant, plant parts, fruit, seed or soil or substrate in which the plant grows. Suitable substrates that can be used to cultivate plants include inorganic substrates, such as mineral wool, in particular asbestos, perlite, sand or gravel; organic substrates, such as peat, pine bark or sawdust; and petroleum substrates, such as polymer foams or plastic beads. An effective and plant-compatible amount is an amount that is sufficient to control or destroy fungi present or likely to appear on farmland and does not produce any obvious phytotoxic symptoms to the crop. Such an amount may vary over a wide range, depending on the fungi to be controlled, the crop type, the crop growth stage, the climatic conditions and the corresponding compound or composition of the invention used. This amount can be determined by systematic field trials within the capabilities of a person skilled in the art.

[0295] Plants and plant parts

[0296] The compounds of formula (I) and compositions comprising the same can be applied to any plant or plant part.

[0297] Plants are understood to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnology and genetic engineering methods or a combination of these methods, including transgenic plants (GMO or transgenic plants) and plant varieties which are or are not protected by plant variety property rights.

[0298] Plant parts are understood to mean all above-ground and below-ground parts and organs of plants, such as buds, leaves, flowers and roots, including, for example, leaves, needles, stalks, stems, flowers, fruiting bodies, fruits and seeds, and also roots, tubers and rhizomes. Plant parts also include crop material and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, shoots and seeds.

[0299] Plants that can be treated according to the method of the present invention include: cotton, flax, grapevines, fruits, vegetables, such as Rosaceae sp. (e.g., Rosaceae fruits such as apples and pears, and stone fruits such as apricots, cherries, almonds and peaches, and soft fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (e.g., banana trees and plantations), Rubiaceae sp. (e.g., coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (e.g., lemons, oranges and grapefruits), Solanaceae sp. sp.) (e.g., tomato), Liliaceae sp., Asteraceae sp. (e.g., lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (e.g., cucumber), Alliaceae sp. (e.g., leek, onion), Papilionaceae sp. (e.g., peas); major crop plants, such as Gramineae sp. (e.g., corn, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (e.g., sunflower), Brassicaceae sp. (e.g., white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pakchoi, kohlrabi, radish and rapeseed, mustard, horseradish and watercress), Fabacaesp. (e.g., beans), Papilionaceae sp. (e.g., sp.) (e.g. soybean), Solanaceae sp. (e.g. potato), Chenopodiaceae sp. (e.g. beet, fodder beet, Swiss chard, beetroot), useful plants for gardens and woodlands and ornamental plants; and transgenic varieties of each of these plants.

[0300] In some preferred embodiments, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods such as hybridization or protoplast fusion, and parts thereof are treated according to the methods of the invention.

[0301] In some other preferred embodiments, transgenic plants and plant cultivars obtained by genetic engineering methods are treated according to the method of the invention, if appropriate in combination with conventional methods (transgenic organisms) and parts thereof according to the method of the invention. More preferably, plants of commercially available or in use plant cultivars are treated according to the invention. Plant cultivars are understood to mean plants with new properties ("traits") and obtained by conventional breeding, mutagenesis or recombinant DNA technology. They can be cultivars, variants, biotypes or genotypes.

[0302] The method according to the present invention can be used to process genetically modified organisms (GMOs), such as plants or seeds.Genetically modified plants (or transgenic plants) are plants in which heterologous genes have been stably integrated into the genome.The term "heterologous gene" refers essentially to a gene provided or assembled outside the plant, when introduced into the nuclear, chloroplast or mitochondrial genome, by expressing a target protein or polypeptide or by down-regulating or silencing other genes present in the plant (e.g., using antisense technology, co-suppression technology, RNA interference-RNAi-technology or microRNA-miRNA-technology).The heterologous gene located in the genome is also referred to as transgenic.The transgenic defined by its specific position in the plant genome is called transformation or transgenic event.

[0303] Plants and plant cultivars which can be treated by the methods disclosed above include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and / or biotechnological means).

[0304] Plants and plant cultivars that can be treated by the above disclosed methods include plants and plant cultivars that are resistant to one or more biotic stresses, ie the plants exhibit improved resistance to animal and microbial pests, such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.

[0305] Plants and plant cultivars that can be treated by the above disclosed methods include those plants that are resistant to one or more abiotic stresses. Abiotic stress conditions can include, for example, drought, low temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, and shade avoidance.

[0306] Plants and plant cultivars that can be processed by the above-mentioned disclosed method include those plants characterized by the yield characteristics of improvement. The output increased by the plant can be, for example, to improve plant physiology, growth and development, such as water use efficiency, water retention efficiency, improve nitrogen utilization, strengthen carbon assimilation, improve photosynthesis, improve germination efficiency and accelerate the result of maturation. Output can also be subject to the impact of plant structure improvement (under stress and non-stress conditions), including but not limited to early flowering, flowering control, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number of each pod or ear, seed quality, strengthen seed filling degree, reduce seed scattering, reduce pod cracking and lodging. Other yield traits include seed composition, such as carbohydrate content and composition, such as cotton or starch, protein content, oil content and composition, nutritional value, reduce anti-nutritional compounds, improve processability and better storage stability.

[0307] Plants and plant cultivars that can be treated by the above disclosed methods include plants and plant cultivars that are hybrid plants that have shown characteristics of heterosis or hybrid vigor, which generally results in higher yields, vigor, health, and resistance to biotic and abiotic stresses. Plants and plant cultivars that can be treated by the above disclosed methods (obtained by plant biotechnology methods such as genetic engineering) include plants and plant cultivars that are herbicide-tolerant plants, i.e., plants that tolerate one or more given herbicides. Such plants can be obtained by genetic transformation or by selecting plants that contain mutants that confer such herbicide tolerance.

[0308] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that may be treated by the methods disclosed above include plants and plant cultivars that are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that impart such insect resistance.

[0309] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that may be treated by the methods disclosed above include plants and plant cultivars that are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such stress resistance.

[0310] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may be treated by the methods disclosed above include plants and plant cultivars which display altered quantity, quality and / or storage stability of the harvested products and / or altered properties of specific components of the harvested products.

[0311] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated by the above disclosed methods include plants and plant cultivars with altered fiber properties, such as cotton plants. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such fiber properties alterations.

[0312] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated by the above disclosed methods include plants and plant cultivars with altered oil content, such as rapeseed or related Brassica species. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such altered oil content.

[0313] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that may be treated by the above disclosed methods include plants and plant cultivars with altered seed shattering characteristics, such as rapeseed or related Brassica species. Such plants can be obtained by genetic transformation or by selection of plants containing mutations imparting such altered seed shattering characteristics, including, for example, rapeseed plants with delayed or reduced seed shattering.

[0314] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may be treated according to the methods disclosed above include plants and plant cultivars, such as tobacco plants, with altered patterns of post-translational protein modifications.

[0315] Pathogens and diseases

[0316] The methods disclosed above can be used to control disease-causing microorganisms, in particular phytopathogenic microorganisms such as phytopathogenic fungi, for example:

[0317] Diseases caused by powdery mildew pathogens, such as Blumeria species (e.g. Blumeria graminis), Podosphaera species (e.g. Podosphaera leucotricha), Sphaerotheca species (e.g. Sphaerotheca fuliginea), Uncinula species (e.g. Uncinula necator);

[0318] Diseases caused by rust pathogens, for example Gymnosporangium species (e.g. Gymnosporangium sabinae), Hemileia species (e.g. Hemileia vastatrix), Phakopsora species (e.g. Phakopsora pachyrhizi or Phakopsora meibomiae), Puccinia species (e.g. Puccinia recondite, Puccinia graminis or Puccinia striiformis), Uromyces species (e.g. Uromyces appendiculatus);

[0319] Diseases caused by oomycete pathogens, for example Albugo species (e.g. Albugocandida), Bremia species (e.g. Bremia lactucae), Peronospora species (e.g. Peronospora pisi or P. brassicae), Phytophthora species (e.g. Phytophthora infestans), Plasmopara species (e.g. Plasmopara viticola), Pseudoperonospora species (e.g. Pseudoperonospora humuli or Pseudoperonospora cubensis), Pythium species (e.g. Pythium ultimum);

[0320] Leaf spot and leaf blight caused by pathogens such as Alternaria species (e.g. Alternaria solani), Cercospora species (e.g. Cercospora beticola), Cladiosporium species (e.g. Cladiosporium cucumerinum), Cochliobolus species (e.g. Cochliobolus sativus) (conidial forms: Drechslera, Helminthosporium or Cochliobolus miyabeanus), Colletotrichum species (e.g. Colletotrichum lindemuthanium), Cycloconium species (e.g. Cycloconium oleiferum), oleaginum), Diaporthe species (e.g., Diaporthe citri), Elsinoe species (e.g., Elsinoe fawcettii), Gloeosporium species (e.g., Gloeosporium laeticolor), Glomerella species (e.g., Glomerella cingulate), Guignardia species (e.g., Guignardia bidwelli), Leptosphaeria species (e.g., Leptosphaeria maculans), Magnaporthe species (e.g., Magnaporthe grisea), Microdochium species (e.g., Microdochium nivale), Mycosphaerella species (e.g. Mycosphaerellagraminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis), Phaeosphaeria species (e.g. Phaeosphaeria nodorum), Pyrenophora species (e.g. Pyrenophora teres or Pyrenophora tritici repentis), Ramularia species (e.g. Ramularia collo-cygni or Ramularia areola), Rhynchosporium species (e.g. Rhynchosporium secalis), Septoria species (e.g. Septoria apii or Septorialycopersici), Stagonospora species) (e.g. Stagonosporanodorum), Typhula species (e.g. Typhula incarnate), Venturia species (e.g. Venturia inaequalis),

[0321] Root and stem diseases caused by pathogens such as Corticium species (e.g. Corticium graminearum), Fusarium species (e.g. Fusarium oxysporum), Gaeumannomyces species (e.g. Gaeumannomyces graminis), Plasmodiophora species (e.g. Plasmodiophora brassicae), Rhizoctonia species (e.g. Rhizoctonia solani), Sarocladium species (e.g. Sarocladium oryzae), Sclerotium species (e.g. Sclerotium oryzae), Tapesia species (e.g. Tapesia acuformis), Thielaviopsis species (e.g. species) (e.g., Thielaviopsis basicola);

[0322] Ear and inflorescence diseases (including cobs) caused by pathogens such as Alternaria species (e.g. Alternaria spp.), Aspergillus species (e.g. Aspergillus flavus), Cladosporium species (e.g. Cladosporium cladosporioides), Claviceps species (e.g. Claviceps purpurea), Fusarium species (e.g. Fusarium culmorum), Gibberella species (e.g. Gibberella zeae), Monographella species (e.g. Monographella nivalis), Stagnospora species (e.g. Stagnospora nodorum);

[0323] Diseases caused by smut fungi, for example Sphacelotheca species (e.g. Sphacelotheca reiliana), Tilletia species (e.g. Tilletia caries or Tilletia controversa), Urocystis species (e.g. Urocystis occulta), Ustilago species (e.g. Ustilago nuda);

[0324] Fruit rot caused by pathogens such as Aspergillus species (e.g. Aspergillus flavus), Botrytis species (e.g. Botrytis cinerea), Penicillium species (e.g. Penicillium expansum),

[0325] (Penicillium expansum or Penicillium purpurogenum), Rhizopus species (e.g. Rhizopus stolonifer), Sclerotinia species (e.g. Sclerotinia sclerotiorum), Verticilium species (e.g. Verticilium alboatrum);

[0326] Seed- and soil-borne rots and wilts, and seedling diseases, caused by pathogens such as Alternaria species (e.g., Alternaria brassicicola), Aphanomyces species (e.g., Aphanomyces euteiches), Ascochyta species (e.g., Ascochyta lentis), Aspergillus species (e.g., Aspergillus flavus), Cladosporium species (e.g., Cladosporium herbarum), Cochliobolus species (e.g., Cochliobolus sativus) (conidial forms: Drechslera, Bipolaris Syn: Helminthosporium), Colletotrichum ), Fusarium species (e.g., Fusarium culmorum), Gibberella species (e.g., Gibberella zeae), Macrophomina species (e.g., Macrophomina phaseolina), Microdochium species (e.g., Microdochium nivale), Monographella species (e.g., Monographella nivalis), Penicillium species (e.g., Penicillium expansum), Phoma species (e.g., Phoma lingam), Phomopsis species (e.g., Phomopsis spp.), sojae), Phytophthora species (e.g. Phytophthora cactorum), Pyrenophoraspecies) (e.g., Pyrenophora graminea), Pyricularia species (e.g., Pyricularia oryzae), Pythium species (e.g., Pythium ultimum), Rhizoctonia species (e.g., Rhizoctonia solani), Rhizopus species (e.g., Rhizopus oryzae), Sclerotium species (e.g., Sclerotium rolfsii), Septoria species (e.g., Septoria nodorum), Typhula species (e.g., Typhula incarnate), Verticillium species (e.g., Verticillium dahlia);

[0327] Cancer, crown gall and witches' broom caused by pathogens such as Nectria species (e.g. Nectria galligena); wilt caused by pathogens such as Monilinia species (e.g. Monilinia laxa);

[0328] Leaf, flower and fruit deformations caused by pathogens such as Exobasidium species (e.g. Exobasidium vexans), Taphrina species (e.g. Taphrina deformans);

[0329] Degenerative diseases of woody plants caused by pathogens such as Esca species (e.g. Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea), Ganoderma species (e.g. Ganoderma boninense);

[0330] Flower and seed diseases caused by pathogens such as Botrytis species (e.g. Botrytis cinerea); tuber diseases caused by pathogens such as Rhizoctonia species (e.g. Rhizoctonia solani), Helminthosporium species (e.g. Helminthosporium solani);

[0331] Diseases caused by bacterial pathogens, for example Xanthomonas species (e.g. Xanthomonas campestris pv. Oryzae), Pseudomonas species (e.g. Pseudomonas syringae pv. Lachrymans), Erwinia species (e.g. Erwinia amylovora).

[0332] Seed treatment

[0333] The method for controlling undesirable microorganisms can be used to protect seeds from attack by phytopathogenic microorganisms such as fungi.

[0334] As used herein, the term "seed" includes dormant seeds, seeds to be germinated, germinated seeds, and seeds with roots and leaves sprouted.

[0335] Therefore, the present invention also relates to a method for protecting seeds and / or crops from harmful microorganisms such as bacteria or fungi, which comprises the step of treating seeds with one or more compounds of formula (I) or compositions comprising the same. Treating seeds with compounds of formula (I) or compositions comprising the same not only protects seeds from plant pathogenic microorganisms, but also protects germinating plants, germinating seedlings and plants after germination.

[0336] Seed treatment can be carried out before sowing, during sowing or shortly after sowing. When seed treatment is carried out before sowing (e.g., so-called application on seeds), the following seed treatment can be carried out: the seeds can be placed in a mixer with a desired amount of a compound of formula (I) or a composition comprising it (as is or after dilution), and the seeds and the compound of formula (I) or a composition comprising it are mixed until uniform distribution on the seeds is achieved. Then, if suitable, the seeds can be dried.

[0337] The present invention also relates to seeds treated with one or more compounds of formula (I) or compositions comprising the same. As previously mentioned, the use of treated seeds can not only protect the seeds from unwanted microorganisms such as phytopathogenic fungi before and after sowing, but also protect the germinating plants and the seedlings grown from the treated seeds. Most of the damage caused by harmful organisms to crops is caused by infection of the seeds before sowing or after plant germination. This stage is particularly critical because the roots and shoots of growing plants are particularly sensitive and even small damage may lead to plant death.

[0338] Therefore, the present invention also relates to a method for protecting seeds, germinating plants and germinating seedlings, more generally to a method for protecting crops from phytopathogenic microorganisms, which comprises the step of treating the seeds with one or more compounds of formula (I) or a composition comprising the same.

[0339] Preferably, the seed is treated in a state where it is sufficiently stable to not be damaged during the treatment process. In general, the seed can be treated at any time between harvesting and shortly after sowing. It is customary to use seeds that are separated from the plant and do not have cobs, shells, stems, skins, hairs or pulp. For example, seeds that have been harvested, cleaned and dried to a moisture content of less than 15% by weight can be used. Alternatively, dried seeds can also be used, for example, seeds that have been treated with water and then dried again, or seeds just after germination, or seeds stored under germination conditions or pre-germinated seeds, or seeds sown on seedling trays, tapes or paper.

[0340] The amount of the compound of formula (I) or the composition comprising it applied to the seed is generally such that the germination of the seed is not affected, or the resulting plant is not damaged. This must be ensured in particular in the case where the active ingredient exhibits phytotoxic effects at certain application rates. When determining the amount of the compound of formula (I) or the composition comprising it applied to the seed, the intrinsic phenotype of the transgenic plant should also be taken into account, so that the compound of formula (I) or the composition comprising it is used in the least amount for optimal seed and germination plant protection.

[0341] As mentioned above, the compound of formula (I) can be applied directly to the seed, i.e. without any other components and without dilution, or a composition comprising the compound of formula (I) can be applied. Preferably, the composition is applied to the seed in any suitable form. Examples of suitable formulations include solutions, emulsions, suspensions, powders, foams, slurries or in combination with other coating compositions of the seed, such as film-forming materials, granulating materials, fine iron or other metal powders, granules, coating materials for inactivating seeds, and ULV formulations. The formulation can be a ready-to-use formulation or can be a concentrate that needs to be diluted before use.

[0342] These formulations are prepared in a known manner, for example by mixing the active ingredients or mixtures thereof with customary additives, such as customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, auxiliary thickeners, binders, gibberellins, and also water.

[0343] These formulations are prepared in a known manner by mixing the active ingredients or active ingredient combinations with customary additives, such as customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, binders, gibberellins, and also water.

[0344] Useful dyes that may be present in the seed dressing formulations are all dyes that are commonly used for such purposes. Pigments that are slightly soluble in water or dyes that are soluble in water can be used. Examples include dyes named Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1. Useful wetting agents that may be present in the seed dressing formulations are all substances that promote wetting that are commonly used to formulate agrochemical active ingredients. Alkylnaphthalene sulfonates, such as diisopropyl- or diisobutylnaphthalene sulfonates, are preferably used. Useful dispersants and / or emulsifiers that may be present in the seed dressing formulations are all nonionic, anionic and cationic dispersants that are conventionally used for active agrochemical ingredient preparations. Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants are preferably used. Useful nonionic dispersants include ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, as well as phosphated or sulfated derivatives thereof. Suitable anionic dispersants are in particular lignin sulfonates, polyacrylates and aryl sulfonate / formaldehyde condensates. Defoamers that may be present in the seed dressing formulation are all antifoaming substances that are commonly used to formulate agrochemical active ingredients. Silicone defoamers and magnesium stearate can be preferably used. Preservatives that may be present in the seed dressing formulation are all substances that can be used in agrochemical compositions for such purposes. Examples include dichlorobenzene and benzyl alcohol hemiformal. Secondary thickeners that may be present in the seed dressing formulation are all substances that can be used in agrochemical compositions for such purposes. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays and finely divided silica. Adhesives that may be present in the seed dressing formulation are all commonly used adhesives that can be used for seed dressing products. Preferred examples include polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

[0345] The compound of formula (I) and the composition comprising it are suitable for protecting the seeds of any plant variety used for agriculture, greenhouse, forest or gardening. More specifically, it is the seeds of cereals (such as wheat, barley, rye, millet, triticale and oats), rape, corn, cotton, soybean, rice, potato, sunflower, beans, coffee, peas, beets (such as beets and fodder beets), peanuts, vegetables (such as tomatoes, cucumbers, onions and lettuce), lawns and ornamental plants. Particularly important is the processing of wheat, soybean, rape, corn and rice seeds.

[0346] The compounds of formula (I) or compositions comprising them can be used to treat transgenic seeds, in particular plant seeds capable of expressing proteins against pests, herbicide damage or abiotic stress, thereby improving protection. Synergistic effects may also occur in the interaction with the substances formed by expression.

[0347] Nematodes

[0348] In the present context, the term "nematodes" encompasses all species of the phylum Nematoda, and in particular species here which parasitize plants or fungi (e.g. species of the orders Aphelenchida, Meloidogyne, Tylenchida, etc.) or humans and animals (e.g. species of the orders Trichinellida, Tylenchida, Rhabditina and Spirurida) and cause damage in or on these living organisms, as well as other parasitic helminths.

[0349] As described herein, nematicides in crop protection control nematodes.

[0350] The term "controlling nematodes" means killing the nematodes or preventing or retarding their development or their growth or preventing or retarding their penetration into plant tissue or sucking on plant tissue.

[0351] Here, the efficacy of the compound is determined by comparing mortality, gall formation, cyst formation, nematode density per volume of soil, nematode density per root, number of nematode eggs per soil volume, mobility of nematodes between plants or plant parts treated with compounds of formula (I) or treated soil and untreated plants or plant parts or untreated soil (100%). Preferably, a reduction of 25-50%, particularly preferably 51-79%, is achieved compared to untreated plants, plant parts or untreated soil, very particularly preferably complete killing or complete prevention of the development and growth of nematodes, a reduction of 80% to 100%. Controlling nematodes as described herein also comprises controlling the proliferation of nematodes (development of cysts and / or eggs). The compounds of formula (I) can also be used to maintain the health of plants or animals, and they can be used therapeutically, preventively or systemically for controlling nematodes. The person skilled in the art knows methods for determining mortality, gall formation, cyst formation, nematode density per volume of soil, nematode density per root, number of nematode eggs per volume of soil, mobility of nematodes.

[0352] The use of compounds of formula (I) can maintain plant health and also include reducing damage caused by nematodes and increasing harvest yields.

[0353] As used herein, the term "nematode" refers to plant nematodes, including all nematodes that damage plants. Plant nematodes include plant parasitic nematodes and soil-borne nematodes. Plant parasitic nematodes include ectoparasites, such as Xiphinema spp., Longidorus spp., and Trichodorus spp.; hemiparasites, such as Tylenchulus spp.; migratory endoparasites, such as Pratylenchus spp., Radophholus spp., and Scutellonema spp.; non-migratory parasites, such as Heterodera spp., Globodera spp., and Meloidogyne spp., as well as stem and leaf endoparasites, such as Ditylenchus spp., Aphelenchoides spp. And Hirschmaniella spp.. Particularly harmful root parasitic soil nematodes are, for example, cyst-forming nematodes of the genus Heterodera or Globodera, and / or root gall nematodes of the genus Meloidogyne. The destructive species of these genera are, for example, southern root-knot nematodes (Meloidogyne incognita), soybean cyst nematodes (Heterodera glycines), potato white nematodes (Globodera pallida) and potato golden wireworms (Globodera rostochiensis) (yellow potato cyst nematodes), which are effectively controlled by the compounds described herein. However, the use of the compounds described herein is by no means limited to these genera or species, but is extended to other nematodes in the same manner.

[0354] Plant nematodes include, for example, Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Aphelenchoides fragaria; and stem and leaf parasites of Aphelenchoides spp., Belonolaimus gracilis,

[0355] (Belonolaimus longicaudatus), Belonolaimus nortoni, Coconut red ring nematode

[0356] Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus and Bursaphelenchus spp., Cacopaurus pestis, Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax and Criconemella spp., Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum and Criconemoides spp., Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus and stem and leaf parasites of Ditylenchus spp., Dolichodorus heterocephalus, Globodera pallida (= Heterodera pallida), Globodera rostochiensis (yellow potato cyst nematode), Globodera solanacearum, Globodera tabacum, Globodera Virginia and Globodera spp.), Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus erythrine, Helicotylenchus multicinctus, Helicotylenchus nannus, Helicotylenchus pseudorobustus, and Helicotylenchus spp., Hemicriconemoides, Hemicycliophora arenaria, Hemicycliophora nudata, Hemicycliophora parvana, Heterodera avenae, Heterodera cruciferae, Heterodera glycines (soya cyst nematode), Heterodera spp. bean cyst nematode), Heterodera oryzae, Heterodera schachtii, Heterodera zeae, and Heterodera spp., non-migratory cyst-forming parasites, Hirschmaniella gracilis, Hirschmaniella oryzae, Hirschmaniella spinicaudata, and Hirschmaniella spp.), Hoplolaimus aegyptii, Hoplolaimus californicus, Hoplolaimus columbus, Hoplolaimus galeatus, Hoplolaimus indicus, Hoplolaimus magnistylus, Hoplolaimus pararobustus, Longidorus africanus, Longidorus breviannulatus, Longidorus elongatus, Longidorus laevicapitatus, Longidorus vineacola, and Longidorus spp.), sorghum root-knot nematode (Meloidogyne acronea), African root-knot nematode (Meloidogyne africana), peanut root-knot nematode (Meloidogyne arenaria), Meloidogynearenaria thamesi, cabbage root-knot nematode (Meloidogyne artiella), Qi's root-knot nematode (Meloidogynechitwoodi), coffee root-knot nematode (Meloidogyne coffeicola), Ethiopian root-knot nematode (Meloidogyne ethiopica), short root-knot nematode (Meloidogyne exigua), pseudo root-knot nematode (Meloidogyne fallax), grass root-knot nematode (Meloidogyne graminicola), grass root-knot nematode (Meloidogyne graminis), northern root-knot nematode (Meloidogyne hapla), southern root-knot nematode (Meloidogyne incognita), Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne kikuyensis, Meloidogyne minor, Meloidogyne naasi, Meloidogyne paranaensis, Meloidogyne thamesi, and non-migratory parasites of Meloidogyne spp., Meloinema spp., Nacobbus aberrans, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Paratrichodorus allius, Paratrichodorus lobatus, Paratrichodorus minor), Paratrichodorus nanus, Paratrichodorus porosus, Paratrichodorus teres, and Paratrichodorus spp.), Paratylenchus hamatus, Paratylenchus minutus, Paratylenchus projectus and Paratylenchus spp., Pratylenchus agilis, Pratylenchus alleni, Pratylenchus andinus, Pratylenchus brachyurus, Pratylenchus cerealis, Pratylenchus coffeae, Pratylenchus crenatus, Pratylenchus delattrei, Pratylenchus giibbicaudatus, Pratylenchus goodeyi, Pratylenchus hamatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus, Pratylenchus zeae, and migratory endoparasites of Pratylenchus spp., Pseudohalenchus minutus, Psilenchus magnidens, Psilenchus tumidus, Punctodera chalcoensis, Quinisulciusacutus, Radopholus citrophilus, Radopholus similis, Radopholus spp.), Rotylenchulus borealis, Rotylenchulus parvus, Rotylenchulus reniformis and Rotylenchulus spp., Rotylenchus laurentinus, Rotylenchus macrodoratus, Rotylenchus robustus, Rotylenchus uniformis and Rotylenchulus spp.

[0357] ), migratory endoparasites of Scutellonema brachyurum, Scutellonema bradys, Scutellonema clathricaudatum and Scutellonema species, ectoparasites of Subanguina radiciola, Tetylenchus nicotianae, Trichodorus cylindricus, Trichodorus minor, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus and Trichodorus species, and ectoparasites of Tylenchorhynchus agri), Tylenchorhynchus brassicae, Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus vulgaris, and Tylenchorhynchus spp., Tylenchorhynchus semipenetrans, and hemiparasites of Tylenchulus spp., Xiphinema americanum, Xiphinema brevicolle, Xiphinema dimorphica udatum, Xiphinema index) and ectoparasites of Xiphinema spp.

[0358] Nematodes that can be controlled using the compounds of formula (I) include nematodes of the genus Meloidogyne, for example the southern root-knot nematode (Meloidogyne incognita), the Java root-knot nematode (Meloidogyne javanica), the northern root-knot nematode (Meloidogyne hapla) and the peanut root-knot nematode (Meloidogyne arenaria); nematodes of the genus Ditylenchus, for example the potato rot nematode (Ditylenchus destructor) and the stem and bulb nematode (Ditylenchus dipsaci); nematodes of the genus Pratylenchus, for example the corn root-damaging nematode (Pratylenchus penetrans), the chrysanthemum root-damaging nematode (Pratylenchus pseudobrachiatus); fallax), coffee root-damaging nematodes (Pratylenchus coffeae), tea root-damaging nematodes (Pratylenchus loosi), and walnut root-damaging nematodes (Pratylenchus vulnus); nematodes of the genus Globodera, such as the yellow potato cyst nematode (Glechoma longituba),

[0359] rostochiensis) and white potato cyst nematode (Globodera pallida); nematodes of the genus Heterodera, such as soybean cyst nematode (Heterodera glycines) and sugar beet cyst nematode (Heteroderaschachtii); nematodes of the genus Aphelenchoides, such as rice stem tip nematode (Aphelenchoides besseyi), chrysanthemum leaf nematode (Aphelenchoidesritzemabosi) and strawberry nematode (Aphelenchoides fragariae); nematodes of the genus Aphelenchus, such as fungi-feeding nematode (Aphelenchus avenae), and fungi-feeding nematode (Aphelenchus spp.). avenae); nematodes of the genus Radopholus, such as the burrowing nematode (Radopholus similis); nematodes of the genus Tylenchulus, such as the citrus root nematode (Tylenchulus semipipenetrans); nematodes of the genus Rotylenchulus, such as the kidney-shaped nematode (Rotylenchulus reniformis); nematodes present in trees, such as the pine wood nematode (Bursaphelenchus xylophilus) and the red ring nematode (Bursaphelenchus cocophilus), etc.

[0360] Plants that can be protected using the compounds of formula (I) include the following: for example, cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), legumes (soybeans, red beans, kidney beans, broad beans, peas, peanuts, etc.), fruit trees / fruits (apples, citrus species, pears, grapes, peaches, Japanese apricots, cherries, walnuts, almonds, bananas, strawberries, etc.), vegetable species (cabbage, tomatoes, spinach, broccoli, lettuce, onions, green onions, bell peppers, etc.), root crops (carrots, potatoes, sweet potatoes, radish, lotus root, turnip, etc.), industrial raw material crops (cotton, paper mulberry, three-leaf mulberry, rapeseed, beet, hop, sugarcane, sugar beet, olive, rubber, palm tree, coffee, tobacco, tea, etc.), melons (pumpkin, cucumber, watermelon, melon, etc.), forage plants (duckgrass, sorghum, timothy, alfalfa, purple alfalfa, etc.), lawn grass (zoysia, bentgrass, etc.), spice plants (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), and flowers (chrysanthemum, rose, orchid, etc.).

[0361] The compounds of formula (I) are particularly suitable for controlling nematodes in coffee, especially Brachyura brachyura, Brachyura coffee, short root-knot nematodes, southern root-knot nematodes, coffee root-knot nematodes, spiral nematodes, and Parana root-knot nematodes, spiral nematodes, Xiphinema species, dwarf nematodes, and shield nematodes.

[0362] The compounds of formula (I) are particularly suitable for controlling nematodes in potatoes, in particular Brachyura short-tailed, Pratylenchus prausnitzii, Pratylenchus scribneri, Pratylenchus penetrans, Pratylenchus coffee, Ditylenchus truncatus, as well as Pratylenchus allensis, Pratylenchus andean, Pratylenchus cerealis, Pratylenchus notch, Pratylenchus six-lobed, Pratylenchus louse, Pratylenchus lost, Pratylenchus smooth, Pratylenchus sorrelii, Pratylenchus wounded, Long-tailed thorn nematode, Barrel burr nematode, Dark Burr nematode, adjacent burr nematode, similar burr nematode, rare burr nematode, lesser pseudo-burr nematode, onion pseudo-burr nematode, short pseudo-burr nematode, smooth pseudo-burr nematode, peanut root-knot nematode, pseudo-root-knot nematode, northern root-knot nematode, Thames root-knot nematode, southern root-knot nematode, Qi's root-knot nematode, Java root-knot nematode, abnormal pearl nematode, potato golden nematode, potato white nematode, destructive stem nematode, similar piercing nematode, kidney-shaped small spiral nematode, Neotylenchus vigissi, false wall grass Heterotype nematode (Paraphelenchus pseudoparietinus), strawberry Heterotype nematode and spherical nematode species.

[0363] The compounds of formula (I) are particularly suitable for controlling nematodes in tomatoes, in particular the peanut root-knot nematode, the northern root-knot nematode, the java root-knot nematode, the southern root-knot nematode, the puncturing Pratylenchus penetrans, as well as the short-tailed Pratylenchus, the coffee Pratylenchus, the scribner Pratylenchus, the wounding Pratylenchus, the lesser pseudoburr nematode, the short root-knot nematode, the abnormal pearl nematode, the eggplant spherical nematode, Dolichodorus heterocephalus and the reniform spiral nematode.

[0364] The compounds of formula (I) are particularly suitable for controlling nematodes in cucumber plants, in particular the peanut root-knot nematode, the northern root-knot nematode, the javanic root-knot nematode, the southern root-knot nematode, the reniform spiral nematode, and the sowerby's nematode.

[0365] The compounds of formula (I) are particularly suitable for controlling nematodes in cotton, in particular L. longicaudalis, M. incognita, L. columbiformis, L. cap-shaped, and L. reniformis.

[0366] The compounds of formula (I) are particularly suitable for controlling nematodes in corn, in particular the long-tailed thorn nematode, the lesser pseudo-burr nematode, and the short-tailed thorn nematode, the delat thorn nematode, the six-lobed thorn nematode, the puncturing thorn nematode, the corn thorn nematode, (the fine thorn nematode), Belonolaimus nortoni, the short-ringed long needle nematode, the peanut root knot nematode, Meloidogyne arenariathamesi, the grass root knot nematode, the southern root knot nematode, Meloidogyne incognita acrita, the Java root knot nematode, the Nasi root knot nematode, the avenous nematode, the rice nematode, the corn nematode, the charcoal spot nematode, the teasel grass stem nematode, the Egyptian tie nematode, the large needle tie nematode, the cap tie nematode, the Indian tie nematode, the double-horned spiral nematode, the double palace spiral nematode, the false strong spiral nematode, the American sword nematode, the Dolichodorus heterocephalus, the small decorative ring nematode, the small Ouni ring nematode, the similar piercing nematode, the small northern spiral nematode, the small kidney-shaped nematode, the farmland dwarf nematode, the clear dwarf nematode, the Clayton dwarf nematode, the largest dwarf nematode, the naked dwarf nematode, the common dwarf nematode, the sharp five-grooved nematode, the microscopic needle nematode, the microscopic sheath nematode, the soil rough-grained film mat nematode, the wheat grain gall nematode, the peanut pseudo-slippery blade nematode, the small-tailed shield nematode, and the root gall sub-granular nematode.

[0367] The compounds of formula (I) are particularly suitable for controlling nematodes in soybeans, in particular Brachyura short-tailed, Brachyura savannae, Brachyura penetrating, Brachyura scribneri, Brachyura longicaudatus, Heterodera soybean, and Brachyura columella, as well as Brachyura coffee, Brachyura six-lobed, Brachyura lost, Brachyura notched, Brachyura Allenii, Brachyura agile, Brachyura corn, Brachyura injured, (fine thorn nematode), peanut root-knot nematode, southern root-knot nematode, Java root-knot nematode, northern root-knot nematode, Columbian nematode, cap-shaped nematode and kidney-shaped spiral nematode.

[0368] The compounds of formula (I) are particularly suitable for controlling nematodes in tobacco, especially the southern root-knot nematode, the javanic root-knot nematode, and the short-tailed Braybody nematode, the grassland Braybody nematode, the six-lobed Braybody nematode, the piercing Braybody nematode, the defeated Braybody nematode, the notched Braybody nematode, the sow's Braybody nematode, the disabled Braybody nematode, the corn Braybody nematode, the escaped long needle nematode, Paratrichodorus lobatus, the burr nematode, the peanut root-knot nematode, the northern root-knot nematode, the tobacco ball skin nematode, the soya ball skin nematode, the virginia ball skin nematode, the teasel grass stem nematode, the spiral nematode, the spiral nematode, the American sword nematode, the small ring nematode, the kidney-shaped small spiral nematode, the Clayton dwarf nematode, the needle nematode and the tobacco fine pad nematode.

[0369] The compounds of formula (I) are particularly suitable for controlling nematodes in citrus, in particular Braytria coffee, as well as Braytria short-tailed, Braytria injured, Long-tailed thorn nematode, Lesser thorn nematode, Pseudothorn burr nematode, Trichodina spp., Meloidogyne incognita acrita, Meloidogyne incognita acrita, Javan root-knot nematode, Macrocystis spp., Xiphinema americana, Xiphinema short-necked, Xiphinema standard, Microcirculina species, Hemicycline spp., Similar puncture nematode and Citrus citrus puncture nematode, Peanut sheath nematode, Hemicycliophora nudata and Semipuncture nematode.

[0370] The compounds of formula (I) are particularly suitable for controlling nematodes in banana, in particular Pratylenchus coffee, P. simulans, and Pratylenchus giibbicaudatus, Pratylenchus louse, Meloidogyne species, Helicoverpa multitapes, Helicoverpa divaricata and Helicoverpa microstomata species.

[0371] The compounds of formula (I) are particularly suitable for controlling nematodes in pineapples, in particular Pratylenchus zeae, Pratylenchus pratylenchus, Brachyura caudatus, Pratylenchus goodeyi, Root-knot nematode species, Microhelicidinus reniformis, as well as Longidorus laevicapitatus, Dusky burr nematode, Microhelicidinus microcarpa, Ditylenchus species, Ditylenchus californicus, Ditylenchus robustus, Ditylenchus indica, Helicidinus dimorphica, Brachyhelicidinus multitape, Helicidinus erythrinae, Xiphinema dimorphicaudatum, Similar piercing nematode, Digital dwarf nematode, Tylenchorhynchus ebriensis, Micronematode microcarpa, Scutellonema clathricaudatum, Slow shield nematode, Caudal thick naked lance nematode, Psilenchus magnidens, Pseudohalenchus minutus, the Vernia, the Ouni, and the Ornamental.

[0372] The compounds of formula (I) are particularly suitable for controlling nematodes in grapes, in particular Pratylenchus injuris, Root-knot nematodes of peanuts, Root-knot nematodes of the south, Root-knot nematodes of java, Xiphinema americana, Xiphinema standard, as well as Pratylenchus prausnitzii, Pratylenchus scribneri, Pratylenchus fallis, Pratylenchus brachyura, Pratylenchus sorrelii and Pratylenchus semipenetratingensis.

[0373] The compounds of formula (I) are particularly suitable for controlling nematodes in tree crops - pome fruits, in particular Pratylenchus penetrans, as well as Pratylenchus injuris, Longissimus escapingus, southern root-knot nematodes and northern root-knot nematodes.

[0374] The compounds of formula (I) are particularly suitable for controlling nematodes in tree crops - stone fruits, in particular the puncturing nematode, the wounding nematode, the peanut root-knot nematode, the northern root-knot nematode, the Java root-knot nematode, the southern root-knot nematode, the thin-leaved ring nematode, as well as the short-tailed nematode, the coffee nematode, the scribner's nematode, the corn nematode, the long-tailed thorn nematode, the double-house spiral nematode, the American sword nematode, the curved wheel nematode, the Clayton dwarf nematode, the hook needle nematode, the protruding needle nematode, the small-tailed shield nematode and the cap-shaped tie nematode.

[0375] The compounds of formula (I) are particularly suitable for controlling nematodes in tree crops, sugar cane and rice, in particular Trichodina species, Microcircuitella species, and also Pratylenchus species, Pseudocranulus species, Meloidogyne species, Heliconematode species, Dwarfing nematode species, Aphelenchoidea species, Heterodera species, Xiphinema species and Cacopaurus pestis.

[0376] application

[0377] The compounds of formula (I) can be applied as such or, for example, as ready-to-use solutions, emulsions, water-based or oil-based suspensions, dusts, wettable powders, pastes, soluble powders, powders, soluble granules, granules for broadcasting, suspoemulsions, natural products impregnated with the compounds of formula (I), synthetic substances impregnated with the compounds of formula (I), fertilizers or microcapsules in polymers.

[0378] Application is done in a conventional manner, for example by watering, spraying, atomizing, broadcasting, dusting, foaming, smearing, etc. It can also be applied by ultra-low volume method, by drip irrigation system or drenching, by furrowing the compound of formula (I) or injecting it into the soil stem or trunk. It can also be applied by wound sealing, coating or other wound dressing.

[0379] The effective and phytocompatible amount of a compound of formula (I) applied to plants, plant parts, fruits, seeds or soil will depend on various factors, such as the compound / composition used, the object of treatment (plant, plant part, fruit, seed or soil), the type of treatment (dusting, spraying, seed dressing), the purpose of the treatment (curative and protective), the type of microorganism, the development stage of the microorganism, the sensitivity of the microorganism, the crop growth stage and the environmental conditions.

[0380] When the compound of formula (I) is used as fungicide, the rate of application can change in a relatively wide range according to the type used. For the processing of plant parts such as leaves, the rate of application can be 0.1 to 10000g / ha, preferably 10 to 1000g / ha, more preferably in the range of 50 to 300g / ha (when applied by the mode of watering or drip irrigation, the amount of application can even be reduced, particularly when using inert substrates such as rock wool or perlite). For the processing of seeds, the rate of application can be 0.1 to 200g per 100kg seeds, preferably 1 to 150g per 100kg seeds, more preferably 2.5 to 25g per 100kg seeds, even more preferably 2.5 to 12.5g per 100kg seeds. For the processing of soil, the scope of the amount of application can be 0.1 to 10000g / ha, preferably 1 to 5000g / ha.

[0381] These application rates are merely examples and are not intended to limit the scope of the invention.

[0382] Material protection

[0383] The compounds and compositions of the invention can also be used for protecting materials, especially industrial materials, from attack and destruction by harmful microorganisms.

[0384] Furthermore, the compounds and compositions of the present invention can be used as antifouling compositions alone or in combination with other active ingredients.

[0385] In this article, industrial materials are understood to mean inanimate materials that are ready for industrial use. For example, industrial materials that are protected from microbial changes or destruction may be adhesives, glues, paper, wallpaper and board / cardboard, textiles, carpets, leather, wood, fibers and tissue paper, paints and plastic products, cooling lubricants and other materials that may be infected or destroyed by microorganisms. Components of production plants and buildings, such as cooling water circuits, cooling and heating systems and ventilation and air conditioning units, which may be damaged by the growth of microorganisms, may also be mentioned within the scope of the materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, coatings, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.

[0386] The compounds and compositions of the present invention can prevent adverse effects such as rotting, decay, discoloration, fading or mold formation.

[0387] In the case of the treatment of wood, the compounds and compositions according to the invention may also be used to combat fungal diseases liable to grow on or in wood.

[0388] Wood refers to all types of wood, as well as all types of wood processing used for construction, such as solid wood, high-density wood, laminated wood and plywood. In addition, the compounds and compositions according to the invention can be used for protecting objects which come into contact with salt or brackish water, in particular hulls, screens, nets, buildings, rigging and signalling systems, from contamination.

[0389] The compounds and compositions of the present invention can also be used to protect stored goods. Stored goods are understood to refer to natural substances of plant or animal origin or processed products of their natural origin, and require long-term protection. Stored goods of plant origin, such as plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, can be protected by (pre) drying, moistening, crushing, grinding, compressing or baking after fresh harvest or processing. Stored goods also include unprocessed wood, such as building wood, poles and barriers, or wood in finished form, such as furniture. Stored goods of animal origin are, for example, hides, leather, fur and hair. The compounds and compositions of the present invention can prevent adverse effects, such as rotting, decay, discoloration, fading or mold formation.

[0390] Microorganisms capable of degrading or modifying industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. The compounds and compositions of the invention are preferably active against fungi, especially molds, wood-discoloring and wood-destroying fungi (ascomycetes, basidiomycetes, deuteromycetes and zygomycetes), as well as against slime organisms and algae. Examples include microorganisms of the genera Alternaria, such as Alternaria spp.; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp. spp.), Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria spp., Serpula spp., and Tyromyces spp., Cladosporium spp., Paecilomyces spp., Mucor spp., Escherichia spp., such as Escherichia coli; Pseudomonas spp., such as Pseudomonas aeruginosa. aeruginosa); Staphylococcus spp., such as Staphylococcus aureus, Candida spp., and Saccharomyces spp., such as Saccharomyces cerevisae.

[0391] Aspects of the teachings herein may be further understood in light of the following examples, which should not be construed as limiting the scope of the present teachings in any way.

[0392] Example

[0393] Synthesis of compounds of formula (I)

[0394] Preparation Example 1 : Preparation of S-ethyl 1-{[(3,4,5-trichloro-2-thienyl)carbonyl]amino}cyclopropanethiocarboxylate (Compound I.011)

[0395] Step 1 :Preparation of 1-{[(3,4,5-trichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylic acid ethyl ester

[0396] To a solution of 1.90 g (11.2 mmol) 2-chloro-1,3-dimethylimidazoline chloride dissolved in 11.2 mL dichloromethane was added a solution of 2.00 g (9.47 mmol) 3,4,5-trichlorothiophene-2-carboxylic acid and 6.47 mL (37.1 mmol) N,N-diisopropylethylamine dissolved in 75 mL dichloromethane. After stirring for 5 min, 2.86 g (17.2 mmol) 1-aminocyclopropanecarboxylic acid ethyl ester hydrochloride (1:1) was added and stirred at room temperature for 24 hours. Water was added and the reaction mixture was extracted twice with dichloromethane. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient dichloromethane / ethyl acetate) to give 2.48 g (98% purity, 84% yield) of the title compound as a white solid. LogP = 3.41. (M+H) = 342.

[0397] step 2: Preparation of 1-{[(3,4,5-trichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylic acid

[0398] 4.1 mL of 1M potassium hydroxide aqueous solution (4.1 mmol) was added dropwise to a solution of 640 mg (1.86 mmol) of ethyl 1-{[(3,4,5-trichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate in 11.5 mL of tetrahydrofuran. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was then carefully acidified to pH 1 with 1.0 M hydrochloric acid solution at 0°C and extracted three times with ethyl acetate. The combined organic layers were purified by Chem EIut TM The filtrate was filtered and concentrated under reduced pressure to give 551 mg (100% purity, 94% yield) of the title compound as a white solid. LogP = 2.39. (M+H) = 314.

[0399] step3: Preparation of S-ethyl 1-{[(3,4,5-trichloro-2-thienyl)carbonyl]amino}cyclopropanecarbothioate (Compound I.011)

[0400] Under an inert atmosphere, 332 μL (1.90 mmol) of N,N-diisopropylethylamine and 363 mg (0.95 mmol) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridine 3-oxide hexafluorophosphate were added to a solution of 200 mg (0.63 mmol) of 1-{[(3,4,5-trichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylic acid in 6.3 mL of anhydrous dichloromethane at room temperature. After stirring at room temperature for 15 min, 59 mg (0.95 mmol) of ethanethiol were added and the reaction mixture was stirred at room temperature for 18 hours. Saturated aqueous sodium bicarbonate solution was added and the reaction mixture was extracted twice with dichloromethane. The combined organic layer was filtered through a silica gel column and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient n-heptane / ethyl acetate) to give 217 mg (100% purity, 95% yield) of the title compound as a white solid. LogP = 4.01. (M+H) = 358.

[0401] Preparation Example 2 : Preparation of N-[(3,4,5-trichloro-2-thienyl)thiocarbonyl]glycine methyl ester (Compound I.038)

[0402] Step 1 :N-[(3,4,5-trichloro-2-thienyl)carbonyl]glycine methyl ester

[0403] To a solution of 250 mg (1.08 mmol) 3,4,5-trichlorothiophene-2-carboxylic acid and 210 mg (1.67 mmol) glycine ethyl ester hydrochloride (1:1) dissolved in 4.2 mL tetrahydrofuran was added 0.23 mL (1.62 mmol) triethylamine, followed by 1.0 mL (1.68 mmol) 50% (w / w) propanephosphonic anhydride in ethyl acetate. The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was cooled with water and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient n-heptane / ethyl acetate) to give 178 mg (93% purity, 51% yield) of the title compound as a white solid. LogP = 2.8. (M+H) = 302.

[0404] Step 2 : Preparation of N-[(3,4,5-trichloro-2-thienyl)thiocarbonyl]glycine methyl ester (Compound I.038)

[0405] To a solution of 2.50 g (8.26 mmol) of N-[(3,4,5-trichloro-2-thienyl)carbonyl]glycine methyl ester in 40 mL of dichloromethane was added 1.67 g (4.13 mmol) of Lawesson's reagent. The reaction mixture was stirred at 50°C for 72 hours. An additional 1.67 g (4.13 mmol) of Lawesson's reagent was added and the reaction mixture was stirred at 50°C for 24 hours. The resulting reaction mixture was diluted with dichloromethane and purified by alkaline Filter through an alumina cartridge and concentrate under reduced pressure. The residue is purified by silica gel column chromatography (gradient n-heptane / ethyl acetate) to give 1.26 g (98% purity, 47% yield) of the title compound as a yellow solid. LogP = 4.05. (M+H) = 318.

[0406] Preparation Example 3: Preparation of N-[(3,4,5-trichloro-2-thienyl)thiocarbonyl]glycine (Compound I.022)

[0407] 1.72 mL of 1 M potassium hydroxide aqueous solution (1.72 mmol) was added dropwise to a solution of 250 mg (0.78 mmol) of N-[(3,4,5-trichloro-2-thienyl)thiocarbonyl]glycine methyl ester (Compound I.038) in 6.4 mL of tetrahydrofuran. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was then carefully acidified to pH 1 with 1.0 M aqueous hydrochloric acid at 0°C and extracted three times with ethyl acetate. The combined organic layers were purified by Chem EIut TM The resulting mixture was filtered and concentrated under reduced pressure to afford 230 mg (98% purity, 94% yield) of the title compound as an orange solid. LogP = 3.17. (MH) = 302.

[0408] Preparation Example 4: Preparation of N-[(3,4,5-trichloro-2-thienyl)thiocarbonyl]glycine (Compound 1.022)

[0409] To a solution of 200 mg (0.63 mmol) of 1-{[(3,4,5-trichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylic acid, 73 mg (97% purity, 0.76 mmol) of aminoacetonitrile hydrochloride (1:1) and 290 mg (0.76 mmol) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridine 3-oxide hexafluorophosphate dissolved in 5 mL of N,N-dimethylformamide at room temperature, 332 μL (1.90 mmol) of N,N-diisopropylethylamine was added. The reaction mixture was stirred at room temperature for 66 hours. Water was added and the resulting reaction mixture was extracted twice with dichloromethane. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (gradient acetonitrile / aqueous formic acid solution (1%)) to give 195 mg (purity 100%, yield 87%) of the title compound as a yellow solid. LogP=2.41. (M+H)=352.

[0410] Preparation Example 5: Preparation of 3,4,5-trichloro-N-(cyanomethyl)thiophene-2-carboxamide (Compound I.025)

[0411] Under an inert atmosphere, 0.55 mL (3.94 mmol) of triethylamine, 198 mg (0.87 mmol) of 1-(3-dimethylaminopropyl)-3-carbodiimide hydrochloride and 118 mg (0.87 mmol) of 1-hydroxybenzotriazole were added to a solution of 150 mg (0.64 mmol) of 3,4,5-trichlorothiophene-2-carboxylic acid in 12 mL of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 18 hours. Water was added and the resulting reaction mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient n-heptane / ethyl acetate) to give 103 mg (100% purity, 59% yield) of the title compound as a white solid. LogP = 2.59. (M+H) = 269.

[0412] Preparation Example 6: Preparation of N-(2-amino-2-oxoethyl)-3,4,5-trichlorothiophene-2-carboxamide (Compound I.066)

[0413] Step 1 :Preparation of N-[(3,4,5-trichloro-2-thienyl)carbonyl]glycine

[0414] To a solution of 178 mg (0.59 mmol) of N-[(3,4,5-trichloro-2-thienyl)carbonyl]glycine methyl ester dissolved in 3 mL of tetrahydrofuran was added dropwise 1.3 mL of 1 M aqueous lithium hydroxide solution (1.3 mmol). The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate, water and saturated aqueous sodium bicarbonate solution. The organic layer was washed twice with saturated aqueous sodium bicarbonate solution. The combined aqueous layers were carefully acidified with 37% (w / w) aqueous hydrochloric acid at 0°C and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 159 mg (98% purity, 92% yield) of N-[(3,4,5-trichloro-2-thienyl)carbonyl]glycine as a white solid. LogP = 2.14. (MH) = 286.

[0415] Step 2 : Preparation of N-(2-amino-2-oxoethyl)-3,4,5-trichlorothiophene-2-carboxamide (Compound I.066)

[0416] To a solution of 400 mg (1.39 mmol) of N-[(3,4,5-trichloro-2-thienyl)carbonyl]glycine in 20 mL of anhydrous dichloromethane at room temperature under an inert atmosphere, 111 mg (2.08 mmol) of ammonium chloride, 399 mg (2.08 mmol) of 1-[bis(dimethylamino)methylene]-1H-1,2,3 triazolo[4,5-b]pyridine 3-oxide hexafluorophosphate and 359 mg (2.77 mmol) of N,N-diisopropylethylamine were added. The reaction mixture was stirred at room temperature for 2 hours. Saturated aqueous sodium bicarbonate solution was added, and the resulting reaction mixture was extracted twice with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (gradient acetonitrile / aqueous ammonium bicarbonate solution [10 mmol / L]) to give 255 mg (98% purity, 63% yield) of the title compound as a white solid. LogP = 1.89. (M+H) = 287.

[0417] Preparation Example 7 : Preparation of N-(2-amino-2-sulfanylideneethyl)-3,4,5-trichlorothiophene-2-carboxamide (Compound I.104)

[0418] Under an inert atmosphere, 400 mg (4.13 mmol) of Lawesson's reagent was added to a solution of 200 mg (0.66 mmol) of N-(2-amino-2-oxoethyl)-3,4,5-trichlorothiophene-2-carboxamide in 10 mL of toluene. The reaction mixture was stirred at 60 ° C for 5 hours. The resulting reaction mixture was concentrated under reduced pressure, diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (gradient acetonitrile / formic acid aqueous solution (0.1%)) to give 85 mg (45% purity, 99% yield) of the title compound as a white solid. LogP = 2.53. (M + H) = 303.

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431] NMR peak list

[0432] Table A provides NMR data for some of the compounds disclosed in the above table ( 1 H).

[0433] Selected Embodiments 1 H-NMR data 1 H-NMR peaks are written in the form of a list. Each signal peak is listed with the δ value in ppm and the signal intensity in parentheses. The signal intensity pairs between δ values ​​are separated by semicolons.

[0434] The peak list thus has the following form:

[0435] δ1(intensity 1); δ2(intensity 2); ...δ i (strength i );……δ n (strength n )

[0436] In the example of a printed NMR spectrum in centimeters, the intensity of a sharp signal is related to the height of the signal and shows the true relationship of the signal strength. From a broad signal, several peaks or intermediate signals of the signal can be shown and their relative intensities compared to the strongest signal in the spectrum.

[0437] For calibration 1 For the chemical shifts of H spectra, we use the chemical shift of tetramethylsilane and / or the solvent used, particularly in cases where the spectra were measured in DMSO. Therefore, in the NMR peak list, tetramethylsilane peaks may, but do not necessarily, appear.

[0438] 1 The H-NMR peak list is similar to the classical 1 H-NMR printed diagrams therefore usually contain all peaks which are listed in a classical NMR description.

[0439] Furthermore, they may show the classical peaks of solvents, stereoisomers of the target compound (also the object of the present invention) and / or impurity peaks. 1 H-NMR printing signals.

[0440] To show the compound signals in the delta range of solvent and / or water, common peaks of solvents such as DMSO peak and water peak in DMSO-D6 are shown in our 1 In the H-NMR peak list, the peaks generally have high intensities on average.

[0441] The average intensity of the stereoisomer peaks and / or impurity peaks of the target compound is usually lower than that of the target compound peak (eg, purity > 90%).

[0442] Such stereoisomers and / or impurities may be typical for a particular preparation process. Therefore, their peaks help to identify the reproduction of our preparation process by "by-product fingerprint".

[0443] Experts who calculate the peaks of target compounds using known methods (MestreC, ACD simulation, and empirically evaluated expectation values) can selectively use additional intensity filters to separate the peaks of target compounds as needed. This separation is similar to classical 1 Relevant peak detection in H-NMR interpretation.

[0444] You can find further details on NMR data descriptions and peak lists in the publication "Citation of NMR Peaklist Data within Patent Applications" with Research Disclosure Database Number 564025.

[0445] Table A : NMR peak list

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476] Biological data

[0477] Example A described below shows that compounds according to formula (1) induce defense gene expression in Arabidopsis thaliana, in particular stimulation of the salicylic acid pathway. Thus, these compounds can induce host defense, thereby protecting plants from a variety of pathogens including bacteria and fungi.

[0478] Examples B, C, D and E described below show in vitro cell assays for direct inactivation of compounds according to formula (1) against various pathogens including bacteria and fungi, thereby illustrating the mode of action of compounds according to formula (1) as plant host defense inducers.

[0479] Examples F, G, H, I and J described below show the in vivo activity of compounds according to formula (1) in plants by stimulating plant defences against various pathogens infecting plants including bacteria and fungi.

[0480] Examples K, L, M, N and O described below show a comparison of the in planta activity of the comparative compounds CMP1, CMP2, CMP3, CMP4, CMP5 and CMP6 prepared according to the teaching of EP0450355 and the compounds according to the invention.

[0481] Comparison of the activities of CMP1, CMP2, CMP3, CMP4, CMPS and CMP6 with the compounds of the present invention shows that these prior art compounds have significantly lower activities and therefore cannot provide the beneficial technical effects of the compounds of the present invention.

[0482] Example A: Inducing defense gene expression in Arabidopsis thaliana

[0483] Arabidopsis reporter plants containing a green fluorescent protein (GFP) coding sequence linked to the salicylic acid-responsive promoter sequence of the PR1 (pathogenesis-related protein 1) gene (AT2G14610) were grown for 5 days and then sprayed with the compounds. On the 3rd day after spraying, plant fluorescence was assessed using a MacroFluo instrument from Leica Microsystems (Wetzlar, Germany). Fluorescence was quantified using Meta-Morph microscope automation and image analysis software (Molecular Devices, Sunnyvale, CA, United States).

[0484] The background fluorescence of mock-treated leaves was set to 1.00. The relative fluorescence value of salicylic acid treatment (300 ppm) was 2.70, demonstrating the effectiveness of the test system.

[0485] During the course of the examination, the compound in the lower row of the basic book has a high degree of concentration of 300ppm and is as low as 2 times.I.001;I.003;I.006;I.007;I.008;I.009;I.010;I.011; I.012; I.013; I.015; I.016; I.017; I.018; I.019; I.020; I.021; I.023; I.025; I.026; I.029; I.031; I.032; I.03 3;I.034;I.035;I.036;I.037;I.038;I.039;I.040;I.041;I.042;I.043;I.044;I.045;I.046;I.048;I.049;I. 050;I.051;I.052;I.054;I.055;I.056;I.057;I.058;I.059;I.061;I.062;I.064;I.065;I.066;I.067;I.068;I .069;I.072;I.073;I.074;I.075;I.076;I.078;I.079;I.080;I.089;I.090;I.091;I.092;I.093;I.094;I.095 ;I.097;I.098;I.099;I.100;I.101;I.102;I.103;I.104;I.105;I.106;I.107;I.108;I.109;I.111;I.112;I.1 13;I.114;I.115;I.116;I.117;I.118;I.119;I.120;I.121;I.123;I.124;I.125;I.126;I.127;I.128;I.129;I .130; I.133; I.134; I.136; I.137; I.138; I.139; I.140; I.141; I.142; I.143; I.144; I.145; I.146; I.148;

[0486] In this test, the following compounds according to the invention showed relative fluorescence values ​​of at least greater than 2 at a compound concentration of 75 ppm: 1.001; 1.003; 1.007; 1.008; 1.009; 1.011; 1.012; 1.015; 1.016; 1.017; 1.018; 1.019; 1.020; 1.021; 1.022; I.023; I.025; I.029; I.036; I.037; I.040; I.041; I.042; I.043; I.046; I.048; I. 051;I.052;I.054;I.056;I.058;I.059;I.061;I.066;I.067;I.068;I.069;I.07 5;I.076;I.078;I.079;I.080;I.089;I.090;I.092;I.093;I.098;I.099;I.100; I.101; I.102; I.103; I.104; I.106; I.107; I.108; I.109; I.112; I.113; I.115; I. 117; I.118; I.119; I.120; I.121; I.123; I.124; I.127; I.128; I.131; I.136; I.13 7; I.138; I.139; I.140; I.141; I.142; I.143; I.144; I.145; I.146; I.148; I.149.

[0487] Salicylate is the primary defense hormone against plant pathogens. All of the above compounds stimulate the salicylate pathway and thus protect plants from a wide range of pathogens.

[0488] Example B: Alternaria alternata in vitro cell assay

[0489] Solvent: DMSO

[0490] Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g mycopeptone (Oxoid),

[0491] 1.4 g granulated yeast extract (Merck), QSP 1 liter

[0492] Inoculum: Spore suspension

[0493] The bactericide was dissolved in DMSO and this solution was used to prepare the desired concentration range. The final concentration of DMSO used in the assay was ≤ 1%.

[0494] A spore suspension of Alternaria alternifolia was prepared and diluted to the desired spore density.

[0495] The ability of fungicides to inhibit spore germination and mycelial growth was evaluated in a liquid culture test. The desired concentration of the compound was added to the medium containing the spores. After 5 days of incubation, the fungal toxicity of the compound was determined by spectroscopic measurement of mycelial growth. Inhibition of fungal growth was determined by comparing the absorbance values ​​in the wells containing the fungicide with the absorbance values ​​in the control wells without the fungicide.

[0496] In this test, the following compounds of the invention showed no direct activity (efficacy less than or equal to 30%) at an active ingredient concentration of 20 ppm: I.001; I.002; I.004; I.005; I.006; I.007; I.008; I.009; I.010; I.011; I.014; I.015; I.016; I.018; I.022 ;I.023;I.026;I.027;I.028;I.030;I.031;I.032;I.033;I.034;I.035;I.038;I.0 39; I.040; I.041; I.044; I.046; I.047; I.048; I.049; I.050; I.051; I.052; I.053; I .054; I.055; I.056; I.058; I.060; I.062; I.063; I.064; I.066; I.067; I.068; I.069 ;I.070;I.071;I.072;I.073;I.074;I.075;I.076;I.077;I.078;I.079;I.080;I.1 12;I.113;I.114;I.115;I.119;I.121;I.122;I.123;I.126;I.127;I.128;I.130;I .134; I.136; I.137; I.138; I.139; I.142; I.143; I.144; I.145; I.147; I.148; I.149.

[0497] Example C: In vitro cell test on bean anthracnose (Colletotrichum lindemuthianum)

[0498] Solvent: DMSO

[0499] Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g mycopeptone (Oxoid),

[0500] 1.4 g granulated yeast extract (Merck), QSP 1 liter

[0501] Inoculum: Spore suspension

[0502] The bactericide was dissolved in DMSO and this solution was used to prepare the desired concentration range. The final concentration of DMSO used in the assay was ≤ 1%.

[0503] A spore suspension of Colletotrichum spp. was prepared and diluted to the desired spore density.

[0504] The ability of fungicides to inhibit spore germination and mycelial growth was evaluated in a liquid culture test. The desired concentration of the compound was added to the medium containing the spores. After 6 days of incubation, the fungal toxicity of the compound was determined by spectroscopic measurement of mycelial growth. Inhibition of fungal growth was determined by comparing the absorbance values ​​in the wells containing the fungicide with the absorbance values ​​in the control wells without the fungicide.

[0505] In this test, the following compounds of the invention showed no direct activity (efficacy less than or equal to 30%) at an active ingredient concentration of 20 ppm: I.001; I.002; I.003; I.004; I.005; I.006; I.007; I.008; I.009; I.010; I.011; I.012; I.014; I.015; I.016; I.018; I.022; I.026; I.027; I.028; I.030 ;I.035;I.038;I.039;I.041;I.044;I.046;I.047;I.048;I.049;I.05 0;I.051;I.052;I.053;I.054;I.055;I.056;I.057;I.058;I.060;I.0 61; I.062; I.063; I.064; I.066; I.067; I.068; I.069; I.073; I.074; I. 075;I.113;I.114;I.115;I.119;I.121;I.122;I.123;I.125;I.128;I .129; I.134; I.135; I.137; I.139; I.141; I.143; I.147; I.148; I.149.

[0506] Example D: Cruciferous vegetable black rot fungus (Xanthomonas campestris pv. Campestris) in vitro Cell assay

[0507] Solvent: DMSO

[0508] Culture medium: LB broth (Luria Broth Miller) Sigma

[0509] Inoculum: Bacterial suspension

[0510] The bactericide was dissolved in DMSO and this solution was used to prepare the desired concentration range. The final concentration of DMSO used in the assay was ≤ 1%.

[0511] Inoculum was prepared from a bacterial preculture grown in liquid medium and diluted to the desired optical density (OD).

[0512] The ability of compounds to inhibit bacterial growth was evaluated in a liquid culture assay. The desired concentration of the compound was added to a culture medium containing a bacterial suspension. After 24 hours of incubation, the efficacy of the compound was determined by spectroscopic measurement of bacterial growth. Inhibition was determined by comparing the absorbance values ​​in the wells containing the compound with the absorbance values ​​in the control wells without active ingredient.

[0513] In this test, the following compounds of the invention showed no direct activity (efficacy less than or equal to 30%) at an active ingredient concentration of 20 ppm: I.001; I.002; I.003; I.004; I.005; I.006; I.007; I.008; I.009; I.010; I.011; I.012; I.013; I.014; I.015; I.016; I.018; I.019; I.020; I.021; I.022; I.023; I.024; I.025; I.026; I.027; I.028; I.029; I.030; I.031; I.032; I.033; I.034; I.035; I.036; I.037; I.038; I.039; I.040; I.041; I.042; I.043; I.044; I.045; I.046; I.047; I.048; I.049; I.050; I.051; I.052 022;I.023;I.025;I.026;I.027;I.028;I.029;I.030;I.031;I.032;I.033;I.034;I.035;I.036;I.03 7;I.038;I.039;I.040;I.041;I.042;I.043;I.044;I.046;I.047;I.048;I.049;I.050;I.051;I.052;I .053; I.054; I.055; I.056; I.057; I.058; I.059; I.060; I.061; I.062; I.063; I.064; I.065; I.066; I.0 67; I.068; I.069; I.070; I.071; I.072; I.073; I.074; I.075; I.076; I.077; I.078; I.079; I.080; I.112; I.113;I.114;I.115;I.119;I.121;I.122;I.123;I.124;I.125;I.126;I.127;I.128;I.129;I.130;I.1 34; I.135; I.136; I.137; I.138; I.139; I.140; I.141; I.142; I.143; I.144; I.145; I.146; I.147; I.149.

[0514] Example E: In vitro cell test on tomato bacterial spot pathogen (Pseudomonas syrinua epv. tomato)

[0515] Solvent: DMSO

[0516] Culture medium: LB broth (Luria Broth Miller) Sigma

[0517] Inoculum: Bacterial suspension

[0518] The bactericide was dissolved in DMSO and this solution was used to prepare the desired concentration range. The final concentration of DMSO used in the assay was ≤ 1%.

[0519] Inoculum was prepared from a bacterial preculture grown in liquid medium and diluted to the desired optical density (OD).

[0520] The ability of compounds to inhibit bacterial growth was evaluated in a liquid culture assay. The desired concentration of the compound was added to a culture medium containing a bacterial suspension. After 24 hours of incubation, the efficacy of the compound was determined by spectroscopic measurement of bacterial growth. Inhibition was determined by comparing the absorbance values ​​in the wells containing the compound with the absorbance values ​​in the control wells without active ingredient.

[0521] In this test, the following compounds of the present invention did not show direct activity (efficacy less than or equal to 30%) at an active ingredient concentration of 20 ppm: I.001; I.002; I.003; I.004; I.005; I.006; I.007; I.008; I.009; I.010; I.011; I.012; I.013; I.014; I.015; I.016; I.018; I.019; I.020; I.021; I.022; I.023; I.025; I.026; I.027; I.028; I.029; I.030; I.031; I.032; I.033; I.034; I.035; I.036; I.038; I.039; I.040; I.041; I.042; I.043; I.044; I.045; I.046; I.047; I.048; I.049; I.050; I.051; I.052; I.053; I.054; I.055; I.056; I.057; I.058; I.059; I.060; I.061; I.062; I.063; I.064; I.065; I.066; I.067; I.068; I.069; I.070; I.071; I.072; I.073; I.074; I.075; I.076; I.077; I.078; I.079; I.080; I.112; I.113; I.114; I.115; I.119; I.121; I.122; I.123; I.124; I.125; I.126; I.127; I.128; I.129; I.130; I.134; I.135; I.136; I.137; I.138; I.139; I.140; I.141; I.142; I.143; I.144; I.145; I.146; I.147; I.148; I.149.

[0522] Example F: In vivo prevention of Colletotrichum lindemuthianum (Bean Anthracnose) Anti-test

[0523] The active ingredient to be tested was prepared by homogenization in a mixture of acetone / dimethyl sulfoxide / and then diluted with water to obtain the desired concentration of the active material.

[0524] The seedlings of beans were treated by spraying the active ingredient prepared as described above. The control plants were treated only with an aqueous solution of acetone / dimethyl sulfoxide /

[0525] After 72 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of spores of Colletotrichum phaeocaulis. The contaminated bean plants were incubated at 20°C and 100% relative humidity for 24 hours and then at 20°C and 90% relative humidity for 5 days.

[0526] The test is evaluated 6 days after inoculation. 0% means an efficacy which corresponds to that of the control plants, while an efficacy of 100% means that no disease is observed.

[0527] In this test, the following compounds according to the invention showed an efficacy of 70% to 79% at an active ingredient concentration of 500 ppm: 1.091; 1.095; 1.111; 1.116.

[0528] In this test, the following compounds of the invention showed an efficacy of 80% to 89% at an active ingredient concentration of 500 ppm: 1.013; 1.020; 1.023; 1.026; 1.039; 1.048; 1.064; 1.104; 1.14.

[0529] In this test, the following compounds of the invention showed an efficacy of 90% to 100% at an active ingredient concentration of 500 ppm: I.009; I.010; I.012; I.016; I.019; I.022; .040;I.041;I.042;I.045;I.046;I.059;I.070;I.078;I.079;I.080; I.089; I.090; I.108; I.109; I.113; I.117; I.118; I.119; I.120; I.128.

[0530] In this test, the following compounds of the invention showed an efficacy of 70% to 79% at an active ingredient concentration of 31 ppm: 1.006; 1.010; 1.022; 1.041; 1.059; 1.061; 1.062; 1.066; 1.17; 1.119; 1.120; 1.127; 1.139; 1.143.

[0531] In this test, the following compounds of the invention showed an efficacy of 80% to 89% at an active ingredient concentration of 31 ppm: 1.004; 1.016; 1.046; 1.123; 1.137; 1.142; 1.144.

[0532] In this test, the following compounds of the invention showed an efficacy of 90% to 100% at an active ingredient concentration of 31 ppm: 1.025; 1.031; 1.036; 1.038; 1.043; 1.121; 1.124.

[0533] Example G: Peronospora parasitica (Cruciferous Vegetable Downy Mildew In vivo prevention study of Crucifer downymildew

[0534] By acetone / dimethyl sulfoxide / The active ingredients to be tested were prepared by homogenizing a mixture of 1% ethanol and then diluting with water to obtain the desired concentration of active material.

[0535] Seedlings of cabbage were treated by spraying with the active ingredient prepared as described above. Control plants were treated only with acetone / DMSO / of aqueous solution treatment.

[0536] After 72 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of spores of Peronospora parasitica. The contaminated cabbage plants were incubated at 20°C and 100% relative humidity for 5 days.

[0537] The test is evaluated 5 days after inoculation. 0% means an efficacy which corresponds to that of the control plants, while an efficacy of 100% means that no disease is observed.

[0538] In this test, the following compounds according to the invention showed an efficacy of 70% to 79% at an active ingredient concentration of 500 ppm: 1.076; 1.110.

[0539] In this test, the following compounds according to the invention showed an efficacy of 80% to 89% at an active ingredient concentration of 500 ppm: 1.041; 1.072; 1.077; 1.093.

[0540] In this test, the following compounds of the invention showed 90% to 100% efficacy at an active ingredient concentration of 500 ppm: I.008; I.009; I.010; I.011; I.012; I.013; I.016; I.020; I.022; I.023; I.025; I.029; I.031; I.036; I.037; I.038; I.039; I.040; I.041; I.042; I.043; I.044; I.045; I.046; I.047; I.048; I.049; I.050; I.051; I.052; I.053; I.054; I.055; I.056; I.057; I.058; I.059; I.060; I.061; I.062; I.063; I.064; I.065 .042; I.043; I.046; I.048; I.059; I.064; I.078; I.079; I.080; I.089; I.090; I.091; I.094; I.095; I.104; I.108; I.109; I.111; 1.113; 1.116; 1.117; 1.118; 1.120; 1.128; 1.129; 1.147.

[0541] In this test, the following compounds according to the invention showed an efficacy of 70% to 79% at an active ingredient concentration of 31 ppm: 1.012; 1.028; 1.095; 1.122.

[0542] In this test, the following compounds of the invention showed an efficacy of 80% to 89% at an active ingredient concentration of 31 ppm: 1.013; 1.025; 1.041; 1.059; 1.063; 1.064; 1.065; 1.113.

[0543] In this test, the following compounds of the invention showed an efficacy of 90% to 100% at an active ingredient concentration of 31 ppm: I.006; I.007; I.008; I.009; I.010; I.011; I.015; I.016; I.018; I.0 22; I.023; I.029; I.031; I.034; I.036; I.037; I.038; I.040; I.042; I.043; I.046; I.048; I.054; I.061; I.062; I.066; I. 067; I.069; I.073; I.074; I.078; I.079; I.080; I.089; I.090; I.091; I.104; I.108; I.109; I.117; I.118; I.119; I.120; I .121; I.123; I.124; I.125; I.126; I.127; I.128; I.136; I.137; I.138; I.139; I.140; I.142; I.143; I.144; I.145; I.146.

[0544] In this test, the following compounds of the invention showed an efficacy of 70% to 79% at an active ingredient concentration of 125 ppm: 1.059.

[0545] In this test, the following compounds of the invention showed an efficacy of 80% to 89% at an active ingredient concentration of 125 ppm: 1.025; 1.041; 1.049; 1.050; 1.057; 1.069; 1.073; 1.111.

[0546] In this test, the following compounds of the invention showed an efficacy of 90% to 100% at an active ingredient concentration of 125 ppm: I.006; ;I.023;I.029;I.031;I.034;I.036;I.037;I.038;I.039;I.040;I.0 42;I.043;I.046;I.048;I.052;I.054;I.061;I.062;I.063;I.064;I .065; I.066; I.067; I.074; I.078; I.079; I.080; I.089; I.090; I.091 ;I.095;I.104;I.108;I.109;I.113;I.117;I.118;I.119;I.120;I.1 21;I.122;I.123;I.124;I.125;I.126;I.127;I.128;I.129;I.136;I .137; I.138; I.139; I.140; I.142; I.143; I.144; I.145; I.146; I.147.

[0547] Example H: Cruciferous vegetable black rot fungus (Xanthomonas campestris pv. campestris) (Brassica oleracea In vivo prevention test of black rot

[0548] By acetone / dimethyl sulfoxide / The active ingredients to be tested were prepared by homogenizing a mixture of 1% ethanol and then diluting with water to obtain the desired concentration of active material.

[0549] Seedlings of cabbage were treated by spraying with the active ingredient prepared as described above. Control plants were treated only with acetone / DMSO / of aqueous solution treatment.

[0550] After 72 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of spores of Pseudomonas aeruginosa. The contaminated cabbage plants were incubated at 27°C and 95% relative humidity for 8 or 10 days.

[0551] The tests are evaluated 8 or 10 days after inoculation. 0% means an efficacy which corresponds to that of the control plants, while an efficacy of 100% means that no disease is observed.

[0552] In this test, the following compounds of the invention showed an efficacy of 70% to 79% at an active ingredient concentration of 31 ppm: 1.010; 1.025; 1.029; 1.055; 1.069; 1.090; 1.110; 1.128; 1.129; 1.138.

[0553] In this test, the following compounds of the invention showed an efficacy of 80% to 89% at an active ingredient concentration of 31 ppm: 1.008; 1.012; 1.018; 1.019; 1.031; 1.038; 1.074; 1.080; 1.113; 1.120; 1.126; 1.136; 1.137; 1.142; 1.144.

[0554] In this test, the following compounds of the invention showed an efficacy of 90% to 100% at an active ingredient concentration of 31 ppm: 1.009; 1.015; 1.016; 1.042; 1.043; 1.046; 1.059; 1.108; 1.140; 1.143; 1.145.

[0555] In this test, the following compounds of the invention showed an efficacy of 70% to 79% at an active ingredient concentration of 125 ppm: 1.018; 1.064; 1.109; 1.110; 1.111; 1.125; 1.136.

[0556] In this test, the following compounds of the invention showed an efficacy of 80% to 89% at an active ingredient concentration of 125 ppm: 1.013; 1.029; 1.038; 1.079; 1.080; 1.096; 1.129; 1.143.

[0557] In this test, the following compounds of the invention showed an efficacy of 90% to 100% at an active ingredient concentration of 125 ppm: 1.009; 1.019; 1.042; 1.043; 1.046; 1.048; 1.142; 1.145.

[0558] Example I: In vivo prevention test of Uromvces appendiculatus (bean rust)

[0559] By acetone / dimethyl sulfoxide / The active ingredients to be tested were prepared by homogenizing a mixture of 1% ethanol and then diluting with water to obtain the desired concentration of active material.

[0560] Bean seedlings were treated by spraying with the active ingredient prepared as described above. Control plants were treated only with acetone / DMSO / of aqueous solution treatment.

[0561] After 72 hours, Puccinia vulgaris The plants were contaminated by spraying the leaves with an aqueous suspension of the spores. The contaminated bean plants were incubated at 20°C and 100% relative humidity for 24 hours and then at 20°C and 70-80% relative humidity for 9 days.

[0562] The test is evaluated 10 days after inoculation. 0% means an efficacy which corresponds to that of the control plants, while an efficacy of 100% means that no disease is observed.

[0563] In this test, the following compounds according to the invention showed an efficacy of 70% to 79% at an active ingredient concentration of 500 ppm: 1.077; 1.091.

[0564] In this test, the following compounds of the invention showed an efficacy of 80% to 89% at an active ingredient concentration of 500 ppm: 1.010; 1.023; 1.041; 1.072; 1.129.

[0565] In this test, the following compounds of the invention showed 90% to 100% efficacy at an active ingredient concentration of 500 ppm: I.008; I.009; I.012; I.013; I.016; I.019; I.020; I.022; I.026; I.029; I.031; I.036; I.037; I.038; I.039; I.040; I.042; I.043; I.044; I.045; I.046; I.047; I.048; I.049; I.050; I.051; I.052; I.053; I.054; I.055; I.056; I.057; I.058; I.059; I.060; I.061; I.062; I.063; I.064; I.065 .045; I.046; I.048; I.059; I.064; I.078; I.079; I.080; I.089; I.090; I.093; I.094; I.095; I.104; I.108; I.109; I.110; I.111; I.113; I.116; I.117; I.118; I.119; I.120; I.128; I.147.

[0566] In this test, the following compounds of the invention showed an efficacy of 70% to 79% at an active ingredient concentration of 125 ppm: 1.008; 1.013; 1.037; 1.052; 1.104; 1.110; 1.130.

[0567] In this test, the following compounds of the invention showed an efficacy of 80% to 89% at an active ingredient concentration of 125 ppm: 1.015; 1.019; 1.026; 1.039; 1.041; 1.063; 1.074; 1.090; 1.091; 1.093; 1.095; 1.125; 1.129.

[0568] In this test, the following compounds of the invention showed 90% to 100% efficacy at an active ingredient concentration of 125 ppm: I.006; I.007; I.009; I.016; I.018; I.023; I.029; I.031; I.032; I.034; I.036; I.040; I.042; I.043; I.045; I.046; I.048; I.049; I.050; I.054; I.059; I.061; I.062; I.063; 5;I.066;I.067;I.078;I.079;I.080;I.089;I.108;I.109;I.111;I.113;I.116;I.117;I.118;I.119;I.120;I. 121; I.123; I.124; I.126; I.127; I.128; I.137; I.138; I.139; I.140; I.142; I.143; I.144; I.145; I.146; I.147.

[0569] Example J: Pseudomonas syringa epv. Tomato (Tomato Bacterial Spot) In vivo prevention trial

[0570] By acetone / dimethyl sulfoxide / The active ingredients to be tested were prepared by homogenizing a mixture of 1% ethanol and then diluting with water to obtain the desired concentration of active material.

[0571] Tomato seedlings were treated by spraying with the active ingredient prepared as described above. Control plants were treated only with acetone / DMSO / of aqueous solution treatment.

[0572] After 72 hours, the plants were contaminated by spraying the leaves with an aqueous bacterial suspension of tomato bacterial spot. The contaminated tomato plants were incubated for 4 days in a saturated atmosphere of 22°C day / 20°C night-70% HR, and then for 1 or 2 days at 22°C day / 20°C night and 70-80% relative humidity.

[0573] The tests are evaluated 5 or 6 days after inoculation. 0% means an efficacy which corresponds to that of the control plants, while an efficacy of 100% means that no disease is observed.

[0574] In this test, the following compounds of the invention showed an efficacy of 70% to 79% at an active ingredient concentration of 500 ppm: 1.008; 1.038; 1.040; 1.042; 1.048.

[0575] In this test, the following compounds of the invention showed an efficacy of 80% to 89% at an active ingredient concentration of 500 ppm: 1.025; 1.093; 1.094; 1.095; 1.104; 1.108; 1.109; 1.111; 1.117; 1.128.

[0576] In this test, the following compounds of the invention showed an efficacy of 90% to 100% at an active ingredient concentration of 500 ppm: 1.009; 1.016; 1.019; 1.020; 1.022; 1.036; 1.059; 1.089; 1.090; 1.118; 1.119.

[0577] In this test, the following compounds of the invention showed an efficacy of 70% to 79% at an active ingredient concentration of 31 ppm: 1.016; 1.055; 1.104; 1.119; 1.140; 1.142.

[0578] In this test, the following compounds of the invention showed an efficacy of 80% to 89% at an active ingredient concentration of 31 ppm: 1.006; 1.007; 1.015; 1.065; 1.066; 1.117; 1.121; 1.124; 1.139; 1.144; 1.145.

[0579] In this test, the following compounds of the invention showed an efficacy of 90% to 100% at an active ingredient concentration of 31 ppm: 1.018; 1.049; 1.054; 1.061; 1.062; 1.089; 1.090; 1.138; 1.143.

[0580] Example K: Comparative Example

[0581] exist Cruciferous vegetable black rot (cabbage black rot) In the in vivo prevention assay, compounds CMP1, CMP2, CMP3 and CMP4 were tested under the same conditions as described in Example H.

[0582] Compounds CMP1, CMP2, CMP3 and CMP4 were prepared according to the teaching of EP0450355.

[0583] The results are shown in the following table.

[0584]

[0585] *Efficacy not measured due to over 80% phytotoxicity observed

[0586] The compounds of formula (1) of the present invention in the following table show better efficacy than the structurally related compound CMP1.

[0587]

[0588] When tested at a concentration of 125 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP1.

[0589] More specifically, at a concentration of 125 ppm, compound I.111 showed an efficacy of 70%, whereas CMP1 showed an efficacy of less than 10% at the same concentration.

[0590] When tested at a concentration of 31 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP1.

[0591] More specifically, at a concentration of 31 ppm, compound I.113 showed an efficacy of at least 80%, whereas CMP1 showed an efficacy of less than 40% at the same concentration.

[0592] The compounds of formula (1) of the present invention in the following table show better efficacy than the structurally related compound CMP2.

[0593]

[0594] When tested at a concentration of 125 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP2.

[0595] More specifically, at a concentration of 125 ppm, compounds I.109, I.136, I.142 showed 70% efficacy, while CMP2 showed more than 80% phytotoxicity at the same concentration.

[0596] When tested at a concentration of 31 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP2.

[0597] More specifically, at a concentration of 31 ppm, compounds I.008, I.015, I.016, I.108, I.136, I.140, I.142, I.144 showed an efficacy of at least 80%, whereas CMP2 showed an efficacy of less than 40% at the same concentration.

[0598] The compounds of formula (1) of the present invention in the following table show better efficacy than the structurally related compound CMP3.

[0599]

[0600] When tested at a concentration of 125 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP3.

[0601] More specifically, at a concentration of 125 ppm, compounds I.009, I.013, I.064, I.046, I.048, I.059, I.110, I.143, I.145 showed 70% efficacy, while CMP3 showed more than 80% phytotoxicity at the same concentration.

[0602] When tested at a concentration of 31 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP3.

[0603] More specifically, at a concentration of 31 ppm, compounds I.009, I.110, I.120, I.046, I.059, I.138, I.137, I.143, I.145 showed an efficacy of at least 70%, whereas CMP3 showed no efficacy at the same concentration.

[0604] The compounds of formula (1) of the present invention in the following table show better efficacy than the structurally related compound CMP4.

[0605]

[0606] When tested at a concentration of 125 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP4.

[0607] More specifically, at a concentration of 125 ppm, compounds I.096, I.136, I.142 showed 70% efficacy, while CMP4 showed no efficacy at the same concentration.

[0608] When tested at a concentration of 31 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP4.

[0609] More specifically, at a concentration of 31 ppm, compounds I.008, I.015, I.016, I.136, I.140, I.142, I.144 showed an efficacy of at least 80%, whereas CMP4 showed an efficacy of less than 40% at the same concentration.

[0610] Example L: Comparative Example

[0611] exist Tomato bacterial spot (Tomato bacterial spot) In an in vivo prevention assay, compounds CMP1 and CMP4 were tested under the same conditions as described in Example J.

[0612] Compounds CMP1 and CMP4 were prepared according to the teaching of EP0450355.

[0613] The results are shown in the following table.

[0614]

[0615]

[0616] The compounds of formula (1) of the present invention in the following table show better efficacy than the structurally related compound CMP1.

[0617]

[0618] When tested at a concentration of 500 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP1.

[0619] More specifically, at a concentration of 500 ppm, compounds I.111, I.119 showed an efficacy of at least 80%, whereas CMP1 showed an efficacy of less than 20% at the same concentration.

[0620] The compounds of formula (1) of the present invention in the following table show better efficacy than the structurally related compound CMP4.

[0621]

[0622] When tested at a concentration of 31 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP4.

[0623] More specifically, at a concentration of 31 ppm, compounds 1.007, 1.012, 1.015, 1.016, 1.124, 1.139, 1.140, 1.142, 1.144 showed an efficacy of at least 70%, whereas CMP4 showed no efficacy at the same concentration.

[0624] Example M: ​​Comparative Example

[0625] exist Colletotrichum phaeocaulis (Bean Anthracnose) In an in vivo prevention assay, compound CMP1 was tested under the same conditions as described in Example F.

[0626] Compound CMP1 was prepared according to the teaching of EP0450355.

[0627] The results are shown in the following table.

[0628]

[0629] The compounds of formula (1) of the present invention in the following table show better efficacy than the structurally related compound CMP1.

[0630]

[0631] When tested at a concentration of 31 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP1.

[0632] More specifically, at a concentration of 31 ppm, compound I.119 showed an efficacy of at least 70%, whereas CMP1 showed an efficacy of less than 20% at the same concentration.

[0633] Example N: Comparative Example

[0634] exist Parasitic mildew (downy mildew of cruciferous vegetables) In an in vivo prevention assay, compounds CMP2 and CMP3 were tested under the same conditions as described in Example G.

[0635] Compounds CMP2 and CMP3 were prepared according to the teaching of EP0450355.

[0636] The results are shown in the following table.

[0637]

[0638] *Efficacy not measured due to over 80% phytotoxicity observed

[0639] The compounds of formula (1) of the present invention in the following table show better efficacy than the structurally related compound CMP2.

[0640]

[0641]

[0642] When tested at a concentration of 500 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP2.

[0643] More specifically, at a concentration of 500 ppm, compounds I.008, I.012, I.016, I.091, I.109, I.117 showed 90% efficacy, while CMP2 showed more than 80% phytotoxicity at the same concentration.

[0644] The compounds of formula (1) of the present invention in the following table show better efficacy than the structurally related compound CMP3.

[0645]

[0646] When tested at a concentration of 500 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP3.

[0647] More specifically, at a concentration of 500 ppm, compounds I.009, I.013, I.046, I.048, I.059, I.064, I.078, I.089, I.108, I.110, I.118, and I.120 showed 70% efficacy, while CMP3 showed more than 80% phytotoxicity at the same concentration.

[0648] Example O: Comparative Example

[0649] exist Puccinia vulgaris (bean rust) In an in vivo prevention assay, compounds CMP5 and CMP6 were tested under the same conditions as described in Example 1.

[0650] Compounds CMP5 and CMP6 were prepared according to the teaching of EP0450355.

[0651] The results are shown in the following table.

[0652]

[0653]

[0654] The compounds of formula (1) of the present invention in the following table show better efficacy than the structurally related compound CMP5.

[0655]

[0656] When tested at a concentration of 8 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP5.

[0657] More specifically, at a concentration of 8 ppm, compound 1.147 showed an efficacy of at least 90%, whereas CMP5 showed an efficacy of less than 20% at the same concentration.

[0658] The compounds of formula (1) of the present invention in the following table show better efficacy than the structurally related compound CMP6.

[0659]

[0660] When tested at a concentration of 31 ppm, the compound of formula (1) of the present invention showed better efficacy than the structurally related compound CMP6.

[0661] More specifically, at a concentration of 500 ppm, compounds I.009, I.013, I.048, I.059, I.064, I.078, I.090, I.094 showed an efficacy of at least 90%, whereas CMP6 showed an efficacy of less than 40% at the same concentration.

Claims

1. Compounds of formula (I): in R 1 , R 2 and R 3 Each is chlorine; R 4 and R 5 independently selected from hydrogen, halogen, cyano, hydroxyl, C1-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, -OC(=O)-C1-C6-alkyl, C3-C6-carbocycle, 4-, 5- or 6-membered non-aromatic heterocyclic group, -C(=O)-NH2, -C(=O)-NH(C1-C6-alkyl), -C(=O)-N(C1-C6-alkyl)2, -C(=O)-OH, -C(=O)-O-C1-C6-alkyl, aryl, 5- to 9-membered heteroaryl C1-C6-alkyl-C1-C6-alkoxy, -C1-C6-alkyl-C1-C6-haloalkyl, -C1-C6-alkyl-C3-C6-carbocycle, -C1-C6-alkyl-4-membered, 5-membered or 6-membered non-aromatic heterocyclic group, -C1-C6-alkyl-aryl, -C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl-5-membered to 9-membered heteroaryl, -C1-C6-alkyl-S-C1-C6-alkyl, -C1-C6-alkyl-SC(=O)-C1-C6-alkyl, -C1-C6-alkyl -O-(C=O)-C1-C6-alkyl, -C1-C6-alkyl-C(=O)-NH2, -C1-C6-alkyl -C(=O)-NH(C1-C6-alkyl), -C1-C6-alkyl-C(=O)-N(C1-C6-alkyl)2, -C1-C6-alkyl -C(=O)-OH, -C1-C6-alkyl-C(=O)-O-C1-C6-alkyl, -C1-C6-alkyl -NH-C(=NH)-NH2, -S-C1-C6-alkyl, -SC(=O)-C1-C6-alkyl, -SC(=O)-O-C1-C6-alkyl, -SC(=S)-O-C1-C6-alkyl, -SC(=O)-S-C1-C6-alkyl, -SC(=O)-NH2, -SC(=O)-NH(C1-C6-alkyl), -SC(=O)-NH(C1-C6-alkyl)2, -SC(=S)-NH2, -SC(=S)-NH(C1-C6-alkyl), -SC(=S)-NH(C1-C6-alkyl)2, -C1-C6-alkyl-SC(=O)-O-C1-C6-alkyl, -C1-C6-alkyl-SC(=O)-S-C1-C6-alkyl, -C1-C6-alkyl-SC(=O)-NH2, -C1-C6-alkyl-SC(=O)-NH(C1-C6-alkyl), -C1-C6-alkyl-SC(=O)-NH(C1-C6-alkyl)2, -C1-C6-alkyl-SC(=S)-NH2, -C1-C6-alkyl -SC(=S)-NH(C1-C6-alkyl), -C1-C6-alkyl-SC(=S)-NH(C1-C6-alkyl)2, wherein the cyclic R 4 , R 5 The group may be one or more R x Substituent substitution, where R 4 and R 5 At least one is hydrogen, C1-C6-alkyl or C3-C6-carbocycle, or R 4 and R 5 Together with the carbon atoms to which they are attached, they form a C3-C6-carbocyclic ring or a 3- to 6-membered heterocyclic ring, wherein the C3-C6-carbocyclic ring and the 3- to 6-membered heterocyclic ring may be replaced by one or more R x Substituent substitution, where R x Independently selected from the following groups: halogen, nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-λ 6 -sulfanyl, formyl, carbamoyl, carbamate, C1-C8-alkyl, C3-C7-cycloalkyl, C1-C8-haloalkyl having 1 to 5 halogen atoms, C3-C7-halocycloalkyl having 1 to 5 halogen atoms, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkylamino, di-C1-C8-alkylamino, C1-C8-alkoxy, C1-C8-haloalkoxy having 1 to 5 halogen atoms, C1-C8-alkylsulfanyl, C1-C8-haloalkylsulfanyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyl, C1-C8-haloalkylcarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbamoyl, di-C1-C8-alkylcarbamoyl, C1-C8-alkoxycarbonyl, C1-C8-alkylsulfanyl having 1 to 5 halogen atoms C1-C8-haloalkoxycarbonyl, C1-C8-alkylcarbonyloxy, C1-C8-haloalkylcarbonyloxy having 1 to 5 halogen atoms, C1-C8-alkylcarbonylamino, C1-C8-haloalkylcarbonylamino having 1 to 5 halogen atoms, C1-C8-alkylsulfanyl, C1-C8-haloalkylsulfanyl having 1 to 5 halogen atoms, C1-C8-alkylsulfinyl, C1-C8-haloalkylsulfinyl having 1 to 5 halogen atoms, C1-C8-alkylsulfonyl, C1-C8-haloalkylsulfonyl having 1 to 5 halogen atoms; C1-C8-alkylsulfonylamino, C1-C8-haloalkylsulfonyl having 1 to 5 halogen atoms; sulfamoyl; C1-C8-alkylsulfamoyl and di-C1-C8-alkylsulfamoyl; R 6 and R 7 are independently selected from hydrogen, C1-C6-alkyl, C3-C6-carbocycle; or R 6 and R 7 Together with the carbon atoms to which they are attached, they form a C3-C6-carbocyclic ring or a 3- to 6-membered heterocyclic ring; n is 0 or 1; W is oxygen or sulfur; Y is NR 8 , R 8 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, hydroxy, C1-C6-alkoxy or C3-C6-carbocycle; Z is selected from -C(=O)-OR a , -C(=O)-SR a 、-C(=O)-NR b R c , -C(=S)-NR b R c or -C(=O)-NH-CR d R e -C(=O)-OR a , where R a It can form a 4- to 7-membered heterocyclic ring together with R4 and the atoms to which they are attached. b Can be used with R 4 Together with the atoms to which they are attached, they form a 4- to 7-membered heterocyclic ring, R d and R e independently selected from hydrogen, cyano, hydroxyl, C1-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, -OC(=O)-C1-C6-alkyl, C3-C6-carbocycle, -C(=O)-NH2, -C(=O)-NH(C1-C6-alkyl), -C(=O)-N(C1-C6-alkyl)2, -C(=O)OH, -C(=O)-O- C1-C6-alkyl, aryl, 5- to 9-membered heteroaryl, -C1-C6-alkyl-C1-C6-alkoxy, -C1-C6-alkyl-C3-C6-carbocycle, -C1-C6-alkyl-aryl, -C1-C6-alkyl-hydroxyaryl, -C1-C6-alkyl-5- to 9-membered heteroaryl, -C1-C6-alkyl-S-C1-C6-alkyl, -C1-C6-alkyl -SC(=O)-C1-C6-alkyl, -C1-C6-alkyl-O-(C=O)-C1-C6-alkyl, -C1-C6-alkyl -C(=O)-NH2, -C1-C6-alkyl-C(=O)-NH(C1-C6-alkyl), -C1-C6-alkyl -C(=O)-N(C1-C6-alkyl)2, -C1-C6-alkyl-C(=O)-OH, -C1-C6-alkyl-C(=O)-O-C1-C6-alkyl, -C1-C6-alkyl-NH-C(=NH)-NH2, wherein R d and R e At least one is hydrogen, C1-C6-alkyl or C3-C6 carbocycle, or R d and R e Together with the carbon atom to which they are attached they form a carbonyl group, a C3-C6-carbocycle or a 3- to 6-membered heterocycle.

2. The compound according to claim 1, wherein W is oxygen.

3. A compound according to any one of claims 1 to 2, wherein Y is NR 8 , R 8 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, hydroxy, C1-C6-alkoxy or C3-C6-carbocycle, and wherein Y is preferably NR 8 , R 8 It's hydrogen.

4. The compound according to any one of claims 1 to 3, wherein Z is selected from -C(=O)SR a , -C(=S)-NR b R c or -C(=O)-NH-CR d R e -C(=O)-OR a , and wherein Z is preferably selected from -C(=O)-OR a 、C(=O)-NR b R c .

5. A composition comprising at least one compound of formula (I) according to any one of claims 1 to 4 and at least one agriculturally suitable adjuvant.

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