Phenyl Oxazolone and Analogs

Abstract

The present disclosure relates to substituted thiophene carboxamide derivatives, their use for controlling plant pathogenic microorganisms, and compositions containing same.

Description

Technical Field

[0001] The present invention relates to substituted thiophenecarboxamide derivatives, their use for controlling phytopathogenic microorganisms, and compositions containing the same.

Background Art

[0002] To date, numerous microbicides have been developed, but the development of new microbicidal compounds is still needed to meet the ever-increasing environmental and economic requirements imposed on modern crop protection agents and compositions. This includes, for example, improvements in the spectrum of action, safety profile, selectivity, application rate, residue formation, and preferred formulation ability. It may also be desirable to have new compounds to prevent the emergence of resistance.

[0003] The present invention provides new compounds having advantages over known compounds and compositions in at least some of these aspects.

[0004] Unpublished application PCT / EP2019 / 067824 discloses thiophenecarboxamide derivatives useful for protecting plants from attack by phytopathogenic microorganisms. International Publication No. WO 2004 / 062361 discloses compounds said to be effective in controlling fungal diseases. These exert their action through a direct effect on undesirable microorganisms, but also thanks to an effect of inducing resistance in plants. International Publication No. WO 2004 / 062361 also suggests that these compounds may be useful for controlling bacterial diseases, but does not provide evidence of such activity. The inventors have found that these compounds are not very efficient against Xanthomonas campestris pv. campestris at low doses.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

[0006] The present invention relates to compounds of formula (I) listed herein, as well as their isomers, polymorphs, salts, N-oxides and solvates.

[0007] The present invention relates to a composition comprising at least one compound of formula (I) as defined herein and at least one agriculturally suitable carrier.

[0008] The present invention relates to a method for preparing the compounds of formula (I) described herein and their intermediates.

[0009] The present invention relates to a method for controlling phytopathogenic microorganisms, comprising the step of applying at least one compound of formula (I) as defined herein or a composition as defined herein to a plant, a plant part, a seed, a fruit or the soil in which the plant grows.

[0010] Definitions For example, the term "alkyl" as used herein in the context of alkyl or alkylsulfonyl, alkylsulfinyl, alkylthio, alkylamino preferably means branched and unbranched alkyl, for example methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, sec-butyl, pentyl, iso-pentyl, hexyl, heptyl, octyl, nonyl and decyl and their isomers.

[0011] As used herein, the term "alkenyl" is preferably understood to mean branched and unbranched alkenyl, such as vinyl, propen-1-yl, propen-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-propa-2-en-1-yl, or 2-methyl-propa-1-en-1-yl groups.

[0012] As used herein, the term "alkynyl" is preferably understood to mean branched and unbranched alkynyl, such as ethynyl, propa-1-in-1-yl, but-1-in-1-yl, but-2-in-1-yl, or but-3-in-1-yl groups.

[0013] As used herein, the term "halogen" or "Hal" is preferably understood to mean fluorine, chlorine, bromine or iodine.

[0014] The terms "halo" or "halogeno" (e.g., haloalkyl, "C1-C6-haloalkyl" or "C1-C8-halogenoalkyl") indicate the presence of any one or more halogen substituents, which may be the same or different.

[0015] As used herein, the term "haloalkyl" is preferably understood to mean branched and unbranched alkyl as defined above, wherein one or more hydrogen substituents are substituted with halogen in the same or different ways. Particularly preferably, the haloalkyl is, for example, chloromethyl, fluoropropyl, fluoromethyl, difluoromethyl, trichloromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, bromobutyl, trifluoromethyl, iodoethyl, and isomers thereof.

[0016] As used herein, the term "haloalkenyl" should be understood to mean branched and unbranched alkenyl as defined above, wherein one or more hydrogen substituents are preferably substituted with halogen in the same or different ways.

[0017] As used herein, the term "haloalkynyl" should be understood to mean branched and unbranched alkynyl as defined above, wherein one or more hydrogen substituents are preferably substituted with halogen in the same or different ways.

[0018] As used herein, the term "alkoxy" refers to a group of the formula (alkyl)-O-, where 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.

[0019] As used herein, the term "halogenated alkoxy" refers to an alkoxy group as defined above, wherein one or more hydrogen atoms are substituted with one or more halogen atoms, which may be the same or different. Examples of C1-C8-halogenated alkoxy include, but are not limited to, chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chloro-difluoro-methoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoro-ethoxy, 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, pentafluoro-ethoxy and 1,1,1-trifluoropropan-2-oxy.

[0020] 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, methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, butylsulfanyl, sec-butylsulfanyl, isobutylsulfanyl, tert-butylsulfanyl, pentylsulfanyl, isopentylsulfanyl, hexylsulfanyl groups.

[0021] As used herein, the term "halogenated alkylsulfanyl" refers to an alkylsulfanyl as defined above, wherein one or more hydrogen atoms are substituted with one or more halogen atoms, which may be the same or different.

[0022] As used herein, the term "alkylsulfinyl" refers to a saturated straight-chain or branched group of the formula (alkyl)-S(=O)-, where 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 to 8, preferably 1 to 6, more preferably 1 to 4 carbon atoms, such as (but not limited to) methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methyl-ethyl-sulfinyl, butylsulfinyl, 1-methyl-propyl-sulfinyl, 2-methylpropylsulfinyl, 1,1-dimethyl-ethyl-sulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methyl-butylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethyl-propylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methyl-pentyl-sulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutyl-sulfinyl, 1,2-dimethyl-butylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethyl-butyl-sulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methyl-propyl-sulfinyl and 1-ethyl-2-methylpropylsulfinyl.

[0023] As used herein, the term "halogenoalkylsulfinyl" refers to an alkylsulfinyl as defined above, wherein one or more hydrogen atoms are substituted with one or more halogen atoms, which may be the same or different.

[0024] As used herein, the term "alkylsulfonyl" refers to a saturated straight-chain or branched group of the formula (alkyl)-S(=O)2-, where 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.

[0025] As used herein, the term "halogenoalkylsulfonyl" refers to a C1-C8-alkylsulfonyl as defined above, substituted with one or more halogen atoms, which may be the same or different, and where one or more hydrogen atoms may be the same or different.

[0026] As used herein, the term "alkylcarbonyl" refers to a saturated straight-chain or branched group of the formula (alkyl)-C(=O)-, where the term "alkyl" is as defined herein.

[0027] As used herein, the term "halogenoalkylcarbonyl" refers to an alkylcarbonyl as defined above, wherein one or more hydrogen atoms are substituted with one or more halogen atoms which may be the same or different.

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

[0029] As used herein, the term "haloalkoxycarbonyl" refers to an alkoxycarbonyl as defined above, wherein one or more hydrogen atoms are substituted with one or more halogen atoms which may be the same or different.

[0030] As used herein, the term "cycloalkyl" refers to a non-aromatic monocyclic carbon-containing ring having 3 to 8 carbon atoms. Examples of saturated cycloalkyls include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl groups.

[0031] As used herein, the term "heterocyclyl" refers to a 4-, 5- or 6-membered saturated or partially unsaturated heterocyclic ring containing 1 to 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur. When the ring contains two or more oxygen atoms, these are not directly adjacent.

[0032] 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 is further understood that when the aryl group is substituted with one or more substituents, the (one or more) substituents may be at any position on the (one or more) aryl rings. In particular, when the aryl is a phenyl group, the (one or more) substituents may occupy one or both ortho positions, one or both meta positions, or the para position, or any combination of these positions. This definition also applies to aryl as part of a complex substituent (e.g., aryloxy).

[0033] As used herein, the term "aralkyl" refers to C1-C6-alkyl substituted by aryl as defined herein. An example of aralkyl is the benzyl group (-CH2-C6H5).

[0034] 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 the group consisting of 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 through any carbon or nitrogen atom contained within the heterocycle.

[0035] As used herein, the term "C1-C6" in the context of the definition of, for example, "C1-C6-alkyl" or "C1-C6-alkoxy" should be understood to mean a group having a finite number of carbon atoms, namely 1 to 6 carbon atoms, i.e., 1, 2, 3, 4, 5, or 6 carbon atoms.

[0036] As used herein, the term "C1-C8-alkyl" or "C1-C8-alkoxy" in the context of the definition, for example, the term "C1-C8" means a group having a finite number of carbon atoms, i.e., 1 to 8 carbon atoms, that is, 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, and is to be understood accordingly.

[0037] As used herein, the term "oxo" refers to an oxygen atom bonded to a carbon atom or a sulfur atom via a double bond.

[0038] As used herein, the term "leaving group" is to be understood to mean a group that is expelled from a compound in a substitution or elimination reaction, such as a halogen atom, a trifluoromethanesulfonate ("triflate") group, an alkoxy group, a methanesulfonate group, a p-toluenesulfonate group, etc.

Mode for Carrying Out the Invention

[0039] The present invention relates to a compound of formula (I):

Chemical formula

[0040] R 1 is preferably selected from the group consisting of halogen and cyano groups.

[0041] According to another preferred embodiment, R 2 is halogen.

[0042] R 3 is also preferably selected from the group consisting of halogen, cyano, C1-C6-alkyl, and C1-C6-haloalkyl.

[0043] R 1 and R 2 are independently selected from each other from the group consisting of halogen, cyano, C1-C6-alkyl, and C1-C6-haloalkyl; R 3 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, and C1-C6-haloalkyl; W and Y are independently selected from each other from the group consisting of oxygen and sulfur; R 4 and R 5 are independently selected from each other from the group consisting of hydrogen, C1-C6-alkyl, aryl-C1-C6-alkyl, or C3-C6-carbocyclic ring, and the acyclic R 4 and R 5 groups may be substituted with one or more R a substituents, and the cyclic R 4 and R 5 groups may be substituted with one or more R b substituents; or R 4 and R 5 together with the carbon atom to which they are attached form a C3-C6-carbocyclic ring or a 3- to 6-membered heterocyclic ring, and the C3-C6-carbocyclic ring and the 3- to 6-membered heterocyclic ring have one or more R bmay be substituted with a substituent, R a is nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-λ 6 -sulfanyl, formyl, carbamoyl, carbamate, C3-C7-cycloalkyl, C3-C7-halogenocycloalkyl having 1 to 5 halogen atoms, C1-C8-alkylamino, di-C1-C8-alkylamino, C1-C8-alkoxy, C1-C8-halogenoalkoxy having 1 to 5 halogen atoms, C1-C8-alkylsulfanyl, C1-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyl, C1-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbamoyl, di-C1-C8-alkylcarbamoyl, C1-C8-alkoxycarbonyl, C1-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyloxy, C1-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C1-C8-alkylcarbonylamino, C1-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, C1-C8-alkylsulfinyl, C1-C8-halogenoalkylsulfinyl having 1 to 5 halogen atoms, C1-C8-alkyl-sulfonyl, C1-C8-halogenoalkylsulfonyl having 1 to 5 halogen atoms; C1-C8-alkyl-sulfonylamino, C1-C8-halogenoalkylsulfonylamino having 1 to 5 halogen atoms; sulfamoyl; C1-C8-alkylsulfamoyl and di-C1-C8-alkylsulfamoyl, independently selected from the group consisting of, R b is a halogen atom, nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-λ 6- independently selected from the group consisting of sulfanyl, formyl, carbamoyl, carbamate, C1-C8-alkyl, C3-C7-cycloalkyl, C1-C8-halogenoalkyl having 1 to 5 halogen atoms, C3-C7-halogenocycloalkyl having 1 to 5 halogen atoms, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkylamino, di-C1-C8-alkylamino, C1-C8-alkoxy, C1-C8-halogenoalkoxy having 1 to 5 halogen atoms, C1-C8-alkylsulfanyl, C1-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyl, C1-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbamoyl, di-C1-C8-alkylcarbamoyl, C1-C8-alkoxycarbonyl, C1-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyloxy, C1-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C1-C8-alkylcarbonylamino, C1-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, C1-C8-alkylsulfanyl, C1-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, C1-C8-alkylsulfinyl, C1-C8-halogenoalkylsulfinyl having 1 to 5 halogen atoms, C1-C8-alkylsulfonyl, C1-C8-halogenoalkylsulfonyl having 1 to 5 halogen atoms, C1-C8-alkylsulfonylamino, C1-C8-halogenoalkylsulfonylamino having 1 to 5 halogen atoms, sulfamoyl, C1-C8-alkylsulfamoyl and di-C1-C8-alkylsulfamoyl; provided that R 1 is halogen, when R 2 is halogen, R 3 is selected from the group consisting of halogen, cyano, C1-C6-alkyl or C1-C6-haloalkyl, provided that when R 1 and R 2 are the same and are bromine or chlorine, R 3is cyano or C1-C6-haloalkyl, or W is sulfur, or R 4 and R 5 do not form cyclopropyl together with the carbon atom to which they are attached is also preferred.

[0044] R 3 is preferably selected from the group consisting of halogen, C1-C6-alkyl.

[0045] R 4 and R 5 also preferably form a C3-C6 carbocyclic ring together with the carbon atom to which they are attached, the compound of formula (I).

[0046] In another preferred embodiment, W is oxygen.

[0047] The compound of formula (I) where Y is oxygen is also preferred.

[0048] In another preferred embodiment, R 1 is selected from the group consisting of halogen, cyano; R 2 is halogen; R 3 is selected from the group consisting of halogen, C1-C6-alkyl; R 4 and R 5 form a C3-C6 carbocyclic ring together with the carbon atom to which they are attached; W is oxygen; Y is oxygen.

[0049] In another preferred embodiment, R 1 is selected from the group consisting of Cl, Br, cyano; R 2 is Cl, Br; R 3 is selected from the group consisting of H, F, Cl, Br, I, CH3; R 4and R 5 together with the carbon atom to which they are attached form a C3-carbon ring; W is oxygen; Y is oxygen.

[0050] In another embodiment, R 1 is halogen, cyano, C1-C6-alkyl or C1-C6-haloalkyl. In another embodiment, R 1 is halogen, cyano, C1-C3-alkyl or C1-C3-haloalkyl. In another embodiment, R 1 is halogen, cyano, methyl, trifluoromethyl or difluoromethyl. In another embodiment, R 1 is halogen. In another embodiment, R 1 is cyano, trifluoromethyl or difluoromethyl.

[0051] In another embodiment, R 2 is halogen, cyano, C1-C6-alkyl or C1-C6-haloalkyl. In another embodiment, R 2 is halogen, cyano, C1-C3-alkyl or C1-C3-haloalkyl. In another embodiment, R 2 is halogen, cyano, methyl, trifluoromethyl or difluoromethyl. In another embodiment, R 2 is halogen. In another embodiment, R 2 is cyano, trifluoromethyl or difluoromethyl.

[0052] In another embodiment, R 3 is hydrogen, halogen, cyano, C1-C6-alkyl or C1-C6-haloalkyl. In another embodiment, R 3 is hydrogen, halogen, cyano, C1-C3-alkyl or C1-C3-haloalkyl. In another embodiment, R 3 is hydrogen, halogen, cyano, methyl, trifluoromethyl or difluoromethyl. In another embodiment, R 3 is halogen. In another embodiment, R3 is hydrogen. In another embodiment, R 3 is cyano, methyl, trifluoromethyl or difluoromethyl.

[0053] In another embodiment, R 4 and R 5 are independently selected from the group consisting of hydrogen, C1-C6-alkyl, aryl-C1-C6-alkyl or C3-C6-carbocyclic ring, and the acyclic R 4 , R 5 groups may be substituted with one or more R a substituents, and the cyclic R 4 , R 5 groups may be substituted with one or more R b substituents. In another embodiment, R 4 and R 5 together with the carbon atom to which they are attached form a C3-C6-carbocyclic ring or a 3- to 6-membered heterocyclic ring, and the C3-C6-carbocyclic ring and the 3- to 6-membered heterocyclic ring may be substituted with one or more R b substituents. In another embodiment, R 4 and R 5 together with the carbon atom to which they are attached form a C3-C6-carbocyclic ring, and the C3-C6-carbocyclic ring may be substituted with one or more R b substituents. In another embodiment, R 4 and R 5 together with the carbon atom to which they are attached form cyclopropyl or cyclobutyl, and the cyclopropyl or cyclobutyl may be substituted with one or more R b substituents.

[0054] In another embodiment, W is oxygen. In another embodiment, W is sulfur. In another embodiment, Y is oxygen. In another embodiment, Y is sulfur.

[0055] Compounds I.01 to I.26 disclosed in the experimental section are also preferred.

[0056] Compounds obtained from combinations that are contrary to the natural laws and thus would be excluded by a person skilled in the art based on their expertise are not included herein. For example, a ring structure having three or more adjacent oxygen atoms is excluded.

[0057] Depending on the nature of the substituents, the compounds of formula (I) may exist in different stereoisomeric forms. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the present invention encompasses both pure stereoisomers and any mixtures of these isomers. When a compound may exist in two or more tautomeric forms in equilibrium, a reference to a compound by way of description of one tautomer should be considered to include all tautomeric forms.

[0058] Any of the compounds of the present invention may also exist in one or more geometric isomeric forms depending on the number of double bonds in the compound. Geometric isomers due to the nature of the double bond or the substituents around the ring may exist in the cis (=Z-) or trans (=E-) form. Accordingly, the present invention is equally relevant to all geometric isomers and all possible mixtures in all proportions.

[0059] The compounds of formula (I) may appropriately be in their free form, salt form, N-oxide form or solvate form (e.g., hydrate).

[0060] Depending on the nature of the substituents, the compounds of formula (I) may exist in the form of the free compound and / or its salts, for example, agrochemically active salts.

[0061] The agrochemically active salts include acid addition salts of inorganic and organic acids and salts of conventional 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 acidic salts such as sodium bisulfate and potassium bisulfate. Useful organic acids include, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and 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 sulfuric acid monoesters, alkylsulfonic acids (sulfonic acids having a straight-chain or branched alkyl group having 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic groups such as phenyl and naphthyl having one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having a straight-chain or branched alkyl group having 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic groups such as phenyl and naphthyl having one or two phosphonic acid groups) (the alkyl group and the aryl group may have further substituents), for example, p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid and the like are included.

[0062] The solvate of the compound of formula (I) or its salt is a stoichiometric composition of the compound and the solvent.

[0063] The compound of formula (I) may exist in a plurality of crystalline and / or amorphous forms. The crystalline forms include non-solvated crystalline forms, solvates and hydrates.

[0064] The present invention also relates to any compound of formula (I) disclosed in Table 1, and its use in crop protection (i.e., for controlling phytopathogenic fungi and / or bacteria on plants or plant parts).

[0065] Another aspect of the present invention relates to a composition comprising at least one compound of formula (I) according to the present invention and at least one agriculturally suitable adjuvant.

[0066] Another aspect of the present invention relates to a method for controlling bacterial and / or fungal diseases, comprising the step of applying at least one compound of formula (I) according to the present invention or a composition according to the present invention to a plant, a plant part, a seed, a fruit or the soil in which the plant grows.

[0067] Another aspect of the present invention relates to the use of a compound according to the present invention or a composition according to the present invention for controlling bacterial and / or fungal diseases on a plant or a plant part. Preferably, they are used for controlling fungal diseases on a plant or a plant part.

[0068] Another aspect of the present invention relates to the use of a compound according to the present invention or a composition according to the present invention for controlling nematodes on a plant or a plant part.

[0069] Another aspect of the present invention relates to the use of a compound according to the present invention or a composition according to the present invention for controlling viruses on a plant or a plant part.

[0070] Preferably, the compound or composition according to the present invention is a disease caused by powdery mildew pathogens such as species of the genus Podosphaera (e.g., Podosphaera leucotricha), species of the genus Sphaerotheca (e.g., Sphaerotheca fuliginea); a disease caused by rust pathogens such as species of the genus Uromyces (e.g., Uromyces appendiculatus); a disease caused by pathogens of the group Oomycetes such as species of the genus Peronospora (e.g., Peronospora parasitica), species of the genus Phytophthora (e.g., Phytophthora infestans), species of the genus Plasmopara (e.g., Plasmopara viticola), species of the genus Pseudoperonospora (e.g., Pseudoperonospora humuli or Pseudoperonospora cubensis), species of the genus Pythium (e.g., Pythium ultimum); leaf blight and leaf withering diseases caused by, for example, species of the genus Alternaria (e.g., Alternaria solani), species of the genus Cercospora (e.g., Cercospora beticola), species of the genus Colletotrichum (e.g., Colletotrichum lindemuthanium), species of the genus Venturia (e.g., Venturia inaequalis).It is used against diseases caused by bacterial pathogens, such as species of the genus Xanthomonas (e.g., Xanthomonas campestris pv. campestris), species of the genus Pseudomonas (e.g., Pseudomonas syringae pv. tomato), species of the genus Erwinia (e.g., Erwinia amylovora), species of the genus Liberibacter (e.g., Liberibacter Candidatus), species of the genus Ralstonia (e.g., Ralstonia solanacearum).;

[0071] According to a further aspect of the present invention, the compound or composition according to the present invention is a plant defense activator in use. The plant defense inducer according to the present invention is a compound or composition that stimulates the plant's own defense system.

[0072] Method for preparing the compound of formula (I) The present invention relates to a method for preparing a compound of formula (I). The compound of formula (I) can be prepared by various routes in the same manner as the known methods described in Helvetica Chimica Acta, 69(2), 374 - 388, 1986; Helvetica Chimica Acta, 70(4), 1001 - 1011, 1987; Chimia, 36(2), 78 - 81, 1982; Helvetica Chimica Acta, 71(8), 2071 - 2084, 1988; Heterocyclic Communications, 9(2), 129 - 134; 2003; International Publication No. 2007080885; International Publication No. 2007003536, Chemical Communications (Cambridge, United Kingdom), 55(39), 5547 - 5550; 2019; and other references therein, or by one or more of the following synthetic routes described below and in the experimental section.

[0073] General synthetic route to the compound of formula (I) Unless otherwise indicated, hereinafter, R 1 、R 2 、R 3 、R 4 、R 5 、W, Y have the same meanings as shown above for the compound of formula (I).

[0074] Method A The compound of formula (I) as defined herein can be prepared by Method A from a compound of formula (IIa) or a salt thereof in which R 6 is hydrogen by the cyclization reaction exemplified in the following reaction scheme:

Chemical formula

[0075] Method A can be carried out as described in Journal of Heterocyclic Chemistry, 25(1), 209 - 215; 1988; International Publication No. 2007003536.

[0076] Method A can be carried out, where appropriate, in the presence of a suitable Bronsted acid, Lewis acid or other condensing agent, where appropriate, in the presence of a suitable acid binder, and where appropriate, in the presence of a solvent.

[0077] Lewis acids suitable for carrying out Method A can be inorganic and organic Lewis acids customary for such reactions. Metal halides such as aluminum(III) chloride, iron(III) chloride, zinc(II) chloride, titanium tetrachloride, boron trifluoride; triflates such as scandium(III) triflate, bismuth(III) triflate or ytterbium(III) triflate, and also iodine are preferably used.

[0078] Bronsted acids suitable for carrying out Method A can be inorganic and organic Bronsted acids customary for such reactions. Hydrogen halides such as hydrogen chloride or hydrogen bromide; sulfonic acids such as p-toluenesulfonic acid, camphorsulfonic acid, methanesulfonic acid or trifluoromethanesulfonic acid, and also polyphosphoric acid, phosphoric acid, sulfuric acid, potassium bisulfite, trifluoroacetic acid or acetic acid are preferably used.

[0079] Other suitable condensing agents for carrying out Method A may be selected from the non-limiting list consisting of acid halide forming agents such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus trichloride oxide, oxalyl chloride or thionyl chloride; anhydride forming agents such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; anhydrides such as trifluoroacetic anhydride or acetic anhydride; carbodiimides such as N,N'-dicyclohexylcarbodiimide (DCC), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC), or phosphorus pentoxide, polyphosphoric acid, bis(2-oxo-3-oxazolidinyl)phosphinic acid chloride, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU), (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate, N,N'-carbonyl-diimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / tetrachloro-methane, 4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholinium chloride hydrate, bis(2-oxo-3-oxazolidinyl)phosphinic acid chloride (BOP-Cl), bromo-tripyrrolidinophosphonium hexafluorophosphate (PyBroP), 2-chloro-1,3-dimethylimidazolinium chloride (DMC), or other conventional condensing agents such as propane phosphonic anhydride (T3P).

[0080] The acid binders suitable for carrying out method A according to the present invention are, in each case, all inorganic and organic bases customary for such reactions. 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-dimethylpyridin-4-amine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU), or aromatic bases such as pyridine are preferred.

[0081] The solvent suitable for carrying out Method A is not particularly limited. These can be conventional inert organic solvents as long as they do not dissolve the compound for reacting with the compound and do not show specific interaction with the compound. Aliphatic, alicyclic or aromatic hydrocarbons which may be halogenated such as petroleum ether, pentane, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene, decalin, ISOPAR™ E or ISOPAR™ G, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or trichloroethane; Ethers such as 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 such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile; Amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Ureas such as 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, or sulfones such as sulfolane; And mixtures thereof are preferably used.

[0082] Method A can be carried out in an inert atmosphere. When carrying out Method A, 0.01 to 5 mol% of a suitable acid or condensing agent per mole of the compound of formula (IIa) and 0.01 to 5 mol of an acid binder per mole of the compound of formula (IIa) can be used. It is also possible to use the reaction components in other ratios. The work-up is carried out by known methods.

[0083] R 6 For the compound of formula (IIa) in which R 6It can be prepared from the compound of formula (IIb) wherein C1-C6-alkyl is represented by a well-known method such as hydrolysis. Examples of the hydrolysis reagent include lithium hydroxide, potassium hydroxide, sodium hydroxide, and trimethyltin hydroxide. The hydrolysis can be carried out as described in WO 2008 / 157844; WO 2006 / 002099; WO 2005 / 0256107; Angewandte Chemie, International Edition (2005), 44(9), 1378-1382.

[0084] Method B R 6 The compound of formula (IIc) wherein R represents hydrogen or C1-C6-alkyl can be prepared by Method B which includes reacting one of the compounds of formula (III) or a salt thereof with one of the compounds of formula (IV) or a salt thereof as exemplified by the following reaction scheme:

Chemical formula

[0085] U 1When representing hydroxy, method B is preferably carried out in the presence of a condensing agent. Suitable condensing agents include acid halide forming agents such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride or thionyl chloride; 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 phosphorus pentoxide, polyphosphoric acid, bis(2-oxo-3-oxazolidinyl)phosphinic acid chloride, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU), (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate, N,N'-carbonyl-diimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, 4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholinium chloride hydrate, bis(2-oxo-3-oxazolidinyl)phosphinic acid chloride (BOP-Cl), bromo-tripyrrolidinophosphonium hexafluorophosphate (PyBroP), 2-chloro-1,3-dimethylimidazolinium chloride (DMC), propane phosphonic anhydride (T3P) and 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT) and other conventional condensing agents can be selected from the non-limiting list consisting of.

[0086] U 1When [[ID=]] represents a halogen, Method B is preferably carried out in the presence of an acid binder. Suitable acid binders for carrying out Method B are, in each case, all inorganic and organic bases customary for such reactions. 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-dimethylpyridin-4-amine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU), or aromatic bases such as pyridine are preferred.

[0087] U 1 When [[ID=]] represents C1-C6-alkoxy, Method B may be carried out in the presence of a Lewis acid such as trimethylaluminum using an excess of amine component.

[0088] Where appropriate, Method B can be carried out in the presence of a base, and where appropriate in the presence of a solvent, preferably under anhydrous conditions.

[0089] The solvent suitable for carrying out Method B is not particularly limited. These can be conventional inert organic solvents as long as they do not dissolve the compound for reacting with the compound and do not show specific interaction with the compound. Aliphatic, alicyclic or aromatic hydrocarbons which may be halogenated such as petroleum ether, pentane, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene, decalin, ISOPAR™ E or ISOPAR™ G, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or trichloroethane; Ethers such as 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 such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile; Amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Ureas such as 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, or sulfones such as sulfolane; And mixtures thereof are preferably used.

[0090] Method B can be carried out in an inert atmosphere such as an argon or nitrogen atmosphere. When carrying out Method B, 1 mol or an excess of the compound of formula (IV) and 1 to 5 mol of a base can be used per 1 mol of the compound of formula (III). It is also possible to use the reaction components in other ratios. The post-treatment is carried out by a known method.

[0091] The compound of formula (IV) is commercially available or can be prepared by a well-known method.

[0092] U 1 The compound of formula (IIIa) in which U represents hydroxy is commercially available, U1 can be prepared from a compound of formula (IIIb) wherein U represents C1-C6-alkoxy by a well-known method such as base hydrolysis, or can be prepared by a known method (Beilstein J.Org.Chem.2007,3,No.23).

[0093] U 1 A compound of formula (IIIc) wherein U represents halogen is commercially available or U 1 can be prepared from a compound of formula (IIIa) wherein U represents hydroxy by a well-known method.

[0094] U 1 A compound of formula (IIIb) wherein U represents C1-C6-alkoxy can be prepared from a compound of formula (IIIa) wherein U 1 represents hydroxy by a well-known method.

[0095] Method C R 6 A compound of formula (IId) wherein R represents hydrogen or C1-C6-alkyl can be prepared from a compound of formula (IIc) wherein R 6 represents hydrogen or C1-C6-alkyl by Method C by carrying out a vulcanization reaction as exemplified in the following reaction scheme.

Chemical formula

[0096] Method C according to the present invention is carried out in the presence of a vulcanizing agent.

[0097] Sulfurizing agents suitable for carrying out Method C according to the present invention may be sulfur (S), hydrogen sulfide (H₂S), sodium sulfide (Na₂S), sodium hydrosulfide (NaHS), boron trisulfide (B₂S₃), bis(diethylaluminum) sulfide ((AlEt₂)₂S), ammonium sulfide ((NH₄)₂S), phosphorus pentasulfide (P₂S₅), Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane 2,4-disulfide) or a polymer-supported sulfurizing reagent as described in Journal of the Chemical Society, Perkin 1 (2001), 358, even in the presence of a catalytic amount or a stoichiometric amount or an excess amount of a base, such as an inorganic base and an organic base. It is preferable to use alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate; heterocyclic aromatic bases such as pyridine, picoline, lutidine, collidine; and also tertiary amines such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylpyridin-4-amine or N-methyl-piperidine.

[0098] Solvents suitable for carrying out Method C according to the present invention can be conventional inert organic solvents. It is preferable to use aliphatic, alicyclic or aromatic hydrocarbons which may be halogenated, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane; nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; and sulfur solvents such as sulfolane or carbon disulfide.

[0099] When carrying out Method C according to the present invention, 1 mole or an excess of sulfur equivalent of a sulfurizing agent and 1 to 3 moles of a base can be used per mole of the amide reactant (IIc).

[0100] It is also possible to use the reaction components in other ratios. The work-up is carried out by known methods.

[0101] Intermediate for preparing the compound of formula (I) The present invention relates to an intermediate for preparing the compound of formula (I).

[0102] Compound of formula (II):

Chemical formula

[0103] Compositions and formulations The present invention further relates to a composition comprising one or more compounds of formula (I), in particular a composition for controlling unwanted microorganisms. The composition is preferably a fungicidal composition.

[0104] The composition typically comprises one or more compounds of formula (I) and one or more acceptable carriers, in particular one or more agriculturally acceptable carriers.

[0105] The carrier is generally an inert solid or liquid, natural or synthetic, organic or inorganic substance. The carrier generally improves, for example, the application of a compound to a plant, plant part or seed. Examples of suitable solid carriers include, but are not limited to, ammonium salts, kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, such as natural rock powders, as well as synthetic rock powders such as particulate silica, alumina and silicates. Examples of typically useful solid carriers for preparing granules include, but are not limited to, natural rocks such as ground and fractionated calcite, marble, pumice, sepiolite and dolomite, synthetic granules of inorganic and organic powders, and granules of organic materials such as paper, sawdust, coconut shells, corn cobs and tobacco stems. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents and combinations thereof. Examples of suitable solvents include, for example, aromatic and non-aromatic hydrocarbons (cyclohexane, paraffin, alkylbenzene, xylene, toluene, alkylnaphthalene, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, etc.), alcohols and polyols (which may be substituted, etherified and / or esterified, such as butanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (such as dimethylformamide), lactams (such as N-alkylpyrrolidone) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide), polar and non-polar organic chemical liquids of the classes. The carrier may also be a liquefied gaseous diluent, i.e., a liquid that is gaseous under standard temperature and pressure, such as an aerosol propellant such as a halogenated hydrocarbon, butane, propane, nitrogen and carbon dioxide. The amount of the carrier typically ranges from 1 to 99.99% by weight of the composition, preferably 5 to 99.9% by weight, more preferably 10 to 99.5% by weight, and most preferably 20 to 99% by weight.

[0106] The composition may further comprise one or more acceptable auxiliaries customary for formulating the composition (e.g., an agrochemical composition), such as one or more surfactants.

[0107] The surfactant can be an ionic (cationic or anionic) or non-ionic surfactant, such as an ionic or non-ionic (one or more) emulsifier, (one or more) foaming agent, (one or more) dispersant, (one or more) wetting agent, and any mixture thereof. Examples of suitable surfactants include, but are not limited to, salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene and / or propylene oxide with fatty alcohols, fatty acids or fatty amines (polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic esters, taurine derivatives (preferably alkyltaurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of compounds containing sulfates, sulfonates, phosphates (e.g., alkylsulfonates, alkylsulfates, arylsulfonates), as well as protein hydrolysates, lignosulfite waste liquors and methylcellulose. The surfactant is typically used when the compound of formula (I) and / or the carrier is insoluble in water and the application is carried out using water. In that case, the amount of the surfactant is typically in the range of 5 to 40% by weight of the composition.

[0108] As further examples of customary auxiliaries for formulating the agrochemical composition, there are water repellents, desiccants, binders (adhesives, tackifiers, fixing agents such as carboxymethyl cellulose, 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, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tyrosin), thickeners, stabilizers (e.g., low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents that improve chemical and / or physical stability), dyes or pigments (e.g., inorganic pigments such as iron oxide, titanium oxide and Prussian blue; organic dyes such as alizarin, azo and metal phthalocyanine dyes), defoamers (e.g., silicone defoamers and magnesium stearate), preservatives (e.g., dichlorophene and benzyl alcohol hemi formal), secondary thickeners (cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and fine silica), spreading agents, gibberellin and processing aids, mineral and vegetable oils, fragrances, waxes, nutrients (including micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc), protective colloids, thixotropic substances, penetrants, sealants and complexing agents.

[0109] The choice of auxiliaries is related to the intended manner of application and / or physical properties of the compound of formula (I). Furthermore, the auxiliaries can be selected to impart specific properties (technical, physical and / or biological properties) to the composition or the use forms prepared therefrom. The choice of auxiliaries can make it possible to customize the composition to specific needs.

[0110] The composition can be in any customary form such as a solution (e.g., aqueous solution), emulsion, wettable powder, water- and oil-based suspension, powder, dust, paste, soluble powder, soluble granule, spreading granule, suspoemulsion concentrate, natural or synthetic product impregnated with the compound of the invention, fertilizer, and also microencapsulation in polymeric substances. The compound of formula (I) can be present in suspended, emulsified or dissolved form.

[0111] 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 means of a suitable device such as a spraying or spreading device. Alternatively, the composition can be provided to the end user in the form of a concentrate which preferably has to be diluted with water before use.

[0112] The composition can be prepared in a conventional manner, for example, by mixing the compound of formula (I) with one or more suitable auxiliaries as disclosed above in the present specification.

[0113] The composition generally contains from 0.01 to 99% by weight, from 0.05 to 98% by weight, preferably from 0.1 to 95% by weight, more preferably from 0.5 to 90% by weight, most preferably from 1 to 80% by weight of the compound of formula (I).

[0114] (One or more) compounds and (one or more) compositions containing them can be mixed with other active ingredients such as fungicides, bactericides, acaricides, nematicides, insecticides, herbicides, fertilizers, growth regulators, phytotoxicity reducing agents or semiochemicals. This can make it possible to broaden the activity spectrum or prevent the development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides and bactericides are disclosed in the Pesticide Manual, 17th Edition.

[0115] The active ingredients specified herein by common name are known and are described, for example, in The Pesticide Manual (16 th Ed. British Crop Protection Council) or can be searched for on the Internet (for example, www.alanwood.net / pesticides).

[0116] When the compound (A) or the compound (B) can exist in a tautomeric form, such compounds are understood to include the corresponding tautomeric forms herein above and below, where applicable, even if they are not specifically mentioned in each case.

[0117] Examples of fungicides that can be mixed with the compound(s) of formula (I) and the compositions of the present invention are as follows: 1) Inhibitors of ergosterol biosynthesis, such as (1.001) cyproconazole, (1.002) difenoconazole, (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 sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (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) tridemorph, (1.025) triticonazole, (1.026) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.027) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)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, (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.(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, (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-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.039)1-{[3-(2-Chlorophenyl)-2-(2,4-difluorophenyl)oxolan-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.040)1-{[rel(2R,3R)-3-(2-Chlorophenyl)-2-(2,4-difluorophenyl)oxolan-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.041)1-{[rel(2R,3S)-3-(2-Chlorophenyl)-2-(2,4-difluorophenyl)oxolan-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.042)2-[(2R,4R,5R)-1-(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-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-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4. -Triazole-3-thione, (1.044) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-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-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-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-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.048) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-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-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (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-chlorophenoxy)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) Mefentrifluconazole, (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-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-difluorophenyl)oxiran-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)oxiran-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-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.063) N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidformamide, (1.064) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidformamide, (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidformamide, (1.066) N'-(2,5-Dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidohydroxamic acid, (1.067) N'-(2,5-Dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidohydroxamic acid, (1.068) N'-(2,5-Dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidohydroxamic acid, (1.069) N'-(2,5-Dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidohydroxamic acid, (1.070) N'-(2,5-Dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidohydroxamic acid, (1.071) N'-(2,5-Dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidohydroxamic acid, (1.072) N'-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidohydroxamic acid, (1.073) N'-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidohydroxamic acid, (1.074) N'-[5-Bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidohydroxamic acid, (1.075) N'-{4-[(4,5-Dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidohydroxamic acid, (1.076) N'-{5-Bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidohydroxamic acid, (1.077) N'-{5-Bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidohydroxamic acid, (1.078) N'-{5-Bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidohydroxamic acid, (1.079) N'-{5-Bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidohydroxamic acid, (1.080) N'-{5-Bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidohydroxamic acid, (1.081) Ipflufentrifluconazole, (1.082) 2-[4-(4-Chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.083) 2-[6-(4-Bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.084) 2-[6-(4-Chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.085) 3-[2-(1-Chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, (1.086) 4-[[6-[rac-(2R)-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, (1.087) N-Isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methylimidohydroxamic acid, (1.088) N'-{5-Bromo-2-methyl-6-[(1-propoxypropan-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylimidohydroxamic acid, (1.089) Methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate.

[0118] 2) Inhibitors of the respiratory chain in 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) flutriafol, (2.009) isofetamid, (2.010) isopyrazam (anti-epimer enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimer enantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimer racemate 1RS,4SR,9SR), (2.013) isopyrazam (mixture of syn-epimer racemate 1RS,4SR,9RS and anti-epimer racemate 1RS,4SR,9SR), (2.014) isopyrazam (syn-epimer enantiomer 1R,4S,9R), (2.015) isopyrazam (syn-epimer enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimer racemate 1RS,4SR,9RS), (2.017) penthiopyrad, (2.018) penthiopyrad, (2.019) pyridiflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-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) Imidacloprid, (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]quinazolin-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) Isoflucipram, (2.039) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-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-carbothioamide, (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-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-Cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.057) Pyrapropion, (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) Flubeneteram.

[0119] 3) Inhibitors of the respiratory chain in complex III, such as (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) cumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (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) pyra-metostrobin, (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-dimethylpent-3-enamide, (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-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.030) methyltetraprole, (3.031) Florilpicoxamide.

[0120] 4) Inhibitors of mitosis and cell division, such as (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) penthiopyrad, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) pyridachloromethyl, (4.010) 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-pyrazole-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.017) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.018) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.020) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-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) Fluopyram.

[0121] 5) Compounds capable of having multi-site action, for example, (5.001) Bordeaux mixture, (5.002) Captan, (5.003) Captan, (5.004) Chlorothalonil, (5.005) Copper hydroxide, (5.006) Copper naphthenate, (5.007) Copper oxide, (5.008) Copper oxychloride, (5.009) Copper(II) sulfate, (5.010) Dithianon, (5.011) Dodine, (5.012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Metiram, (5.016) Metiram zinc, (5.017) Copper oxine, (5.018) Propineb, (5.019) Sulfur and sulfur preparations containing calcium polysulfide, (5.020) Thiram, (5.021) Dinneb, (5.022) Dithiram, (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.

[0122] 6) Compounds capable of inducing host defense, for example, (6.001) Acibenzolar-S-methyl, (6.002) Isothianyl, (6.003) Probenazole, (6.004) Thiadinyl.

[0123] 7) Inhibitors of amino acid and / or protein biosynthesis, such as (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.

[0124] 8) Inhibitors of ATP production, such as (8.001) Silthiopham.

[0125] 9) Inhibitors of cell wall synthesis, such as (9.001) Benalaxyl-M (Kiralaxyl), (9.002) Dimethomorph, (9.003) Flumorph, (9.004) Iprovalicarb, (9.005) Mandipropamid, (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.

[0126] 10) Inhibitors of lipid and membrane synthesis, such as (10.001) Propamocarb, (10.002) Propamocarb hydrochloride, (10.003) Tolfenpyrad-methyl.

[0127] 11) Inhibitors of melanin biosynthesis, such as (11.001) Tricyclazole, (11.002) Tolprocarb.

[0128] 12) Inhibitors of nucleic acid synthesis, such as (12.001) Benalaxyl, (12.002) Benalaxyl-M (Kiralaxyl), (12.003) Metalaxyl, (12.004) Metalaxyl-M (Mefenoxam).

[0129] 13) Inhibitors of signal transduction, for example, (13.001) fluazinam, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin.

[0130] 14) Compounds that can act as uncoupling agents, for example, (14.001) fluazinam, (14.002) meptyldinocap.

[0131] (15)(15.001) Abscisic acid, (15.002) Benziothiazole, (15.003) Benzoxazine, (15.004) Capsimycin, (15.005) Carboxylic, (15.006) Quinomethionate, (15.007) Cufraneb, (15.008) Ciflufenamide, (15.009) Simoxanil, (15.010) Cyprosulfamide, (15.011) Flutianil, (15.012) Phosphorous acid aluminum salt, (15.013) Phosphorous acid calcium salt, (15.014) Phosphorous acid sodium salt, (15.015) Methyl isothiocyanate, (15.016) Metrafenone, (15.017) Mildiomycin, (15.018) Natamycin, (15.019) Nickel dimethyldithiocarbamate, (15.020) Nitrothal isopropyl, (15.021) Oxamocarb, (15.022) Oxathiapiprolin, (15.023) Oxyphenthiine, (15.024) Pentachlorophenol and its salts, (15.025) Phosphorous acid and its salts, (15.026) Propamocarb-fosetylate, (15.027) Pyriofenone (Chlazafenone), (15.028) Tebufenozide, (15.029) Tecnazene, (15.030) Tolinifanide, (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]ethanone, (15.032) 1-(4-{4-[(5S)-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]ethanone, (15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034) Diphenamidone, (15.(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]ethanone, (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]ethanone, (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]ethanone, (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-chlorophenylmethanesulfonate, (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-chlorophenylmethanesulfonate, (15.041) Ipflufenoquin, (15.042) 2-{2-Fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (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}phenylmethanesulfonate, (15.045) 2-Phenylphenol and salts, (15.046) 3-(4,4,5-Trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.047) quinopharmine, (15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.049) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.050) 5-amino-1,3,4-thiadiazole-2-thiol, (15.051) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide, (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-benzoxazepine, (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) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057) phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate, (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) 5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one, (15.063) aminopyrifen, (15.064) (N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidformamide), (15.065) (N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylimid-formamide), (15.(066)(2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol), (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-dihydrothieno[2,3-c]pyridin-7-yl)quinoline), (15.069)(1-(4,5-dimethyl-1H-benzimidazol-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)methyl {4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamate, (15.075)(N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-cyclopropane-carboxamide), (15.076)N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-benzamide, (15.077)N-[(E)-methoxyiminomethyl]-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)N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-cyclopropane-carboxamide, (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-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]acetamide, (15.083) N-[(E)-N-methoxy-C-methyl-carboximidoyl]-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-benzamide, (15.084) N-[(Z)-N-methoxy-C-methyl-carboximidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.085) N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-methyl]-propanamide, (15.086) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-pyrrolidin-2-one, (15.087) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-benzenecarbothioamide, (15.088) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.089) N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide, (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]cyclopropanecarboxamide, (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)-cycl. ropane-carboxamide, (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) 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]isoxazolidin-3-one, (15.103) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-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]-azepan-2-one, (15.106) 4,4-dimethyl-2-[[4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-phenyl]methyl]isoxazolidin-3-one, (15.107) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-phenyl]methyl]isoxazolidin-3-one, (15.108) Ethyl 1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazole-4-carboxylate, (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) 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}propanamide, (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-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-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-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.123) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-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, which are further fungicides selected from the group consisting of.

[0132] All designated mixing partners of classes (1) to (15) may form salts with appropriate bases or acids, if their functional groups permit this.

[0133] Another aspect of the invention relates to one or more of the following compound combinations: (I.01)+(1.001), (I.01)+(1.002), (I.01)+(1.003), (I.01)+(1.004), (I.01)+(1.005), (I.01)+(1.006), (I.01)+(1.007), (I.01)+(1.008), (I.01)+(1.009), (I.01)+(1.010), (I.01)+(1.011), (I.01)+(1.012), (I.01)+(1.013), (I.01)+(1.014), (I.01)+(1.015), (I.01)+(1.016), (I.01)+(1.017), (I.01)+(1.018), (I.01)+(1.019), (I.01)+(1.020), (I.01)+(1.021), (I.01)+(1.022), (I.01)+(1.023), (I.01)+(1.024), (I.01)+(1.025), (I.01)+(1.026), (I.01)+(1.027), (I.01)+(1.028), (I.01)+(1.029), (I.01)+(1.030), (I.01)+(1.031), (I.01)+(1.032), (I.01)+(1.033), (I.01)+(1.034), (I.01)+(1.035), (I.01)+(1.036), (I.01)+(1.037), (I.01)+(1.038), (I.01)+(1.039), (I.01)+(1.040), (I.01)+(1.041), (I.01)+(1.042), (I.01)+(1.043), (I.01)+(1.044), (I.01)+(1.045), (I.01)+(1.046), (I.01)+(1.047), (I.01)+(1.048), (I.01)+(1.049), (I.01)+(1.050), (I.01)+(1.051), (I.01)+(1.052), (I.01)+(1.053), (I.01)+(1.054), (I.01)+(1.055), (I.01)+(1.056), (I.01)+(1.057), (I.01)+(1.058), (I.01)+(1.059), (I.01)+(1.060), (I.01)+(1.061), (I.01)+(1.062), (I.01)+(1.063), (I.01)+(1.064), (I.01)+(1.065), (I.01)+(1.066), (I.01)+(1.067), (I.01)+(1.068), (I.01)+(1.069), (I.01)+(1.070), (I.01)+(1.071), (I.01)+(1.072), (I.01)+(1.073), (I.01)+(1.074), (I.01)+(1.075), (I.01)+(1.076), (I.01)+(1.077), (I.01)+(1.078), (I.01)+(1.079), (I.01)+(1.080), (I.01)+(1.081), (I.01)+(1.082), (I.01)+(1.083), (I.01)+(1.084), (I.01)+(1.085), (I.01)+(1.086), (I.01)+(1.087), (I.01)+(1.088), (I.01)+(1.089), (I.01)+(2.001), (I.01)+(2.002), (I.01)+(2.003), (I.01)+(2.004), (I.01)+(2.005), (I.01)+(2.006), (I.01)+(2.007), (I.01)+(2.008), (I.01)+(2.009), (I.01)+(2.010), (I.01)+(2.011), (I.01)+(2.012), (I.01)+(2.013), (I.01)+(2.014), (I.01)+(2.015), (I.01)+(2.016), (I.01)+(2.017), (I.01)+(2.018), (I.01)+(2.019), (I.01)+(2.020), (I.01)+(2.021), (I.01)+(2.022), (I.01)+(2.023), (I.01)+(2.024), (I.01)+(2.025), (I.01)+(2.026), (I.01)+(2.027), (I.01)+(2.028), (I.01)+(2.029), (I.01)+(2.030), (I.01)+(2.031), (I.01)+(2.032), (I.01)+(2.033), (I.01)+(2.034), (I.01)+(2.035), (I.01)+(2.036), (I.01)+(2.037), (I.01)+(2.038), (I.01)+(2.039), (I.01)+(2.040), (I.01)+(2.041), (I.01)+(2.042), (I.01)+(2.043), (I.01)+(2.044), (I.(I.01)+(2.045), (I.01)+(2.046), (I.01)+(2.047), (I.01)+(2.048), (I.01)+(2.049), (I.01)+(2.050), (I.01)+(2.051), (I.01)+(2.052), (I.01)+(2.053), (I.01)+(2.054), (I.01)+(2.055), (I.01)+(2.056), (I.01)+(2.057), (I.01)+(2.058), (I.01)+(2.059), (I.01)+(2.060), (I.01)+(3.001), (I.01)+(3.002), (I.01)+(3.003), (I.01)+(3.004), (I.01)+(3.005), (I.01)+(3.006), (I.01)+(3.007), (I.01)+(3.008), (I.01)+(3.009), (I.01)+(3.010), (I.01)+(3.011), (I.01)+(3.012), (I.01)+(3.013), (I.01)+(3.014), (I.01)+(3.015), (I.01)+(3.016), (I.01)+(3.017), (I.01)+(3.018), (I.01)+(3.019), (I.01)+(3.020), (I.01)+(3.021), (I.01)+(3.022), (I.01)+(3.023), (I.01)+(3.024), (I.01)+(3.025), (I.01)+(3.026), (I.01)+(3.027), (I.01)+(3.028), (I.01)+(3.029), (I.01)+(3.030), (I.01)+(3.031), (I.01)+(4.001), (I.01)+(4.002), (I.01)+(4.003), (I.01)+(4.004), (I.01)+(4.005), (I.01)+(4.006), (I.01)+(4.007), (I.01)+(4.008), (I.01)+(4.009), (I.01)+(4.010), (I.01)+(4.011), (I.01)+(4.012), (I.01)+(4.013), (I.01)+(4.014), (I.01)+(4.015), (I.01)+(4.016), (I.01)+(4.017), (I.01)+(4.018), (I.01)+(4.019), (I.01)+(4.020), (I.01)+(4.021), (I.01)+(4.022), (I.01)+(4.023), (I.01)+(4.024), (I.01)+(4.025), (I.01)+(4.026), (I.01)+(5.001), (I.01)+(5.002), (I.01)+(5.003), (I.01)+(5.004), (I.01)+(5.005), (I.01)+(5.006), (I.01)+(5.007), (I.01)+(5.008), (I.01)+(5.009), (I.01)+(5.010), (I.01)+(5.011), (I.01)+(5.012), (I.01)+(5.013), (I.01)+(5.014), (I.01)+(5.015), (I.01)+(5.016), (I.01)+(5.017), (I.01)+(5.018), (I.01)+(5.019), (I.01)+(5.020), (I.01)+(5.021), (I.01)+(5.022), (I.01)+(5.023), (I.01)+(6.001), (I.01)+(6.002), (I.01)+(6.003), (I.01)+(6.004), (I.01)+(7.001), (I.01)+(7.002), (I.01)+(7.003), (I.01)+(7.004), (I.01)+(7.005), (I.01)+(7.006), (I.01)+(8.001), (I.01)+(9.001), (I.01)+(9.002), (I.01)+(9.003), (I.01)+(9.004), (I.01)+(9.005), (I.01)+(9.006), (I.01)+(9.007), (I.01)+(9.008), (I.01)+(9.009), (I.01)+(10.001), (I.01)+(10.002), (I.01)+(10.003), (I.01)+(11.001), (I.01)+(11.002), (I.01)+(12.001), (I.01)+(12.002), (I.01)+(12.003), (I.01)+(12.004), (I.01)+(13.001), (I.01)+(13.002), (I.01)+(13.003), (I.01)+(13.004), (I.01)+(13.005), (I.01)+(13.006), (I.01)+(14.001), (I.(01)+(14.002), (I.01)+(15.001), (I.01)+(15.002), (I.01)+(15.003), (I.01)+(15.004), (I.01)+(15.005), (I.01)+(15.006), (I.01)+(15.007), (I.01)+(15.008), (I.01)+(15.009), (I.01)+(15.010), (I.01)+(15.011), (I.01)+(15.012), (I.01)+(15.013), (I.01)+(15.014), (I.01)+(15.015), (I.01)+(15.016), (I.01)+(15.017), (I.01)+(15.018), (I.01)+(15.019), (I.01)+(15.020), (I.01)+(15.021), (I.01)+(15.022), (I.01)+(15.023), (I.01)+(15.024), (I.01)+(15.025), (I.01)+(15.026), (I.01)+(15.027), (I.01)+(15.028), (I.01)+(15.029), (I.01)+(15.030), (I.01)+(15.031), (I.01)+(15.032), (I.01)+(15.033), (I.01)+(15.034), (I.01)+(15.035), (I.01)+(15.036), (I.01)+(15.037), (I.01)+(15.038), (I.01)+(15.039), (I.01)+(15.040), (I.01)+(15.041), (I.01)+(15.042), (I.01)+(15.043), (I.01)+(15.044), (I.01)+(15.045), (I.01)+(15.046), (I.01)+(15.047), (I.01)+(15.048), (I.01)+(15.049), (I.01)+(15.050), (I.01)+(15.051), (I.01)+(15.052), (I.01)+(15.053), (I.01)+(15.054), (I.01)+(15.055), (I.01)+(15.056), (I.01)+(15.057), (I.01)+(15.058), (I.01)+(15.059), (I.01)+(15.060), (I.01)+(15.061), (I.01)+(15.(I.01)+(15.063), (I.01)+(15.064), (I.01)+(15.065), (I.01)+(15.066), (I.01)+(15.067), (I.01)+(15.068), (I.01)+(15.069), (I.01)+(15.070), (I.01)+(15.071), (I.01)+(15.072), (I.01)+(15.073), (I.01)+(15.074), (I.01)+(15.075), (I.01)+(15.076), (I.01), (I.01)+(15.077), (I.01)+(15.078), (I.01)+(15.079), (I.01)+(15.080), (I.01)+(15.081), (I.01)+(15.082), (I.01)+(15.083), (I.01)+(15.084), (I.01)+(15.085), (I.01)+(15.086), (I.01)+(15.087), (I.01)+(15.088), (I.01)+(15.089), (I.01)+(15.090), (I.01)+(15.091), (I.01)+(15.092), (I.01)+(15.093), (I.01)+(15.094), (I.01)+(15.095), (I.01)+(15.096), (I.01)+(15.097), (I.01)+(15.098), (I.01)+(15.099), (I.01)+(15.100), (I.01)+(15.101), (I.01)+(15.102), (I.01)+(15.103), (I.01)+(15.104), (I.01)+(15.105), (I.01)+(15.106), (I.01)+(15.107), (I.01)+(15.108), (I.01)+(15.109), (I.01)+(15.110), (I.01)+(15.111), (I.01)+(15.112), (I.01)+(15.113), (I.01)+(15.114), (I.01)+(15.115), (I.01)+(15.116), (I.01)+(15.117), (I.01)+(15.118), (I.01)+(15.119), (I.01)+(15.120), (I.01)+(15.121), (I.01)+(15.122), (I.01)+(15.123), (I.01)+(15.124), (I.01) + (15.125), (I.01) + (15.126), (I.01) + (15.127).

[0134] In these combinations, the first component is a compound of formula (I) as defined in Table 1 (e.g., I.01), and the second component is a fungicide selected from groups 1 to 15 as defined herein. For example, the combination (I.01) + (1.001) corresponds to a combination comprising compound I.01 of Table 1 and cyproconazole (1.001).

[0135] In some other embodiments, the compound combination corresponds to the above combinations in which compound (I.01) is replaced by any one of the compounds listed in Table 1.

[0136] The compound of formula (I) and the fungicide selected from groups (1) to (15) can be present in a weight ratio in the range of 100:1 to 1:100 (compound of formula (I): 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. Further examples of the weight ratio range 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, 2:1 to 1:2.

[0137] A further fungicide selected from groups 1 to 15 as defined herein can be added to the compound combination.

[0138] The compound of formula (I) and the composition containing it can be combined with one or more biological control agents.

[0139] Examples of biological control agents that can be combined with the compound of formula (I) and the composition containing it are as follows: (A) An antibacterial agent selected from the following group: (A1) Bacteria, such as (A1.1) Bacillus subtilis, particularly strain QST713 / AQ713 (having NRRL accession number B21661 and described in U.S. Patent No. 6,060,051, available from Bayer CropScience LP, USA as SERENADE OPTI or SERENADE ASO); (A1.2) Bacillus amyloliquefaciens, particularly strain D747 (having accession number FERM BP-8234 and disclosed in U.S. Patent No. 7,094,592, available from Certis, USA as Double Nickel™); (A1.3) Bacillus pumilus, particularly strain BU F-33 (having NRRL accession number 50185); (A1.4) Bacillus subtilis var. amyloliquefaciens strain FZB24 (available from Novozymes, USA as Taegro®); (A1.5) A strain of the genus Paenibacillus having accession number NRRL B-50972 or accession number NRRL B-67129 and described in International Publication No. 2016 / 154297; and (A2) Fungi, such as (A2.1) The blastospore of Aureobasidium pullulans, particularly strain DSM14940; (A2.2) The blastospore of Aureobasidium pullulans strain DSM 14941; (A2.3) Aureobasidium pullulans, particularly a mixture of the blastospores of strains DSM14940 and DSM14941; (B) A fungicide selected from the following group: (B1) Bacteria, such as (B1.1) Bacillus subtilis, particularly strain QST713 / AQ713 (having NRRL deposit number B21661, described in U.S. Patent No. 6,060,051, available from Bayer CropScience LP, USA as SERENADE OPTI or SERENADE ASO); (B1.2) Bacillus pumilus, particularly strain QST2808 (having deposit number NRRL B-30087, described in U.S. Patent No. 6,245,551, available from Bayer CropScience LP, USA as SONATA®); (B1.3) Bacillus pumilus, particularly strain GB34 (available from Bayer AG, Germany as Yield Shield®); (B1.4) Bacillus pumilus, particularly strain BU F-33 (having NRRL deposit number 50185); (B1.5) Bacillus amyloliquefaciens, particularly strain D747 (having deposit number FERM BP-8234, disclosed in U.S. Patent No. 7,094,592, available from Certis, USA as Double Nickel™); (B1.6) Bacillus subtilis Y1336 (registered numbers 4764, 5454, 5096 and 5277, registered as a biocide in Taiwan, available from Bion-Tech, Taiwan as BIOBAC® WP); (B1.7) Bacillus amyloliquefaciens strain MBI 600 (available from BASF SE as SUBTILEX); (B1.8) Bacillus subtilis strain GB03 (available from Bayer AG, Germany as Kodiak®); (B1.9) Bacillus subtilis var. amyloliquefaciens strain FZB24 (available from Novozymes Biologicals Inc., Salem, Virginia or Syngenta Crop Protection, LLC, Greensboro, North Carolina as fungicide TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)); (B1.10) Bacillus mycoides, isolate J (available from Certis USA as BmJ TGAI or WG); (B1.11) Bacillus licheniformis, particularly strain SB3086 (available from Novozymes as EcoGuard™ Biofungicide and Green Releaf); (B1.12) a strain of the genus Paenibacillus having accession number NRRL B-50972 or accession number NRRL B-67129 and described in International Publication No. WO 2016 / 154297.

[0140] In some embodiments, the biological control agent is a strain of Bacillus subtilis or Bacillus amyloliquefaciens that produces fengycin or prepastatin-type compounds, iturin-type compounds and / or surfactin-type compounds. For background, see the following review article: Ongena, M., et al., ‘‘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 (having NRRL accession number B21661, described in U.S. Patent No. 6,060,051, available from Bayer CropScience LP, USA as SERENADE OPTI or SERENADE ASO); Bacillus amyloliquefaciens strain D747 (having accession number FERM BP-8234, disclosed in U.S. Patent No. 7,094,592, available from Certis, USA as Double Nickel™); Bacillus subtilis MBI600 (available from Becker Underwood, USA as SUBTILEX® EPA registration number 71840-8); Bacillus subtilis Y1336 (registered numbers 4764, 5454, 5096 and 5277, registered as a biopesticide in Taiwan, available from Bion-Tech, Taiwan as BIOBAC® WP); Bacillus amyloliquefaciens, particularly strain FZB42 (available from ABiTEP, Germany as RHIZOVITAL®); and Bacillus subtilis var. amyloliquefaciens FZB24 (available from Novozymes Biologicals Inc., Salem, Virginia or Syngenta Crop Protection, LLC, Greensboro, North Carolina as fungicide TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)); and. (B2) Fungi, for example: (B2.1) Coniothyrium minitans, in particular strain CON / M / 91-8 (deposit number DSM-9660; for example, Contans® by Bayer); (B2.2) Metschnikowia fructicola, in particular strain NRRL Y-30752 (for example, Shemer®); (B2.3) Microsphaeropsis ochracea (for example, Microx® by Prophyta); (B2.5) Trichoderma atroviride species, including strain SC1, as described in international application number PCT / IT2008 / 000196; (B2.6) Trichoderma harzianum rifai strain KRL-AG2 (also known as strain T-22 / ATCC 208479, for example, PLANTSHIELD T-22G, Rootshield® and TurfShield by BioWorks, USA); (B2.14) Gliocladium roseum, strain 321U, manufactured by W.F. Stoneman Company LLC; (B2.35) Talaromyces flavus, strain V117b; (B2.36) Trichoderma asperellum, strain ICC 012, manufactured by Isagro; (B2.37) Trichoderma asperellum, strain SKT-1 (for example, ECO-HOPE® by Kumiai Chemical Industry); (B2.38) Trichoderma atroviride, strain CNCM I-1237 (for example, Esquive® WP by Agrauxine, France); (B2.39) Trichoderma atroviride, strain number V08 / 002387; (B2.40) Trichoderma atroviride, strain NMI number V08 / 002388; (B2.41) Trichoderma atroviride, strain NMI number V08 / 002389; (B2.42) Trichoderma atroviride, strain NMI number V08 / 002390; (B2.43) Trichoderma atroviride, strain LC52 (e.g., Tenet manufactured by Agrimm Technologies Limited); (B2.44) Trichoderma atroviride, strain ATCC 20476 (IMI 206040); (B2.45) Trichoderma atroviride, strain T11 (IMI352941 / CECT20498); (B2.46) Trichoderma harmatum; (B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum rifai T39 (e.g., Trichodex® manufactured by Makhteshim, USA); (B2.49) Trichoderma harzianum, especially strain KD (e.g., Trichoplus manufactured by Biological Control Products, SA (acquired by Becker Underwood)); (B2.50) Trichoderma harzianum, strain ITEM 908 (e.g., Trianum-P manufactured by Koppert); (B2.51) Trichoderma harzianum, strain TH35 (e.g., Root-Pro manufactured by Mycontrol); (B2.52) Trichoderma virens (also known as Gliocladium virens), particularly strain GL-21 (e.g., SoilGard 12G, manufactured by Certis in the United States); (B2.53) Trichoderma viride, strain TV1 (e.g., Trianum-P, manufactured by Koppert); (B2.54) Ampelomyces quisqualis, particularly strain AQ 10 (e.g., AQ 10®, manufactured by IntrachemBio Italia); (B2.56) Aureobasidium pullulans, particularly blastospores of strain DSM14940; (B2.57) Aureobasidium pullulans, particularly blastospores of strain DSM 14941; (B2.58) Aureobasidium pullulans, particularly a mixture of blastospores of strains DSM14940 and DSM14941 (e.g., Botector®, manufactured by bio-ferm in China); (B2.64) Cladosporium cladosporioides, strain H39 (manufactured by Stichting Dienst Landbouwkundig Onderzoek); (B2.69) Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulate) strain J1446 (e.g., Prestop®, manufactured by AgBio Inc. and also e.g., Primastop®, manufactured by Kemira Agro Oy); (B2.70) Lecanicillium lecanii (formerly known as Verticillium lecanii) conidia of strain KV01 (e.g., Vertalec®, manufactured by Koppert / Arysta); (B2.71) Penicillium vermiculatum; (B2.72) Pichia anomala, strain WRL-076 (NRRL Y-30842); (B2.75) Trichoderma atroviride, strain SKT-1 (FERM P-16510); (B2.76) Trichoderma at. Trichoderma atroviride, strain SKT-2 (FERM P-16511); (B2.77) Trichoderma atroviride, strain SKT-3 (FERM P-17021); (B2.78) Trichoderma gamsii (formerly Trichoderma viride), strain ICC080 (IMI CC 392151 CABI, for example BioDerma manufactured by AGROBIOSOL DE MEXICO, S.A.DE C.V.); (B2.79) Trichoderma harzianum, strain DB 103 (for example, T-Gro 7456 manufactured by Dagutat Biolab); (B2.80) Trichoderma polysporum, strain IMI 206039 (for example, Binab TF WP manufactured by BINAB Bio-Innovation AB, Sweden); (B2.81) Trichoderma stromaticum (for example, Tricovab manufactured by Ceplac, Brazil); (B2.83) Ulocladium oudemansii, particularly strain HRU3 (for example, Botry-Zen (registered trademark) manufactured by Botry-Zen Ltd, New Zealand); (B2.84) Verticillium albo-atrum (formerly Verticillium dahliae), strain WCS850 (CBS 276.92; for example, Dutch Trig manufactured by Tree Care Innovations); (B2.86) Verticillium chlamydosporium; (B2.87) A mixture of Trichoderma asperellum strain ICC 012 and Trichoderma gamsii strain ICC 080 (for example, a product known as BIO-TAM (trademark) manufactured by Bayer CropScience LP, USA).

[0141] Examples of biological control agents that can be combined with the compounds of formula (I) and compositions containing them are as follows: Bacteria selected from the group consisting of Bacillus cereus, in particular Bacillus cereus strain CNCM I-1562 and Bacillus firmus, strain I-1582 (deposit number CNCM I-1582), Bacillus subtilis strain OST 30002 (deposit number NRRL B-50421), Bacillus thuringiensis, in particular Bacillus thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (deposit number ATCC 1276), Bacillus thuringiensis subspecies aizawai, in particular strain ABTS-1857 (SD-1372), Bacillus thuringiensis subspecies kurstaki strain HD-1, Bacillus thuringiensis subspecies tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria sp. (Rotylenchulus reniformis nematode)-PR3 (deposit number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), and Streptomyces galbus strain AQ 6047 (deposit number NRRL 30232); Fungi and yeasts selected from the group consisting of Beauveria bassiana, in particular strain ATCC 74040, Lecanicillium species, in particular strain HRO LEC 12, Metarhizium anisopliae, in particular strain F52 (DSM3884 or ATCC 90448), Paecilomyces fumosoroseus (currently: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (deposit number ATCC 20874), and Paecilomyces lilacinus, in particular Paecilomyces lilacinus strain 251 (AGAL 89 / 030550); Viruses selected from the group consisting of Adoxophyes orana (apple tortrix) granulosis virus (GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV, and Spodoptera littoralis (African cotton leafworm) NPV; Bacteria and fungi that can be added to plants, plant parts, or plant organs as "inoculum materials" and that promote plant growth and plant health by virtue of their specific properties. Examples include species of the genus Agrobacterium, Azorhizobium caulinodans, Azospirillum species, Azotobacter species, Bradyrhizobium species, Burkholderia species, particularly Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora species, or Gigaspora monosporum, Glomus species, Laccaria species, Lactobacillus buchneri, Paraglomus species, Pisolithus tinctorus, Pseudomonas species, Rhizobium species, particularly Rhizobium trifolii, Rhizopogon species, Scleroderma species, Suillus species, and Streptomyces species.

[0142] Products formed by plant extracts and microorganisms, including proteins and secondary metabolites that can be used as biological control agents, such as garlic (Allium sativum), wormwood (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, "Requiem (trademark) insecticide", rotenone, ryania / ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, veratrine, Viscum album, Brassicaceae extracts, especially rapeseed powder or mustard powder.

[0143] Examples of insecticides, acaricides and nematicides that can be mixed with the compounds of formula (I) and compositions containing them are as follows: (1) Acetylcholinesterase (AChE) inhibitors, such as carbamates, such as alanycarb, aldicarb, benfuracarb, benfurocarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, methocarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, such as acephate, azamethiphos,azinphos-ethyl, azinphos-methyl, kazusaphos, chlorethoxyfos, chlorfenvinphos, chlormethos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dichlorvos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, etoprophos, famphur, fenamiphos, fenitrothion, fenthion, fostiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinolphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thimeton, triazophos, trichlorfon and vamidothion.

[0144] (2) GABAergic chloride channel blockers, such as cyclodiene organochlorines, such as chlordane and endosulfan or phenylpyrazoles (fiproles), such as ethiprole and fipronil.

[0145] (3) Sodium channel modulators, such as pyrethroids, such as acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, permethrin, alpha-permethrin, beta-permethrin, theta-permethrin, zeta-permethrin, silafluofen [(1R)-trans-isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenobucarb, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R)-trans-isomer], prallethrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin and transfluthrin or DDT or methoxychlor.

[0146] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, such as neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.

[0147] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, such as spinosyns, such as spinetoram and spinosad.

[0148] (6) Glutamate-gated chloride channel (GluCl) allosteric modulators, such as avermectin / milbemycin, such as abamectin, emamectin benzoate, lepimectin and milbemycin.

[0149] (7) Juvenile hormone mimics, for example, juvenile hormone analogs such as hydroprene, kinoprene, and methoprene, or fenoxycarb or pyriproxyfen.

[0150] (8) Various miscellaneous non-specific (multi-site) inhibitors, for example, alkyl halides such as methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic or methyl isocyanate generators such as diazomethane and metam.

[0151] (9) Modulators of the stridulatory organ, for example, pymetrozine or flonicamid.

[0152] (10) Mite growth inhibitors, for example, clofentezine, hexythiazox, and diflovidazin or etoxazole.

[0153] (11) Microbial disruptors of the insect midgut, for example, Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, and B.t. plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1.

[0154] (12) Inhibitors of mitochondrial ATP synthase, for example, diafenthiuron or organotin compounds such as azocyclotin, cyhexatin, and fenbutatin oxide, or ATP disruptors such as propargite or tetradifon.

[0155] (13) Uncoupling agents of oxidative phosphorylation via proton gradient destruction, such as chlorfenapyr, DNOC, and sulfiramid.

[0156] (14) Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, thiram, and thiosultap sodium.

[0157] (15) Inhibitors of chitin biosynthesis, type 0, such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

[0158] (16) Inhibitors of chitin biosynthesis, type 1, such as buprofezin.

[0159] (17) Molting inhibitors (especially for Diptera, i.e., Diptera), such as cyromazine.

[0160] (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.

[0161] (19) Octopamine receptor agonists, such as amitraz.

[0162] (20) Mitochondrial complex III electron transport inhibitors, such as hydramethylnon, acequinocyl, or fluacrypyrim.

[0163] (21) Mitochondrial complex I electron transport inhibitors, such as those in the group of METI acaricides, such as phenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, and tolfenpyrad, or rotenone (Derris).

[0164] (22) Voltage-dependent sodium channel blockers, such as indoxacarb or metaflumizone.

[0165] (23) Inhibitors of acetyl-CoA carboxylase, such as tetronic acid derivatives and tetramic acid derivatives, such as spirodiclofen, spirotetramat and spirodiclofen.

[0166] (24) Inhibitors of mitochondrial complex IV electron transport, such as phosphine, such as aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, such as calcium cyanide, potassium cyanide and sodium cyanide.

[0167] (25) Inhibitors of mitochondrial complex II electron transport, such as beta-ketonitrile derivatives, such as cyenopyrafen and cyflumetofen and carboxanilides, such as piflubumide.

[0168] (28) Ryanodine receptor modulators, such as diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide, Further active compounds, such as afidopyropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, chloroprallethrin, cryolite, cyclaniliprole, cycloxaprid, cyhalodiamide, dichloromethoziaz, dicofol, epsilon-methofluthrin, epsilon-momfluthrin, flometokine, fluaazindine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, flufenhexone, fluopyram, fluralaner, fluxametamide, fufenozide, guazipyr, heptafluthrin, imidaclothiz, iprodione, kappa-bifenthrin, kappa-tefluthrin, lotilaner, meperfluthrin, paichongding, pyridalyl, pyrifluquinazone, pyriminostrobin, spirodiclofen, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole, tigolaner, thiazaflufen, thiofluoximate, triflumizopyrim and iodomethane; further preparations based on Bacillus firmus (I-1582, BioNeem, Votivo), and also the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)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-en-1-yl]-5-fluorospiro[indole-3,4'-Piperidin]-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-en-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]deca-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]deca-3-en-4-yl ethyl carbonate (known from EP 2647626 B1) (CAS 1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO 2004 / 099160) (CAS 792914-58-0), PF1364 (known from JP2010 / 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-pyridyl)methyl]-2-pyridylidene]-1,1,1-Trifluoro-propan-2-one (known from WO 2013 / 144213) (CAS 1461743-15-6), N-[3-(Benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO 2010 / 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 the specification of Chinese Patent No. 103232431) (CAS 1449220-44-3), 4-[5-(3,5-Dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxide-3-thietanyl)-benzamide, 4-[5-(3,5-Dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxide-3-thietanyl)-benzamide and 4-[(5S)-5-(3,5-Dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxide-3-thietanyl)benzamide (known from WO 2013 / 050317) (CAS 1332628-83-7), N-[3-Chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide, (+)-N-[3-Chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide and (-)-N-[3-Chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide (known from WO 2013 / 162715, WO 2013 / 162716, the specification of US Patent Application Publication No. 2014 / 0213448) (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 the specification of Chinese Patent No. 101337937) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thiomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (Liudaibenjiaxuanan, known from the specification of Chinese Patent No. 103109816) (CAS 1232543-85-9); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from International Publication No. 2012 / 034403) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from International Publication No. 2011 / 085575) (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 the specification of Chinese Patent No. 101337940) (CAS 1108184-52-6); (2E)-and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide (known from the specification of Chinese Patent No. 101715774) (CAS 1232543-85-9); 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropanecarboxylic acid ester (known from the specification of Chinese Patent No. 103524422) (CAS 1542271-46-4); (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]-indeno[1,2-e][1,3,4] Methyl oxadiazine-4a(3H)-carboxylate (known from the specification of Chinese Patent No. 102391261) (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-mannopyranose (known from the specification of US Patent Application Publication No. 2014 / 0275503) (CAS 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 1253850-56-4), (8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 933798-27-7), (8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (known from International Publication No. 2007040280, International Publication No. 2007040282) (CAS 934001-66-8), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]-propanamide (known from International Publication No. 2015 / 058021, International Publication No. 2015 / 058028) (CAS 1477919-27-9) and N-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from the specification of Chinese Patent No. 103265527) (CAS 1452877-50-7), 5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (known from International Publication No. 2013 / 115391) (CAS 1449021-97-9), 3-(4-chloro-2,6-Dimethylphenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decan-3-en-2-one (known from International Publication No. WO 2010 / 066780 and International Publication No. WO 2011 / 151146) (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 International Publication No. WO 2014 / 187846) (CAS 1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]decan-3-en-4-yl ethyl carboxylate (known from International Publication No. WO 2010 / 066780 and International Publication No. WO 2011 / 151146) (CAS 1229023-00-0), N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoro-acetamide (known from German Patent No. DE 3639877 and International Publication No. WO 2012 / 029672) (CAS 1363400-41-2), [N(E)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoro-acetamide (known from International Publication No. WO 2016 / 005276) (CAS 1689566-03-7), [N(Z)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoro-acetamide (CAS 1702305-40-5), 3-endo-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-9-azabicyclo[3.3.1]nonane (known from International Publication No. WO 2011 / 105506 and International Publication No. WO 2016 / 133011) (CAS 1332838-17-1). de (CAS 1702305-40-5), 3-endo-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-9-azabicyclo[3.3.1]nonane (known from International Publication No. WO 2011 / 105506 and International Publication No. WO 2016 / 133011) (CAS 1332838-17-1).

[0169] Examples of phytotoxicity-reducing agents that can be mixed with the compound of formula (I) and compositions containing the same include, for example, benoxacor, cloquintocet (-mexyl), cimetrinil, cyprosulfamide, dichloramide, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)-amino]phenyl}-sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

[0170] Examples of herbicides that can be mixed with the compound of formula (I) and compositions containing the same are as follows: Acetochlor, Acifluorfen, Acifluorfen Sodium, Acronifen, Aclonifen, 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, Anilophos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamid, Benazolin, Benazolin Ethyl, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron Methyl, Bensulide, Bentazone, Benzobicyclon, Benzofenap, Bicyclopyron, Bifenox, Bilanafos, Bilanafos Sodium, Bispyribac, Bispyribac Sodium, Bromacil, Bromobutide, Bromophenoxim, Bromoxynil, Bromoxynil Butyrate, -Potassium, -Heptanoate and -Octanoate, Busoxinone, Butachlor, Butaphenacil, Butamiphos, Butenachlor, Butralin, Butroxydim, Butyrate, Cafestrol, Carbetamide, Carfentrazone, Carfentrazone Ethyl, Chloramben, Chlorbromuron, Chlorfenac, Chlorfenac Sodium, Chlorfenprop, Chlorflurenol, Chlorflurenol Methyl, Chloridazon, Chlorimuron, Chlorimuron Ethyl, Chlorophthalim, Chlorotoluron, Chlorothal Dimethyl, Chlorsulfuron, Cinidon, Cinidon Ethyl, Cinosulfuron, Clacyfos, Clethodim, Clodinafop, Clodinafop Propargyl, Chromazone, Chlormepropp, Clopyralid, Chloransulam, Chloransulam Methyl, Cumyluron, Cyanamide, Cyanazine, Cycloate, Cyclopyrimorate, Cyclosulfamuron, Cycloxydim, Cyhalofop, Cyhalofop Butyl, Cyprazine, 2,4-D, 2,4-D Butyl (2,4-D-butotyl), -butyl, -dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, dimethoate (dimethoate), dalapon, dazomet, n-decanol, desmedipham, detosylpyrazolate (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, dichlorprop-P, dichlormequat, dichlormequat methyl, dichlormequat-P-methyl, diclomezine, difenzoquat, diflufenican, diflufenazopyr, diflufenazopyr sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron methyl, ethiozin, ethofumesate, ethoxyphene, ethoxyphene ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, that is, N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5-oxo-4,5-dihydro-1H-tetrazol-1-yl]phenyl}ethanesulfonamide, F-7967, that is, 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, florasulam, flucarbazone, flucarbazone sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, fluazinam, flumiclorac, flumiclorac pentyl, flumioxazin, flumetsulam, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, fluopropanate, flupyrsulfuron, flupyrsulfuron-methyl sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr meptyl, flurtamon, fluthiacet, fluthiacet-methyl, homesisafen, homesisafen sodium, halosulfuron, hosamine, glufosinate, glufosinate ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, i.e., O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropyl phosphoramidothioate, haloxyfop, haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxybut, haloxybut-P, haloxybut-ethoxyethyl, haloxybut-P-ethoxyethyl, haloxybut-methyl, haloxybut-P-methyl, hexazinone, HW-02, i.e., 1-(dimethoxyphosphoryl)ethyl(2,4-(dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxtynil, ioxtynil-octanoate, -potassium and -sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, carbutilate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium and -butyl, mecoprop-P, mecoprop-P-butyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluizide, mesosulfuron, mesosulfuron-methyl, mesotrione, metobenzthiazone, metam, metamifop, metazachlor, metazosulfuron, metobenzthiazone, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metachlor, S-metachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, i.e., N-(3-chloro-4-isopropylphenyl)-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., [5-(benzyloxy)-1-methyl-1H-pyrazol-4-yl](2,4-dichlorophenyl)-methanone, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orben carb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxadiquat dichloride, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, petoxamide, petroleum, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, Program, propisochlor, propoxycarbazone, propoxycarbazone sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen ethyl, pyrazosulfotole, pyrazolineate (pyrazolate), pyrazosulfuron, pyrazosulfuron ethyl, pyraoxyphen, pyribambenz, pyribambenz isopropyl, pyribambenz propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriflutalid, pyriminobac, pyriminobac methyl, pyrimisulfan, pyrithiobac, pyrithiobac sodium, pyroxasulfone, pyroxasulam, cinchonazine, cinchonine, quinoclamine, quizalofop, quizalofop ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, sulfofenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron methyl, sulfosulfuron, SYN-523, SYP-249, that is, 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, that is, 1-[7-fluoro-3-oxo-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, TCA (trifluoroacetic acid), sodium TCA, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbuthylazine, terbumeton, terbuthylazine, terbutryn, tenilchlor, thiazopyr, triencarbazone, triencarbazone methyl, thifensulfuron, thifensulfuron methyl, thiobencarb, thiafenox, topramezone, traloxydim, triafamone, triazamate, triasulfuron, triaziflam, tribenuron, tribenuron methyl, triclopyr, trietazine, trifloxysulfuron, sodium trifloxysulfuron, triflumizole, trifluralin, triflusulfuron, triflusulfuron methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, that is, 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds: [Chemical formula]

[0171] Examples of plant growth regulators are as follows: Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chloromethocort chloride, chlorpropham, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dicamba, dicamba sodium, endothal, endothal-dipotassium, -disodium, and -mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol butyl, flurprimidol, fluchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, methyl jasmonate, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, paclobutrazol, N-(2-phenylethyl)-β-alanine, N-phenylphthalamic acid, prohexadione, prohexadione calcium, prohydrojasmon, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0172] Methods and uses The compounds of formula (I) and compositions containing them have potent microbicidal activity. These can be used to control unwanted microorganisms such as unwanted fungi and bacteria. These can be particularly useful in crop protection (controlling microorganisms that cause plant diseases) or in protecting materials (e.g., industrial materials, wood, stored products) as described in more detail hereinbelow. More specifically, the compounds of formula (I) and compositions containing them can be used to protect seeds, germinated seeds, sprouted seedlings, plants, plant parts, fruits, harvests and / or the soil in which the plants grow from unwanted microorganisms.

[0173] As used herein, controlling or to control includes protective, curative, and eradication treatments of unwanted microorganisms. The unwanted microorganisms can be pathogenic bacteria, pathogenic viruses, pathogenic oomycetes, or pathogenic fungi, more specifically phytopathogenic bacteria, phytopathogenic viruses, phytopathogenic oomycetes, or phytopathogenic fungi. As detailed below, these phytopathogenic microorganisms are the cause of a wide range of plant diseases.

[0174] More specifically, the compounds of formula (I) and compositions containing 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 for the control of unwanted fungi such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, and Deuteromycetes and / or the control of Oomycetes, more preferably for the control of Basidiomycetes (causing rust diseases).

[0175] The invention also relates to a method for controlling unwanted microorganisms such as phytopathogenic fungi, oomycetes, and bacteria, comprising the step of applying at least one compound of formula (I) or at least one composition containing the same to the microorganisms and / or their habitats (plants, plant parts, seeds, fruits, or the soil in which the plants grow).

[0176] Typically, when the compounds and compositions of the present invention are used in a curative or protective method for controlling phytopathogenic fungi and / or phytopathogenic oomycetes, the effective and plant-compatible amount thereof is applied to plants, plant parts, fruits, seeds or the soil or substrate in which the plants grow. Suitable substrates that can be used for cultivating plants include inorganic substrates such as mineral wool, especially stone wool, perlite, sand or gravel; organic substrates such as peat, pine bark or sawdust; and petroleum-based substrates such as polymer foams or plastic beads. The effective and plant-compatible amount is sufficient to control or destroy fungi present in or likely to appear in agricultural land and means an amount that does not cause recognizable symptoms of phytotoxicity to the said crops. Such amounts can vary widely depending on the fungi to be controlled, the type of crop, the growth stage of the crop, the climatic conditions and the respective compounds or compositions of the present invention used. This amount can be determined by systematic field trials within the capabilities of those skilled in the art.

[0177] Plants and plant parts The compounds of formula (I) and compositions containing the same can be applied to any plant or plant part.

[0178] Plants means all plants and plant populations, for example desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants obtainable by conventional breeding and optimization methods or biotechnology and genetic engineering methods or combinations of these methods, including genetically modified plants (GMOs or transgenic plants) and plant cultivars that can and cannot be protected by plant breeders' rights.

[0179] Plant parts are understood to mean all above-ground and underground parts and organs of plants such as shoots, leaves, flowers and roots, examples of which include leaves, needles, petioles, stems, flowers, fruiting bodies, fruits and seeds, and also roots, tubers and rhizomes. Plant parts also include harvested material and vegetative and reproductive propagation material, such as cuttings, tubers, rhizomes, grafts and seeds.

[0180] Plants that can be processed by the method of the present invention include the following: cotton, flax, grapes, fruits, vegetables, such as Rosaceae species (e.g., not only pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, as well as soft fruits such as strawberries), Ribesioidae species, Juglandaceae species, Betulaceae species, Anacardiaceae species, Fagaceae species, Moraceae species, Oleaceae species, Actinidaceae species, Lauraceae species, Musaceae species (e.g., banana trees and plantations), Rubiaceae species (e.g., coffee), Theaceae species, Sterculiceae species, Rutaceae species (e.g., lemons, oranges and grapefruits); Solanaceae species (e.g., tomatoes), Liliaceae species, Asteraceae species (e.g., lettuce), Umbelliferae species, Cruciferae species, Chenopodiaceae species, Cucurbitaceae species (e.g., cucumbers), Alliaceae species (e.g., leeks, onions), Papilionaceae species (e.g., peas);Major crop plants, such as Gramineae species (e.g., maize, turfgrass, cereals, such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae species (e.g., sunflower), Brassicaceae species (e.g., white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, bok choy, kohlrabi, radish, and rape, mustard, wasabi and cress), Fabacae species (e.g., beans, peanuts), Papilionaceae species (e.g., soybean), Solanaceae species (e.g., potato), Chenopodiaceae species (e.g., sugar beet, fodder beet, spinach beet, beetroot); useful plants and ornamental plants for gardens and green areas; and genetically modified varieties of each of these plants.;

[0181] In some preferred embodiments, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods such as crossing or protoplast fusion, and parts thereof are treated by the method of the present invention.

[0182] In some other preferred embodiments, transgenic plants and plant cultivars obtained by genetic engineering methods, optionally in combination with conventional methods (genetically modified organisms), and parts thereof are treated by the method of the present invention. More preferably, plants of plant cultivars that are commercially available or in use are treated by the present invention. Plant cultivars are understood to mean plants having new characteristics ("traits") and obtained by conventional breeding, mutagenesis or recombinant DNA techniques. These can be cultivars, varieties, biotypes or genotypes.

[0183] The method according to the invention can be used for the treatment of genetically modified organisms (GMOs), such as plants or seeds. A genetically modified plant (or transgenic plant) is a plant in which a foreign gene has been stably integrated into the genome. The expression "foreign gene" essentially means a gene that is provided or constructed outside the plant and, when introduced into the nuclear, chloroplast or mitochondrial genome, expresses a protein or polypeptide of interest or down-regulates or silences one or more other genes present in the plant (for example, using antisense technology, co-suppression technology, RNA interference - RNAi - technology or microRNA - miRNA - technology), thereby conferring new or improved agronomic or other characteristics to the transformed plant. A foreign gene located in the genome is also called a transgene. A transgene defined by its specific position in the plant genome is called a transformation or transgenic event.

[0184] Plants and plant cultivars that can be treated by the method disclosed above include all plants having genetic material that confers particularly advantageous and useful traits to these plants (regardless of whether they are obtained by breeding and / or biotechnological means).

[0185] Plants and plant cultivars that can be treated by the method disclosed above include plants and plant cultivars that are resistant to one or more biotic stresses, i.e., the plants show better defense against animal and microbial pests such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.

[0186] Plants and plant cultivars that can be treated by the method disclosed above include plants that are resistant to one or more abiotic stresses. Abiotic stress conditions can include, for example, drought, cold exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limitation of nitrogen nutrient availability, limitation of phosphorus nutrient availability, shade avoidance.

[0187] Plants and plant cultivars that can be processed by the methods disclosed above include plants characterized by enhanced yield characteristics. The increase in yield in said plants can be the result of improvements in plant physiology, growth and development such as, for example, improved water use efficiency, water retention efficiency, nitrogen utilization, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. Yield can further be affected by, but is not limited to, early flowering, flowering control for hybrid seed production, seed viability, plant size, number and distance of internodes, root growth, seed size, fruit size, pod size, number of pods or ears, number of seeds per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod shattering and lodging resistance, in improved plant architecture (under stress and non-stress conditions). Further yield traits include seed composition, such as carbohydrate content and composition, such as cotton or starch, protein content, oil content and composition, nutritional value, reduction of anti-nutritional compounds, improved processability and better storage stability.

[0188] Plants and plant cultivars that can be processed by the methods disclosed above include hybrid plants and plant cultivars in which the characteristics of heterosis or hybrid vigor, which generally result in higher yields, vigor, health and resistance to biotic and abiotic stresses, are already expressed.

[0189] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be processed by the methods disclosed above include herbicide-tolerant plants, i.e., plants and plant cultivars that are resistant to one or more given herbicides. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that confer such herbicide tolerance.

[0190] Plants and plant cultivars that can be processed by the methods disclosed above (obtained by plant biotechnology methods such as genetic engineering) include insect-resistant transgenic plants, i.e., plants and plant cultivars that are resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that confer such insect resistance.

[0191] Plants and plant cultivars that can be processed by the methods disclosed above (obtained by plant biotechnology methods such as genetic engineering) include plants and plant cultivars that are resistant to abiotic stress. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that confer such stress resistance.

[0192] Plants and plant cultivars that can be processed by the methods disclosed above (obtained by plant biotechnology methods such as genetic engineering) include plants and plant cultivars that exhibit changes in the quantity, quality and / or storage stability of the harvest and / or changes in the properties of specific components of the harvest.

[0193] Plants and plant cultivars that can be processed by the methods disclosed above (obtained by plant biotechnology methods such as genetic engineering) include plants and plant cultivars such as cotton plants having altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that confer such altered fiber properties.

[0194] Plants and plant cultivars that can be processed by the method disclosed above (obtained by plant biotechnology methods such as genetic engineering) include plants and plant cultivars such as Brassica or related Brassica plants having altered oil profile characteristics. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that confer such altered oil profile characteristics.

[0195] Plants and plant cultivars that can be processed by the method disclosed above (obtained by plant biotechnology methods such as genetic engineering) include plants and plant cultivars such as Brassica or related Brassica plants having altered seed threshing characteristics. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that confer such seed threshing characteristics, including plants such as Brassica plants with delayed or reduced seed threshing.

[0196] Plants and plant cultivars that can be processed by the method disclosed above (obtained by plant biotechnology methods such as genetic engineering) include plants and plant cultivars such as tobacco plants having altered post-translational protein modification patterns.

[0197] Pathogens and diseases Using the method disclosed above, microorganisms, in particular diseases caused by powdery mildew pathogens such as species of Blumeria (e.g., Blumeria graminis), Podosphaera (e.g., Podosphaera leucotricha), Sphaerotheca (e.g., Sphaerotheca fuliginea), Uncinula (e.g., Uncinula necator); Diseases caused by rust pathogens such as 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 recondita, Puccinia graminis or Puccinia striiformis), Uromyces species (e.g., Uromyces appendiculatus); Diseases caused by pathogens of the group Oomycetes such as Albugo species (e.g., Albugo candida), Bremia species (e.g., Bremia lactucae), Peronospora species (e.g., Peronospora pisi or Peronospora 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); For example, species of the genus Alternaria (e.g., Alternaria solani), species of the genus Cercospora (e.g., Cercospora beticola), species of the genus Cladiosporium (e.g., Cladiosporium cucumerinum), species of the genus Cochliobolus (e.g., Cochliobolus sativus (conidial form: Drechslera, synonym: Helminthosporium) or Cochliobolus miyabeanus), species of the genus Colletotrichum (e.g., Colletotrichum lindemuthanium), species of the genus Cycloconium (e.g., Cycloconium oleaginum), species of the genus Diaporthe (e.g., Diaporthe citri), species of the genus Elsinoe (e.g., Elsinoe fawcettii), species of the genus Gloeosporium (e.g., Gloeosporium laeticolor), species of the genus Glomerella (e.g., Glomerella cingulate), species of the genus Guignardia (e.g., Guignardia bidwelli), species of the genus Leptosphaeria (e.g., Leptosphaeria maculans), species of the genus Magnaporthe (e.g., Magnaporthe grisea), species of the genus Microdochium (e.g., Microdochium nivaleleaf blight and leaf blight caused by species of nivale)), Mycosphaerella (e.g., Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis), Phaeosphaeria (e.g., Phaeosphaeria nodorum), Pyrenophora (e.g., Pyrenophora teres or Drechslera tritici repentis), Ramularia (e.g., Ramularia collo-cygni or Ramularia areola), Rhynchosporium (e.g., Rhynchosporium secalis), Septoria (e.g., Septoria apii or Septoria lycopersici), Stagonospora (e.g., Stagonospora nodorum), Typhula (e.g., Typhula incarnate), Venturia (e.g., Venturia inaequalis); For example, root and stem diseases caused by species of the genus Corticium (e.g., Corticium graminearum), Fusarium (e.g., Fusarium oxysporum), Gaeumannomyces (e.g., Gaeumannomyces graminis), Plasmodiophora (e.g., Plasmodiophora brassicae), Rhizoctonia (e.g., Rhizoctonia solani), Sarocladium (e.g., Sarocladium oryzae), Sclerotium (e.g., Sclerotium oryzae), Tapesia (e.g., Tapesia acuformis), Thielaviopsis (e.g., Thielaviopsis basicola); For example, diseases of ears and panicles caused by species of Alternaria (e.g., Alternaria species), Aspergillus (e.g., Aspergillus flavus), Cladosporium (e.g., Cladosporium cladosporioides), Claviceps (e.g., Claviceps purpurea), Fusarium (e.g., Fusarium culmorum), Gibberella (e.g., Gibberella zeae), Monographella (e.g., Monographella nivalis), Stagnospora (e.g., Stagnospora nodorum) (including the cob of maize); Diseases caused by smut fungi, such as species of Sphacelotheca (e.g., Sphacelotheca reiliana), Tilletia (e.g., Tilletia caries or Tilletia controversa), Urocystis (e.g., Urocystis occulta), Ustilago (e.g., Ustilago nuda); For example, fruit rot caused by Aspergillus species (e.g., Aspergillus flavus), Botrytis species (e.g., Botrytis cinerea), Penicillium species (e.g., Penicillium expansum or Penicillium purpurogenum), Rhizopus species (e.g., Rhizopus stolonifer), Sclerotinia species (e.g., Sclerotinia sclerotiorum), Verticilium species (e.g., Verticilium alboatrum); For example, species of the genus Alternaria (e.g., Alternaria brassicicola), species of the genus Aphanomyces (e.g., Aphanomyces euteiches), species of the genus Ascochyta (e.g., Ascochyta lentis), species of the genus Aspergillus (e.g., Aspergillus flavus), species of the genus Cladosporium (e.g., Cladosporium herbarum), species of the genus Cochliobolus (e.g., Cochliobolus sativus (conidial form: Drechslera, synonym: Helminthosporium)), species of the genus Colletotrichum (e.g., Colletotrichum coccodes), species of the genus Fusarium (e.g., Fusarium culmorum), species of the genus Gibberella (e.g., Gibberella zeae), species of the genus Macrophomina (e.g., Macrophomina phaseolina), species of the genus Microdochium (e.g., Microdochium nivale), species of the genus Monographella (e.g., Monographella nivalis), species of the genus Penicillium (e.g., Penicillium expansum), species of the genus Phoma (e.g., Phoma lingam), species of the genus Phomopsis (e.g., Phomopsis sojaeseed and soil-borne rot and blight diseases, as well as seedling diseases caused by, for example, species of Fusarium (e.g., Fusarium sojae), Phytophthora (e.g., Phytophthora cactorum), Pyrenophora (e.g., Pyrenophora graminea), Pyricularia (e.g., Pyricularia oryzae), Pythium (e.g., Pythium ultimum), Rhizoctonia (e.g., Rhizoctonia solani), Rhizopus (e.g., Rhizopus oryzae), Sclerotium (e.g., Sclerotium rolfsii), Septoria (e.g., Septoria nodorum), Typhula (e.g., Typhula incarnate), Verticillium (e.g., Verticillium dahlia); for example, cankers, galls and witches' broom diseases caused by species of Nectria (e.g., Nectria galligena); for example, blight diseases caused by species of Monilinia (e.g., Monilinia laxa); for example, leaf, flower and fruit deformities caused by species of Exobasidium (e.g., Exobasidium vexans), Taphrina (e.g., Taphrina deformans); For example, tree diseases caused by Esca species (e.g., Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea), Ganoderma species (e.g., Ganoderma boninense); For example, diseases of flowers and seeds caused by Botrytis species (e.g., Botrytis cinerea); For example, diseases of tubers caused by Rhizoctonia species (e.g., Rhizoctonia solani), Helminthosporium species (e.g., Helminthosporium solani); Bacterial pathogens, e.g., diseases caused by Xanthomonas species (e.g., Xanthomonas campestris pv. Oryzae), Pseudomonas species (e.g., Pseudomonas syringae pv. Lachrymans), Erwinia species (e.g., Erwinia amylovora) It is possible to control phytopathogenic microorganisms such as phytopathogenic fungi that cause diseases such as these.

[0198] Seed treatment Methods for controlling unwanted microorganisms can be used to protect seeds from phytopathogenic microorganisms such as fungi.

[0199] As used herein, the term "(one or more) seeds" includes dormant seeds, primed seeds, pre-germinated seeds, and seeds having emerged roots and leaves.

[0200] Accordingly, the present invention also relates to a method for protecting seeds and / or crops from unwanted microorganisms such as bacteria or fungi, the method comprising treating the seeds with one or more compounds of formula (I) or a composition comprising the same. Treatment of the seeds with the (one or more) compounds of formula (I) or a composition comprising the same not only protects the seeds from phytopathogenic microorganisms, but also protects germinated plants, germinated seedlings and plants after emergence.

[0201] The seed treatment can be carried out before sowing, at sowing or immediately thereafter.

[0202] When the seed treatment is carried out before sowing (e.g., so-called on-seed application), the seed treatment can be carried out as follows: The seeds are placed in a mixer together with the desired amount of the (one or more) compounds of formula (I) or a composition comprising the same (either as such or after dilution), and the seeds and the (one or more) compounds of formula (I) or a composition comprising the same are mixed until a uniform distribution on the seeds is achieved. If appropriate, the seeds can then be dried.

[0203] The present invention also relates to seeds treated with one or more compounds of formula (I) or a composition comprising the same. As described above, the use of the treated seeds not only makes it possible to protect the seeds before and after sowing from unwanted microorganisms such as phytopathogenic fungi, but also makes it possible to protect the germinated plants and seedlings emerging from the treated seeds. Most of the damage to crop plants caused by pests is induced by infection of the seeds before or after sowing of the plants. This stage is particularly important because the roots and shoots of growing plants are particularly sensitive and even minor damage can lead to the death of the plant.

[0204] Accordingly, the present invention also relates to a method of protecting seeds, germinating plants and germinated seedlings, and more generally to a method of protecting crops from phytopathogenic microorganisms, which comprises the step of using seeds treated with one or more compounds of formula (I) or a composition comprising the same.

[0205] Preferably, the seeds are treated in a sufficiently stable state so as not to be damaged during the treatment process. Generally, the seeds can be treated at any point in time between harvest and immediately after sowing. It is customary to use seeds separated from the plant with the rachis, husk, stalk, skin, hair or pulp removed. For example, it is possible to use seeds that have been harvested, washed and dried to a water content of less than 15% by weight. Alternatively, after drying, seeds treated with water, for example, and then dried again, or seeds immediately after priming, or seeds stored or pre-germination seeds under primed conditions, or seeds sown on a seedling tray, tape or paper can also be used.

[0206] The amount of the compound(s) of formula (I) or the composition comprising the same applied to the seeds is typically an amount such that the germination of the seeds is not impaired or the resulting plants are not damaged. This must be particularly ensured if the active ingredient exhibits phytotoxic effects at a certain application rate. When determining the amount of the compound(s) of formula (I) or the composition comprising the same applied to the seeds in order to achieve optimal protection of the seeds and germinating plants using the minimum amount, the specific phenotype of the transgenic plants should also be taken into account.

[0207] As shown above, the compound of formula (I) can be applied directly to the seeds as such, i.e., without using other components and without dilution, or a composition containing the compound of formula (I) can be applied. Preferably, the composition is applied to the seeds in any suitable form. Examples of suitable formulations include solutions, emulsions, suspensions, powders, foams, slurries, or other coating compositions for seeds, such as film-forming materials, pellet materials, fine iron or other metal powders, granules, coating materials for inactivated seeds, and combinations with ULV formulations. The formulation may be a ready-to-use formulation or a concentrate that needs to be diluted before use.

[0208] These formulations are prepared by known methods, for example, by mixing the active ingredient or its mixture with conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersing agents, emulsifying agents, defoaming agents, preservatives, secondary thickeners, adhesives, gibberellins and also water.

[0209] These formulations are prepared by known methods by mixing the active ingredient or a combination of active ingredients with conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersing agents, emulsifying agents, defoaming agents, preservatives, secondary thickeners, adhesives, gibberellins and also water.

[0210] Useful dyes that may be present in the seed film coating formulation are all dyes customary for such purposes. It is possible to use either pigments poorly soluble in water or water-soluble dyes. Examples include dyes known by the names of rhodamine B, C.I. Pigment Red 112, and C.I. Solvent Red 1. Useful wetting agents that may be present in the seed film coating formulation are all substances customary for use in the formulation of active pesticidal ingredients that promote wetting. Alkylnaphthalenesulfonates, such as diisopropyl- or diisobutylnaphthalenesulfonate, can preferably be used. Useful dispersants and / or emulsifiers that may be present in the seed film coating formulation are all nonionic, anionic, and cationic dispersants customary for use in the formulation of active pesticidal ingredients. Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants can preferably be used. Useful nonionic dispersants include, in particular, ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers, and tristyrylphenol polyglycol ethers, as well as their phosphorylated or sulfated derivatives. Suitable anionic dispersants are, in particular, lignosulfonates, polyacrylates, and arylsulfonate / formaldehyde condensates. Useful antifoaming agents that may be present in the seed film coating formulation are all foam-inhibiting substances customary for use in the formulation of active pesticidal ingredients. Silicone antifoaming agents and magnesium stearate can preferably be used. Preservatives that may be present in the seed film coating formulation are all substances that can be used for such purposes in pesticidal compositions. Examples include dichlorophene and benzyl alcohol hemiformal. Secondary thickeners that may be present in the seed film coating formulation are all substances that can be used for such purposes in pesticidal compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays, and fine silica. Adhesives that may be present in the seed film coating formulation are all customary binders that can be used in seed film coating products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and tyrosin.

[0211] The compounds of formula (I) and compositions containing them are suitable for protecting the seeds of any plant variety used in agriculture, greenhouses, forests or horticulture. More specifically, the seeds are cereals (e.g., wheat, barley, rye, millet, triticale, and oats), rapeseed, corn, cotton, soybeans, rice, potatoes, sunflowers, legumes, coffee, peas, beets (e.g., sugar beets and fodder beets), peanuts, vegetables (e.g., tomatoes, cucumbers, onions, lettuce), lawns and ornamental plant seeds. Of particular importance is the treatment of the seeds of wheat, soybeans, rapeseed, corn and rice.

[0212] The compounds of formula (I) or compositions containing them can be used to treat transgenic seeds, in particular the seeds of plants that can express proteins that act against pests, herbicide damage or abiotic stress, thereby enhancing the protective effect. A synergistic effect can also occur in the interaction with the substances formed by the expression.

[0213] Nematodes In this context, the term "nematodes" refers to all species of the phylum Nematoda, here in particular species that act as parasites on plants or fungi (e.g., species of the order Aphelenchida, the genus Meloidogyne, the order Tylenchida, etc.) or humans and animals (e.g., species of the order Trichinellida, the order Tylenchida, the order Rhabditina and the order Spirurida), causing damage in or on these organisms, and also includes other parasitic helminths.

[0214] The nematicides in crop protection can control nematodes as described herein.

[0215] The term "controlling nematodes" means killing nematodes, or preventing or interfering with the generation or growth of nematodes, or preventing or interfering with the invasion of nematodes into plant tissues or the sucking on plant tissues.

[0216] Here, the effectiveness of the compound is determined by comparing the dead worm rate, gall formation, cyst formation, nematode density per soil volume, nematode density per root, number of nematode eggs per soil volume, and nematode mobility between the plant or plant part or treated soil treated with the compound of formula (I) and the untreated plant or plant part or untreated soil (100%). Preferably, the reduction achieved is a complete killing of nematodes or a complete prevention of generation and growth by a 25 - 50% reduction, particularly preferably a 51 - 79% reduction, and very particularly preferably an 80 - 100% reduction compared to the untreated plant, plant part or untreated soil. The control of nematodes described herein also includes the control of nematode proliferation (cyst and / or egg generation). The compounds of formula (I) can also be used to keep plants or animals healthy and can be used curatively, prophylactically or systemically for the control of nematodes.

[0217] Those skilled in the art know the methods for determining the mortality rate, gall formation, cyst formation, nematode density per soil volume, nematode density per root, number of nematode eggs per soil volume, and nematode mobility.

[0218] The use of the compounds of formula (I) can keep plants healthy and also includes a reduction in damage caused by nematodes and an increase in yield.

[0219] In this context, 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 species of the genus Xiphinema, Longidorus, and Trichodorus; hemiparasites such as species of the genus Tylenchulus; migratory endoparasites such as species of the genus Pratylenchus, Radopholus, and Scutellonema; sedentary parasites such as species of the genus Heterodera, Globodera, and Meloidogyne, and also foliar endoparasites such as species of the genus Ditylenchus, Aphelenchoides, and Hirschmaniella. Particularly harmful root-parasitic soil nematodes are, for example, cyst-forming nematodes of the genus Heterodera or Globodera, and / or root-knot nematodes of the genus Meloidogyne. Harmful species of these genera are, for example, Meloidogyne incognita, Heterodera glycines (soybean cyst nematode), Globodera pallida, and Globodera rostochiensis (potato white cyst nematode), and these species are effectively controlled by the compounds described in this document. However, the use of the compounds described in this document is not limited to these genera or species, but extends equally to other nematodes.

[0220] Plant nematodes include, for example, Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Aphelenchoides fragaria, and Aphelenchoides species that are internal parasites of stems and leaves, Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, and Bursaphelenchus species, Cacopaurus pestis, Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), and Criconemella species, Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, and Criconemoides species, Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagusmyceliophagus) and also Ditylenchus species which are endophytes in stems and leaves, Dolichodorus heterocephalus, Globodera pallida (= Heterodera pallida), Globodera rostochiensis (potato cyst nematode), Globodera solanacearum, Globodera tabacum, Globodera virginia and Globodera species which are non-motile cyst-forming parasites, Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus erythrine, Helicotylenchus multicinctus, Helicotylenchus nannus, Helicotylenchus pseudorobustus and Helicotylenchus species, Hemicriconemoides, Hemicycliophora arenaria, Hemicycliophora nudata, Hemicycliophora parvana, Heterodera avenae, Heterodera cruciferae, Heterodera glycines (soybean cyst nematode), Heterodera oryzae, Heterodera schachtii, Heterodera zeae (Heteroderazea), and sedentary cyst-forming parasites such as Heterodera species, Hirschmaniella gracilis, Hirschmaniella oryzae, Hirschmaniella spinicaudata, and Hirschmaniella species that are endoparasites of stems and leaves, 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 species that are ectoparasites, Meloidogyne acronea, Meloidogyne africana, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Meloidogyne artiella, Meloidogyne chitwoodi, Meloidogyne coffeicola, Meloidogyne ethiopica, MeloidogyneEthiopica), Meloidogyne exigua, Meloidogyne fallax, Meloidogyne graminicola, Meloidogyne graminis, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne kikuyensis, Meloidogyne minor, Meloidogyne naasi, Meloidogyne paranaensis, Meloidogyne thamesi and sedentary parasitic Meloidogyne species, Meloinema species, Nacobbus aberrans, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Paratrichodorus allius, Paratrichodorus lobatus, Paratrichodorus minor, Paratrichodorus nanus, Paratrichodorus porosus, Paratrichodorus teres and Paratrichodorus species, Paratylenchus hamatus, Paratylenchus minutatusMinutus), Paratylenchus projectus and Paratylenchus species, 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 Pratylenchus species which are migratory endoparasites, Pseudohalenchus minutus, Psilenchus magnidens, Psilenchus tumidas (Psilenchustumidus), Punctodera chalcoensis, Quinisulcius acutus, Radopholus citrophilus, Radopholus similis, Radopholus species which are migratory endoparasites, Rotylenchus borealis Hemicriconemoides borealis, Rotylenchulus parvus, Rotylenchulus reniformis and Rotylenchulus species, Rotylenchus laurentinus, Rotylenchus macrodoratus, Rotylenchus robustus, Rotylenchus uniformis and Rotylenchus species, Scutellonema brachyurum, Scutellonema bradys, Scutellonema clathricaudatum and Scutellonema species which are migratory endoparasites, Subanguina radiciola, Tetylenchus nicotianae, Trichodorus cylindricus, Trichodorus minor, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus and Trichodorus species which are ectoparasites, Tylenchorhynchus agri, Tylenchorhynchus brassicae, Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus digitatusdigitatus), Tylenchorhynchus ebriensis, Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus vulgaris and Tylenchorhynchus species, Tylenchulus semipenetrans and Tylenchulus species which are hemiparasites, Xiphinema americanum, Xiphinema brevicolle, Xiphinema dimorphicaudatum, Xiphinema index and Xiphinema species which are ectoparasites are included.

[0221] Nematodes against which the compounds of formula (I) can be used for control include nematodes of the genus Meloidogyne, such as the sweet potato root-knot nematode (Meloidogyne incognita), the Javanese 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, such as the potato rot nematode (Ditylenchus destructor) and the stem nematode (Ditylenchus dipsaci); nematodes of the genus Pratylenchus, such as the northern lesion nematode (Pratylenchus penetrans), the citrus lesion nematode (Pratylenchus fallax), the southern lesion nematode (Pratylenchus coffeae), the banana lesion nematode (Pratylenchus loosi), and the walnut lesion nematode (Pratylenchus vulnus); nematodes of the genus Globodera, such as the potato cyst nematode (Globodera rostochiensis) and the pale potato cyst nematode (Globodera pallida); nematodes of the genus Heterodera, such as the soybean cyst nematode (Heterodera glycines) and the sugar beet cyst nematode (Heterodera schachtii);Nematodes of the genus Aphelenchoides, such as the rice slender nematode (Aphelenchoides besseyi), the strawberry bud nematode (Aphelenchoides ritzemabosi), and the strawberry nematode (Aphelenchoides fragariae); nematodes of the genus Aphelenchus, such as the mycophagous nematode (Aphelenchus avenae); nematodes of the genus Radopholus, such as the burrowing nematode (Radopholus similis); nematodes of the genus (Tylenchulus), such as the citrus nematode (Tylenchulus semipenetrans); nematodes of the genus Rotylenchulus, such as the reniform nematode (Rotylenchulus reniformis); nematodes that inhabit trees, such as the pine wood nematode (Bursaphelenchus xylophilus) and the red ring nematode (Bursaphelenchus cocophilus), etc. are included.;

[0222] Plants for which the compounds of formula (I) can be used for their protection include cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), legumes (soybean, adzuki bean, broad bean, pea, peanut, etc.), fruit trees / fruits (apple, citrus fruits, pear, grape, peach, plum, cherry, walnut, almond, banana, strawberry, etc.), vegetable species (cabbage, tomato, spinach, broccoli, lettuce, onion, leek, pepper, etc.), root vegetables (carrot, potato, sweet potato, radish, lotus root, turnip, etc.), plants for industrial raw materials (cotton, hemp, castor oil plant, euonymus, rape, beet, hop, sugarcane, sugar beet, olive, rubber, palm tree, coffee, tobacco, tea, etc.), gourds (pumpkin, cucumber, watermelon, melon, etc.), forage plants (Japanese lawngrass, sorghum, large cricket, clover, alfalfa, etc.), lawns (Zoysia grass, bentgrass, etc.), spice plants, etc. (lavender, rosemary, thyme, parsley, pepper, ginger, etc.) and flowers (chrysanthemum, rose, orchid, etc.).

[0223] The compounds of formula (I) are particularly suitable for controlling coffee nematodes, especially Pratylenchus brachyurus, Pratylenchus coffeae, Meloidogyne exigua, Meloidogyne incognita, Meloidogyne coffeicola, species of the genus Helicotylenchus and Meloidogyne paranaensis, species of the genus Rotylenchus, species of the genus Xiphinema, species of the genus Tylenchorhynchus and species of the genus Scutellonema.

[0224] The compounds of formula (I) are nematodes of potatoes, especially Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus penetrans, Pratylenchus coffeae, Ditylenchus dipsaci and Pratylenchus alleni, Pratylenchus andinus, Pratylenchus cerealis, Pratylenchus crenatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus, Belonolaimus longicaudatus, Trichodorus cylindricus, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus, Paratrichodorus minor, Paratrichodorus allius, Paratrichodorus nanus, Paratrichodorus teresIt is particularly suitable for controlling Pratylenchus penetrans, Meloidogyne arenaria, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne thamesi, Meloidogyne incognita, Meloidogyne chitwoodi, Meloidogyne javanica, Nacobbus aberrans, Globodera rostochiensis, Globodera pallida, Ditylenchus destructor, Radopholus similis, Rotylenchulus reniformis, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Aphelenchoides fragariae and Meloinema species.

[0225] The compounds of formula (I) are particularly suitable for controlling tomato nematodes, especially Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Pratylenchus penetrans and also Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus vulnus, Paratrichodorus minor, Meloidogyne exigua, Nacobbus aberrans, Globodera solanacearum, Dolichodorus heterocephalus and Rotylenchulus reniformis.

[0226] The compounds of formula (I) are particularly suitable for controlling cucumber plant nematodes, especially Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Rotylenchulus reniformis and Pratylenchus thornei.

[0227] The compounds of formula (I) are particularly suitable for controlling nematodes, especially Belonolaimus longicaudatus, Meloidogyne incognita, Hoplolaimus columbus, Hoplolaimus galeatus and Rotylenchulus reniformis.

[0228] The compounds of formula (I) are useful against nematodes of maize, especially Belonolaimus longicaudatus, Paratrichodorus minor and also Pratylenchus brachyurus, Pratylenchus delattrei, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus zeae, (Belonolaimus gracilis), Belonolaimus nortoni, Longidorus breviannulatus, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Meloidogyne graminis, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne naasi, Heterodera avenae, Heterodera oryzae, Heterodera zeae, Punctodera chalcoensis, Ditylenchus dipsaci, Hoplolaimus aegyptii, Hoplolaimus magnistylus, Hoplolaimus galeatus, Hoplolaimus indicusIt is particularly suitable for controlling Meloidogyne incognita, Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus pseudorobustus, Xiphinema americanum, Dolichodorus heterocephalus, Criconemella ornata, Criconemella onoensis, Radopholus similis, Rotylenchulus borealis, Rotylenchulus parvus, Tylenchorhynchus agri, Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus vulgaris, Quinisulcius acutus, Paratylenchus minutus, Hemicycliophora parvana, Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Scutellonema brachyurum and Subanguina radiciola.

[0229] The compounds of formula (I) are particularly suitable for controlling soybean nematodes, especially Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus penetrans, Pratylenchus scribneri, Belonolaimus longicaudatus, Heterodera glycines, Hoplolaimus columbus, and also Pratylenchus coffeae, Pratylenchus hexincisus, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus alleni, Pratylenchus agilis, Pratylenchus zeae, Pratylenchus vulnus, (Belonolaimus gracilis), Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne hapla, Hoplolaimus columbus, Hoplolaimus galeatus and Rotylenchulus reniformis.

[0230] The compounds of formula (I) are particularly suitable for controlling tobacco nematodes, especially Meloidogyne incognita, Meloidogyne javanica and also Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus thornei, Pratylenchus vulnus, Pratylenchus zeae, Longidorus elongatu, Paratrichodorus lobatus, Trichodorus species, Meloidogyne arenaria, Meloidogyne hapla, Globodera tabacum, Globodera solanacearum, Globodera virginiae, Ditylenchus dipsaci, Rotylenchus species, Helicotylenchus species, Xiphinema americanum, Criconemella species, Rotylenchulus reniformis, Tylenchorhynchus claytoni, Paratylenchus species and Tetylenchus nicotianae.

[0231] The compounds of formula (I) are particularly suitable for controlling citrus nematodes, especially Pratylenchus coffeae and also Pratylenchus brachyurus, Pratylenchus vulnus, Belonolaimus longicaudatus, Paratrichodorus minor, Paratrichodorus porosus, Trichodorus spp., Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Rotylenchus macrodoratus, Xiphinema americanum, Xiphinema brevicolle, Xiphinema index, Criconemella spp., Hemicriconemoides, Radopholus similis and Radopholus citrophilus, Hemicycliophora arenaria, Hemicycliophora nudata and Tylenchulus semipenetrans.

[0232] The compounds of formula (I) are particularly suitable for controlling banana nematodes, especially Pratylenchus coffeae, Radopholus similis and also Pratylenchus giibbicaudatus, Pratylenchus loosi, Meloidogyne species, Helicotylenchus multicinctus, Helicotylenchus dihystera and Rotylenchulus species.

[0233] The compounds of formula (I) are effective against pine nematodes, in particular Pratylenchus zeae, Pratylenchus pratensis, Pratylenchus brachyurus, Pratylenchus goodeyi, Meloidogyne species, Rotylenchulus reniformis and also Longidorus elongatus, Longidorus laevicapitatus, Trichodorus primitivus, Trichodorus minor, Heterodera species, Ditylenchus myceliophagus, Hoplolaimus californicus, Hoplolaimus pararobustus, Hoplolaimus indicus, Helicotylenchus dihystera, Helicotylenchus nannus, Helicotylenchus multicinctus, Helicotylenchus erythrine, Xiphinema dimorphicaudatum, Radopholus similis, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Paratylenchus minutus, ScutellonemaIt is particularly suitable for controlling Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Xiphinema americanum, Xiphinema index, as well as Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus neglectus, Pratylenchus brachyurus, Pratylenchus thornei and Tylenchulus semipenetrans.

[0234] The compound of formula (I) is particularly suitable for controlling grape nematodes, especially Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Xiphinema americanum, Xiphinema index, as well as Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus neglectus, Pratylenchus brachyurus, Pratylenchus thornei and Tylenchulus semipenetrans.

[0235] The compounds of formula (I) are particularly suitable for controlling nematodes in tree crops - pomaceous fruits, in particular Pratylenchus penetrans and also Pratylenchus vulnus, Longidorus elongatus, Meloidogyne incognita and Meloidogyne hapla.

[0236] The compounds of formula (I) are particularly suitable for controlling nematodes in tree crops, especially stone fruit nematodes, in particular Pratylenchus penetrans, Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Criconemella xenoplax and Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus zeae, Belonolaimus longicaudatus, Helicotylenchus dihystera, Xiphinema americanum, Criconemella curvata, Tylenchorhynchus claytoni, Paratylenchus hamatus, Paratylenchus projectus, Scutellonema brachyurum and Hoplolaimus galeatus.

[0237] The compounds of formula (I) are particularly suitable for controlling nematodes in tree crops, sugar cane and rice, in particular species of the genus Trichodorus, Criconemella and also Pratylenchus, Paratrichodorus, Meloidogyne, Helicotylenchus, Tylenchorhynchus, Aphelenchoides, Heterodera, Xiphinema and Cacopaurus pestis.

[0238] Application The compounds of formula (I) can be applied as such or in the form of, for example, ready-to-use solutions, emulsions, aqueous or oily suspensions, powders, wettable powders, pastes, soluble powders, dusts, soluble granules, spreading granules, suspoemulsion concentrates, natural products impregnated with the compounds of formula (I), synthetic substances impregnated with the compounds of formula (I), microencapsulated in fertilizers or polymeric substances.

[0239] Application is achieved by customary methods, for example by watering, spraying, atomizing, spreading, dusting, foaming, diffusion, etc. It is also possible to develop the compounds of formula (I) by the ultra-low volume method via a drip irrigation system or perfusion application and apply it in furrows or inject it into the soil stem or trunk. Furthermore, it is possible to apply the compounds of formula (I) by means of a wound seal, paint or other wound covering material.

[0240] The effective and plant-compatible amount of the compounds of formula (I) applied to plants, plant parts, fruits, seeds or soil depends 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 treatment (curative and protective), the type of microorganism, the development stage of the microorganism, the sensitivity of the microorganism, the crop growth stage and environmental conditions.

[0241] When the compound of formula (I) is used as a fungicide, the application rate can vary within a relatively wide range depending on the type of application. For the treatment of plant parts such as leaves, the application rate can be in the range of 0.1 to 10000 g / ha, preferably 10 to 1000 g / ha, more preferably 50 to 300 g / ha (in the case of application by spraying or perfusion, especially when using an inert substrate such as rock wool or perlite, it is even possible to reduce the application rate). For the treatment of seeds, the application rate can be in the range of 0.1 to 200 g per 100 kg of seeds, preferably 1 to 150 g per 100 kg of seeds, more preferably 2.5 to 25 g per 100 kg of seeds, and even more preferably 2.5 to 12.5 g per 100 kg of seeds. For the treatment of soil, the application rate can be in the range of 0.1 to 10000 g / ha, preferably 1 to 5000 g / ha.

[0242] These application rates are merely examples and are not intended to limit the scope of the present invention.

[0243] Material protection The compounds and compositions of the present invention can also be used for the protection of materials, particularly for the protection of industrial materials against attack and destruction by undesirable microorganisms.

[0244] Furthermore, the compounds and compositions of the present invention can be used as antifouling compositions, either alone or in combination with other active ingredients.

[0245] Industrial materials in this context are understood to mean inanimate materials prepared for industrial use. For example, industrial materials to be protected from alteration or destruction by microorganisms can be adhesives, gums, paper, wallpaper and board / cardboard, textiles, carpets, leather, wood, fibers and tissues, paint and plastic articles, cooling lubricants, and other materials that can be infected by or destroyed by microorganisms. Parts of manufacturing plants and buildings that can be impaired by the growth of microorganisms, such as cooling water circuits, cooling and heating systems, and ventilation and air conditioning units, can also be mentioned within the scope of materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, sizing agents, paper and cardboard, leather, wood, paint, cooling lubricants and heat transfer fluids, more preferably wood.

[0246] The compounds and compositions of the present invention can prevent harmful effects such as putrefaction, decay, discoloration, decolorization or mold formation.

[0247] In the case of treating wood, the compounds and compositions of the present invention can also be used against fungal diseases that tend to grow on the surface or inside of lumber.

[0248] Lumber means any kind of wood and any kind of processing of this wood for construction purposes, for example, solid wood, high-density wood, laminated wood, and plywood. Furthermore, the compounds and compositions of the present invention can be used to protect objects in contact with salt water or brackish water, particularly ship hulls, screens, nets, buildings, mooring equipment and signal systems from fouling.

[0249] The compounds and compositions of the present invention can also be used to protect stored goods. Stored goods are understood to mean natural substances or products of natural origin derived from plants or animals and their processed products for which long-term protection is desired. Stored goods of plant origin, for example, plants or plant parts such as stems, leaves, tubers, seeds, fruits, grains, etc., can be protected when freshly harvested or after processing by (pre-)drying, wetting, grinding, milling, pressing or roasting. Stored goods include raw wood such as construction timber, utility poles and barriers, or wood in the form of finished products such as furniture. Stored goods of animal origin are, for example, skins, leathers, furs and hairs. The compounds and compositions of the present invention can prevent harmful effects such as decay, disintegration, discoloration, decolorization or mold formation.

[0250] Microorganisms capable of decomposing or altering industrial materials include, for example, bacteria, fungi, yeasts, algae, and slime organisms. The compounds and compositions of the present invention preferably act against fungi, particularly molds, wood-staining and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes, and Zygomycetes), as well as slime organisms and algae. Examples include microorganisms of the following genera: Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride;Species of Ophiostoma, Ceratocystis, Humicola, Petriella, Trichurus, Coriolus, Gloeophyllum, Pleurotus, Poria, Serpula and Tyromyces, Cladosporium species, Paecilomyces species, Mucor species, Escherichia, for example Escherichia coli; Pseudomonas, for example Pseudomonas aeruginosa; Staphylococcus, for example Staphylococcus aureus, Candida species and Saccharomyces species, for example Saccharomyces cerevisiae.;

Example

[0251] Synthesis of the compound of formula (I) Preparation Example 1: Preparation of 5-(4,5-dibromo-3-fluoro-2-thienyl)-6-thia-4-azaspiro[2.4]hept-4-en-7-one (Compound I.03) Step 1: Preparation of methyl 1-{[(4,5-dibromo-3-fluoro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate In a 100 mL round-bottomed flask vial under an inert atmosphere, a solution of 733 mg (4.33 mmol) of 2-chloro-1,3-dimethylimidazolidinium chloride dissolved in 4.3 mL of dichloromethane was added to a solution of 1.0 g (3.33 mmol) of 4,5-dibromo-3-fluorothiophene-2-carboxylic acid and 2.50 mL (14.3 mmol) of N,N-diisopropylethylamine dissolved in 35 mL of dichloromethane. After stirring for 15 minutes, 1.0 g (6.66 mmol) of methyl 1-aminocyclopropanecarboxylate hydrochloride (1:1) was added, and the reaction mixture was stirred at room temperature for 72 hours. Water was added, and the resulting reaction mixture was extracted twice with dichloromethane. The combined organic layers were filtered through a Chem Elut™ cartridge and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient dichloromethane / ethyl acetate) to obtain 1.24 g of the title compound (purity 100%, yield 93%) as a white solid. LogP = 2.77. (M+H) = 400.

[0252] Step 2: Preparation of methyl 1-{[(4,5-dibromo-3-fluoro-2-thienyl)carbonothioyl]amino}cyclopropanecarboxylate To a solution of 265 mg (0.65 mmol) of methyl 1-{[(4,5-dibromo-3-fluoro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate in 5 mL of 1,2-dimethoxyethane was added 267 mg (0.66 mmol) of Lawesson's reagent. The reaction mixture was stirred at 50 °C for 42 hours. The resulting reaction mixture was diluted with dichloromethane, filtered through a basic Chromabond® alumina cartridge, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient n-heptane / ethyl acetate) to obtain 158 mg of the title compound (purity 100%, yield 57%) as a yellow solid. LogP = 3.91. (M+H) = 416.

[0253] Step 3: Preparation of 1-{[(4,5-dibromo-3-fluoro-2-thienyl)carbonothioyl]amino}cyclopropanecarboxylic acid A solution of 271 mg (0.47 mmol) of methyl 1-{[(4,5-dibromo-3-fluoro-2-thienyl)carbonothioyl]amino}cyclopropanecarboxylate in 7 mL of 1,2-dichloroethane was added with 203 mg (0.47 mmol) of trimethylstannyl hydroxide. The reaction mixture was stirred at 60 °C for 18 hours. The resulting reaction mixture was concentrated under reduced pressure, dissolved in acetyl acetate, and washed three times with 1.0 M aqueous hydrochloric acid. The combined organic layers were filtered through a Chem Elut™ cartridge and concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (gradient acetonitrile / aqueous formic acid (1%)) to obtain 135 mg (purity 100%, yield 54%) of the title compound as a yellow solid. LogP = 2.95. (M+H) = 402.

[0254] Step 4: Preparation of 5-(4,5-dibromo-3-fluoro-2-thienyl)-6-thia-4-azaspiro[2.4]hept-4-en-7-one (Compound I.03) A solution of 70 mg (0.17 mmol) of 1-{[(4,5-dibromo-3-fluoro-2-thienyl)carbonothioyl]amino}cyclopropanecarboxylic acid in 2 mL of dichloromethane was added with 43 mg (0.22 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The reaction mixture was stirred at room temperature for 18 hours. Water was added, and the resulting reaction mixture was extracted twice with dichloromethane. The combined organic layers were filtered through a Chem Elut™ cartridge and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient n-heptane / ethyl acetate) to obtain 51 mg (purity 94%, yield 72%) of the title compound as a light pink solid. LogP = 5.08. (M+H) = 384.

[0255] Preparation Example 2: Preparation of 3-bromo-4-methyl-5-(7-oxo-6-oxa-4-azaspiro[2.4]hept-4-en-5-yl)thiophene-2-carbonitrile (Compound I.06) Step 1: Preparation of 4-bromo-5-cyano-3-methylthiophene-2-carboxylic acid A solution of 150 mg (0.86 mmol) of methyl 4-bromo-5-cyano-3-methylthiophene-2-carboxylate in 3.9 ml of tetrahydrofuran was added dropwise with 0.7 ml (0.7 mmol) of 1.1 M aqueous lithium hydroxide solution. The reaction mixture was stirred at room temperature for 1 hour. The resulting reaction mixture was carefully acidified with 1.0 M aqueous hydrochloric acid at 0 °C and extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain 142 mg (purity 97%, yield 97%) of the title compound as a white solid. LogP = 2.05. (M+H) = 246.

[0256] Step 2: Preparation of methyl 1-{[(4-bromo-5-cyano-3-methyl-2-thienyl)carbonyl]amino}cyclopropanecarboxylate A solution of 1.34 g (7.92 mmol) of 2-chloro-1,3-dimethylimidazolidinium chloride dissolved in 7.9 mL of dichloromethane was added to a solution of 1.50 mg (6.09 mmol) of 4-bromo-5-cyano-3-methylthiophene-2-carboxylic acid and 4.57 mL (26.2 mmol) of N,N-diisopropylethylamine dissolved in 50 mL of dichloromethane. After stirring for 15 minutes, 1.85 g (12.1 mmol) of methyl 1-aminocyclopropanecarboxylate hydrochloride (1:1) was added, and the reaction mixture was stirred at room temperature for 72 hours. Water was added, and the resulting reaction mixture was extracted twice with dichloromethane. The resulting reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient dichloromethane / ethyl acetate) to obtain 1.55 g (purity 96%, yield 71%) of the title compound as a white solid. LogP = 2.31. (M+H) = 343.

[0257] Step 3: Preparation of 1-{[(4-bromo-5-cyano-3-methyl-2-thienyl)carbonyl]amino}cyclopropanecarboxylic acid To a solution of 400 mg (1.16 mmol) of methyl 1-{[(4-bromo-5-cyano-3-methyl-2-thienyl)carbonyl]amino}cyclopropanecarboxylate in 8.0 mL of tetrahydrofuran was added dropwise 1.5 mL (0.7 mmol) of 1.0 M aqueous lithium hydroxide solution. The reaction mixture was stirred at room temperature for 2 hours. The resulting reaction mixture was 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 filtered through a Chem Elut™ cartridge and concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (gradient acetonitrile / aqueous formic acid (1%)) to give 301 mg (purity 92%, yield 72%) of the title compound as a white solid. LogP = 1.88. (M+H) = 329.

[0258] Step 3 bis: Alternative preparation of 1-{[(4-bromo-5-cyano-3-methyl-2-thienyl)carbonyl]amino}cyclopropanecarboxylic acid In a first round-bottomed flask, to a solution of 120 mg (0.48 mmol) of 4-bromo-5-cyano-3-methylthiophene-2-carboxylic acid in 4 mL of dehydrated dichloromethane were added 47 μL (0.53 mmol) of oxalyl chloride and 1 drop of N,N-dimethylformamide at room temperature. After stirring at room temperature for 45 minutes, the reaction mixture was concentrated under reduced pressure and dissolved in 2 mL of dehydrated 1,4-dioxane to obtain a solution of the acyl chloride. In a second round-bottomed flask, to a solution of 134 mg (0.97 mmol) of 1-aminocyclopropanecarboxylic acid hydrochloride (1:1) in 1 mL of water was added 1.46 mL (1.46 mmol) of 1.0 M aqueous sodium hydroxide solution. The reaction mixture was stirred at room temperature for 30 minutes and then slowly added to the previously prepared solution of the acyl chloride at 0 °C. The resulting reaction mixture was stirred at room temperature for 24 hours, diluted with water, carefully acidified to pH 1 with 1.0 M aqueous hydrochloric acid at 0 °C and extracted with ethyl acetate. The combined organic layers were filtered through a Chem Elut™ cartridge and concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (gradient acetonitrile / aqueous formic acid (1%)) to give 65 mg (purity 100%, yield 41%) of the title compound as a white solid. LogP = 1.84. (M+H) = 329.

[0259] Step 4: Preparation of 3-bromo-4-methyl-5-(7-oxo-6-oxa-4-azaspiro[2.4]hept-4-en-5-yl)thiophene-2-carbonitrile (Compound I.06) In a 100 mL round bottom flask vial under an inert atmosphere, a solution of 80 mg (0.47 mmol) of 2-chloro-1,3-dimethylimidazolidinium chloride dissolved in 0.47 mL of dichloromethane was added to a solution of 1.0 g (3.33 mmol) of 1-{[(4-bromo-5-cyano-3-methyl-2-thienyl)carbonyl]amino}cyclopropanecarboxylic acid and 0.19 mL (1.09 mmol) of N,N-diisopropylethylamine dissolved in 4 mL of dichloromethane. The reaction mixture was stirred at room temperature for 18 hours. Water was added and the resulting reaction mixture was extracted twice with dichloromethane. The combined organic layers were filtered through a Chem Elut™ cartridge and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient n-heptane / ethyl acetate) to obtain 87 mg (purity 100%, yield 77%) of the title compound as a white solid. LogP = 3.37. (M+H) = 311.

[0260] Exemplary compounds The exemplary compounds according to the present invention shown in Table 1 were prepared in the same manner as the examples provided above and / or according to the general description of the methods disclosed herein.

[0261] The following Table 1 shows, without limitation, examples of compounds according to formula (I).

Chemical formula

[0262]

Table 1

[0263] In the above table, the LogP value was measured by HPLC (High Performance Liquid Chromatography) on a reverse phase column using the following method in accordance with Annex V.A8 of EEC Directive 79 / 831: [a] The LogP value is determined by LC-UV measurement in the acidic range using 0.1% formic acid in water and acetonitrile (linear gradient from 10% to 95% acetonitrile) as the eluent.

[0264] [b] The LogP value is determined by LC-UV measurement in the neutral range using 0.001 molar aqueous ammonium acetate solution and acetonitrile (linear gradient from 10% to 95% acetonitrile) as the eluent.

[0265] [c] The LogP value is determined by LC-UV measurement in the acidic range using 0.1% phosphoric acid and acetonitrile (linear gradient from 10% to 95% acetonitrile) as the eluent.

[0266] If two or more LogP values are available within the same method, all values are shown and separated by "+".

[0267] Calibration was performed using straight-chain alkan-2-ones (having 3 to 16 carbon atoms) with known LogP values (measurement of LogP values using retention time by linear interpolation between consecutive alkanones). The λmax value was determined using the UV spectrum from 200 nm to 400 nm and the peak value of the chromatographic signal.

[0268] NMR peak list Table A provides the NMR data ( 1 H) of some of the compounds disclosed in the above table.

[0269] For the selected examples 1 The 1H-NMR data are 1It is written in the form of an H-NMR peak list. For each signal peak, the δ value is listed in ppm, and the signal intensity is listed within parentheses. There is a semicolon as a delimiter between the δ value-signal intensity pairs.

[0270] Therefore, a peak list for one example has the following form: δ 1( intensity 1); δ 2( intensity 2);........; δ i( intensity i );......; δ n( intensity n ) The intensity of a sharp signal correlates with the height (cm) of the signal in the printed example of the NMR spectrum and shows the true relationship of the signal intensity. In the case of a broad signal, the relative intensity compared to the center of several peaks or signals and the strongest signal in the spectrum can be shown.

[0271] 1 To calibrate the chemical shift of the H spectrum, especially for spectra measured in DMSO, the chemical shift of tetramethylsilane and / or the solvent is used. Therefore, in the NMR peak list, a tetramethylsilane peak may or may not be present.

[0272] 1 The list of H-NMR peaks is the same as a classical 1 H-NMR print and thus usually includes all the peaks enumerated in classical NMR interpretation.

[0273] Furthermore, these may show the solvent, as well as the signals of the stereoisomers of the target compound which is the subject of the present invention, and / or the peaks of impurities, in the same way as a classical 1 H-NMR print.

[0274] To show the compound signals in the delta range of the solvent and / or water, those of the present inventors 1The list of H-NMR peaks shows the normal solvent peaks, such as the peak of DMSO and the peak of water in DMSO-D6, which usually have a relatively high intensity on average.

[0275] The peaks of stereoisomers and / or impurities of the target compound usually have a relatively low intensity on average compared to the peak of the target compound (e.g., having a purity of more than 90%).

[0276] Such stereoisomers and / or impurities may be typical of a particular preparation method. Therefore, these peaks can help to recognize the reproduction of the inventors' preparation method by referring to the "by-product fingerprint".

[0277] Experts who calculate the peaks of the target compound by known methods (using not only MestreC and ACD simulations but also empirically evaluated expected values) can isolate the peaks of the target compound by using, if necessary, an additional intensity filter. This isolation would be similar to the relevant peak picking in classical 1 H-NMR interpretation.

[0278] Further details of the description of NMR data by the peak list can be found in "Citation of NMR Peaklist Data within Patent Applications" of Research Disclosure Database Number 564025, which is a publication.

[0279]

Table 2

[0280] Biological data Example A described below shows the induction of defense gene expression in Arabidopsis thaliana by the compounds of formula (I), specifically the stimulation of the salicylic acid pathway. Thus, these compounds would be able to induce host defense and thereby protect plants from a wide range of pathogens including bacteria and fungi.

[0281] Examples B and C described below show the direct inactivity of the compounds of formula (I) in in vitro cell tests against various pathogens including bacteria and fungi, thus exemplifying the mode of action of the compounds of formula (I) as plant host defense inducers.

[0282] Examples D, E, F and G described below show the in vivo activity of the compounds in planta of formula (I) by stimulating plant defense against various pathogens infecting plants including bacteria and fungi.

[0283] Examples H, I and J described below show the in vivo activity in planta of comparative compound CMP1 prepared according to the teachings of WO 2004 / 062361 and the compounds according to the invention. Comparative compound CMP1 has R 3 being hydrogen and at the same time R 1 and R 2 being halogen (bromine), and is structurally different from the compounds of the invention. When comparing the activity of CMP1 with the activity of the compounds of the invention, this prior art compound is clearly less active and thus shown not to provide the beneficial technical effects of the compounds of the invention.

[0284] Example A: Induction of Defense Gene Expression in Arabidopsis thaliana An Arabidopsis thaliana reporter plant containing the coding sequence of green fluorescent protein (GFP) linked to the salicylate-responsive promoter sequence of the PR1 (infection-specific protein I) gene (AT2G14610) was grown for 5 days and then the compound was sprayed. On the 3rd day after spraying, plant fluorescence was evaluated using a MacroFluo instrument manufactured by Leica Microsystems (Wetzlar, Germany). Fluorescence was quantified using Meta-Morph Microscopy Automation & Image Analysis Software (Molecular Devices, Sunnyvale, California, USA).

[0285] The background fluorescence in the mock-treated leaves was set to 1.00. Salicylic acid treatment (300 ppm) resulted in a relative fluorescence value of 2.70, demonstrating the validity of the test system.

[0286] In this test, the following compounds according to the present invention showed relative fluorescence values exceeding at least 2 at a compound concentration of 300 ppm: I.01; I.02; I.03; I.04; I.06; I.07; I.08; I.09; I.12; I.15; I.16; I.17.

[0287] In this test, the following compounds according to the present invention showed relative fluorescence values exceeding at least 2 at a compound concentration of 75 ppm: I.02; I.06; I.07; I.08; I.09; I.11; I.16; I.17.

[0288] Salicylic acid is a major defense hormone against plant pathogens. All of the above compounds may stimulate the salicylic acid pathway and thus protect plants from a wide range of pathogens.

[0289] Example B: Colletotrichum lindemuthianum in vitro cell test Solvent: DMSO Culture medium: 14.6 g of anhydrous D-glucose (VWR), 7.1 g of peptone for fungi (Oxoid), 1.4 g of granular yeast extract (Merck), QSP 1 liter Inoculum: Spore suspension The fungicide was solubilized in DMSO and the solution was used to prepare the required concentration range. The final concentration of DMSO used in the assay was 1% or less.

[0290] A spore suspension of Colletotrichum lindemuthianum was prepared and diluted to the desired spore density.

[0291] The fungicide was evaluated for its ability to inhibit spore germination and hyphal growth in a liquid culture assay. The compound was added to the culture medium containing spores at the desired concentration. After 6 days of incubation, the fungitoxicity of the compound was determined by spectrophotometry of hyphal growth. The inhibition of fungal growth was determined by comparing the absorbance value of the wells containing the fungicide with the absorbance of the control wells without the fungicide.

[0292] In this test, the following compounds according to the invention did not show direct activity at a concentration of 20 ppm of the active ingredient (efficacy of 30% or less): I.02; I.03; I.04; I.05; I.06; I.07; I.08; I.09; I.11; I.12; I.13; I.14; I.15; I.16; I.17; I.19; I.20; I.21; I.22; I.23; I.24; I.25.

[0293] Example C: Xanthomonas campestris pv. campestris in vitro cell test Solvent: DMSO Culture medium: LB broth medium (Luria broth Miller) Sigma Inoculum: Bacterial suspension The compound was solubilized in DMSO and the solution was used to prepare the required concentration range. The final concentration of DMSO used in the assay was 1% or less.

[0294] The inoculum was prepared from a pre - culture of bacteria grown in liquid medium and diluted to the desired optical density (OD).

[0295] Compounds were evaluated for their ability to inhibit bacterial growth in liquid culture assays. The compounds were added to culture media containing the bacterial suspension at the desired concentrations. After 24 hours of incubation, the effectiveness of the compounds was determined by spectrophotometric measurement of bacterial growth. Inhibition was determined by comparing the absorbance values of the wells containing the compounds to the absorbance of control wells without the active ingredient.

[0296] In this test, the following compounds according to the invention did not show direct activity at an active ingredient concentration of 20 ppm (effectiveness less than 30%): I.01; I.02; I.03; I.04; I.05; I.06; I.07; I.08; I.09; I.11; I.12; I.13; I.14; I.15; I.16; I.17; I.19; I.20; I.21; I.22; I.23; I.24; I.25.

[0297] Example D: In - vivo prophylactic test against Colletotrichum lindemuthianum (anthracnose of beans) The test active ingredient was prepared by homogenizing in a mixture of acetone / dimethyl sulfoxide / Tween® and then diluting with water to obtain the desired active material concentration.

[0298] Bean seedlings were treated by spraying with the active ingredient prepared as described above. Control plants were treated with an aqueous solution of acetone / dimethyl sulfoxide / Tween® only.

[0299] After 72 hours, the plants were contaminated by spraying an aqueous suspension of Colletotrichum lindemuthianum spores onto the leaves. 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.

[0300] The test was evaluated 6 days after inoculation. 0% means an efficacy equivalent to that of the control plants, and 100% efficacy means that no disease was observed.

[0301] In this test, the following compounds according to the invention showed an efficacy between 70% and 79% with an active ingredient concentration of 500 ppm: I.26.

[0302] In this test, the following compounds according to the invention showed an efficacy between 80% and 89% with an active ingredient concentration of 500 ppm: I.07; I.12.

[0303] In this test, the following compounds according to the invention showed an efficacy between 90% and 100% with an active ingredient concentration of 500 ppm: I.06; I.08; I.09; I.11; I.13.

[0304] In this test, the following compounds according to the invention showed an efficacy between 70% and 79% with an active ingredient concentration of 31 ppm: I.09; I.25.

[0305] In this test, the following compound according to the invention showed an efficacy between 80% and 89% with an active ingredient concentration of 31 ppm: I.22.

[0306] Example E: In vivo prophylactic test against Peronospora parasitica (downy mildew of cruciferous plants) The test active ingredient was prepared by homogenizing in a mixture of acetone / dimethyl sulfoxide / Tween® and then diluting with water to obtain the desired active material concentration.

[0307] Cabbage seedlings were treated by spraying with the active ingredient prepared as described above. Control plants were treated with only an aqueous solution of acetone / dimethyl sulfoxide / Tween®.

[0308] After 72 hours, plants were contaminated by spraying an aqueous suspension of Peronospora parasitica spores onto the leaves. The contaminated cabbage plants were incubated at 20 °C and 100% relative humidity for 5 days.

[0309] The test was evaluated 5 days after inoculation. 0% means the effectiveness corresponding to that of the control plants, and 100% effectiveness means that no disease was observed.

[0310] In this test, the following compounds according to the invention showed an effectiveness between 80% and 89% with the active ingredient at a concentration of 125 ppm: I.01; I.20; I.24.

[0311] In this test, the following compounds according to the invention showed an effectiveness between 90% and 100% with the active ingredient at a concentration of 125 ppm: I.05; I.06; I.07; I.08; I.09; I.11; I.12; I.13; I.16; I.17; I.19; I.21; I.22; I.26.

[0312] Example F: In vivo prophylactic test against Xanthomonas campestris pv. campestris (cabbage black rot) The test active ingredients were prepared by homogenizing in a mixture of acetone / dimethyl sulfoxide / Tween® and then diluting with water to obtain the desired concentration of the active material.

[0313] Cabbage seedlings were treated by spraying with the active ingredient prepared as above. Control plants were treated with only an aqueous solution of acetone / dimethyl sulfoxide / Tween®.

[0314] After 72 hours, plants were contaminated by spraying an aqueous bacterial suspension of Xanthomonas campestris pv. campestris onto the leaves. The contaminated cabbage plants were incubated at 27 °C and 95% relative humidity for 8 or 10 days.

[0315] The test was evaluated 8 or 10 days after inoculation. 0% means an efficacy corresponding to the efficacy of the control plants, and 100% efficacy means that no disease was observed.

[0316] In this test, the following compounds according to the invention showed an efficacy between 70% and 79% with an active ingredient concentration of 31 ppm: I.03; I.09; I.11; I.12; I.26.

[0317] In this test, the following compounds according to the invention showed an efficacy between 80% and 89% with an active ingredient concentration of 31 ppm: I.01; I.08.

[0318] In this test, the following compounds according to the invention showed an efficacy between 90% and 100% with an active ingredient concentration of 31 ppm: I.06; I.13.

[0319] In this test, the following compounds according to the invention showed an efficacy between 70% and 79% with an active ingredient concentration of 125 ppm: I.03; I.08; I.15.

[0320] In this test, the following compounds according to the invention showed an efficacy between 80% and 89% with an active ingredient concentration of 125 ppm: I.02; I.13.

[0321] In this test, the following compounds according to the invention showed an efficacy between 90% and 100% with an active ingredient concentration of 125 ppm: I.06; I.11; I.12.

[0322] Example G: In vivo prophylactic test against Uromyces appendiculatus (bean rust) The test active ingredient was prepared by homogenizing in a mixture of acetone / dimethyl sulfoxide / Tween® and then diluting with water to obtain the desired active material concentration.

[0323] The bean seedlings were treated by spraying with the active ingredient prepared as described above. Control plants were treated with an aqueous solution of acetone / dimethyl sulfoxide / Tween® only.

[0324] After 72 hours, the plants were contaminated by spraying an aqueous suspension of Uromyces appendiculatus spores onto the leaves. 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.

[0325] The test was evaluated 10 days after inoculation. 0% means an efficacy corresponding to that of the control plants, and 100% efficacy means that no disease was observed.

[0326] In this test, the following compounds according to the invention showed an efficacy between 70% and 79% with an active ingredient concentration of 500 ppm: I.02.

[0327] In this test, the following compounds according to the invention showed an efficacy between 80% and 89% with an active ingredient concentration of 500 ppm: I.15.

[0328] In this test, the following compounds according to the invention showed an efficacy between 90% and 100% with an active ingredient concentration of 500 ppm: I.01; I.04; I.05; I.06; I.07; I.08; I.09; I.11; I.12; I.13; I.26.

[0329] In this test, the following compounds according to the invention showed an efficacy between 70% and 79% with an active ingredient concentration of 31 ppm: I.06; I.23.

[0330] In this test, the following compounds according to the invention showed an efficacy between 80% and 89% with an active ingredient concentration of 31 ppm: I.11; I.20.

[0331] In this test, the following compounds according to the invention showed an efficacy between 90% and 100% with an active ingredient concentration of 31 ppm: I.08; I.09; I.16; I.19; I.21; I.22; I.25.

[0332] In this test, the following compounds according to the invention showed an efficacy between 70% and 79% with an active ingredient concentration of 125 ppm: I.06; I.20.

[0333] In this test, the following compounds according to the invention showed an efficacy between 90% and 100% with an active ingredient concentration of 125 ppm: I.08; I.09; I.11; I.12; I.13; I.16; I.17; I.19; I.21; I.22; I.24; I.25.

[0334] Example H: Comparative Example Compound CMP1 was tested in an in vivo prophylactic test against Xanthomonas campestris pv. campestris (black rot of cabbage) under the same conditions as described in Example F.

[0335] Compound CMP1 was prepared according to the teachings of International Publication No. WO 2004 / 062361.

[0336] The results are as shown in the following table.

[0337] [Table 3]

[0338] The compounds of formula (I) of the present invention in the following table were shown to exhibit superior efficacy compared to the structurally related compound CMP1.

[0339] [Table 4]

[0340] When tested at a concentration of 125 ppm, the compound of formula (I) of the present invention was shown to exhibit superior efficacy compared to the structurally related compound CMP1.

[0341] More specifically, at a concentration of 125 ppm, compounds I.03; I.08; I.15 were shown to exhibit efficacy between 70% and 79%, compounds I.02; I.13 were shown to exhibit efficacy between 80% and 89%, and compounds I.06; I.11; I.12 were shown to exhibit efficacy between 90% and 100%, while CMP1 was shown to exhibit efficacy of less than 40% at the same concentration.

[0342] When tested at a concentration of 31 ppm, the compound of formula (I) of the present invention was shown to exhibit superior efficacy compared to the structurally related compound CMP1.

[0343] More specifically, at a concentration of 31 ppm, compounds I.03; I.09; I.11; I.12; I.26 were shown to exhibit efficacy between 70% and 79%, compounds I.01; I.08 were shown to exhibit efficacy between 80% and 89%, and compounds I.06; I.13 were shown to exhibit efficacy between 90% and 100%, while CMP1 was shown to exhibit efficacy of less than 40% at the same concentration.

[0344] Example I: Comparative Example Compound CMP1 was tested in an in vivo prophylactic test against Uromyces appendiculatus (bean rust) under the same conditions as described in Example G.

[0345] Compound CMP1 was prepared according to the teachings of International Publication No. 2004 / 062361.

[0346] The results are as shown in the following table.

[0347]

Table 5

[0348] The compounds of formula (I) of the present invention in the following table have been shown to exhibit superior efficacy compared to the structurally related compound CMP1.

[0349]

Table 6

[0350] The compounds of formula (I) of the present invention have been shown to exhibit superior efficacy compared to the structurally related compound CMP1 when tested at a concentration of 125 ppm.

[0351] More specifically, at a concentration of 125 ppm, it has been shown that compounds I.06; I.20 exhibit efficacy between 70% and 79%, and compounds I.08; I.09; I.11; I.12; I.13; I.16; I.17; I.19; I.21; I.22; I.24; I.25 exhibit efficacy between 90% and 100%, while CMP1 has been shown to exhibit 42% efficacy at the same concentration.

[0352] The compounds of formula (I) of the present invention have been shown to exhibit superior efficacy compared to the structurally related compound CMP1 when tested at a concentration of 31 ppm.

[0353] More specifically, at a concentration of 31 ppm, it has been shown that compounds I.06; I.23 exhibit efficacy between 70% and 79%, compounds I.11; I.20 exhibit efficacy between 80% and 89%, and compounds I.08; I.09; I.16; I.19; I.21; I.22; I.25 exhibit efficacy between 90% and 100%, while CMP1 has been shown to exhibit less than 40% efficacy at the same concentration.

[0354] Example J: Comparative Example Compound CMP1 was tested in an in vivo prophylactic test against Colletotrichum lindemuthianum (anthracnose of legumes) under the same conditions as described in Example D.

[0355] Compound CMP1 was prepared according to the teachings of International Publication No. 2004 / 062361.

[0356] The results are as shown in the following table.

[0357]

Table 7

[0358] The compounds of formula (I) of the present invention in the following table were shown to exhibit better efficacy than the structurally related compound CMP1.

[0359]

Table 8

[0360] The compounds of formula (I) of the present invention were shown to exhibit better efficacy than the structurally related compound CMP1 when tested at a concentration of 31 ppm.

[0361] More specifically, at a concentration of 31 ppm, compounds I.09; I.25 were shown to exhibit efficacy between 70% and 79%, compound I.22 was shown to exhibit efficacy between 90% and 100%, while CMP1 was shown to exhibit efficacy of less than 20% at the same concentration.

Claims

1. A compound of formula (I): 【Chemical Formula 1】 (wherein, R １ and R ２ are each independently selected from the group consisting of halogen, cyano, C １ to C ６ -alkyl, C １ to C ６ -haloalkyl; R ３ is selected from the group consisting of halogen, C1-C6-alkyl; W and Y are each independently selected from the group consisting of oxygen and sulfur; R ４ and R ５ are each independently selected from the group consisting of hydrogen and C1-C6-alkyl; or R ４ and R ５ together with the carbon atom to which they are attached form a C3-C6-carbon ring; However, when R １ and R ２ are the same and are bromine or chlorine, W is sulfur, or R ４ and R ５ do not combine with the carbon atom to which they are attached to form cyclopropyl).

2. R １ The compound according to claim 1, wherein R is selected from the group consisting of halogen and cyano.

3. R ２ The compound according to claim 1 or 2, wherein R is halogen.

4. R ４ and R ５ together with the carbon atom to which they are attached form a C ３ -C ６ -carbon ring, a compound according to any one of claims 1 to 3.

5. The compound according to any one of claims 1 to 4, wherein W is oxygen.

6. The compound according to any one of claims 1 to 5, wherein Y is oxygen.

7. A composition comprising a compound of formula (I) according to any one of claims 1 to 6 and at least one agriculturally suitable adjuvant.

8. A method for controlling bacterial and / or fungal diseases in plants, comprising applying a compound of formula (I) according to any one of claims 1 to 6 or the composition according to claim 7 to plants, plant parts, seeds, fruits or the soil in which the plants grow.

9. Use of a compound according to any one of claims 1 to 6 or the composition according to claim 7 for controlling bacterial and / or fungal diseases on plants or plant parts.

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