Microbicide pyrazole derivatives

Abstract

Compounds of formula (I): JPEG2025532977000094.jpg33160, wherein the substituents are as defined in claim 1, and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of these compounds, which may be used as fungicides.

Description

[Technical Field]

[0001] The present invention relates to microbicidal pyrazole derivatives as active ingredients having, for example, microbicidal, particularly fungicidal, activity. The present invention also relates to the preparation of these pyrazole derivatives, intermediates useful in the preparation of these pyrazole derivatives, the preparation of these intermediates, agrochemical compositions comprising at least one of the pyrazole derivatives, the preparation of these compositions, and the use of the pyrazole derivatives or compositions in agriculture or horticulture to control or prevent infestation of plants, harvested food crops, seeds, or non-living materials by phytopathogenic microorganisms, particularly fungi. Summary of the Invention [Means for solving the problem]

[0002] According to a first aspect of the present invention, there is provided a compound of formula (I): [ka] (In the formula, R 1 is selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or C3-C6 cycloalkyl; R 2 is selected from hydrogen, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkylcarbonyl, N—C1-C4 alkoxy-C—C1-C4 alkyl-carbonimidoyl, N-hydroxy-C—C1-C4 alkyl-carbonimidoyl, or C1-C4 alkoxycarbonyl; R 3 is selected from hydrogen, halogen, or C1-C4 alkyl; R 4 is selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, C1-C4 alkylaminocarbonyl, or di(C1-C4 alkylamino)carbonyl; R 5and R 6 are independently selected from hydrogen or C1-C4 alkyl; A 1 is CR 7 or N, A 2 is CR 8 or N; A 3 is CR 9 or N; R 7 , R 8 , and R 9 are independently selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or C1-C4 haloalkyl; Q is Q1, Q2, Q3, Q4, or Q5; [ka] (In the formula, R 10 , R 11 , R 12 and R 13 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, NC 1-4 Alkylamino, N,N-diC 1-4independently selected from alkylamino, C1-C6 alkoxycarbonyl, C1-C4 alkylcarbonyl, N—C1-C4 alkoxy-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C1-C4 alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, amino, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S, and said phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl are unsubstituted or substituted by 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxy; Z 1 is selected from C1-C4 alkyl, phenyl, 5- or 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein any of said 5- or 6-membered heteroaryl contains 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S, and any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, or C2-C4 alkynyl); or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof is provided.

[0003] Surprisingly, it has been found that the compounds of formula (I) have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases caused by fungi.

[0004] According to a second aspect of the present invention there is provided an agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to the present invention. Such an agricultural composition may further comprise at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

[0005] According to a third aspect of the present invention, there is provided a method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, which comprises applying a fungicidally effective amount of a compound of formula (I) according to the present invention, or a composition comprising a compound of formula (I), to the plant, its parts or its habitat.

[0006] According to a fourth aspect of the present invention, there is provided the use of a compound of formula (I) according to the present invention as a fungicide. According to this particular aspect of the present invention, this use may not include methods involving the treatment of the human or animal body by surgery or therapy and diagnostic methods performed on the human or animal body.

[0007] The compounds of formula (I) having at least one basic center can form, for example, acid addition salts with strong inorganic acids, such as mineral acids such as perchloric acid, sulfuric acid, nitric acid, nitrous acid, phosphoric acid, or hydrohalic acids; with strong organic carboxylic acids, such as unsubstituted or halogen-substituted C1-C4 alkanecarboxylic acids, such as acetic acid; with saturated or unsaturated dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, or phthalic acid; with hydroxycarboxylic acids, such as ascorbic acid, lactic acid, malic acid, tartaric acid, citric acid, or benzoic acid; or with organic sulfonic acids, such as unsubstituted or halogen-substituted C1-C4 alkane or arylsulfonic acids, such as methane or p-toluenesulfonic acid. Compounds of formula (I) having at least one acidic group can, for example, form salts with bases, for example mineral salts, for example alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or organic amines, for example morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, for example ethyl, diethyl, triethyl or dimethylpropylamine, or mono-, di- or trihydroxy-lower alkylamines, for example mono-, di- or triethanolamine.

[0008] In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as N-oxides or in salt form, for example in agriculturally useful salt form.

[0009] N-oxides are the oxidized forms of tertiary amines or nitrogen-containing heteroaromatic compounds, as described, for example, in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0010] The compounds of formula (I) according to the invention also include the hydrates which may be formed during salt formation.

[0011] When a substituent is designated as "optionally substituted," it means that such substituent may be substituted with one or more of the same or different substituents, for example, 1, 2, or 3 R x It means that it may or may not have a substituent. For example, C1-C6 alkyl substituted with 1, 2 or 3 halogens includes -CH2Cl, -CHCl2, -CCl 3、 Examples include, but are not limited to, -CHF, -CHF, -CF, -CHCF, or -CFCH groups. As another example, C-C alkoxy substituted with 1, 2, or 3 halogens includes, but is not limited to, CHClO-, CHClO-, CClO-, CHFO-, CHFO-, CFO-, CFCHO-, or CHCFO- groups. Furthermore, the term "optionally substituted," as used herein, means that the referenced group is unsubstituted or substituted. DETAILED DESCRIPTION OF THE INVENTION

[0012] As used herein, the term "halogen" or "halo" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine. This also applies correspondingly to halogen in combination with other meanings, such as haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, and halocycloalkyl.

[0013] As used herein, amino refers to the group —NH 2 .

[0014] As used herein, cyano refers to a -CN group.

[0015] As used herein, the term "hydroxyl" or "hydroxy" refers to an --OH group.

[0016] As used herein, the term "carboxylic acid" refers to a -COOH group.

[0017] As used herein, "C1-C n The term "-alkyl" refers to a saturated straight or branched hydrocarbon radical having 1 to n carbon atoms attached via any of the carbon atoms, such as any one of the radicals methyl, ethyl, n-propyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, n-pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl.

[0018] As used herein, "C2-C n The term "-alkenyl" refers to a straight or branched alkenyl chain moiety having 2 to n carbon atoms and one or two double bonds, for example ethenyl, prop-1-enyl, but-2-enyl.

[0019] As used herein, "C2-C n The term "-alkynyl" refers to a straight or branched alkynyl chain moiety having 2 to n carbon atoms and one triple bond, for example, ethynyl, prop-2-ynyl, but-3-ynyl.

[0020] As used herein, "C3-C n The term "-cycloalkyl" refers to a 3- to n-membered cycloalkyl radical, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0021] As used herein, "C1-C nThe term "C2-C6-alkoxy" refers to a linear or branched saturated alkyl radical having 1 to n carbon atoms (as defined above) attached through an oxygen atom, i.e., any one of the following radicals: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, and 1,1-dimethylethoxy. n The term "-alkenyloxy" refers to a straight or branched alkenyl chain having 2 to n carbon atoms (as defined above) attached through an oxygen atom.

[0022] As used herein, "C1-C nThe term "haloalkyl" refers to a straight or branched saturated alkyl radical having 1 to n carbon atoms bonded via any of the carbon atoms (as defined above), wherein some or all of the hydrogen atoms in these radicals may be replaced by fluorine, chlorine, bromine and / or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl and n-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, or nonafluorobutyl. Thus, the term "C1-C2 fluoroalkyl" refers to any one of C1-C2 alkyl radicals having 1, 2, 3, 4, or 5 fluorine atoms, such as difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, or pentafluoroethyl. Similarly, as used herein, "C2-C n -haloalkenyl" or "C2-C n The term "haloalkynyl" refers to any C-C alkyl group substituted with one or more halogen atoms, which may be the same or different. n Alkenyl or C2-C nSimilarly, as used herein, "C-C" refers to an alkynyl radical. n -halocycloalkyl" or "C1-C n The term "haloalkoxy" refers to any C-C alkyl group substituted with one or more halo atoms, which may be the same or different. n -cycloalkyl radical or C1-C n -refers to alkoxy radicals.

[0023] As used herein, "C1-C n -alkylthio" or "C1-C n The term "-alkylsulfanyl" refers to a C1-C alkyl group linked through a sulfur atom. n -refers to alkyl groups.

[0024] As used herein, "C1-C n The term "-alkylsulfinyl" refers to a C1-C alkylsulfinyl group linked through the sulfur atom of the sulfinyl (or S(=O)-) group. n Refers to an alkyl group.

[0025] As used herein, "C1-C n The term "-alkylsulfonyl" refers to a C1-C2 alkyl group linked through the sulfur atom of the sulfonyl (or S(=O)2-) group. n Refers to an alkyl group.

[0026] As used herein, "C1-C n The term "-alkylcarbonyl" refers to a C1-C alkyl group linked through the carbon atom of a carbonyl (C=O) group. n -refers to alkyl groups.

[0027] As used herein, "C1-C n The term "-alkoxycarbonyl" refers to a C1-C alkoxycarbonyl group linked through the carbon atom of the carbonyl (or C=O) group. n -refers to the alkoxy moiety.

[0028] As used herein, "C1-C nThe term "-alkoxycarbonyl-C1-C6-alkyl" refers to "C1-C n -C1-C substituted with alkoxycarbonyl group n -refers to alkyl radicals.

[0029] As used herein, the term "benzoyl" refers to a phenyl group attached through the carbon atom of a carbonyl (C=O) group.

[0030] As used herein, "C1-C n The term "-alkylaminocarbonyl" refers to a C1-C aryl group linked through the carbon atom of a carbonyl (C=O) group. n -Alkylamino group (or R a NHC(=O)-, where R a is C1~C n -alkyl groups).

[0031] As used herein, the term “N—C1-C4 alkoxy-C—C1-C4 alkyl-carbonimidoyl” refers to a group of the formula —C(R a )=NO(R b )(wherein, R a is a C1-C4 alkyl radical as generally defined above, and R b refers to a radical of the formula (wherein 1 is a C1-C4 alkyl radical as generally defined above).

[0032] As used herein, the term “N-hydroxy-C—Ci-C4 alkyl-carbonimidoyl” refers to a group of the formula —C(R a )=NOH(where R a refers to a radical of the formula (wherein 1 is a C1-C4 alkyl radical as generally defined above).

[0033] As used herein, the term "heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring radical containing 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S. Examples of heteroaryl include, but are not limited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl, or pyridyl. "Heteroaryl-C1-C n -alkyl" or "heteroaryl-C3-C n The term "-cycloalkyl" refers to any C1-C4 alkyl group substituted with a heteroaryl group. n -Alkyl or C3-C n -refers to cycloalkyl radicals. Heteroaryl-C1-C n -Alkyl or Heteroaryl-C3-C n -Cycloalkyl radicals may be optionally substituted on the heteroaryl, alkyl and / or cycloalkyl groups.

[0034] As used herein, the term "control" refers to reducing the number of pests, eradicating pests and / or preventing further pest damage, such that damage to plants or plant-derived products is reduced.

[0035] As used herein, the term "pest" refers to insects and mollusks found in agriculture, horticulture, forestry, and storage of plant-based products (such as fruit, grain, and lumber); pests associated with damage to man-made structures. The term pest encompasses all stages in the life cycle of a pest.

[0036] As used herein, the term "effective amount" refers to the amount of a compound or salt thereof that produces a desired effect upon one or more applications.

[0037] An effective amount is readily determined by one skilled in the art by using known techniques and by observing results obtained under analogous circumstances. In determining an effective amount, several factors are taken into consideration, including, but not limited to: the type of plant or derived product to be applied; the pest to be controlled and its life cycle; the particular compound applied; the type of application; and other relevant circumstances.

[0038] As used herein, the terms "room temperature" or "RT" or "rt" refer to a temperature of about 15° C. to about 35° C. For example, rt can refer to a temperature of about 20° C. to about 30° C.

[0039] The following list refers to compounds of formula (I) of the present invention and defines substituent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , A 1 , A 2 , A 3 , Q (Q1, Q2, Q3, Q4, and Q5) and Z 1 For any one of these substituents, any definition given below can be combined with any definition of any other substituent given below or elsewhere in this specification.

[0040] In one embodiment of the present invention, R 1 is selected from C1 to C4 alkyl. Preferably, R 1 is methyl, ethyl or isopropyl. More preferably, R 1 is methyl.

[0041] In one embodiment of the present invention, R 2is selected from hydrogen, halogen, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C2 alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C2 alkyl-carbonimidoyl, or N-hydroxy-C-C1-C2 alkyl-carbonimidoyl. 2 is selected from hydrogen, halogen, methyl, ethyl, cyclopropyl, C1-C2-alkylcarbonyl, N-C1-C2 alkoxy-C-C1-C2 alkyl-carbonimidoyl, or N-hydroxy-C1-C2 alkyl-carbonimidoyl. 2 is selected from hydrogen, fluorine, chlorine, bromine, methyl, ethyl, cyclopropyl, acetyl, -C(CH3)=NOCH3, -C(CH3)=NOCH2CH3, or -C(CH3)=NOH. Even more preferably, R 2 is selected from hydrogen, fluorine, chlorine, or methyl.

[0042] In one embodiment of the present invention, R 3 is selected from hydrogen, halogen, or C1-C2 alkyl. 3 is hydrogen, fluorine, chlorine, or methyl. More preferably, R 3 is hydrogen or methyl. Even more preferably, R 3 is hydrogen.

[0043] In one embodiment of the present invention, R 4 is hydrogen, halogen, C1-C4 alkyl, cyano, C1-C4-alkylcarbonyl, or C1-C4-alkoxycarbonyl. 4 is hydrogen, chlorine, fluorine, C1-C3-alkyl, cyano, or CO2Me. More preferably, R 4 is hydrogen, methyl, ethyl, isopropyl, or cyano. Even more preferably, R 4 is hydrogen or methyl. In one embodiment, R 4 is hydrogen. In another embodiment, R 4 is methyl.

[0044] In one embodiment of the present invention, R 5 and R 6 are independently selected from hydrogen or C1-C2-alkyl. Preferably, R 5 and R 6 are independently selected from hydrogen or methyl. More preferably, R 5 and R 6 is hydrogen.

[0045] In one embodiment of the invention, Q is Q1, Q2, Q3 or Q4: [ka] (In the formula, R 10 , R 11 , R 12 and R 13 is as defined above).

[0046] Preferably, Q is Q1, Q2, or Q3: [ka] (In the formula, R 10 , R 11 , R 12 and R 13 is as defined above).

[0047] More preferably, Q is Q1: [ka] (In the formula, R 10 , R 11 , R 12 and R 13 is as defined above).

[0048] In one embodiment of the present invention, R 12 and R 13 are independently selected from hydrogen, halogen, cyano, C1-C4 alkyl, or C1-C4 alkoxy. Preferably, R 12 and R 13are independently selected from hydrogen, chlorine, bromine, fluorine, or methyl. More preferably, R 12 and R 13 is hydrogen.

[0049] In one embodiment of the present invention, R 10 and R 11 is hydrogen, halogen, hydroxy, cyano, amino, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, NC 1-4 Alkylamino, N,N-diC 1-4 and wherein said phenyl, 5- or 6-membered heteroaryl and C3-C6-cycloalkyl are independently selected from alkylamino, C1-C6 alkoxycarbonyl, C1-C4 alkylcarbonyl, N—C1-C4 alkoxy-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C1-C4 alkyl-carbonimidoyl, trifluoromethyl, sulfonyloxy, carboxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S, and wherein any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxy.

[0050] In another embodiment of the present invention, R 10 and R 11is hydrogen, halogen, cyano, amino, C1-C3 alkyl, C1-C2 haloalkyl, C1-C3 haloalkoxy, C1-C4 alkoxy, C2-C3 alkenyloxy, C2-C3 alkynyloxy, C1-C2 alkylsulfanyl, C1-C2 alkylsulfinyl, C1-C2 alkylsulfonyl, C1-C2 alkoxy-C1-C2 alkyl, C1-C3 alkoxycarbonyl, C1-C2 alkylcarbonyl, N-C1-C2 alkoxy-C-C1-C2 alkyl-carbonimidoyl, N-hydroxy-C1-C2 alkyl-carbonimidoyl, hydroxy, and independently selected from C1-C2 alkylaminocarbonyl, di(C1-C2 alkylamino)carbonyl, trifluoromethylsulfonyloxy, carboxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains 1 or 2 heteroatoms individually selected from N and O, and wherein any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloalkyl is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from halogen, cyano, or methyl.

[0051] In a preferred embodiment, R 10 and R 11is hydrogen, halogen, cyano, amino, C1-C3 alkyl, C1-C2 haloalkyl, C1-C3 haloalkoxy, C1-C4 alkoxy, C2-C3 alkenyloxy, C2-C3 alkynyloxy, C1-C2 alkylsulfanyl, C1-C2 alkylsulfnyl, C1-C2 alkylsulfonyl, C1-C2 alkoxy-C1-C2 alkyl, C1-C3 alkoxycarbonyl, C1-C2 alkylcarbonyl, N-C1-C2 alkoxy-C-C1-C2 alkyl-carbonimidoyl, N-hydroxy-C1-C2 alkyl-carbonimidoyl, hydroxy, C1-C2 alkylaminocarbonyl, di(C1-C2 alkylamino)carbonyl, trifluoromethylsulfonyloxy, carboxy, phenyl, 2-cyanophenyl, 3-cyanophenyl , 4-cyanophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, [4-(trifluoromethyl)pyrazol-1-yl], [3-(trifluoromethyl)pyrazol-1-yl], (3-cyanopyrazol-1-yl), (4-cyanopyrazol-1-yl), (5-chloropyrazol-1-yl), (4-chloropyrazol-1-yl), (3-chloropyrazol-1-yl), (5-fluoropyrazol-1-yl), (4-fluoropyrazol-1-yl), (3-fluoropyrazol-1-yl), (3,5-dimethylpyrazol-1-yl), (5-methylpyrazol-1-yl), (4-methylpyrazol-1-yl), (3-methylpyrazol-1-yl), pyrazol-1-yl, cyclopropyl, or 1-cyanocyclopropyl.

[0052] More preferably, R 10 and R 11is hydrogen, chloro, fluoro, bromo, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, methoxy, ethoxy, propoxy, allyloxy, prop-2-ynoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, 2-methoxyethoxymethyl, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetyl, propanoyl, -C(CH3)=NOCH3, -C(CH3)=NOCH2CH3, -C(CH3)=NOH, methylaminocarbonyl, di(methylamino)carbonyl, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, and R is independently selected from aryl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, [4-(trifluoromethyl)pyrazol-1-yl], [3-(trifluoromethyl)pyrazol-1-yl], (3-cyanopyrazol-1-yl), (4-cyanopyrazol-1-yl), (5-chloropyrazol-1-yl), (4-chloropyrazol-1-yl), (3-chloropyrazol-1-yl), (5-fluoropyrazol-1-yl), (4-fluoropyrazol-1-yl), (3-fluoropyrazol-1-yl), (3,5-dimethylpyrazol-1-yl), (5-methylpyrazol-1-yl), (4-methylpyrazol-1-yl), (3-methylpyrazol-1-yl), pyrazol-1-yl, cyclopropyl, or 1-cyanocyclopropyl. 10 and R 11is hydrogen, chloro, fluoro, bromo, methyl, trifluoromethyl, difluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, methoxy, propoxy, allyloxy, prop-2-ynoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, 2-methoxyethoxymethyl, methoxycarbonyl, acetyl, propanoyl, -C(CH3)=NOCH3, -C(CH3)=NOCH2CH3, -C(CH3)=NOH, methylaminocarbonyl, di(methylamino)carbonyl, trifluoromethyl-sulfonyloxy, cyano, carboxy, phenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, [4-(

[0039] Even more preferably, R is independently selected from (3-(trifluoromethyl)pyrazol-1-yl), (3-cyanopyrazol-1-yl), (4-cyanopyrazol-1-yl), (5-chloropyrazol-1-yl), (4-chloropyrazol-1-yl), (3-chloropyrazol-1-yl), (5-fluoropyrazol-1-yl), (4-fluoropyrazol-1-yl), (3-fluoropyrazol-1-yl), (3,5-dimethylpyrazol-1-yl), (5-methylpyrazol-1-yl), (4-methylpyrazol-1-yl), (3-methylpyrazol-1-yl), pyrazol-1-yl, cyclopropyl, or 1-cyanocyclopropyl. 10 and R 11are independently selected from hydrogen, chloro, fluoro, bromo, methoxy, cyano, amino, carboxy, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, (3-cyanopyrazol-1-yl), (4-cyanopyrazol-1-yl), (5-chloropyrazol-1-yl), (4-chloropyrazol-1-yl), (3-chloropyrazol-1-yl), (5-fluoropyrazol-1-yl), (4-fluoropyrazol-1-yl), (3-fluoropyrazol-1-yl), (3,5-dimethylpyrazol-1-yl), (5-methylpyrazol-1-yl), (4-methylpyrazol-1-yl), (3-methylpyrazol-1-yl), pyrazol-1-yl, cyclopropyl, and 1-cyanocyclopropyl.

[0053] In yet another embodiment of the present invention, R 10 and R 11 are independently selected from hydrogen, halogen, cyano, amino, C1-C4 alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N, and any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloalkyl is unsubstituted or substituted by one or two substituents independently selected from halogen, cyano, or methyl. More preferably, R 10 and R 11 are independently selected from hydrogen, chloro, bromo, methoxy, cyano, amino, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, (3-cyanopyrazol-1-yl), (4-cyanopyrazol-1-yl), (3,5-dimethylpyrazol-1-yl), (5-methylpyrazol-1-yl), (4-methylpyrazol-1-yl), (3-methylpyrazol-1-yl), pyrazol-1-yl, cyclopropyl, and 1-cyanocyclopropyl. Even more preferably, R 10 and R 11 are independently selected from hydrogen, chloro, bromo, cyano, or amino.

[0054] In certain embodiments of the invention, Q is Q1, Q2, Q3, or Q4: [ka] (In the formula, R 10 and R 11 is independently selected from hydrogen, halogen, cyano, amino, C1-C4 alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N, and any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloalkyl is unsubstituted or substituted by 1 or 2 substituents independently selected from halogen, cyano, or methyl; R 12 and R 13 is hydrogen).

[0055] In another embodiment of the present invention, Q is selected from Q1, Q2, Q3, or Q4, wherein R 10 and R 11 are independently selected from hydrogen, halogen, cyano, or amino; R 12 and R 13 is hydrogen. Preferably, Q is Q1, Q2, or Q3: [ka] (In the formula, R 10 and R 11 are independently selected from hydrogen, halogen, cyano, amino, C1-C4 alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N, and any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloalkyl is unsubstituted or substituted by 1 or 2 substituents independently selected from halogen, cyano, or methyl; R 12 and R 13is hydrogen).

[0056] In another embodiment of the present invention, Q is selected from Q1, Q2, or Q3, wherein R 10 and R 11 are independently selected from hydrogen, halogen, cyano, or amino; R 12 and R 13 is hydrogen.

[0057] More preferably, Q is Q1: [ka] (In the formula, R 10 and R 11 are independently selected from hydrogen, halogen, cyano, amino, C1-C4 alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N, and any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloalkyl is unsubstituted or substituted by 1 or 2 substituents independently selected from halogen, cyano, or methyl; R 12 and R 13 is hydrogen).

[0058] In another embodiment of the present invention, Q is Q1, wherein R 10 and R 11 are independently selected from hydrogen, halogen, cyano, or amino; R 12 and R 13 is hydrogen.

[0059] In one embodiment of the present invention, A 1 is CR 7 or N, and 2 is CR 8 or N, and 3 is CR 9 or N, and 1 , A 2 and A3 At least two of A are selected from N. Preferably, in one embodiment of the present invention, A 1 is CR 7 Selected from A 2 and A 3 is N. Preferably, in another embodiment, A 1 and A 2 is N and A 3 is CR 9 Preferably, in another embodiment, A 1 is N and A 2 is CR 8 and A 3 is N. More preferably, A 1 , A 2 , and A 3 is N.

[0060] In another embodiment of the present invention, A 1 and A 2 is N and A 3 is CR 9 In yet another embodiment of the present invention, A 1 is CR 7 and A 2 is CR 8 and A 3 is N. In yet another embodiment of the present invention, A 1 is N and A 2 is CR 8 and A 3 is CR 9 In yet another embodiment of the present invention, A 1 is CR 7 and A 2 is N and A 3 is CR 9 is.

[0061] In one embodiment of the present invention, R 7 , R 8 , and R 9 are independently selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, or C2-C4 alkynyl. Preferably, R 7 , R 8 , and R9 are independently selected from hydrogen, halogen, methyl, or trifluoromethyl. More preferably, R 7 , R 8 , and R 9 is hydrogen.

[0062] In an embodiment of the present invention, Z 1 is selected from C1-C4 alkyl, phenyl, 5- or 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein said 5- or 6-membered heteroaryl contains 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S, and either of said phenyl and 5- or 6-membered heteroaryl is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkynyl, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, or C1-C4 alkylsulfonyl, and said C3-C6-cycloalkyl is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxy.

[0063] In another embodiment, Z 1 is selected from C1-C3 alkyl, phenyl, 5- or 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein said 5- or 6-membered heteroaryl contains 1, 2, or 3 heteroatoms individually selected from N, O, or S; any of said phenyl and 5- to 6-membered heteroaryl is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from fluoro, chloro, methyl, ethyl, ethynyl, methoxy, or methylsulfonyl; and said C3-C6-cycloalkyl is unsubstituted or substituted with 1 or 2 substituents selected from methyl.

[0064] In another embodiment, Z 1is selected from C1-C3 alkyl, phenyl, 5- to 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein the 5- or 6-membered heteroaryl contains one heteroatom selected from N, O, or S, and either the phenyl and the 5- to 6-membered heteroaryl is unsubstituted or substituted with 1 or 2 substituents independently selected from fluoro, chloro, methyl, ethyl, ethynyl, methoxy, or methylsulfonyl, and the C3-C6-cycloalkyl is unsubstituted or substituted with 1 or 2 substituents selected from methyl.

[0065] Preferably, Z 1 is 1-methylpyrazol-4-yl, 2,3,4-trifluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 2,4,6-trifluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3,5-difluoro-2-pyridyl, 5-fluoro-2-pyridyl, 3-fluoro-2-pyridyl, 2-fluoro-4-methoxy-phenyl, 2-fluoro-4-methylsulfonyl-phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 3,5-difluoro-2-furyl, 3- fluoro-2-furyl, 5-fluoro-2-furyl, 3,5-difluoro-2-thienyl, 3-fluoro-2-thienyl, 5-fluoro-2-thienyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-methoxyphenyl, 4-ethynyl-2-fluoro-phenyl, 4-fluoro-2-methoxy-phenyl, cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclohexyl, cyclopentyl, methyl, n-propyl, or phenyl. More preferably, Z 1is selected from 1-methylpyrazol-4-yl, 2,4,6-trifluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2-chlorophenyl, 2-fluorophenyl, 2-furyl, 2-methylphenyl, 2-thienyl, 3,4-difluorophenyl, 3-chlorophenyl, 3-fluorophenyl, 3-methylphenyl, 3-thienyl, 4-fluoro-2-methoxy-phenyl, 4-fluorophenyl, 4-methylphenyl, cyclobutyl, cyclohexyl, cyclopentyl, methyl, or phenyl. Even more preferably, Z 1 is selected from 1-methylpyrazol-4-yl, 2,4,6-trifluorophenyl, 3,5-difluoro-2-pyridyl, 2,4-difluorophenyl, 2-fluorophenyl, 2-furyl, 2-methylphenyl, 2-thienyl, 3,4-difluorophenyl, 3-chlorophenyl, 3-thienyl, 4-fluoro-2-methoxy-phenyl, 4-fluorophenyl, cyclobutyl, cyclohexyl, cyclopentyl, or phenyl. Even more preferably, Z 1 is selected from 2,4-difluorophenyl, 3,5-difluoro-2-pyridyl, 2-fluorophenyl, 4-fluorophenyl, or phenyl.

[0066] In another embodiment of the present invention, Z 1 is selected from C1-C4 alkyl, phenyl, 5- to 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein said 5- or 6-membered heteroaryl contains 1, 2, or 3 heteroatoms individually selected from N, O, or S, and said phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with 1 or 2 substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, or C1-C4 alkoxy, and said C3-C6-cycloalkyl is unsubstituted or substituted with 1 substituent selected from halogen or C1-C4 alkyl. Preferably, Z 1is selected from phenyl or 5- to 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl contains one heteroatom selected from N or S, and the phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with one or two substituents independently selected from fluoro, chloro, C1-C4 alkyl, or C1-C4 alkoxy. More preferably, Z 1 is selected from 1-methylpyrazol-4-yl, 2,4,6-trifluorophenyl, 2,4-difluorophenyl, 3,5-difluoro-2-pyridyl, 5-fluoro-2-pyridyl, 3-fluoro-2-pyridyl, 2-fluorophenyl, 3,5-difluoro-2-furyl, 3-fluoro-2-furyl, 5-fluoro-2-furyl, 3,5-difluoro-2-thienyl, 3-fluoro-2-thienyl, 5-fluoro-2-thienyl, 2-methylphenyl, 2-thienyl, 3,4-difluorophenyl, 3-chlorophenyl, 3-thienyl, 4-fluoro-2-methoxy-phenyl, 4-fluorophenyl, cyclobutyl, cyclohexyl, cyclopentyl, or methyl. Even more preferably, Z 1 is selected from 2,4-difluorophenyl, 3,5-difluoro-2-pyridyl, 5-fluoro-2-pyridyl, 3-fluoro-2-pyridyl, 3,5-difluoro-2-furyl, 3-fluoro-2-furyl, 5-fluoro-2-furyl, 3,5-difluoro-2-thienyl, 3-fluoro-2-thienyl, 5-fluoro-2-thienyl, 2-fluorophenyl, 4-fluorophenyl, or phenyl.

[0067] In another embodiment of the present invention, Z 1is selected from phenyl, 5- to 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein the 5- or 6-membered heteroaryl contains one heteroatom selected from N or S, the phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with one or two substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, or C1-C4 alkoxy, and the C3-C6-cycloalkyl is unsubstituted or substituted with one substituent selected from halogen or C1-C4 alkyl. Preferably, Z 1 is selected from phenyl or 5- to 6-membered heteroaryl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N or S, and said phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with 1 or 2 substituents independently selected from fluoro, chloro, C1-C4 alkyl, or C1-C4 alkoxy.

[0068] Therefore, the present invention provides 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , A 1 , A 2 , A 3 , Q (Q-1, Q2, Q3, Q4, and Q5) and Z 1 Compounds of formula (I) having the formula: are made available with reference to formula (I) defined above in all combinations / permutations.

[0069] The embodiments according to the present invention are as follows.

[0070] In one embodiment, a compound of formula (I), wherein R 1is selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl; R 2 is selected from hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkylcarbonyl, N—C1-C4 alkoxy-C—C1-C4 alkyl-carbonimidoyl, N-hydroxy-C—C1-C4 alkyl-carbonimidoyl, or C1-C6 alkoxycarbonyl; R 3 is selected from hydrogen, halogen, or C1-C4 alkyl; R 4 is selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, C1-C4 alkylaminocarbonyl, or di(C1-C4 alkylamino)carbonyl; R 5 and R 6 are independently selected from hydrogen or C1-C4 alkyl; A 1 is CR 7 or N, A 2 is CR 8 or N; A 3 is CR 9 or N; R 7 , R 8 , and R 9 are independently selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or C1-C4 haloalkyl; Q is Q1, Q2, Q3, Q4, or Q5; [ka] (In the formula, R 10 , R 11 , R 12 and R 13is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, NC 1-4 Alkylamino, N,N-diC 1-4 independently selected from alkylamino, C1-C6 alkoxycarbonyl, C1-C4 alkylcarbonyl, N—C1-C4 alkoxy-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C1-C4 alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, amino, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S, and wherein any of said phenyl, 5- or 6-membered heteroaryl, or C3-C6-cycloalkyl is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxy; Z 1 is selected from C1-C4 alkyl, phenyl, 5- or 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein said 5- or 6-membered heteroaryl contains 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S, and any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, or C2-C4 alkynyl; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof is provided.

[0071] In one embodiment of the invention, the compound of formula (I) is a compound of formula (Ia): [ka] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q(Q1, Q2, Q3, Q4 and Q5), R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, A is, [ka] (In the formula, [ka] indicates a bond to a C(=O) group, and the arrow indicates a Z 1 indicates a bond to the group, R 7 , R 8 and R 9 may be selected from the group consisting of independently selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or C1-C4 haloalkyl.

[0072] Preferably, in the compound of formula (Ia), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q(Q1, Q2, Q3, Q4 and Q5), R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for compounds of formula (I) according to the invention, A is selected from A1, A2, A3, A4, A5, A6, A7, or A9, and R 7, R 8 and R 9 is hydrogen, halogen, methyl, or trifluoromethyl.

[0073] More preferably, in the compound of formula (Ia), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q(Q1, Q2, Q3, Q4 and Q5), R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for compounds of formula (I) according to the invention, A is selected from A1, A2, A3, A4, A5, A6, A7, or A9, and R 7 , R 8 and R 9 is hydrogen.

[0074] In one embodiment of the present invention, in the compound of formula (Ia), 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q(Q1, Q2, Q3, Q4 and Q5), R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, and A is [ka] (In the formula, [ka] indicates a bond to a C(=O) group, and the arrow indicates a Z 1 indicates a bond to the group, R 7 is selected from hydrogen, C1-C4 alkyl, C1-C4 alkenyl, C1-C4 alkynyl, or C1-C4 haloalkyl).

[0075] Preferably, in the compound of formula (Ia), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q(Q1, Q2, Q3, Q4 and Q5), R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, A is selected from A1, A2 or A3, and R 7 is hydrogen, halogen, methyl, or trifluoromethyl.

[0076] More preferably, in the compound of formula (Ia), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q(Q1, Q2, Q3, Q4 and Q5), R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, A is selected from A1, A2 or A3, and R 7 is hydrogen.

[0077] Another embodiment of the present invention provides compounds of formula (Ia) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q(Q1, Q2, Q3, Q4 and Q5), R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, and A is [ka] (In the formula, [ka] indicates a bond to a C(=O) group, and the arrow indicates a Z 1 (representing a bond to a group).

[0078] Preferably, in the compound of formula (Ia), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q(Q1, Q2, Q3, Q4 and Q5), R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, and A is selected from A1, or A2.

[0079] More preferably, in the compound of formula (Ia), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q(Q1, Q2, Q3, Q4 and Q5), R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, and A is selected from A1, or A2.

[0080] Yet another embodiment of the present invention provides compounds of formula (Ia) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, A is selected from A1 or A2; R 7 is hydrogen; Q is selected from Q1, Q2, Q3, or Q4.

[0081] Yet another embodiment of the present invention provides compounds of formula (Ia) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, A is selected from A1 or A2; R 7 is hydrogen; Q is selected from Q1, Q2, or Q3.

[0082] Yet another embodiment of the present invention provides compounds of formula (Ia) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, A is selected from A1 or A2; R 7 is hydrogen; Q is Q1.

[0083] In one embodiment of the present invention, in the compound of formula (Ia), 1 , R 2 , R 3 , R 4 , R 5 , R 6, Q(Q1, Q2, Q3, Q4 and Q5), R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, and A is [ka] (In the formula, [ka] indicates a bond to a C(=O) group, and the arrow indicates a Z 1 (representing a bond to a group).

[0084] Another embodiment of the present invention provides compounds of formula (Ia) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, A is selected from A1 and Q is selected from Q1, Q2, Q3, or Q4.

[0085] Yet another embodiment of the present invention provides compounds of formula (Ia) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, A is selected from A1 and Q is selected from Q1, Q2 or Q3.

[0086] Yet another embodiment of the present invention provides compounds of formula (Ia) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention, A is selected from A1 and Q is Q1.

[0087] Preferably, in the compound of formula (Ia) of the present invention, R 1 is C1-C4-alkyl, R 2 is hydrogen, fluorine, chlorine, or methyl; R 3 is hydrogen or methyl, R 4 is hydrogen or methyl; R 5 and R 6 are independently selected from hydrogen or methyl; A is A1 or A2; R 7 is hydrogen; Q is Q1, Q2 or Q3; R 10 and R 11 are independently selected from hydrogen, halogen, cyano, amino, C1-C4 alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N, and wherein any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloalkyl is unsubstituted or substituted by 1 or 2 substituents independently selected from halogen, cyano, or methyl; R 12 and R 13 are independently selected from hydrogen; Z 1is selected from phenyl, a 5- to 6-membered heteroaryl, or a C3-C6-cycloalkyl, wherein the 5- or 6-membered heteroaryl contains one heteroatom selected from N or S, and the phenyl and the 5- to 6-membered heteroaryl are unsubstituted or substituted with one or two substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, or C1-C4 alkoxy, and the C3-C6-cycloalkyl is unsubstituted or substituted with one substituent selected from halogen or C1-C4 alkyl.

[0088] Preferably, in the compound of formula (Ia) of the present invention, R 1 is C1-C4-alkyl, R 2 is hydrogen, fluorine, chlorine, or methyl; R 3 is hydrogen or methyl, R 4 is hydrogen or methyl; R 5 and R 6 are independently selected from hydrogen or methyl; A is A1 or A2; R 7 is hydrogen; Q is Q1; R 10 and R 11 are independently selected from hydrogen, halogen, cyano, amino, C1-C4 alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N, and wherein any of said phenyl, 5- or 6-membered heteroaryl and C3-C6 cycloalkyl is unsubstituted or substituted by 1 or 2 substituents independently selected from halogen, cyano or methyl; R 12 and R 13 is selected from hydrogen; Z 1is selected from phenyl, a 5- to 6-membered heteroaryl, or a C3-C6-cycloalkyl, wherein the 5- or 6-membered heteroaryl contains one heteroatom selected from N or S, and the phenyl and the 5- to 6-membered heteroaryl are unsubstituted or substituted with one or two substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, or C1-C4 alkoxy, and the C3-C6-cycloalkyl is unsubstituted or substituted with one substituent selected from halogen or C1-C4 alkyl.

[0089] In one embodiment of the present invention, the compound of formula (Ia) is a compound of formula (Ia-A) where A is A1: [ka] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q(Q1, Q2, Q3, Q4 and Q5), R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention).

[0090] Preferably, in the compound of formula (Ia-A) of the present invention, R 1 is C1-C4-alkyl, R 2 is hydrogen, fluorine, chlorine, or methyl; R 3 is hydrogen or methyl, R 4 is hydrogen or methyl; R 5 and R 6 are independently selected from hydrogen or methyl; Q, R 10 , R 11 , R12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0091] In another embodiment, in the compound of formula (Ia-A) of the present invention, R 1 is C1-C4-alkyl, R 2 is hydrogen, fluorine, chlorine, or methyl; R 3 is hydrogen or methyl, R 4 is hydrogen or methyl; R 5 and R 6 are independently selected from hydrogen or methyl; Q is Q1, Q2, or Q3; R 10 and R 11 are independently selected from hydrogen, halogen, cyano, amino, C1-C4 alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N, and wherein any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloalkyl is unsubstituted or substituted by 1 or 2 substituents independently selected from halogen, cyano, or methyl; R 12 and R 13 are independently selected from hydrogen; Z 1 is selected from phenyl or 5- to 6-membered heteroaryl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N or S, and said phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with 1 or 2 substituents independently selected from fluoro, chloro, C1-C4 alkyl, or C1-C4 alkoxy.

[0092] In yet another embodiment, in the compound of formula (Ia-A) of the present invention, R1 is C1-C4-alkyl, R 2 is hydrogen, fluorine, chlorine, or methyl; R 3 is hydrogen or methyl, R 4 is hydrogen or methyl; R 5 and R 6 are independently selected from hydrogen or methyl; Q is Q1, R 10 and R 11 are independently selected from hydrogen, halogen, cyano, amino, C1-C4 alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N, and wherein any of said phenyl, 5- or 6-membered heteroaryl and C3-C6 cycloalkyl is unsubstituted or substituted by 1 or 2 substituents independently selected from halogen, cyano or methyl; R 12 and R 13 are independently selected from hydrogen; Z 1 is selected from phenyl or 5- to 6-membered heteroaryl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N or S, and said phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with 1 or 2 substituents independently selected from fluoro, chloro, C1-C4 alkyl, or C1-C4 alkoxy.

[0093] In one embodiment of the present invention, the compound of formula (Ia) is a compound of formula (Ia-B) wherein A is A2: [ka] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6, Q(Q1, Q2, Q3, Q4 and Q5), R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention).

[0094] Preferably, in the compound of formula (Ia-B) of the present invention, R 1 is C1-C4-alkyl, R 2 is hydrogen, fluorine, chlorine, or methyl; R 3 is hydrogen or methyl, R 4 is hydrogen or methyl; R 5 and R 6 are independently selected from hydrogen or methyl; Q, R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0095] In another embodiment, in the compound of formula (Ia-B) of the present invention, R 1 is C1-C4-alkyl, R 2 is hydrogen, fluorine, chlorine, or methyl; R 3 is hydrogen or methyl, R 4 is hydrogen or methyl; R 5 and R 6 are independently selected from hydrogen or methyl; Q is Q1, Q2, or Q3; R 10 and R 11are independently selected from hydrogen, halogen, cyano, amino, C1-C4 alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N, and wherein any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloalkyl is unsubstituted or substituted by 1 or 2 substituents independently selected from halogen, cyano, or methyl; R 12 and R 13 is hydrogen; Z 1 is selected from phenyl or 5- to 6-membered heteroaryl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N or S, and said phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with 1 or 2 substituents independently selected from fluoro, chloro, C1-C4 alkyl, or C1-C4 alkoxy.

[0096] In yet another embodiment, in the compound of formula (Ia-B) of the present invention, R 1 is C1-C4-alkyl, R 2 is hydrogen, fluorine, chlorine, or methyl; R 3 is hydrogen or methyl, R 4 is hydrogen or methyl; R 5 and R 6 are independently selected from hydrogen or methyl; Q is Q1; R 10 and R 11are independently selected from hydrogen, halogen, cyano, amino, C1-C4 alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N, and wherein any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloalkyl is unsubstituted or substituted by 1 or 2 substituents independently selected from halogen, cyano, or methyl; R 12 and R 13 is hydrogen; Z 1 is selected from phenyl or 5- to 6-membered heteroaryl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N or S, and said phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with 1 or 2 substituents independently selected from fluoro, chloro, C1-C4 alkyl, or C1-C4 alkoxy.

[0097] In one embodiment of the present invention, the compound of formula (Ia) can be a compound of formula (Ia-C), wherein A is A3 and R 7 is hydrogen): [ka] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q(Q1, Q2, Q3, Q4 and Q5), R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for the compounds of formula (I) according to the invention).

[0098] Preferably, in the compound of formula (Ia-C) of the present invention, R 1 is C1-C4-alkyl, R 2is hydrogen, fluorine, chlorine, or methyl; R 3 is hydrogen or methyl, R 4 is hydrogen or methyl; R 5 and R 6 are independently selected from hydrogen or methyl; Q, R 10 , R 11 , R 12 , R 13 , and Z 1 is as defined for compounds of formula (II) according to the invention.

[0099] In another embodiment, in the compound of formula (Ia-C) of the present invention, R 1 is C1-C4-alkyl, R 2 is hydrogen, fluorine, chlorine, or methyl; R 3 is hydrogen or methyl, R 4 is hydrogen or methyl; R 5 and R 6 are independently selected from hydrogen or methyl; Q is Q1, Q2 or Q3; R 10 and R 11 are independently selected from hydrogen, halogen, cyano, amino, C1-C4 alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N, and wherein any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloalkyl is unsubstituted or substituted by 1 or 2 substituents independently selected from halogen, cyano, or methyl; R 12 and R 13 is hydrogen; Z 1is selected from phenyl or 5- to 6-membered heteroaryl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N or S, and said phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with 1 or 2 substituents independently selected from fluoro, chloro, C1-C4 alkyl, or C1-C4 alkoxy.

[0100] In yet another embodiment, in the compound of formula (Ia-C) of the present invention, R 1 is C1-C4-alkyl, R 2 is hydrogen, fluorine, chlorine, or methyl; R 3 is hydrogen or methyl, R 4 is hydrogen or methyl; R 5 and R 6 are independently selected from hydrogen or methyl; Q is Q1; R 10 and R 11 are independently selected from hydrogen, halogen, cyano, amino, C1-C4 alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N, and wherein any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloalkyl is unsubstituted or substituted by 1 or 2 substituents independently selected from halogen, cyano, or methyl; R 12 and R 13 is hydrogen; Z 1 is selected from phenyl or 5- to 6-membered heteroaryl, wherein said 5- or 6-membered heteroaryl contains one heteroatom selected from N or S, and said phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with 1 or 2 substituents independently selected from fluoro, chloro, C1-C4 alkyl, or C1-C4 alkoxy.

[0101] The presence of one or more possible asymmetric carbon atoms in any of the compounds of formula (I), (Ia), (Ia-A), (Ia-B) and (Ia-C) according to the present invention means that such compounds can occur in chiral isomeric, i.e. enantiomeric or diastereomeric forms.

[0102] Preferably, the compound of formula (I) according to the present invention is selected from the compounds listed in any one of Tables C-1 to C-21 or the compounds listed in Table P.

[0103] More preferably, the compounds of formula (I) according to the present invention are selected from the compounds listed in Table P.

[0104] In one embodiment of the present invention, the compound of formula (I) is selected from: N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-1-(2,4-difluorophenyl)triazole-4-carboxamide, N-[2-(6-cyano-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)triazole-4-carboxamide, N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)triazole-4-carboxamide, N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-1-(2,4-difluorophenyl)-1,2,4-triazole-3-carboxamide, N-[2-(6-cyano-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)tetrazole-5-carboxamide, N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)tetrazole-5-carboxamide, N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-1-(3,5-difluoro-2-pyridyl)triazole-4-carboxamide, N-[2-(6-bromo-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-1-(2,4-difluorophenyl)triazole-4-carboxamide, or N-[2-(6-cyano-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-1-(2,4-difluorophenyl)triazole-4-carboxamide.

[0105] In one embodiment of the present invention, the compound of formula (I) is selected from: N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-1-(2,4-difluorophenyl)triazole-4-carboxamide, N-[2-(6-cyano-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)triazole-4-carboxamide, N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)triazole-4-carboxamide, N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-1-(2,4-difluorophenyl)-1,2,4-triazole-3-carboxamide, N-[2-(6-cyano-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)tetrazole-5-carboxamide, or N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)tetrazole-5-carboxamide.

[0106] The following intermediates are novel and as such form further aspects of the invention.

[0107] According to a fifth aspect of the present invention, there is provided an intermediate compound of formula (III): [ka] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and Q corresponds to the same definition as for the compounds of formula (I) according to the present invention) or a salt thereof is provided.

[0108] The intermediate compound of formula (III) is R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and Q correspond to the same definitions as for the compounds of formula (I) according to the invention.

[0109] According to a sixth aspect of the present invention, there is provided an intermediate compound of formula (IIb): [ka] (In the formula, R 0 is a C1-C6 alkyl, and A 1 , A 2 , A 3 and Z 1 is as defined for compounds of formula (I) according to the present invention) or a salt thereof.

[0110] The intermediate compound of formula (IIb) is A for the compound of formula (I) according to the present invention. 1 , A 2 , A 3 and Z 1 has the same definition and corresponding preferences as those of

[0111] In one embodiment, the compound of formula (IIb) can be a compound of formula (IIba), wherein R 7 is hydrogen and R 0 is a C1-C6 alkyl, and A1 , A 2 , A 3 is N and Z 1 is as defined for the compounds of formula (I) according to the invention. [ka]

[0112] The presence of one or more possible asymmetric carbon atoms in the compounds of formula (III) according to the invention means that such compounds can occur in chiral isomeric forms, ie in enantiomeric or diastereomeric forms.

[0113] Compounds of formula (I) as defined in any of the embodiments of the present invention can be made as shown in the following Schemes 1-15, where, unless otherwise specified, the definition of each variable is as defined above in any of the embodiments according to the present invention.

[0114] In any of the following schemes 1 to 15, the presence of one or more possible asymmetric carbon atoms in the compounds of formula (I) according to the invention means that the compounds can occur in chiral isomeric forms, i.e. in enantiomeric or diastereomeric forms.

[0115] More specifically, the compound of formula (I) is a compound of formula (III) or a salt thereof (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , R 13 and Q are as defined above for compounds of formula (I)) to a compound of formula (II) 1 , A 2 , A 3 and Z 1can be prepared by reaction of a methyl group with a methyl group, which is as defined above for compounds of formula (I). This reaction is shown in Scheme 1. [ka] Scheme 1

[0116] In Scheme 1, a compound of formula (II) 1 , A 2 , A 3 and Z 1 is as defined above for compounds of formula (I), can be activated to compounds of formula (IIa) by methods known to those skilled in the art and described, for example, in Tetrahedron 2005, 61(46), 10827-10852. For example, compounds of formula (IIa) (wherein G 0 is halogen) is formed by treating a compound of formula (II) with oxalyl chloride or thionyl chloride in the presence of a catalytic amount of N,N-dimethylformamide (DMF) in an inert solvent such as methylene dichloride (CH2Cl2) or tetrahydrofuran (THF) at a temperature between 20°C and 100°C, preferably at a temperature of 25°C. 1 , R 2 , R 3 , R 4 , R 5 , R 6and Q are as defined above for compounds of formula (I), optionally in the presence of a base such as triethylamine or pyridine, provides a compound of formula (I). Alternatively, a compound of formula (I) can be obtained by treating a compound of formula (II) with dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) or 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) in an inert solvent such as pyridine, DMF, acetonitrile, CHCl or THF, optionally in the presence of a base such as triethylamine, at a temperature between 30° C. and 180° C. to give an activated compound of formula (IIa), wherein G 0 is obtained by the reaction of G 01 , G 02 or G 03 Finally, compounds of formula (II) can also be activated by reaction with a coupling reagent such as propanephosphonic anhydride (T3P), as described, for example, in Synthesis 2013, 45, 1569, to give compounds of formula (IIa), where G 0 is described below as G 04 Further reaction of the compound of formula (III) with an amine (or a salt thereof) provides the compound of formula (I). [ka] Scheme 2

[0117] Compounds of formula (II) can be prepared by ester hydrolysis to give compounds of formula (IIb) (wherein A 1 , A 2 , A 3 is N and Z 1 is as described in formula (I), and R 0is C1-C4 alkyl). Various conditions can be used, such as aqueous sodium hydroxide or aqueous lithium hydroxide and an organic water-miscible solvent such as THF or dimethoxyethane or methanol or ethanol. Such ester hydrolysis is well known to those skilled in the art. Compounds of formula (IIb) can also be directly converted to compounds of formula (I) by reacting compounds of formula (IIb) with compounds of formula (III) in the presence of trimethylaluminum or trimethylaluminum-DABCO complex in an inert solvent such as toluene or methylene chloride. Such reactions have been reported in the literature (see Tetrahedron Lett. 1977, 4171-4174 and Tetrahedron Lett. 2006, 5767-5769, and references cited therein).

[0118] Compounds of formula (II) and (IIb) are commercially available or can be synthesized as described below.

[0119] A compound of formula (III) or a salt thereof (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , R 13 and Q are as defined above for compounds of formula (I) can be reacted with a nitrile of formula (IV) (where R 1 , R 2 , R 3 , R 4 , R 10 , R 11 , R 12 , R 13and Q are as defined above for compounds of formula (I) can be prepared by one skilled in the art by reaction of a Grignard reagent R with a suitable nucleophile such as (dimethylsulfide)dihydroboron (BMS). 5 MgBr or R 6 MgBr (wherein, R 5 and R 6 (wherein ##STR1## is as defined above for compounds of formula (I)) may be added sequentially or simultaneously as nucleophiles to compounds of formula (IV) to allow the preparation of more highly substituted amines of formula (III). Such Grignard additions to nitriles can be carried out by reaction of Ti(O- i The reaction is carried out in the presence of a Lewis acid such as Pr)4 (see Synlett 2007, (4), 652-654). This reaction is shown in Scheme 3. [ka] Scheme 3

[0120] A compound of formula (IV) 1 , R 2 , R 3 , R 4 , R 10 , R 11 , R 12 , R 13 and Q is as defined above for compounds of formula (I), can be prepared by one skilled in the art according to known methods. More specifically, compounds of formula (IV), and intermediates thereto, can be prepared from compounds of formula (V) as shown in Scheme 4. [ka] Scheme 4

[0121] For example, a compound of formula (IV) 1 , R 2 , R 3 , R 4 , R 10 , R11 , R 12 , R 13 and Q are as defined above for compounds of formula (I), R 4 is different from hydrogen) can be prepared by the reaction of a compound of formula (IVa) (wherein R 4 is hydrogen and R 1 , R 2 , R 3 and Q are as defined above for compounds of formula (I), followed by deprotonation of the compound (I) with a suitable alkylating agent R, e.g., iodomethane. 4 -X 0 (In the formula, X 0 Compounds of formula (IVa) (wherein R is a halogen) can be prepared by one skilled in the art. 4 is hydrogen and R 1 , R 2 , R 3 , R 10 , R 11 , R 12 , R 13 and Q is as defined above for compounds of formula (I)) can be prepared from alcohols of formula (V) by treatment with cyanotrimethylsilane (TMSCN) in the presence of a base such as lithium carbonate in a non-polar solvent such as dichloromethane at temperatures between 0°C and the boiling point of the reaction mixture. Such transformations are well known in the literature under a variety of conditions, for example as described in Org. Lett. 2008, 10, 4570 and references therein. This reaction is shown in Scheme 4.

[0122] Compounds of formula (V) may be prepared from compounds of formula (VI) either from compounds of formula (VIa), formula (VIb), formula (VIc), formula (VId) or formula (VIe), respectively, as shown in Scheme 5. [ka] Scheme 5

[0123] As shown in Scheme 5, a compound of formula (VII), wherein R 1 , R 2 , R 3 , R 10 , R 11 , R 12 , R 13 is as defined above for compounds of formula (I), and X 01 Metallation of the methyl group (M is bromo or iodo) with a suitable reagent, such as a turboGrignard (isopropylmagnesium chloride-lithium chloride complex) or an alkyllithium such as n-butyllithium, gives the intermediate Grignard or alkyllithium reagent (M is MgX 01 or lithium) is obtained. CX 01 Such metal insertion into the bond is well known to those skilled in the art and is generally carried out in an inert solvent such as an ether, e.g., tert-butyl methyl ether or tetrahydrofuran, at temperatures generally between -78°C and rt. A solution of the metallated species (VIIa) is then treated with a compound of formula (VI), respectively (VIa), (VIb), (VIc), (VId), or (VIe), to give a compound of formula (V). Similar reactions of these types are described, for example, in WO 2012 / 102297 and Bio. Med. Chem. Lett. 2017, 27(17), 4044-4050(X 01 is Br, n-butyllithium) and Angew. Chem. Int. Ed. 2016, 55(17), 5332-5336, U.S. Patent Application Publication No. 2014 / 0349990, WO 2002 / 004424, WO 2021 / 009068 (X 01 is an iodine, turbo Grignard (isopropyl magnesium chloride-lithium chloride complex)).

[0124] Compounds of formula (VI) and formula (VII) are either commercially available or readily prepared by methods known to those skilled in the art.

[0125] Further synthesis of compounds of formula (I) can be achieved by treating compounds of formula (VIII) with a base such as sodium hydride or n-butyllithium in an inert solvent such as tetrahydrofuran, followed by the formation of compounds of formula (IX) (wherein R 4 is as described under formula (I), and X 02 is a leaving group such as a halogen, mesylate, or tosylate) to give a compound of formula (X). This reaction is shown in Scheme 6. [ka] Scheme 6

[0126] Then, a compound of formula (X) (wherein R 1 , R 2 , R 3 , and R 4 is as defined above for compounds of formula (I)) is treated with a strong base such as sodium hydride or an alkyl lithium base such as n-butyllithium in an inert solvent such as tetrahydrofuran or tert-butyl methyl ether at a temperature between −78° C. and room temperature, followed by the conversion of a compound of formula (XI), either a compound of formula (XIa), formula (XIb), formula (XIc), formula (XId) or formula (XIe), respectively, where R 9 , R 10 , R 11 , and R 12 is as defined above for compounds of formula (I), and X 03 is a leaving group such as a halogen, preferably F, Cl or Br), to give compounds of formula (IV). This reaction is shown in Scheme 7. [ka] Scheme 7

[0127] Compounds of formula (IV) are converted to compounds of formula (I) as previously described in Schemes 1, 2, and 3. One skilled in the art will recognize that the conversion of compound (VIII) to compounds of formula (IV) may be carried out sequentially or in the same reaction vessel to provide a streamlined conversion of compounds of formula (VIII) to compounds of formula (IV), as described in further detail in the preparative examples.

[0128] A compound of formula (Ia) 1 , R 2 , R 3 , R 5 , Q, R 10 , R 11 , R 12 , R 13 , A 1 , A 2 , A 3 and Z 1 is as described above for compounds of formula (I), and R 4 and R 6 is hydrogen) can also be prepared by converting a compound of formula (VI), respectively a compound of formula (VIa), formula (VIb), formula (VIc), formula (VId) or formula (VIe), into a compound of formula (XII), wherein R 5 can be prepared by treating a compound of formula (XIII) with an anhydride such as trifluoroacetic anhydride in an inert solvent such as methylene chloride in the presence of a base, for example triethylamine. This reaction is shown in Scheme 8. [ka] Scheme 8

[0129] Those skilled in the art will understand that compounds of formula (VI) can be converted to compounds of formula (XIV) without isolating the intermediate of formula (XIII). Such a reaction, known as the Henry reaction, is well described in the literature, as evidenced by Tetrahedron 2001, 57(6), 915-945, and the references cited therein. Compounds of formula (XIV) can be converted to compounds of formula (XV) by treating them with compounds of formula (VIIa) in an inert solvent such as tetrahydrofuran (see Scheme 5), known to those skilled in the art as the Michael reaction of organometallics to nitroalkenes. This reaction is shown in Scheme 9. [ka] Scheme 9

[0130] Similar Michael addition of organometallics to nitroalkenes has been reported, for example, in Org. Lett. 2007, 9, 85-87. Compounds of formula (IIIa) (wherein R 1 , R 2 , R 3 , R 5 , R 10 , R 11 , R 12 , R 13 and Q are as defined above for compounds of formula (I), and R 4 and R 6 Reduction of the nitro group of a compound of formula (XV) to an amine to give (wherein is hydrogen) can be achieved by a number of methods generally known to those skilled in the art, such as a Bechamp reduction or reduction with hydrogen in the presence of a metal catalyst. This reaction is shown in Scheme 10. [ka] Scheme 10

[0131] Compounds of formula (IIIa) are converted to compounds of formula (Ia) by the methods described in Schemes 1 and 2.

[0132] Compounds of formula II are either commercially available or can be synthesized as described below.

[0133] A compound of formula (IIb) 1 , A 2 , A 3 is N and Z 1 is as described for formula (I), i.e., compounds of formula (IIba) [ka] ) is a diazonium salt of formula (XVI) [ka] (In the formula, Z 1 is as defined under formula (I) above, and Y - is a counter ion depending on the conditions under which the diazotization process is carried out, e.g. Cl - Or BF4 - and a compound of formula (XVII) [ka] (In the formula, R 0 is C1-C6 alkyl). This reaction can be catalyzed by various silver salts (preferably silver acetate) and carried out in various solvents, such as THF, DMF, or toluene, or mixtures thereof, usually at temperatures between 0°C and 25°C, in the presence of at least one equivalent of a base, such as sodium carbonate. These dipolar [3+2] cycloadditions are highly regioselective and are described, for example, in Tetrahedron 2020, 76(14), 131063. Compounds of formula (XVI) as defined immediately above can be prepared from primary amines of formula (XVIII) by reaction with a diazotization reagent, such as a salt of nitrous acid, e.g., sodium nitrite. The solvent can be an aqueous solution of an acid, such as dilute hydrochloric acid or tetrafluoroboric acid. The counterion Y -is defined by the acid used. Diazotization reactions are commonly used in organic synthesis, even on an industrial scale, and are known to those skilled in the art.

[0134] To reduce the risk of decomposition of the intermediate of formula (XVI), the diazotization and cycloaddition steps can be carried out sequentially without the need to isolate (XVI). This variant is described in Tetrahedron 2020, 76(14), 131063. The chemical reaction is summarized in Scheme 11. [ka] Scheme 11

[0135] The compound of formula (XVII) can be prepared by reacting a compound of formula (XVII) (e.g., R 0 is methyl and is commercially available as CAS [6832-16-2].

[0136] Very similarly, the compound of formula (IIba) 1 , A 2 , A 3 is N and Z 1 are as described for formula (I)) to form a compound of formula (XIX): [ka] (In the formula, R 0 is C1-C6 alkyl, and Ar 1is phenyl or p-tolyl) with a compound of formula (XVI) in the presence of a base, for example, pyridine, at a temperature between -50°C and 50°C to give a compound of formula (IIba). Such a reaction has good precedent in the literature, for example, Chem. Comm. 2017, 53(69), 9620-9623; Angew. Chem. Int. Ed. 2017, 56(47), 15044-15048; and J. Am. Chem. Soc. 2016, 138(44), 14609-14615. Compounds of formula (XXVIII) are prepared as described in the above literature and are exemplified in the preparative examples of the present application.

[0137] Alternatively, a compound of formula (IIba) 1 , A 2 and A 3 is N and Z 1 is as defined in formula (I)) is a compound of formula (XX) [ka] (In the formula, A 1 , A 2 and A 3 is N and R 0 is as defined above) and a boronic acid derivative of formula (XXI) [ka] (In the formula, Z 1 is as defined in formula I). ​​This Chan-Lam type coupling reaction is usually carried out in a solvent such as dichloromethane, in the presence of a catalytic amount of a copper-based catalyst, at a mild reaction temperature, in the presence of a base such as potassium carbonate, in air or under oxygen. Compounds of formula (XX) (wherein A 1 , A 2 and A 3 Note that ═N exists in tautomeric forms. [ka]

[0138] Those skilled in the art will appreciate that the coupling product of this reaction may be one of the regioisomers or a mixture thereof, but when the reaction conditions are selected as described in J. Org. Chem. 2014, 79, 6703-6707, this reaction exhibits excellent regioselectivity for the compound of formula (IIba). Those skilled in the art will appreciate that this Chan-Lam coupling is a general method for the preparation of the compound of formula (IIb). An example is the compound of formula (IIbb). [ka] (In the formula, Z 1 , R 12a , and R 0 is as defined above) have been shown in the literature (see J. Med. Chem. 2018, 61, 8, 3370-3388 and WO 14 / 041106), and compounds of formula (IIbc) and formula (IIbd) [ka] (In the formula, Z 1 , R 12a , R 13a , R 14a , and R 0 Formula (I) (wherein is as defined below) has been shown in the literature (see WO 15 / 155626, EP 2390252), and compounds of formula (IIbe) [ka] (In the formula, Z 1 , R 12a , R 13a , R 14a , and R 0 is as defined under formula (I)) are shown in the literature (see J. Med. Chem. 2017, 60(14), 6166-6190, Org. Lett. 2008, 10(8), 1653-1655, and Bio. Med. Chem. Lett. 2009, 19(5), 1451-1456) (each as a representative example).

[0139] A compound of formula (IIba) 1 , A 2 and A 3 A further method for the preparation of (wherein Z is N and Z1 is as defined in formula (I)) is shown in Scheme 12. [ka] Scheme 12 As shown in Scheme 12, the sequence begins with the diazotization of a compound of formula (XVIII) as previously described, followed by the diazotization of a compound of formula (XXII) (wherein R 0 is C1-C6 alkyl) to give a compound of formula (XXIII). 1 and R 0 (wherein is as defined above) is treated with aqueous ammonia in a miscible organic solvent, such as tetrahydrofuran or 2-methyltetrahydrofuran, at a temperature between 0°C and 30°C to give a compound of formula (XXIV). Finally, compound of formula (XXIV) is diazotized with a salt of nitrous acid, such as sodium nitrite, in a weakly acidic medium, such as aqueous acetic acid or hydrochloric acid, at a temperature between -20°C and 0°C, whereby the formed diazonium salt spontaneously cyclizes to give the tetrazole compound of formula (IIba). The reaction sequence has been previously described in WO 13 / 087805.

[0140] The compound of formula (IIb) can also be a compound of formula (XX) [ka] Compound of formula (XXIV) Z 1 -X 0 (XXIV) (In the formula, Z 1 is as previously described under formula I, and X 0can be prepared by alkylation with a halogen, preferably chlorine, bromine, or iodine, in the presence of a base, e.g., an alkaline earth metal base such as NaOH, KOH, LiOH, CsCO, or KCO, in an inert aprotic or protic solvent. Such alkylation is well known to those skilled in the art and has been used in this context to prepare compounds of formula (IIb), as described, for example, in WO 14 / 168221; WO 10 / 043000; and WO 14 / 32498. Those skilled in the art will recognize that this can result in a mixture of regioisomeric compounds that can be separated by chromatographic techniques, or that pure isomers can be obtained by flexible selection of conditions and additives (e.g., palladium catalysts for the so-called Buchwald amination). Z 1 When is heteroaryl or aryl, the SnAr reaction (with or without copper catalysis) can be used to prepare compounds of formula (IIb) (see, e.g., Polyhedron 2019, 165, 22-30; US Patent Application Publication No. 2018 / 0170909; Org. Lett. 2022, 24(20), 3620-3625; J. Org. Chem. 2017, 82(14), 7420-7427; Chem. Comm. 2021, 57(57), 7047-7050; ACS Catalysis 2019, 9(12), 10674-10679; Synthesis 2017, 49(23), 5120-5130, J. Org. Chem. 2019, 84(12), 8160-8167, and references cited therein).

[0141] Further compounds according to the invention may be prepared by derivatization using key central intermediates later in the synthesis. For example, compounds of formula (I) (where Q is Q1 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , A 1 , A2 , A 3 and Z 1 is as defined above for compounds of formula (I), and X 04 is a halogen, preferably bromine or chlorine, for example in compounds of formula (Ia): [ka] ) are capable of further chemistry such as palladium-catalyzed carbonylation, Suzuki reactions, Stille couplings, copper-catalyzed introduction of sulfonyl groups, haloalkyl groups, and cyano moieties, as well as SnAr reactions with various nucleophiles.

[0142] An example of such a reaction is shown in Scheme 13. [ka] Scheme 13 As shown in Scheme 13, compounds of formula (I) (wherein Q is Q1 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , A 1 , A 2 , A 3 and Z 1 is as defined above for compounds of formula (I), and R 9is cyano, i.e., compounds of formula (Ib)) can be obtained from compounds of formula (Ia) by treatment with an inorganic cyanide source, such as CuCN, in an inert solvent, such as dimethylformamide (DMF) or N-methyl-2-pyrrolidone, at temperatures between 0°C and 150°C. Such reactions are well known in the literature, for example, in J. Het. Chem. 1987, 24(2), 373-6; Liebigs Ann. Chem. 1994, (10), 1049-53; and Org. Prep. Proc. Int. 1985, 17(6), 391-9. Other methods for introducing a cyano group by substitution of a halogen atom are known in the art. See, for example, Science of Synthesis 2004, 19, 173-195.

[0143] A compound of formula (I) wherein Q is Q1 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , A 1 , A 2 , A 3 and Z 1 is as defined above for compounds of formula (I), and R 9a is C1-C4 haloalkyl, i.e., the compound of formula (Ic)) can be converted to the compound of formula (Ia) (wherein Q is Q1 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , A 1 , A 2 , A 3 and Z 1 is as defined above for compounds of formula (I), and X 04is a halogen, preferably bromine) to a compound of formula (XXV) 9a is C1-C4 haloalkyl). Such a reaction is known in the literature (Org. Lett. 2014, 16(6), 1744-1747). Compounds of formula (I) (wherein Q is Q1 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , A 1 , A 2 , A 3 and Z 1 is as defined above for compounds of formula (I), and R 9b is phenyl, a 5- or 6-membered heteroaryl, or a C3-C6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S, and wherein any of said phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloaryl is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, and C1-C4 alkoxy, i.e., compounds of formula (Id)) can be prepared by Suzuki reaction (as shown in Scheme 13), which can, for example, be prepared by reacting compounds of formula (Ia) (wherein X 04 is a leaving group such as, for example, chlorine, bromine or iodine) to a compound of formula (XXVIa) b1 is, for example, B(OH)2 or B(OR b1 )2, and R b1 can be a C1-C4 alkyl group or two groups OR b1(which may, together with the boron atom, form a five-membered ring, e.g., pinacolboronic acid ester). This reaction is catalyzed by a palladium-based catalyst, e.g., tetrakis(triphenylphosphine)-palladium or (1,1'-bis(diphenylphosphino)-ferrocene)dichloropalladium-dichloromethane (1:1 complex), in the presence of a base such as sodium carbonate or cesium fluoride in a solvent or solvent mixture, e.g., a mixture of 1,2-dimethoxyethane and water, or a mixture of dioxane and water, or a mixture of methyltetrahydrofuran and water, preferably under an inert atmosphere. The reaction temperature can range preferentially from room temperature to the boiling point of the reaction mixture. Such Suzuki reactions are well known to those skilled in the art and are reviewed, for example, in J. Organomet. Chem. 1999, 576, 147-168.

[0144] Alternatively, the compound of formula (Ic) may be a compound of formula (XXVIb) b2 can also be prepared by the Stille reaction of a compound of formula (Ia) with a trialkyltin derivative, preferably tri-n-butyltin. Such a Stille reaction is carried out in the presence of a palladium catalyst, such as tetrakis(triphenylphosphine)palladium(0) or (1,1'-bis(diphenylphosphino)-ferrocene)dichloropalladium-dichloromethane (1:1 complex), in an inert solvent such as DMF, acetonitrile, or dioxane, optionally in the presence of an additive such as cesium fluoride or lithium chloride, and optionally in the presence of a further catalyst, such as copper(I) iodide. Such Stille couplings are also well known to those skilled in the art and are described, for example, in J. Org. Chem. 2005, 70, 8601-8604; J. Org. Chem. 2009, 74, 5599-5602; and Angew. Chem. Int. Ed. 2004, 43, 1132-1136. Many compounds of formula (XXVIa) and formula (XXVIb) are commercially available or can be prepared by one skilled in the art.

[0145] Further compounds accessible from compounds of formula (Ia) are shown in Scheme 14. [ka] Scheme 14 As shown in Scheme 14, compounds of formula (I) (wherein Q is Q1 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , A 1 , A 2 , A 3 and Z 1 is as defined above for compounds of formula (I), and X 04 is a leaving group such as chlorine, bromine, or iodine, i.e., a compound of formula (Ia) can be treated with a compound of formula (XXVII) under Stille reaction conditions to give a compound of formula (Ie). The compound of formula (Ie) can be isolated or directly hydrolyzed under aqueous acidic conditions to give a compound of formula (If). Such reactions are known in the literature and are described, for example, in Synthesis 2001, (10), 1551-1555 and Tetrahedron 2001, 57(13), 2507-2514. A compound of formula (If) can be prepared by converting a compound of formula (If) to a compound of formula (XXVIII) (or a salt thereof) (wherein R 13 is hydrogen or C1-C4 alkyl) to give a compound of formula (Ig) 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , A 1 , A 2 , A 3 and Z 1is as defined above for compounds of formula (I), and R 13 is hydrogen or C1-C4 alkyl). Many examples of the preparation of such oximes are known in the literature (see, for example, Molecules 2019, 24, 2470 and the references cited therein) and are familiar to those skilled in the art.

[0146] A compound of formula (I) wherein Q is Q1 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , A 1 , A 2 , A 3 and Z 1 is as defined above for compounds of formula (I), and X 04 is a leaving group such as, for example, chlorine, bromine or iodine, ie, compounds of formula (Ia), further compounds that can be prepared from these are shown in Scheme 15. [ka] Scheme 15 As shown in Scheme 15, compounds of formula (Ia) can be carbonylated to give compounds of formula (I), i.e., R 14 Compounds of formula (Ih) having C1-C4 alkyl, where Q is Q1 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , A 1 , A 2 , A 3 and Z 1is as defined above for compounds of formula (I), and in such alkoxycarbonylation, compounds of formula (Ia) are typically alkoxylated with alcohols (R) under pressure in the presence of a palladium catalyst (e.g., palladium(II) acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (Pd(dppf)Cl), bis(triphenylphosphine)palladium(II) dichloride (PdCl(PPh)) or bis(diphenylphosphino)propane]palladium(II) (PdCl(dippp)), optionally in the presence of a phosphine ligand such as triphenylphosphine or 1,1-bis(diphenylphosphino)ferrocene. 14 OH) (typically methanol or ethanol) (wherein R 14is C1-C4 alkyl), optionally in the presence of a co-solvent (e.g., toluene, dioxane, or N,N-dimethylformamide), and preferably in the presence of a base, such as trimethylamine, at a temperature of 20°C to 200°C, preferably 50°C to 180°C. Such carbonylation reactions are well known to those skilled in the art and are well known in the literature (see J. Org. Chem. 2008, 73, 7102-7107 and references cited therein). Such compounds of formula (Ih) can be readily saponified to compounds of formula (Ii) under conditions known to those skilled in the art, such as aqueous sodium, potassium, or lithium hydroxide solutions in methanol, ethanol, tetrahydrofuran, or dioxane at room temperature, or up to reflux. Alternatively, the carboxylic acid compound of formula (Ii) may be produced by treating the ester compound of formula (Ih) with a halide anion, preferably a chloride anion, derived from, for example, lithium chloride (or alternatively, sodium or potassium chloride), in a solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, or N-methyl-2-pyrrolidone. The reaction temperature for such O-demethylation may preferably range from 20°C to the boiling point of the reaction mixture, or the reaction may be carried out under microwave irradiation. The compound of formula (Ii) can be converted into the amide of formula (I) (i.e., a compound of formula (Ij) in which R 15 and R 16 are independently hydrogen or C1-C4 alkyl, where Q is Q1, and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , A 1 , A 2 , A 3 and Z 1 is as defined for compounds of formula (I). Such reactions typically involve activation of the carboxyl group followed by conversion of compound R 15 R 16NH or by using a coupling agent to form a compound of formula R 15 R 16 These methods involve the direct conversion of acids to amides by treatment with NH compounds. These methods are discussed in Schemes 1 and 2, referenced above.

[0147] Further compounds of formula (Ij) may be prepared by reacting compounds of formula (I) (i.e., R 9 Compounds of formula (Ik) having an amino group, wherein Q is Q1 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , A 1 , A 2 , A 3 and Z 1can be converted to the corresponding amine of formula (Ik) by the so-called Curtius rearrangement. In the Curtius rearrangement, the compound of formula (Ij) is treated with an organic azide in the presence of a suitable base, and optionally with or without a Lewis acid, in an inert solvent at a temperature between 50°C and 200°C. Examples of organic azides include TMSN3, sodium azide, diphenylphosphoryl azide, or tosyl azide, and suitable solvents can be toluene, xylene, THF, or acetonitrile. An example of a suitable Lewis acid can be Zn(OTf)2, among others. The isocyanate formed in this rearrangement is reacted with water to form a carbamate, which, upon decarboxylation under the reaction conditions, gives the corresponding amine of formula (Ik). Alternatively, these reactions can be carried out in an alcohol, such as t-butyl alcohol, allowing the isolation of the t-butyl carbamate. These are then cleaved in a separate step by an acid (such as trifluoroacetic acid) by methods known to those skilled in the art to give compounds of formula (Ik). Examples of such Curtius reactions are reported, for example, in Org. Lett. 2005, 7, 4107-4110, J. Med. Chem. 2006, 49(12), 3614-3627, and Tetrahedron 1974, 30, 2151-2157. Compounds of formula (Ik) thus obtained can be treated with compounds of formula (XIX) according to the amidation method described above to give compounds of formula (Im) (wherein Q is Q1 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , A 1 , A 2 , A 3 and Z 1 is as defined above for compounds of formula (I), and R 18is a C1-C4 alkyl). Those skilled in the art will appreciate that in any of the compounds of formula (I) where Q is Q1, Q2, Q3, Q4, or Q5, when the latter group is a leaving group such as a halogen atom, it may be amidated at any position of the heterocycle of formula Q (i.e., R 9 , R 10 , R 11 or R 12 ) and will recognize that such chemistry can be applied.

[0148] A compound of formula (I) as defined in any of the embodiments of the present invention can be converted in a manner known per se into another compound as defined in any of the embodiments of the present invention by replacing one or more substituents of the starting compound with one or more other substituents according to the present invention in a conventional manner. Those skilled in the art will also understand that a compound of formula (I) can be further transformed into a further derivative of formula (I) by, for example, alkylation, nucleophilic substitution, elimination, C—C bond forming reactions in the presence of a metal catalyst, heteroatom-carbon bond formation in the presence of a metal catalyst, oxidation, and reduction.

[0149] Depending on the reaction conditions and the choice of starting materials suitable in each case, it may, for example, only be possible in one reaction step to replace one substituent with another substituent according to the invention, or it may be possible to replace several substituents with other substituents according to the invention in the same reaction step.

[0150] Salts of compounds of formula (I) can be prepared in a manner known per se: thus, for example, acid addition salts of compounds of formula (I) can be obtained by treatment with a suitable acid or with a suitable ion exchange reagent, and salts with bases can be obtained by treatment with a suitable base or with a suitable ion exchange reagent.

[0151] Salts of compounds of formula (I) can be converted in a customary manner, for example into the free compounds I (acid addition salts) by treatment with a suitable basic compound or a suitable ion exchange reagent, or into salts with a base, for example by treatment with a suitable acid or a suitable ion exchange reagent.

[0152] Salts of compounds of formula (I) can be converted into other salts (acid addition salts, e.g. other acid addition salts) of compounds of formula (I) in a manner known per se, for example by treating the salt of an inorganic acid, such as hydrochloric acid, with a suitable metal salt of the acid, such as sodium, barium or silver salt (e.g. silver acetate), in a suitable solvent (in which inorganic salts that form, for example, silver chloride, are insoluble and therefore precipitate from the reaction mixture).

[0153] Depending on the procedure or reaction conditions, compounds of formula (I) that have salt-forming properties may be available in the free form or in salt form.

[0154] The compounds of formula (I) and, where appropriate, their tautomers, in each free or salt form, can exist in the form of pure isomers, such as enantiomers and / or diastereomers, or as isomeric mixtures, such as enantiomeric mixtures, such as racemates, diastereomeric mixtures or racemic mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms occurring in the molecule and / or depending on the configuration of non-aromatic double bonds occurring in the molecule; the invention relates to the pure isomers and also to all possible isomeric mixtures, and is to be understood in this sense above and below, respectively, even if details of the stereochemistry are not specifically stated in each case.

[0155] The compounds of formula (I) of the present invention exhibit an asymmetric carbon atom at the bis-benzyl position: Those skilled in the art will appreciate that both enantiomers are within the scope of the present invention.

[0156] Diastereomeric or racemic mixtures of compounds of formula (I), in free or salt form, depending on which starting materials and procedures are selected, can be separated in known manner on the basis of the physical chemical differences of the components into pure diastereomers or racemates, for example by fractional crystallization, distillation and / or chromatography.

[0157] Enantiomeric mixtures, such as racemates, which may be obtained in a similar manner can be resolved into their optical antipodes by known methods, for example by recrystallization from optically active solvents, by chromatography on chiral adsorbents, for example by high-performance liquid chromatography (HPLC) on acetylcellulose using suitable microorganisms, by cleavage with specific immobilized enzymes, in which only one enantiomer is complexed, for example via the formation of inclusion compounds with chiral crown ethers, or by conversion to diastereomeric salts, for example by reacting the basic end-product racemate with an optically active acid, such as a carboxylic acid, for example camphoric acid, tartaric acid or malic acid, or a sulfonic acid, for example camphorsulfonic acid, and separating the diastereomeric mixtures which may thereby be obtained, for example by fractional crystallization according to their different solubilities, from which the desired enantiomer can be liberated by the action of a suitable agent, for example a basic agent.

[0158] Pure diastereomers or enantiomers can be obtained according to the present invention not only by separating the appropriate isomeric mixture, but also by diastereoselective or enantioselective synthesis, which is a method known in the art, e.g., by carrying out the process according to the present invention using starting materials with the appropriate stereochemistry.

[0159] When the individual components have different biological activities, it may be advantageous to isolate or synthesize the respective more biologically active isomer, e.g., enantiomer or diastereomer, or mixture of isomers, e.g., mixture of enantiomers or diastereomers.

[0160] As an example, compounds with two or more asymmetric carbon atoms may exist in diastereomeric forms which can optionally be separated using, for example, supercritical fluid chromatography (SFC) chromatography with a chiral column. Such diastereomers may exhibit different fungicidal activity profiles, but all isomers and diastereomers form part of the present invention.

[0161] The compounds of formula (I) of the present invention exhibit two asymmetric carbon atoms. The relationship between the enantiomers and diastereomers of the compounds of formula (I) is shown below. [ka] Those skilled in the art will recognize that the compounds of formula (I) (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , A 1 , A 2 , A 3 , Q, R 10 , R 11 , R 12 , R 13 , and Z 1 It is well recognized that such diastereomers and enantiomers of formula (I) are within the scope of the present invention.

[0162] Furthermore, those skilled in the art will recognize that the above diastereomers and enantiomers are represented by formula (Ia), formula (Ia-A), formula (Ia-B) and formula (Ia-C) (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , A 1 , A 2 , A 3 , Q, R 10 , R 11 , R12 , R 13 , and Z 1 is as defined for formula (I)) is applicable to compounds of formula (I) and is within the scope of the present invention.

[0163] The compounds of formula (I) and, where appropriate, their tautomers may each be available in free form or in salt form, where appropriate also in the form of hydrates, and / or may include other solvents, such as those that may have been used for the crystallization of compounds present in solid form.

[0164] As stated above, it has now surprisingly been found that the compounds of formula (I) of the present invention have a very advantageous level of biological activity for practical use in protecting plants from diseases caused by fungi.

[0165] The compounds of formula (I) according to the present invention can be used in the agricultural sector and related fields of use, for example, as active ingredients for controlling plant pests or against non-living organisms for the control of spoilage microorganisms or organisms potentially harmful to humans.The novel compounds are distinguished by excellent activity at low application rates, by being well tolerated by plants, and by being environmentally safe.They have very useful curative, preventive, and systemic properties and can be used to protect a large number of cultivated plants.The compounds of formula (I) can be used to suppress or eradicate pests that appear on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while simultaneously protecting those parts of the plant that grow later, for example, from phytopathogenic microorganisms.

[0166] The present invention further relates to a method for controlling or preventing infestation of susceptible plants or plant propagation material and / or harvested food crops by microorganisms by treating the plants or plant propagation material and / or harvested food crops, in which an effective amount of a compound of formula (I) according to the invention is applied to the plant, its part or its habitat.

[0167] As used herein, the term "controlling," when used in the context of infestation of plants or plant propagation material and / or harvested food crops, refers to reducing the number of pests, eradicating the pests and / or preventing further pest damage, such that damage to the plants or plant-derived products is reduced.

[0168] The term "preventing" when used in the context of infestation of plants or plant propagation material and / or harvested food crops refers to the avoidance of symptoms due to microbial attack or fungal infection (fungal growth).

[0169] The compound of formula (I) according to the present invention can also be used as a fungicide. As used herein, the term "fungicide" refers to a compound that controls, modifies, or prevents the growth of fungi. When used, the term "fungicidally effective amount" refers to the amount of such a compound or a combination of such compounds that can produce an effect on the growth of fungi. Controlling or modifying effects include all deviations from natural occurrence, such as killing, delaying, etc., and prevention includes the formation of a barrier or other defense in plants to prevent fungal infection.

[0170] To protect against fungal infections and phytopathogenic fungi occurring in the soil, the compounds of formula (I) according to the present invention may also be used as dressings for treating plant propagation material, such as seeds, such as fruits, tubers, or grains, or plant cuttings. The propagation material can be treated with a composition containing a compound of formula (I) before planting: for example, seeds can be treated with a dressing before sowing. The active compounds of formula (I) can also be applied to seeds (coatings) by impregnating the seeds in a liquid formulation or coating them with a solid formulation. This composition can also be applied to the planting site, for example, in the sowing furrow during sowing, when the propagation material is planted. The present invention also relates to a method for treating such plant propagation material, and to the plant propagation material treated in this way.

[0171] Furthermore, the compounds of formula (I) according to the invention can be used to control fungi in related fields, for example in the protection of industrial materials, including wood and wood-related industrial products, food storage, hygiene control.

[0172] Additionally, the present invention can be used to protect non-living materials such as timber, wallboard and paint from fungal attack.

[0173] The compounds of formula (I) according to the invention are active, for example, against disease-causing fungi and fungal vectors as well as phytopathogenic bacteria and viruses. Fungi and fungal vectors as well as plant pathogenic bacteria and viruses involved in these diseases are, for example: Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Botryosphaeria spp. including B. dermatitidis, Blumeria graminis, Bremia lactucae, B. dothidea, and B. obtusa; Botrytis spp. including B. cinerea; Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, and C. tropicalis; Cephaloascus fragrans fragrans, Ceratocystis spp., Cercospora spp. including C. arachidicola, Cercosporidium personatum, Cladosporium spp.), Claviceps purpurea, Coccidioides immitis, Cochliobolus spp., Colletotrichum spp. including C. musae, Cryptococcus neoformans, Diaporthe spp., Didymella spp., Drechslera spp., Elsinoe spp., Epidermophyton spp., Erwinia amylovora Erysiphe spp. including E. amylovora, E. cichoracearum, Eutypa lata, F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani, Fusarium spp. including Gaeumannomyces graminis, Gibberella fujikuroi, fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp., Hemileia spp., H. capsulatumHistoplasma spp. including Histoplasma capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp., Monilinia spp., Mucor spp., Mycosphaerella spp. including M. graminicola, M. pomi, Oncobasidium theobromaeon theobromaeon, Ophiostoma piceae, Penicillium spp. including Paracoccidioides spp., P. digitatum, P. italicum, Petriellidium spp., Peronosclerospora spp. including P. maydis, P. philippinensis and P. sorghi, Peronosclerospora spp., Peronospora spp., Phaeosphaeria nodorum, Phakopsora pachyrhizi pachyrhizi, Phellinus igniarus, Phialophora spp., Phoma spp., Phomopsis viticola, Phytophthora spp. including P. infestans, P. halstedii, P. viticolaPlasmopara spp. including P. viticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp., Pseudoperonospora spp. including P. cubensis and P. humuli, Pseudoperonospora spp. including P. tracheophila, Pseudoperonospora spp. including P. cubensis and P. humuli, Pseudoperonospora spp. including P. tracheophila, Pseudoperonospora spp. including P. humuli, Pseudoperonospora spp. including P. graminis, ... Puccinia spp. including P. tracheiphila, P. hordei, P. recondita, P. striiformis, P. triticina, Pyrenopeziza spp., Pyrenophora spp., Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum, Ramularia spp., Rhizoctonia spp., Rhizomucor pusillus, Rhizopus alitus arrhizus, Rhynchosporium spp., Scedosporium spp. including S. apiospermum and S. prolificans, Schizothyrium pomi, Sclerotinia spp., Sclerotium spp., Sclerotium spp., S. nodorum, S. triticiSeptoria spp. including (Septoria tritici), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp., Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia Trichoderma spp., including T. harzianum, T. pseudokoningii, and T. viride, Trichophyton spp., Typhula spp., Uncinula necator, Urocystis spp., Ustilago spp., Venturia spp., including V. inaequalis, Verticillium spp., and Xanthomonas spp.

[0174] The compounds of formula (I) according to the invention may be used, for example, on turf, ornamental plants such as flowers, shrubs, broad-leaved trees or evergreen trees such as conifers, as well as for trunk injections, pest management, etc.

[0175] Within the scope of the present invention, target crops and / or useful plants to be protected are typically berry plants, such as blackberries, blueberries, cranberries, raspberries and strawberries; cereals, such as barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, such as cotton, flax, hemp, jute and sisal; field crops, such as sugar and fodder beet, coffee, hops, mustard, rapeseed (canola), poppy, sugarcane, sunflower, tea and tobacco; fruit trees, such as apple, apricot, avocado, banana, cherry, citrus fruit, nectarine, peach, pear and plum; grasses, such as bermudagrass, bluegrass, bentgrass, centipedegrass, fescue, ryegrass, St. Augustine grass and zoysiagrass. herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes such as beans, lentils, peas and soybeans; nuts such as almonds, cashews, groundnuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms such as oil palm; ornamental plants such as flowers, shrubs and trees; other trees such as cocoa, coconut, olives and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and perennial and annual crops such as grapes.

[0176] The term "useful plants" should also be understood to include useful plants that have been rendered tolerant to herbicides such as bromoxynil or to certain classes of herbicides (e.g., HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyroyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) by conventional methods of breeding or genetic engineering. Crops that have been rendered tolerant to imidazolinones, such as imazamox, by conventional methods of breeding (mutagenesis) include, for example, Clearfield® rapeseed (Canola). Examples of crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-tolerant corn varieties commercially available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0177] It should be understood that the term "useful plants" also includes useful plants that have been transformed using recombinant DNA techniques so as to be able to synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly bacteria of the genus Bacillus.

[0178] Examples of such plants are YieldGard® (a corn variety expressing a CryIA(b) toxin); YieldGard Root-Feeding Nematode® (a corn variety expressing a CryIIIB(b1) toxin); YieldGard Plus® (a corn variety expressing a CryIA(b) and a CryIIIB(b1) toxin); Starlink® (a corn variety expressing a Cry9(c) toxin); Herculex I® (a corn variety expressing a CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing a CryIA(c) toxin); Bollgard I® (a cotton variety expressing a CryIA(c) toxin); Bollgard II® (a cotton variety expressing CryIA(c) and CryIIA(b) toxins); VIPCOT® (a cotton variety expressing VIP toxin); NewLeaf® (a potato variety expressing CryIIIA toxin); Nature-Gard® Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), Agrisure® RW (corn root nematode trait), and Protecta®.

[0179] The term "crop plant" should also be understood to include crop plants that have been transformed using recombinant DNA techniques to be able to synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly those belonging to the genus Bacillus.

[0180] Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins from Photorhabdus luminescens, Xenorhabdus nematophilus, for example Photorhabdus spp. or Xenorhabdus spp. insecticidal proteins of nematode-symbiotic bacteria such as nematode toxins; toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycete toxins, plant lectins such as pea lectin, barley lectin or snowdrop lectin; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin and papain inhibitors; ricin, Ribosome-inactivating proteins (RIPs) such as maize RIP, abrin, rufin, saporin or bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as sodium or calcium blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0181] Furthermore, in the context of the present invention, delta-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or trophic insecticidal proteins (Vip), such as Vip1, Vip2, Vip3, or Vip3A, are also understood to be, in particular, hybrid toxins, truncated toxins, and modified toxins. Hybrid toxins are produced recombinantly by combining different domains of these proteins (see, for example, WO 2002 / 015701). For example, truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the natural toxin are replaced. In such amino acid substitutions, preferably a non-naturally occurring protease recognition sequence is inserted into the toxin, for example in the case of Cry3A055 a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see WO 2003 / 018810).

[0182] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP 0 374 753, WO 93 / 07278, WO 95 / 34656, EP 0 427 529, EP 451 878 and WO 2003 / 052073.

[0183] Methods for the preparation of such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP 0 367 474, EP 0 401 979 and WO 90 / 13651.

[0184] The toxins contained in the transgenic plants confer resistance to harmful insects on the plants, which can be from any taxonomic group of insects, but are particularly commonly found among beetles (Coleoptera), two-winged insects (Diptera), and butterflies (Lepidoptera).

[0185] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some are commercially available. Examples of such plants include YieldGard® (a corn variety expressing the Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing the Cry3Bb1 toxin); YieldGard Plus® (a corn variety expressing the Cry1Ab and Cry3Bb1 toxins); Starlink® (a corn variety expressing the Cry9C toxin); Herculex I® (a corn variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing the Cry1Ac toxin); Bollgard I® (a cotton variety expressing the Cry1Ac toxin); Bollgard II® (a cotton variety expressing Cry1Ac and Cry2Ab toxins); VipCot® (a cotton variety expressing Vip3A and Cry1Ab toxins); NewLeaf® (a potato variety expressing Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), and Protecta®.

[0186] Further examples of such transgenic crops are: 1. Bt11 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Genetically engineered maize (Zea mays) resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also achieves tolerance to the herbicide glufosinate-ammonium through transgenic expression of the enzyme PAT. 2. Bt176 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Genetically engineered maize (Zea mays) resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of the Cry1Ab toxin. Bt176 maize also achieves tolerance to the herbicide glufosinate-ammonium through transgenic expression of the enzyme PAT. 3. MIR604 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. This maize is resistant to insects due to the transgenic expression of a modified Cry3A toxin. The toxin is Cry3A055 modified by the insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 2003 / 018810. 4. MON863 maize, registration number C / DE / 02 / 9, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON863 expresses the Cry3Bb1 toxin and confers resistance to certain Coleoptera insects. 5. IPC531 cotton, registration number C / ES / 96 / 02, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. 6. 1507 corn, registration number C / NL / 00 / 10, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium. Maize genetically engineered for expression of the protein Cry1F to achieve resistance to certain Lepidoptera insects and for expression of the PAT protein to achieve tolerance to the herbicide glufosinate ammonium. 7. NK603 x MON810 maize, registration number C / GB / 02 / M3 / 03, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B 1150 Brussels, Belgium. This conventional hybrid maize variety is a cross between the genetically modified varieties NK603 and MON810. NK603 x MON810 maize transgenicly expresses the CP4 EPSPS protein from Agrobacterium sp. strain CP4, which confers resistance to the Roundup® herbicide (containing glyphosate), and the Cry1Ab toxin from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain Lepidoptera, including the European corn borer.

[0187] The compounds of formula (I) according to the invention are effective against diseases caused by plant pathogens, in particular the genus Alternaria in fruits, vegetables and potatoes; Botrytis cinerea in strawberries, tomatoes, sunflowers, pulses, vegetables and grapes; Rhizoctonia solani in potatoes and vegetables; Uncinula necator in grapes; Cladosporium cucumerinum, Didymella bryoniae, Sphaerotheca fuliginea and Glomerella lagenarium in cucurbits; Leveillula taurica in cucurbits and solanaceous crops. taurica; Fusarium spp. in cereals; Leptosphaeria spp. in cereals; and Zymospetoria spp. in cereals.

[0188] As used herein, the term "habitat" means the field in which the plant is growing or in which the seeds of the plant to be cultivated have been sown or will be sown in the soil. It includes the soil, seeds and seedlings, and established vegetation.

[0189] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves and fruits.

[0190] The term "plant propagation material" is understood to refer to reproductive parts, such as seeds, of plants, and vegetative parts, such as cuttings or tubers, for example potatoes, which can be used for their propagation. Examples include seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of plants. Germinated plants and seedlings that are to be transplanted after germination or emergence from the soil may also be mentioned. These seedlings can be protected by a complete or partial immersion treatment before transplanting. Preferably, "plant propagation material" is understood to refer to seeds.

[0191] The compounds of formula (I) according to the present invention can be used in their original form or, preferably, together with adjuvants conventionally used in the formulation art. For this purpose, they can be formulated in a known manner as emulsifiable concentrates, coatable pastes, ready-to-spray or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, dusting powders, granules, or even encapsulated in polymeric materials. The type of composition, as well as the application method (spraying, spraying, dusting, scattering, coating, or pouring) are selected according to the intended purpose and the circumstances. The compositions can also contain further adjuvants, such as stabilizers, defoamers, viscosity modifiers, binders, or tackifiers, as well as fertilizers, sources of trace elements, or other ingredients for achieving special effects.

[0192] Suitable carriers and adjuvants, for example for agricultural applications, can be solid or liquid and are substances useful in formulation technology, such as natural or regenerated inorganic substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 97 / 33890.

[0193] Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations contain anti-settling and dispersing agents and may further contain wetting agents to enhance activity, as well as anti-foaming and crystal growth inhibitors. When used, these concentrates are diluted in water and typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0194] Wettable powders are in the form of finely divided particles that disperse readily in water or other liquid carriers. The particles contain the active ingredient held in a solid matrix. Typical solid matrices include fuller's earth, kaolin clay, silica, and other readily wet organic or inorganic solids. Wettable powders usually contain 5% to 95% of the active ingredient and small amounts of wetting agents, dispersing agents, or emulsifying agents.

[0195] Emulsifiable concentrates are homogeneous liquid compositions that are dispersible in water or other liquids and may consist solely of the active compound and a liquid or solid emulsifier, or may also contain a liquid carrier such as xylene, high-boiling aromatic naphtha, isophorone, and other non-volatile organic solvents. When used, these concentrates are dispersed in water or other liquid and typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0196] Granular formulations include both extrudates and relatively coarse particles, and are usually applied undiluted to the area where treatment is required. Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clay, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, gypsum, wood flour, ground corn cobs, ground peanut shells, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials that can absorb or be coated with the active compound. Granular formulations usually contain 5% to 25% active ingredient, which may include surfactants or vegetable oils such as high-boiling aromatic naphtha, kerosene, and other petroleum fractions; and / or adhesives such as dextrin, glue, or synthetic resins.

[0197] Dusts are free-flowing mixtures of the active ingredient and finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.

[0198] Microcapsules are typically droplets or granules of an active ingredient enclosed in an inert, porous shell that allows the encapsulated material to be released into the environment at a controlled rate. The encapsulated droplets are typically 1 to 50 microns in diameter. The encapsulated liquid typically constitutes 50 to 95% of the capsule's weight and may contain solvent in addition to the active compound. Encapsulated granules are generally porous granules with a porous membrane that seals the pore openings of the granule, retaining the active species in liquid form within the pores of the granule. Granules typically range in diameter from 1 millimeter to 1 centimeter, preferably 1 to 2 millimeters. Granules are formed by extrusion, agglomeration, or prilling, or are naturally occurring. Examples of such materials are vermiculite, calcined clay, kaolin, attapulgite clay, sawdust, and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, and starch xanthates.

[0199] Other useful formulations for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene, and other organic solvents. Pressurized sprayers can also be used, in which the active ingredient is dispersed in finely divided form as a result of evaporation of the low-boiling dispersant solvent carrier. Suitable agricultural adjuvants and carriers useful in formulating the compositions of the present invention in the formulation types described above are well known to those skilled in the art.

[0200] Liquid carriers that can be used include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octyl Examples of suitable carriers include methylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG 400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and higher molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerin, and N-methyl-2-pyrrolidinone. Water is generally the carrier of choice for dilution of concentrates.

[0201] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cottonseed hulls, wheat flour, soy flour, pumice, wood flour, walnut hulls, and lignin.

[0202] A wide variety of surfactants are advantageously employed in both the liquid and solid compositions, especially those designed to be diluted with a carrier before application. These agents, when used, usually constitute from 0.1% to 15% by weight of the formulation. They may be anionic, cationic, nonionic, or polymeric in character and may be used as emulsifying agents, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfates such as diethanolammonium lauryl sulfate; alkylaryl sulfonates, for example, calcium dodecylbenzene sulfone sulfate; alkylphenol-alkylene oxide adducts, for example, nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide adducts, for example, tridecyl alcohol-C.sub.16 ethoxylate; soaps, such as sodium stearate; alkylnaphthalene sulfonates, for example, sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, for example, sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids, for example, polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkyl phosphate esters.

[0203] Other adjuvants commonly used in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, antifoaming agents, sunscreens, compatibilizers, defoamers, sequestering agents, neutralizing and buffering agents, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants and adhesives.

[0204] In addition, other biocidal active ingredients or compositions can be combined with the composition of the present invention and used in the method of the present invention, and can be applied simultaneously or sequentially with the composition of the present invention.When applied simultaneously, these additional active ingredients can be formulated together with the composition of the present invention or mixed, for example, in a spray tank.These additional biocidal active ingredients can be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0205] Pesticides are referred to herein using their common names and are known, for example, from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.

[0206] Additionally, the compositions of the present invention can be applied in conjunction with one or more systemic acquired resistance inducers ("SAR" inducers). SAR inducers are known and are described, for example, in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercially available SAR inducer acibenzolar-S-methyl.

[0207] The compound of formula (I) according to the present invention is usually used in the form of agrochemical compositions, and can be applied to the cropland or the plants to be treated simultaneously or successively with other compounds.These additional compounds can be, for example, fertilizers or sources of trace elements or other preparations that affect plant growth.They can also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, and if necessary, also contain additional carriers, surfactants or application-promoting adjuvants that are commonly used in the technical field of formulations.

[0208] The compounds of formula (I) according to the invention may also be used in the form of (fungicidal) compositions for the control against or protection against phytopathogenic microorganisms, containing as active ingredient at least one compound of formula (I) or at least one preferred individual compound as defined herein, in free form or in the form of an agrochemically available salt, and at least one of the adjuvants mentioned above.

[0209] Therefore, the present invention provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I) according to the present invention, an agriculturally acceptable carrier, and optionally an adjuvant.Agriculturally acceptable carriers are, for example, carriers suitable for agricultural use.Agricultural carriers are well known in the art.Preferably, the composition may contain at least one or more pesticide active compounds, for example, additional fungicidal active ingredients, in addition to the compound of formula (I).

[0210] The compound of formula (I) according to the invention may be the only active ingredient of the composition or, if appropriate, may be mixed with one or more additional active ingredients, such as pesticides, fungicides, synergists, herbicides or plant growth regulators, which may in some cases result in unexpected synergistic effects.

[0211] Examples of suitable additional active ingredients include: acyl amino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides. fungicides, mercury fungicides, morpholine fungicides, organophosphate fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides and zinc fungicides.

[0212] Examples of suitable additional active ingredients include: petroleum, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, 2,4-dichlorophenylbenzenesulfonate, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenylphenylsulfone, acetoprole, aldoxicarb, amidithione, amidothioate, amiton, amiton hydrogen oxalate, amitraz, alamite, arsenic trioxide, azobenzene, azotoate, benomyl, benoxafos, benzyl benzoate, bixafen, brofenvalerate ate, bromocyclen, bromophos, bromopropylate, buprofezin, butocarboxim, butoxycarboxim, butylpyridaben, calcium polysulfide, camphechlor, carbanolate, carbophenothion, cymiazole, chimicianat, chlorbeneside, chlordimeform, chlordimeform hydrochloride, chlorphenetole, chlorfenson, chlorphenesulfide, chlorobenzilate, chloromebuform, chloromethiuron, chloropropylate, chlorthiophos, cinerin I, cinerin II, cinerin, closantel, coumaphos, chlor Rotamiton, Crotoxyphos, Kufraneb, Cyanthoate, DCPM, DDT, Demefion, Demefion-O, Demefion-S, Demeton-methyl, Demeton-O, Demeton-O-methyl, Demeton-S, Demeton-S-methyl, Demeton-S-methyl sulfone, Dichlofluanid, Dichlorvos, Dicrifos, Dienochlor, Dimefox, Zinex, Zinex-diclexin, Dinocap-4, Dinocap-6, Dinocton, Dinopenton, Dinosulfone, Dinotervon, Dioxathion, Diphenylsulfone, Disulfiram, DNOC, Dofenapine, doramectin, endothion, eprinomectin, ethoate-methyl, etrimphos, fenazaflor, fenbutatin oxide, fenothiocarb, fenpyrad, fenpyroximate, fenpyrazamine, fenthone, fentrifanil, flubenzimine, flucycloxuron, fluenethyl, fluorbenside, FMC1137, formetanate, formetanate hydrochloride, formparanate, gamma-HCH, gliodin, halfenprox, hexadecylcyclopropanecarboxylate, isocarbophos, jasmolin I,Jasmolin II, iodofenphos, lindane, malonobene, mecarbam, mefosfolan, mesulfen, methacrifos, methyl bromide, metolcarb, mexacarbate, milbemycin oxime, mipafox, monocrotophos, morphothion, moxidectin, naled, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, nifururidide, nikkomycin, nitrilacarb, nitrilacarb 1:1 zinc chloride complex, omethoate, oxydeprophos, oxydisulfonate Photon, pp'-DDT, parathion, permethrin, fenkapton, phosalone, phospholane, phosphamidon, polychloroterpenes, polynactin, proclonol, promacyl, propoxar, prothidathion, prothoate, pyrethrin I, pyrethrin II, pyrethrins, pyridaphenthion, pirimitate, quinalphos, quinthiofos, R-1492, phosglycine, rotenone, shradan, cebufos, selamectin, sofamid, SSI-121, sulfiram, sulfuramide, sulfotep, sulfur, diflobidazin, tau-fluva Linate, TEPP, Terbam, Tetradifon, Tetrasulf, Thiafanox, Thiocarboxim, Thiofanox, Thiometon, Thioquinox, Thuringiensis, Triamiphos, Triatene, Triazophos, Triazuron, Tripenophos, Trinactin, Vamidothion, Vaniliprole, Bethoxazin, Copper dioctanoate, Copper sulfate, Sibutrin, Dichlorn, Dichlorophen, Endothal, Fentin, Slaked lime, Nabam, Quinoclamine, Quinonamide, Simazine, Triphenyltin acetate, Triphenyltin hydroxide, Crufomate, Pi Perazine, thiophanate, chloralose, fenthion, pyridin-4-amine, strychnine, 1-hydroxy-1H-pyridine-2-thione, 4-(quinoxalin-2-ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bronopol, copper hydroxide, cresol, dipyrithione, dodisin, fenaminosulf, formaldehyde, hydralgafen, kasugamycin, kasugamycin hydrochloride hydrate, Mikkelbis (dimethyldithiocarbamate), nitrapyrin, octhilinone, oxolinic acid, oxytetracycline,Potassium hydroxyquinoline sulfate, probenazole, streptomycin, streptomycin sesquisulfate, tecloftalam, thiomersal, Adoxophyes orana GV, Agrobacterium radiobacter, Amblyseius spp., Anagrapha falcifera NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Autographa californica NPV, Bacillus sphaericus Neide, Beauveria brongniartii, Chrysoperla carnea, Red-spotted ladybird (Cryptolaemus montrouzieri), Codling moth (Cydia pomonella) GV, Leaf-grating wasp (Dacnusa sibirica), Diglyphus isaea, Green house wasp (Encarsia formosa), Desert wasp (Eretmocerus eremicus), Heterorhabditis bacteriophora bacteriophora and H. megidis, ladybug (Hippodamia convergens), Leptomastix dactylopii, Macrolophus caliginosus,Armyworm moth (Mamestra brassicae) NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae, pine sawfly (Neodiprion sertifer) NPV and N. lecontei NPV, Orius spp., Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis, Verticillium lecanii), afolate, visadil, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl afolate, molzide, penfluron, tepa, thiohempa, thiotepa, tretamine, uredepa, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol, (E)-tridec-4-en-1-yl acetate, (E)-6-methylhept-2-en-4-ol, (E, Z)-Tetradeca-4,10-dien-1-yl acetate, (Z)-dodec-7-en-1-yl acetate, (Z)-hexadec-11-enal, (Z)-hexadec-11-en-1-yl acetate, (Z)-hexadec-13-en-11-yn-1-yl acetate, (Z)-icosa-13-en-10-one, (Z)-tetradec-7-en-1-al, (7E,9Z)-dodeca-7,9-dien-1 -yl acetate, (9Z,11E)-tetradec-9,11-dien-1-yl acetate, (9Z,12E)-tetradec-9,12-dien-1-yl acetate, 14-methyloctadec-1-ene, 4-methylnonan-5-ol and 4-methylnonan-5-one, alpha-multistriatin, brevicomin, codrelure, codlemone, curure, disparure, dodec-8-en-1-yl acetate , Dodec-9-en-1-yl acetate, Dodeca-8,10-dien-1-yl acetate, Dominicalua, Ethyl 4-methyloctanoate, Eugenol, Frontalin, Grandolua, Grandolua I, Grandolua II, Grandolua III, Grandolua IV, Hexalua, Ipsdienol, Ipsenol, Japonilua, Lineatin, Littleua, Looplua, Medulua, Megatomoic acid, Methyleugenol,Muscalua, Octadeca-2,13-dien-1-yl acetate, Octadeca-3,13-dien-1-yl acetate, Olfuralua, Orictalua, Ostramon, Siglua, Soldigin, Sulcatol, Tetradec-11-en-1-yl acetate, Trimedulua, Trimedulua A, Trimedulua B1, Trimedulua B2, Trimedulua C, Tranqu-Cole, 2-(Octylthio)ethanol, Butopyronoxyl, Butoxy(Polypropylene Glycol), Dibutyl Adipate, Dibutyl Phthalate, Disuccinate Butyl, diethyl toluamide, dimethylcarbate, dimethyl phthalate, ethyl hexanediol, hexamide, methoquin-butyl, methyl neodecaneamide, oxamate, picaridin, 1-dichloro-1-nitroethane, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane, 1,2-dichloropropane and 1,3-dichloropropene, 1-bromo-2-chloroethane, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate, 2,2-dichlorovinyl 2-ethylsulfinylethyl Methyl phosphate, 2-(1,3-dithiolan-2-yl)phenyl dimethyl carbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate, 2-(4-chloro-3,5-xylyloxy)ethanol, 2-chlorovinyl diethyl phosphate, 2-imidazolidone, 2-isovalerylindan-1,3-dione, 2-methyl(prop-2-ynyl)aminophenyl methyl carbamate, 2-thiocyanatoethyl laurate , 3-bromo-1-chloroprop-1-ene, 3-methyl-1-phenylpyrazol-5-yldimethylcarbamate, 4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate, acetione, acrylonitrile, aldrin, allosamidin, allylxycarb, alpha-ecdysone, aluminum phosphide, aminocarb, anabasine, adidathion, azamethiphos, Bacillus thuringiensis delta-endotoxin, barium hexafluorosilicate, barium polysulfide, bartholin,Bayer 22 / 190, Bayer 22408, beta-cyfluthrin, beta-cypermethrin, bioethanomethrin, biopermethrin, bis(2-chloroethyl)ether, borax, bromfenvinphos, bromo-DDT, bufencarb, butacarb, butathiophos, butonate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, sevadine, chlorbicyclen, chlordane, chlordecone, chloroform, chloropicrin, chlorphoxim, chlorprazophos, cis-resmethrin, cismethrin, clocitrin, acetoarsenous acid Copper, copper arsenate, copper oleate, cumitoate, cryolite, CS708, cyanofenphos, cyanophos, cyclethrin, cythioate, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidaphos, dikapton, diclofenthion, dicresyl, dicyclanil, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dilol, dimefluthrin, dimethane, dimethrin, dimethylvinphos, dimethyllan, dinoprop, dinosam, dinoseb, diofenolan, dioxabenzophos, dicyclophos, DSP, ex Disterone, EI1642, EMPC, EPBP, etaphos, ethiofencarb, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, EXD, fenchlorphos, fenetacarb, fenitrothion, fenoxacrim, fenpyritrin, fensulfothion, fenthion-ethyl, flucofuron, fosmetiran, fospirate, fostietan, furathiocarb, fretrin, guazatine, guazatine acetate, sodium tetrathiocarbonate, halfenprox, HCH, HEOD, heptachlor, heterophos, HHDN, Hydrogen cyanide, hikincarb, IPSP, isazophos, isobenzan, isodrin, isofenphos, isolane, isoprothiolane, isoxathion, juvenile hormone I, juvenile hormone II, juvenile hormone III, kerevan, kinoprene, arsenic lead, leptophos, lilimphos, ritidathion, m-cumenylmethylcarbamate, magnesium phosphide, magidox, mecarfone, menasone, mercurous chloride, mesulfenphos, metam, metam-potassium, metam-sodium, methanesulfonyl fluoride, metoclofos, methoprene, methotrin,Methoxychlor, methyl isothiocyanate, methyl chloroform, methylene chloride, methoxadiazone, Mirex, naphthalophos, naphthalene, NC-170, nicotine, nicotine sulfate, nithiazine, nornicotine, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate, O,O,O',O'-tetrapropyl dithiopyrophosphate, oleic acid, para-dichlorobenzene, parathion-methyl, pentachlorophenol, pentachlorophenyl laurate, PH60-38, fenkapton, phosniclor, phosphine, phoxim-methyl, pyrimetaphos, polychlorodicyclopentadiene isomers, potassium arsenite, potassium thiocyanate Anate, precocene I, precocene II, precocene III, primidophos, profluthrin, promecarb, prothiofos, pyrazophos, pyresmethrin, quassia, quinalphos-methyl, quinothion, lafoxanide, resmethrin, rotenone, kadethrin, ryania, ryanodine, sabadila, shradan, cebufos, SI-0009, tiapronil, sodium arsenite, sodium cyanide, sodium fluoride, sodium hexafluorosilicate, sodium pentachlorophenoxide, sodium selenate, sodium thiocyanate, sulcofuron, sulcofuron-sodium, sulfuryl fluoride, sulprofos, tar oil, tazimcarb, TDE, tebupirimfos, temephos, telalethrin, tetrachloroethane, cyclofos, thiocyclam, thiocyclam hydrogen oxalate, thionazine, thiosultap, thiosultap-sodium Tralomethrin, transpermethrin, triazamate, trichlormethaphos-3, trichloronat, trimethacarb, tolprocarb, triclopyricarb, triplen, veratridine, veratrine, XMC, zetamethrin, zinc phosphide, zolaprofos, meperfluthrin, tetramethylfluthrin, bis(tributyltin) oxide, bromoacetamide, ferric phosphate, niclosamide-olamine, tributyltin oxide, pyrimorph, triphenmorph, 1,2- Dibromo-3-chloropropane, 1,3-dichloropropane, 3,4-dichlorotetrahydrothiophene 1,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid, 6-isopentanylaminopurine, anicifluprine, benclothiaz, cytokinin, DCIP, furfural, isamidophos, kinetin, mulberry dark spot fungus (Myrothecium verrucaria) compound, tetrachlorothiophene, xylenol, zeatin, potassium ethylxanthate, acibenzolar, acibenzolar-S-methyl, giant knotweed (Reynoutria sacharinensis) sachalinensis) extract, alpha-chlorohydrin, antu, barium carbonate, bisthiosemi, brodifacoum, bromadiolone, bromethalin, chlorophacinone, cholecalciferol, coumachlor, coumafuryl, coumatetralyl, crimidine, difenacoum, difethialone, diphacinone, ergocalciferol, flocoumafen, fluoroacetamide, flupropadiene, flupropadiene hydrochloride, norbormide, fosacetim, phosphorus, pindone, pyrinuron, Sciliroside, sodium fluoroacetate, thallium sulfate, warfarin, 2-(2-butoxyethoxy)ethyl piperonylate, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, farnesol and nerolidol, verbutin, MGK264, piperonyl butoxide, piprotal, propyl isomer, S421, sesamex, sesamolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, thiram, zinc naphthenate, ziram, imanine,Ribavirin, chlorinconazide, mercuric oxide, thiophanate-methyl, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furametpyr, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazol, pefurazoate, penconazole, prothioconazole, pyrifenox, prochlorazol, propiconazole , pyrizoxazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, ancymidol, fenarimol, nuarimol, bupirimate, dimethirimol, ethirimol, dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph, cyprodinil, mepanipyrim, pyrimethanil, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace, oxadixyl, carbendazim, debacal bu, fuberidazole, thiabendazole, chlozolinate, dichlozolin, mycrozolin, procymidone, vinclozolin, boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide, dodine, iminooctadine, azoxystrobin, dimoxystrobin, enestrobulin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclost Robin, pyrametostrobin, pyraoxystrobin, ferbam, mancozeb, maneb, metiram, propineb, zineb, captafol, captan, fluoroimide, folpet, tolylfluanid, Bordeaux mixture, copper oxide, mancopper, oxine-copper, nitrothar-isopropyl, edifenphos, iprobenfos, fosdifen, tolclofos-methyl, anilazine, benthiavalicarb, blasticidin-S, chloroneb, chlorothalonil, cyflufenamid, cymoxanil, cyclobutrifluram, diclocymet, diclomedine,Dicloran, diethofencarb, dimethomorph, flumorph, dithianon, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, ferimzone, fluazinam, flumethylsulfolim, fluopicolide, fluoxythioconazole, flusulfamide, fluxapyroxad, fenhexamid, fosetyl-aluminum, hymexazole, iprovalicarb, cyazofamid, metasulfocarb, metrafenone, pencycuron, phthalide, polyoxin, propamocarb, pyribencarb, proquinazid do, pyroquilon, pyriophenone, quinoxyfen, quintozene, tiadinil, triazoxide, tricyclazole, triforine, validamycin, valifenalate, zoxamide, mandipropamide, fluveneteram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, isoflucipram, isotianil, dipimethitrone, 6-ethyl-5,7-dioxo-pyrrolo[ 4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-4-methylphenyl)- 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, fluindapyr, methoxystrobin (jiaxiangjunzhi), rubenmixianan, diclobenthiazox, mandestrobin, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone,2-[2-Fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, oxathiapiproline, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, pyraziflumide, impirfluxam, torolprocarb, mefentrifluconazole, ipfentrifluconazole, 2-(difluoromethyl)-N-[(3R)-3-ethyl -1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4, 5-Dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridyl Dazin, pyridaclomethyl, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one, Aminopyrifen, ametoctrazine, amisulbrom, penflufen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, florylpicoxamide, fenpicoxamide, methallylpicoxamide, tebufloquine, isofetamide, ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate (WO 2020 / 056090 No. 2020 / 056090), ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate (can be prepared from the method described in WO 2020 / 056090), methyl N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate (can be prepared from the method described in WO 2020 / 097012), methyl N-[[4-[1 -(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate (preparable from the method described in WO 2020 / 097012), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (preparable from the method described in WO 2020 / 109391), 6-chloro-N-[2-(2-chloro-4-methyl 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (preparable from the method described in WO 2020 / 109391), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (preparable from the method described in WO 2020 / 109391), N-[2-[2,4-Dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, Benzothiostrobin, Fenamacril, 5-Amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1), Fluopyram, Flufenoxadiazam, Flutianil, Fluopimomide, Enoxastrobin, Methyl (Z)-3-methoxy-2-[2-methyl -5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate, methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate, methyl (Z)-3-meth methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (these compounds can be prepared from the method described in WO 2020 / 193387), 4-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate (these compounds can be prepared from the method described in WO 2020 / 079111), methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (these compounds can be prepared from the method described in WO 2020 / 193387), -[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, trinexapac, cumoxystrobin, zhongshengmycin, copper thiodiazole, zinc thiazole, amethotractin, iprodione, seboxylamine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl] -N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1- N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared from the method described in WO 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared from the method described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine (1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)- 1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro- Quinoline-3-carboxamide, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared by the method described in WO 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6- Trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds can be prepared from the method described in WO 2017 / 025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds can be prepared from the method described in WO 2016 / 156085);N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl) 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-Ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-Dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-3-carboxylate -yl]phenyl]methyl]-1,2,4-triazol-3-amine (these compounds can be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689); 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared from the methods described in WO 2017 / 029179);2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared from the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (this compound can be prepared from the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (this compound can be prepared from the method described in WO 2014 / 006945); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide (which can be prepared from the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound can be prepared from the method described in WO 2018 / 153707); N'- (2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from the method described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared from the method described in WO 2014 / 095675);(5-Methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds can be prepared from the method described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared from the method described in WO 2018 / 065414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxyle acetamide (which can be prepared by the method described in WO 2018 / 158365); 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (which can be prepared by the method described in WO 2018 / 202428);

[0213] The compounds of the present invention may also be used in combination with antiparasitic agents, including compounds selected from the macrocyclic lactone class of compounds, such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin, and milbemycin derivatives, as described in EP 0357460, EP 0444964, and EP 0594291. Additional antiparasitic agents include semi-synthetic and biosynthetic avermectin / milbemycin derivatives, such as those described in U.S. Pat. No. 5,015,630, WO 94 / 15944, and WO 95 / 22552. Additional anthelmintics include benzimidazoles such as albendazole, cambandazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of this class. Additional anthelmintics include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel, or morantel. Additional anthelmintics include flukicides such as triclabendazole and clorsulon, and cestocidal drugs such as praziquantel and epsiprantel.

[0214] The compounds of the present invention can be used in combination with derivatives and analogs of the paraherquamide / markfortin class of anthelmintic agents, as well as anthelmintic oxazolines such as those disclosed in U.S. Pat. No. 5,478,855, U.S. Pat. No. 4,639,771, and German Patent No. 19520936.

[0215] The compounds of the invention may also be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO 96 / 15121, and also with anthelmintic-effective cyclic depsipeptides such as those described in WO 96 / 11945, WO 93 / 19053, WO 93 / 25543, EP 0626375, EP 0382173, WO 94 / 19334, EP 0382173 and EP 0503538.

[0216] The compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide; neonicotinoids such as imidacloprid.

[0217] The compounds of the present invention may also be used in combination with terpene alkaloids, such as those described in WO 95 / 19363 or WO 04 / 72086, particularly the compounds disclosed therein.

[0218] Other examples of such biologically active compounds that may be used in combination with the compounds of the present invention include, but are not limited to, the following: Organic phosphates: Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Bromophos, Bromophos-ethyl, Cadusafos, Chlorethoxyphos, Chlorpyrifos, Chlorfenvinphos, Chlormephos, Demeton, Demeton-S-methyl, Demeton-S-methylsulfone, Dialifos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Disulfoton, Ethion, Ethoprophos, Etrimphos, Famfur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazophos, Fonofos, Formothion, Fosthiazate, Heptenophos, Isazophos, Isothioate, Isoxathion, Malathion, Methac Rifos, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate, phosalone, phospholane, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos-methyl, profenofos, propafos, proetamphos, prothiofos, pyraclofos, pyridapenthione, quinalphos, sulprofos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, timeton, triazophos, trichlorfon, vamidothion. Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl (methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717. Pyrethroids: acrinathrin, allethrin, alphamethrin, (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate 5-benzyl-3-furylmethyl, bifenthrin, β-cyfluthrin, cyfluthrin, α-cypermethrin, β-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, Deltamethrin, empenthrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D-isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, fenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, zeta-cypermethrin. Arthropod growth regulators: a) Chitin synthesis inhibitors: Benzoyl ureas: Chlorfluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Teflubenzuron, Triflumuron, Buprofezin, Diofenolan, Hexythiazox, Etoxazole, Chlorfentadine; b) Ecdysone antagonists: Halofenozide, Methoxyfenozide, Tebufenozide; c) Juvenoids: Pyriproxyfen, Methoprene (including S-Methoprene), Fenoxycarb; d) Lipid biosynthesis inhibitors: Spirodiclofen. Other antiparasitic agents: acequinocyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis thuringiensis), bensultap, bifenazate, binapropacryl, bromopropylate, BTG-504, BTG-505, camfechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidin, cyromazine, diaclor, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, etofenprox, fenazaquin, flumite, MTI-800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzin, flufenprox, fluproxifen, halofen Enprox, hydramethylnon, IKI-220, Kanemite, NC-196, Niemgard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pyridalyl, propargite, protrifenbut, pymetrozine, pyridaben, pyrimidifen, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, cyromazine, spinosad, tebufenpyrad, tetradifon, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosyn, trinactin, verbutin, Bertarec, YI-5301. Biological agents: Bacillus thuringiensis subspecies aizawai, kurstaki, Bacillus thuringiensis delta-endotoxin, baculovirus, entomopathogenic bacteria, viruses and fungi. Fungicides: chlortetracycline, oxytetracycline, streptomycin. Other biological agents: enrofloxacin, febantel, penethamate, meloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel, triclabendazole.

[0219] The following mixtures of compounds of formula (I) with active ingredients are preferred: The abbreviation "TX" means one compound selected from the group consisting of formula (I), formula (Ia), formula (Ia-A), formula (Ia-B) or formula (Ia-C), or one compound selected from the group consisting of the compounds represented in Tables C-1 to C-21 or the compounds listed in Table P (below): Petroleum + TX, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 4-chlorophenyl phenyl sulfone + TX, acetoprole + TX, aldoxicarb + TX, amidithione + TX, amidothioate + TX, amiton + TX, amiton hydrogen oxalate + TX, amitraz + TX, alamite + TX, arsenic trioxide + TX, azobenzene + TX, azotoate + TX, benomyl + TX, benoxafos + T X, benzyl benzoate +TX, bixafen +TX, brofenvalerate +TX, bromocyclen +TX, bromophos +TX, bromopropylate +TX, buprofezin +TX, butocarboxim +TX, butoxycarboxim +TX, butylpyridaben +TX, calcium polysulfide +TX, camphechlor +TX, carbanolate +TX, carbophenothion +TX, cymiazole +TX, chimicianat +TX, chlorbencide +TX, chlorfenson +TX, chlordimeform hydrochloride +TX, chlorphenetole +TX, chlorfenson +TX , Chlorfensulfide +TX, Chlorobenzilate +TX, Chlormebform +TX, Chlormethiuron +TX, Chloropropylate +TX, Chlorthiophos +TX, Cinerin I +TX, Cinerin II +TX, Cinerin +TX, Closantel +TX, Coumaphos +TX, Crotamiton +TX, Crotoxyphos +TX, Kufraneb +TX, Cyanthoate +TX, DCPM +TX, DDT +TX, Demefion +TX, Demefion-O +TX, Demefion-S +TX, Demeton-methyl +TX, Demeton-O +TX, Demeton-O-methyl +TX, De Demeton-S+TX, Demeton-S-methyl+TX, Demeton-S-methylsulfone+TX, Dichlofluanid+TX, Dichlorvos+TX, Dicrifos+TX, Dienochlor+TX, Dimefox+TX, Zinex+TX, Zinex-Diclexin+TX, Dinocap-4+TX, Dinocap-6+TX, Dinocton+TX, Dinopenton+TX, Dinosulfone+TX, Dinotervone+TX, Dioxathion+TX, Diphenylsulfone+TX, Disulfiram+TX, DNOC+TX, Dofenapine+TX, Doramectin+TX, Endothion+TX,Eprinomectin +TX, Ethoate-methyl +TX, Etrimphos +TX, Fenazaflor +TX, Fenbutatin oxide +TX, Fenothiocarb +TX, Fenpyrad +TX, Fenpyroximate +TX, Fenpyrazamine +TX, Fenson +TX, Fentrifanil +TX, Flubenzimine +TX, Flucycloxuron +TX, Fluenethyl +TX, Fluorobenside +TX, FMC1137 +TX, Formetanate +TX, Formetanate Hydrochloride +TX, Formoparanate +TX, Gamma-HCH +TX, Gliodin +TX, Halfenp Rox + TX, Hexadecylcyclopropanecarboxylate + TX, Isocarbophos + TX, Jasmolin I + TX, Jasmolin II + TX, Iodofenphos + TX, Lindane + TX, Malonoben + TX, Mecarbam + TX, Mefosphorane + TX, Mesulfen + TX, Methacrifos + TX, Methyl Bromide + TX, Metolcarb + TX, Mexacarbate + TX, Milbemycin Oxime + TX, Mipafox + TX, Monocrotophos + TX, Morphothion + TX, Moxidectin + TX, Naled + TX, 4-Chloro-2-(2-chloro-2-methyl -propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, Nifluridizide + TX, Nikkomycin + TX, Nitrilacarb + TX, Nitrilacarb 1:1 zinc chloride complex + TX, Omethoate + TX, Oxydeprophos + TX, Oxydisulfoton + TX, pp'-DDT + TX, Parathion + TX, Permethrin + TX, Fenkapton + TX, Phosalone + TX, Phosphorane + TX, Phosphamidon + TX, Polychloroterpenes + TX, Polynactin + TX, Proclonol + TX, Promacyl + TX, Propoxar + TX, Protidathion + TX, Protoate + TX, Pyrethrin I + TX, Pyrethrin II + TX, Pyrethrin + TX, Pyridaphenthion + TX, Pirimitate + TX, Quinalphos + TX, Quinthiofos + TX, R-1492 + TX, Phosglycine + TX, Rotenone + TX, Schradan + TX, Cebufos + TX, Selamectin + TX, Sofamid + TX, SSI-121 + TX, Sulfiram + TX, Sulfuramide + TX, Sulfotep + TX, Sulfur + TX, Diflobidazin + TX, Tau-fluvalinate + TX, TEPP + TX, Thelbam + TX,Tetradifon +TX, Tetrasulf +TX, Thiafanox +TX, Thiocarboxim +TX, Thiofanox +TX, Thiometon +TX, Thioquinox +TX, Thuringiensis +TX, Triamiphos +TX, Triatene +TX, Triazophos +TX, Triazuron +TX, Trifenophos +TX, Trinactin +TX, Vamidothion +TX, Vaniliprole +TX, Bethoxazin +TX, Copper dioctanoate +TX, Copper sulfate +TX, Sibutrin +TX, Dichlorn +TX, Dichlorophen +TX, Endothal +TX, Fentin +TX, Slaked lime +TX, Nabam +TX, Quinoclamine +TX, Quinonamide +TX, Simazine +TX, Triphenyltin acetate +TX, Triphenyltin hydroxide +TX, Crufomate + TX, piperazine + TX, thiophanate + TX, chloralose + TX, fenthion + TX, pyridin-4-amine + TX, strychnine + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 8-hydroxyquinoline sulfate + TX, bronopol + TX, copper hydroxide + TX, cresol + TX, dipyrithione + TX, dodisin + TX, fenaminosulf + TX, formaldehyde + TX, hydralgafen + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, nickel bis(dimethyldithiocarbamate) + TX, nitrapyrin + TX, octhilinone + TX, oxolinic acid + TX, oxytetracycline + TX, Potassium hydroxyquinoline sulfate + TX, probenazole + TX, streptomycin + TX, streptomycin sesquisulfate + TX, tecloftalam + TX, thiomersal + TX, Adoxophyes orana GV + TX, Agrobacterium radiobacter + TX, Amblyseius spp. + TX, Anagrapha falcifera NPV + TX, Anagrus atomus + TX, Aphelinus abdominalis + TX, Aphidius colemani + TX, Aphidoletes aphidimyza + TX, Autographa californica californica NPV+TX, Bacillus sphaericus Neide+TX, Beauveria brongniartii+TX, Chrysoperla carnea+TX, Red-spotted ladybird (Cryptolaemus montrouzieri)+TX, Codling moth (Cydia pomonella) GV+TX, Leaf-grating wasp (Dacnusa sibirica)+TX, Diglyphus isaea)+TX, and Greenhouse wasp (Encarsia formosa) formosa) + TX, desert fire wasp (Eretmocerus eremicus) + TX, Heterorhabditis bacteriophora and H. megidis + TX, ladybug (Hippodamia convergens) + TX,Leptomastix dactylopii + TX, Macrolophus caliginosus + TX, Armyworm moth (Mamestra brassicae) NPV + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, Pine sawfly (Neodiprions ertifer) NPV and N. lecontei NPV + TX, Orius spp. spp.) + TX, Paecilomyces fumosoroseus + TX, Phytoseiulus persimilis + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisi scapterisci + TX, Steinernema spp. + TX, Trichogramma spp. + TX, Typhlodromus occidentalis + TX, Verticillium lecanii + TX, Afolate + TX, Visadil + TX, Busulfan + TX, Dimatif + TX, Hemel + TX, Hempa + TX, Metepa + TX, Methiotepa + TX, Methyl Afolate + TX,Molzide + TX, Penfluron + TX, Tepa + TX, Thiohempa + TX, Thiotepa + TX, Tretamine + TX, Uredepa + TX, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX, (E)-tridec-4-en-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E,Z)-tetradec-4,10-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-11-enal + TX (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-icosa-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradec-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradec-9,12-dien-1-yl acetate Acetate + TX, 14-methyloctadec-1-ene + TX, 4-methylnonan-5-ol and 4-methylnonan-5-one + TX, alpha-multistriatin + TX, Brevicomin + TX, Codrelure + TX, Codlemone + TX, Curure + TX, Disparlure + TX, Dodec-8-en-1-yl acetate + TX, Dodec-9-en-1-yl acetate + TX, Dodec-8 + TX, 10-dien-1-yl acetate + TX, Dominicalure + TX, Ethyl 4-methyloctanoate + TX, Eugenol + TX, Frontalin + TX, Glycerol Landrua + TX, Grandrua I + TX, Grandrua II + TX, Grandrua III + TX, Grandrua IV + TX, Hexalua + TX, Ipsdienol + TX, Ipsenol + TX, Japonilua + TX, Lineatin + TX, Litulua + TX, Lupulua + TX, Medulua + TX, Megatomoic acid + TX, Methyleugenol + TX, Muscalua + TX, Octadeca-2,13-dien-1-yl acetate + TX, Octadeca-3,13-dien-1-yl acetate + TX, Olfrulua + TX, Orictalua + TX, Ostramon + TX,Cigla + TX, Soldigin + TX, Sulcatol + TX, Tetradec-11-en-1-yl acetate + TX, Trimedlure + TX, Trimedlure A + TX, Trimedlure B1 + TX, Trimedlure B2 + TX, Trimedlure C + TX, Trunk-Cole + TX, 2-(octylthio)ethanol + TX, Butopyronoxyl + TX, Butoxy(polypropylene glycol) + TX, Dibutyl adipate + TX, Dibutyl phthalate + TX, Dibutyl succinate + TX, Diethyltoluamide + TX, Dimethylcarbate + TX, Dimethyl phthalate + TX , ethyl hexanediol + TX, hexamide + TX, methoquin-butyl + TX, methyl neodecaneamide + TX, oxamate + TX, picaridin + TX, 1-dichloro-1-nitroethane + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane + TX, 1,2-dichloropropane and 1,3-dichloropropene + TX, 1-bromo-2-chloroethane + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methylphosphate + TX , 2-(1,3-dithiolan-2-yl)phenyl dimethyl carbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-chlorovinyl diethyl phosphate + TX, 2-imidazolidone + TX, 2-isovalerylindan-1,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenyl methyl carbamate + TX, 2-thiocyanatoethyllaurate acetone + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-methyl-1-phenylpyrazol-5-yldimethylcarbamate + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate + TX, acetone + TX, acrylonitrile + TX, aldrin + TX, allosamidin + TX, alixicarb + TX, aluminum phosphide + TX, aminocarb + TX, anabasine + TX, atidathion + TX, azamethiphos + TX,Bacillus thuringiensis delta endotoxin +TX, barium hexafluorosilicate +TX, barium polysulfide +TX, bartholin +TX, Bayer 22 / 190 +TX, Bayer 22408 +TX, beta-cyfluthrin +TX, beta-cypermethrin +TX, bioethanomethrin +TX, biopermethrin +TX, bis(2-chloroethyl) ether +TX, borax +TX, bromfenvinphos +TX, bromo-DDT +TX, bufencarb +TX, butacarb +TX, butathiophos +TX, butonate +TX, calcium arsenate +TX, calcium cyanide +TX, carbon disulfide +TX, carbon tetrachloride +TX, cartap hydrochloride +TX, sevadin +TX, Chlorbicyclen + TX, chlordane + TX, chlordecone + TX, chloroform + TX, chloropicrin + TX, chlorphoxim + TX, chlorprazophos + TX, cis-resmethrin + TX, cismethrin + TX, clocitrin + TX, copper acetoarsenite + TX, copper arsenate + TX, copper oleate + TX, chumithoate + TX, cryolite + TX, CS708 + TX, cyanofenphos + TX, cyanophos + TX, ciclethrin + TX, cythioate + TX, d-tetramethrin + TX, DAEP + TX, dazomet + TX, decarbofuran + TX, diazomethin Midaphos + TX, Dikapton + TX, Diclofenthion + TX, Dicresyl + TX, Dicyclanil + TX, Dieldrin + TX, Diethyl 5-methylpyrazol-3-yl phosphate + TX, Dilol + TX, Dimefluthrin + TX, Dimethane + TX, Dimethryn + TX, Dimethylvinphos + TX, Dimethylan + TX, Dinoprop + TX, Dinosam + TX, Dinoseb + TX, Diofenolan + TX, Dioxabenzophos + TX, Dicyclophos + TX, DSP + TX, Ecdysterone + TX, EI1642 + TX, EMPC + TX, EPBP + TX , Ethaphos + TX, Ethiofencarb + TX, Ethyl formate + TX, Ethylene dibromide + TX, Ethylene dichloride + TX, Ethylene oxide + TX, EXD + TX, Fenchlorphos + TX, Fenetacarb + TX, Fenitrothion + TX, Fenoxacrim + TX, Fenpyrithrin + TX, Fensulfothion + TX, Fenthion-ethyl + TX, Flucofuron + TX, Fosmetilan + TX, Fospirate + TX, Fostietan + TX, Furathiocarb + TX, Frethrin + TX, Guazatine + TX, Guazatine acetate + TX, Sodium tetrathiocarbonate Um+TX, Halfenprox+TX, HCH+TX, HEOD+TX, Heptachlor+TX, Heterofos+TX, HHDN+TX, Hydrogen cyanide+TX, Hikincarb+TX, IPSP+TX, Isazophos+TX, Isobenzane+TX, Isodrin+TX, Isofenphos+TX, Isolane+TX, Isoprothiolane+TX, Isoxathion+TX, Juvenile hormone I+TX, Juvenile hormone II+TX, Juvenile hormone III+TX, Kelevan+TX, Kinoprene+TX, Arsenic lead+TX, Leptophos+TX, Lilimphos+TX, Ritidathion+TX,m-Cumenyl methylcarbamate +TX, Magnesium phosphide +TX, Magidox +TX, Mecarfone +TX, Menasone +TX, Mercurous chloride +TX, Mesulfenphos +TX, Metam +TX, Metam-potassium +TX, Metam-sodium +TX, Methanesulfonyl fluoride +TX, Metoclofos +TX, Methoprene +TX, Methotrin +TX, Methoxychlor +TX, Methyl isothiocyanate +TX, Methylchloroform +TX, Methylene chloride +TX, Methoxadiazone +TX, Mirex +TX, Naphthalophos +TX, Naphthalene +TX, NC- 170 + TX, nicotine + TX, nicotine sulfate + TX, nithiazine + TX, nornicotine + TX, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate + TX, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate + TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate + TX, O,O,O',O'-tetrapropyl dithiopyrophosphate + TX, oleic acid + TX, para-dichlorobenzene + TX, parathion-methyl + TX, pentachloro Phenol + TX, Pentachlorophenyl Laurate + TX, PH60-38 + TX, Fenkapton + TX, Fosniclor + TX, Phosphine + TX, Phoxim-methyl + TX, Pyrimetaphos + TX, Polychlorodicyclopentadiene Isomers + TX, Potassium Arsenite + TX, Potassium Thiocyanate + TX, Precocene I + TX, Precocene II + TX, Precocene III + TX, Primidophos + TX, Profluthrin + TX, Promecarb + TX, Prothiofos + TX, Pyrazophos + TX, Pyresmethrin + TX, Quassia + TX, Quinalphos Methyl + TX, Quinothione + TX, Rafoxanide + TX, Resmethrin + TX, Rotenone + TX, Kadetrin + TX, Riania + TX, Ryanodine + TX, Sabadila + TX, Schradan + TX, Cebufos + TX, SI-0009 + TX, Tiapronil + TX, Sodium arsenite + TX, Sodium cyanide + TX, Sodium fluoride + TX, Sodium hexafluorosilicate + TX, Sodium pentachlorophenoxide + TX, Sodium selenate + TX, Sodium thiocyanate + TX, Sulcofuron + TX, Sulcofuron-sodium + TX,Sulfuryl fluoride +TX, Sulprofos +TX, Tar oil +TX, Thazimcarb +TX, TDE +TX, Tebupirimfos +TX, Temephos +TX, Teralethrin +TX, Tetrachloroethane +TX, Cyclofos +TX, Thiocyclam +TX, Thiocyclam hydrogen oxalate +TX, Thionazine +TX, Thiosultap +TX, Thiosultap-sodium +TX, Tralomethrin +TX, Transpermethrin +TX, Triazamate +TX, Trichlormethaphos-3 +TX, Trichloronaphthalene +TX, Trimethacarb +TX, Tolprocarb +TX, Triclopiricarb +TX, Triplene +TX, Veratridine +TX, Veratrine +TX, XMC +TX, Zetamethrin +TX, Zinc phosphide +TX, Zolaprofos +TX and Meperfluthrin +TX, Tetramethylfluthrin +TX, Bis(tributyltin)oxide Cid + TX, bromoacetamide + TX, ferric phosphate + TX, niclosamide-olamine + TX, tributyltin oxide + TX, pyrimorph + TX, triphenmorph + TX, 1,2-dibromo-3-chloropropane + TX, 1,3-dichloropropane + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid + TX, 6-isopentanylaminopurine + TX, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine + TX, benclothiaz + TX, cytokinin + TX, DCIP + TX, furfural + TX, isamidophos + TX, kinetin + TX, mulberry dark spot fungus (Myrothecium verrucaria) verrucaria)) composition + TX, tetrachlorothiophene + TX, xylenol + TX, Zeatin + TX, Potassium Ethylxanthate + TX, Acibenzolar + TX, Acibenzolar-S-methyl + TX, Giant Knotweed (Reynoutria sachalinensis) Extract + TX, Alpha-Chlorohydrin + TX, Antu + TX, Barium Carbonate + TX, Bisthiosemi + TX, Brodifacoum + TX, Bromadiolone + TX, Bromethalin + TX, Chlorophacinone + TX, Cholecalciferol + TX, Coumachlor + TX, Coumafuryl + TX, Coumatetralyl + TX, Crimidine + TX, Difenacoum + TX, Difethialone + TX, Diphacinone + TX, Ergocalciferol + TX, Flocoumafen + TX , Fluoroacetamide + TX, Flupropaline + TX, Flupropaline hydrochloride + TX, Norbormide + TX, Fosacetim + TX, Phosphorus + TX, Pindone + TX, Pyrinuron + TX, Sciliroside + TX, Sodium Fluoroacetate + TX, Thallium Sulfate + TX, Warfarin + TX, 2-(2-Butoxyethoxy)ethyl Piperonylate + TX, 5-(1,3-Benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, Farnesol and Nerolidol + TX, Verbutin + TX, MGK264+TX, piperonyl butoxide+TX, piprotal+TX, propyl isomers+TX, S421+TX, sesamex+TX, sesamolin+TX, sulfoxide+TX, anthraquinone+TX, copper naphthenate+TX, copper oxychloride+TX, dicyclopentadiene+TX, thiram+TX, zinc naphthenate+TX, ziram+TX, imanin+TX, ribavirin+TX, mercuric oxide+TX, thiophanate-methyl+TX, azaconazole+TX, bitertanol+TX, bromuconazole+TX, cilantrole Proconazole + TX, difenoconazole + TX, diniconazole + TX, epoxiconazole + TX, fenbuconazole + TX, fluquinconazole + TX, flusilazole + TX, flutriafol flusilazole + TX, furametpyr + TX, hexaconazole + TX, imazalil + TX, imibenconazole + TX, ipconazole + TX, metconazole + TX, myclobutanil + TX, paclobutrazol + TX, pefurazoate + TX, penconazole + TX, prothioconazole + TX,Pyrifenox +TX, Prochloraz +TX, Propiconazole +TX, Pyrizoxazole +TX, Simeconazole +TX, Tebuconazole +TX, Tetraconazole +TX, Triadimefon +TX, Triadimenol +TX, Triflumizole +TX, Triticonazole +TX, Ancymidol +TX, Fenarimol +TX, Nuarimol +TX, Bupirimate +TX, Dimethirimol +TX, Ethirimol +TX, Dodemorph +TX, Fenpropidin +TX, Fenpropimorph +TX, Spiroxamine +TX, Tridemorph +TX, Cyprodinil +TX, mepanipyrim +TX, pyrimethanil +TX, fenpiclonil +TX, fludioxonil +TX, benalaxyl +TX, furalaxyl +TX, metalaxyl +TX, R-metalaxyl +TX, ofurace +TX, oxadixyl +TX, carbendazim +TX, debacarb +TX, fuberidazole +TX, thiabendazole +TX, chlozolinate +TX, dichlozolin +TX, mycozolin +TX, procymidone +TX, vinclozolin +TX, boscalid +TX, carboxin +TX, fenfuram +TX, flutolanil +TX, mepronil +TX X, Oxycarboxin +TX, Penthiopyrad +TX, Thifluzamide +TX, Dodine +TX, Iminooctadine +TX, Azoxystrobin +TX, Dimoxystrobin +TX, Enestrobulin +TX, Phenaminestrobin +TX, Flufenoxystrobin +TX, Fluoxastrobin +TX, Kresoxim-methyl +TX, Metominostrobin +TX, Trifloxystrobin +TX, Orysastrobin +TX, Picoxystrobin +TX, Pyraclostrobin +TX, Pyrametstrobin +TX, Pyraoxystrobin +TX, Ferbam + TX, mancozeb + TX, maneb + ​​TX, metiram + TX, propineb + ​​TX, zineb + ​​TX, captafol + TX, captan + TX, fluoroimide + TX, folpet + TX, tolylfluanid + TX, Bordeaux mixture + TX, copper oxide + TX, mancopper + TX, oxine-copper + TX, nitrothal-isopropyl + TX, edifenphos + TX, iprobenfos + TX, phosdifen + TX, tolclofos-methyl + TX, anilazine + TX, benthiavalicarb + TX, blasticidin-S + TX, chloroneb + ​​TX, chlorothalonil + TX,Cyflufenamid + TX, Cymoxanil + TX, Cyclobutrifluram + TX, Diclocymet + TX, Diclomedine + TX, Dicloran + TX, Diethofencarb + TX, Dimethomorph + TX, Flumorph + TX, Dithianon + TX, Ethaboxam + TX, Etridiazole + TX, Famoxadone + TX, Fenamidone + TX, Fenoxanil + TX, Ferimzone + TX, Fluazinam + TX, Fluopicolide + TX, Flusulfamide + TX, Fluxapyroxad + TX, Fenhexamid + TX, Fosetyl-aluminum fluoxetine + TX, hymexazole + TX, iprovalicarb + TX, cyazofamid + TX, methasulfocarb + TX, metrafenone + TX, pencycuron + TX, phthalide + TX, polyoxin + TX, propamocarb + TX, pyribencarb + TX, proquinazid + TX, pyroquilon + TX, pyriophenone + TX, quinoxyfen + TX, quintozene + TX, tiadinil + TX, triazoxide + TX, tricyclazole + TX, triforine + TX, validamycin + TX, valifenalate + TX, zoxamide + TX, mandipro Pamid + TX, fluveneteram + TX, isopyrazam + TX, sedaxane + TX, benzovindiflupyr + TX, pydiflumetofen + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, isoflucipram + TX, isotianil + TX, dipimethitrone + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino(dithiino)[1,2-c]isothiazole-3-carbonitrile + TX, 2-( (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + TX,4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine + TX, fluindapyr + TX, methoxystrobin (jiaxiangjunzhi) + TX, rubenmixianan + TX, diclobenthiazox + TX, mandestrobin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone + TX, 2-[2-fluoro 6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, oxathiapiproline + TX, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, pyraziflumide + TX, impirfluxam + TX, torolprocarb + TX, mefentrifluconazole + TX, ipfentrifluconazole + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl- 1,1-Dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxa tetrazol-5-yl]-3-chlorophenyl] methanesulfonate + TX, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, pyridaclomethyl + TX,3-(Difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, Aminopyrifen + TX, ametoctrazine + TX, amisulbrom + TX, penflufen + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX, florylpicoxamide + TX, fenpicoxamide + TX, tebufloquin + TX, ipflufenoquin + TX, quinofumelin + TX, isofetamide + TX, N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-cal Voxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, benzothiostrobin + TX, fenamacryl + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, fluopyram + TX, flutianil + TX, fluopimomide + TX, pyrapropoin + TX, picarbutrazox + TX, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyrazole Indan-3-carboxamide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, methyltetraprole + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, α- (1,1-Dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol + TX, fluoxapiprolin + TX, enoxastrobin + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, trinexapac + TX, cumoxystrobin + TX, zhongshengmycin + TX, copper thiodiazole + TX, zinc thiazole + TX, ame Cutotractin + TX, iprodione + TX, N-octyl-N'-[2-(octylamino)ethyl]ethane-1,2-diamine + TX; N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds are disclosed in WO 2015 / 15507 No. 5); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared by the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds can be prepared from the method described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl )tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine + TX (these compounds can be prepared from the method described in WO 2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline 8-Fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-Fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl)-8-fluoro-quinoline-3-carboxamide + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX (these compounds can be prepared from the method described in WO 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trimethylpyrazole-3-yl ... Trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4 ,4-difluoro-3,3-dimethyl-isoquinoline + TX (these compounds can be prepared from the method described in WO 2017 / 025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 4,4-Difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole + TX (these compounds can be prepared by the method described in WO 2016 / 156085); N-methoxyN-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N,2-DimethoxyN-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, 1-methoxy3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1,3-dimethoxy1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 3-Ethyl N-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, Ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine + TX. The compounds in this paragraph can be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound can be prepared from the methods described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound can be prepared from the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX (this compound can be prepared from the method described in 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX (this compound can be prepared from the method described in WO 2016 / 156290); (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX (this compound can be prepared from the method described in WO 2016 / 156290). can be prepared from the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrolo-1,3,5,7(2H,6H)-tetrone + TX (this compound can be prepared from the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide + TX;N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX (this compound can be prepared from the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl -formamidine + TX; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared from the method described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX (this compound can be prepared from the method described in WO 2014 / 095675 (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX (these compounds can be prepared from the method described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX (this compound can be prepared from the method described in WO 2018 / 065414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate + TX (this compound can be prepared from the method described in WO 2018 / 158365);2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[ a compound selected from the group of substances consisting of N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX (these compounds can be prepared by the method described in WO 2018 / 202428), chlorinconazide + TX, flumethylsulfolim + TX, fluoxythioconazole + TX, flufenoxadiazam + TX, methallylpicoxamide + TX;

[0220] A reference in parentheses following an active ingredient, such as [3878-19-1], refers to the Chemical Abstracts Registry number. The aforementioned mixing partners are publicly known. When active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: CDS TomLin; The British Crop Protection Council], they are listed therein under the entry number indicated in parentheses above for the particular compound; for example, the compound "abamectin" is listed under entry number (1). When a specific compound listed above is marked with "[CCN]," the compound in question is included in the "Compendium of Pesticide Common Names," accessible via the Internet at [A. Wood; Compendium of Pesticide Common Names, Copyright 1995-2004]; for example, the compound "acetoprole" is listed at the Internet address http: / / www.alanwood.net / pesticides / acetoprole.html.

[0221] Most of the active ingredients listed above are referred to above by so-called "common names," where in each case the relevant "ISO common name" or another "common name" is used. If the name is not a "common name," the nature of the name used instead is given in parentheses for the particular compound; in that case, the IUPAC name, IUPAC / Chemical Abstracts name, "chemical name," "customary name," "compound name," or "development code" is used, or, if none of these names and no "common name" is used, an "alternative name" is utilized. "CAS Registry Number" means the Chemical Abstracts Registry Number.

[0222] The active ingredient mixture of a compound selected from the group consisting of compounds of formula (I), (Ia), (Ia-A), (Ia-B) or (Ia-C), or one compound selected from the group consisting of compounds represented in Tables C-1 to C-21, or a compound listed in Table P (below) is preferably in a mixing ratio of 100:1 to 1:100, in particular 50:1 to 1:50, more in particular 20:1 to 1:20, even more in particular 10:1 to 1:10, and even more in particular 5:1 to 1:5, these mixing ratios being by weight.

[0223] A mixture as described above may be used in a method for controlling pests, the method comprising applying a composition comprising a mixture as described above to the pest or its environment, excluding methods of treating the human or animal body by surgery or therapy or diagnostic methods practiced on the human or animal body.

[0224] A mixture comprising a compound selected from the group consisting of compounds of formula (I), (Ia), (Ia-A), (Ia-B), (Ia-C), or one compound selected from the group consisting of the compounds represented in Tables C-1 to C-21, or a compound listed in Table P (below), and one or more of the above active ingredients may be applied, for example, in the form of a single "prepared ingredient," as a combined spray mixture composed of separate formulations of a single active ingredient, such as a "tank mix," and in combination with a single active ingredient when applied sequentially, i.e., one after the other within a fairly short period of time, such as a few hours or days. The order of applying a compound selected from the group consisting of compounds of formula (I), (Ia), (Ia-A), (Ia-B), (Ia-C), or one compound selected from the group consisting of the compounds represented in Tables C-1 to C-21, or a compound listed in Table P (below), and the above active ingredients, is not essential to the practice of the invention.

[0225] The compositions according to the invention may also comprise further solid or liquid auxiliaries, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (for example epoxidized palm oil, rapeseed oil or soybean oil), antifoaming agents, for example silicone oils, preservatives, viscosity regulators, binders and / or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0226] The compositions according to the invention are prepared in a manner known per se in the absence of auxiliaries, for example by grinding, sieving and / or compressing the solid active ingredient, and in the presence of at least one auxiliary, for example by intimately mixing the active ingredient with one or more auxiliaries and / or grinding. These methods for preparing the compositions and the use of compound (I) for preparing these compositions are also the subject of the present invention.

[0227] Another aspect of the present invention relates to the use of a compound of formula (I) according to the present invention or a preferred individual compound as defined herein, or a composition comprising at least one compound of formula (I) or at least one preferred individual compound as defined herein, or a fungicidal or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as defined herein in admixture with other fungicides or insecticides as defined above, for controlling or preventing infestation on plants, e.g. useful plants such as crop plants, their propagation material, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living material by phytopathogenic microorganisms, e.g. insects or preferably fungal organisms.

[0228] A further aspect of the present invention relates to a method for controlling or preventing infestation of plants, such as useful plants, for example crop plants, their plant propagation material, for example seeds, harvested crops, for example harvested food crops, or non-living material, by plant pathogenic or spoilage microorganisms or organisms, in particular fungal organisms, that are potentially harmful to humans, which method comprises applying a compound of formula (I) according to the present invention or a preferred individual compound as defined herein as active ingredient to the plant, part of the plant or its habitat, its plant propagation material, or any part of the non-living material.

[0229] Control or prevention means reducing infestation by plant pathogenic microorganisms or organisms, such as insects or especially fungal organisms, or spoilage microorganisms or organisms that are potentially harmful to humans, to a level that demonstrates improvement.

[0230] Preferred methods for controlling or preventing infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects include those in which the application of a compound of formula (I) according to the present invention or an agrochemical composition containing at least one compound of formula (I) is a foliar treatment. The frequency and rate of application depend on the risk of infestation by the corresponding pathogen or insect. However, the compounds of formula (I) according to the present invention can also be introduced into the plant through the roots via the soil (systemic action) by drenching the plant habitat with a liquid formulation or by applying the compound to the soil in solid form, for example, in granular form (soil application). In rice crops, such granules can be applied to flooded rice fields. The compounds of formula (I) can also be applied to seeds (coating) by impregnating the seeds or tubers with a liquid formulation of the fungicide or coating them with a solid formulation.

[0231] Formulations, e.g. compositions, containing a compound of formula (I) according to the invention and, if desired, a solid or liquid auxiliary or a monomer encapsulating the compound of formula (I), may typically be prepared in a known manner by intimately mixing and / or grinding the compound with an extender, e.g., a solvent, a solid carrier, and, optionally, a surface-active compound (surfactant).

[0232] Advantageous application rates are usually 5g to 2kg of active ingredient (ai) per hectare (ha), preferably 10g to 1kg ai / ha, most preferably 20g to 600g ai / ha. When used as a seed drench, a convenient dosage is 10mg to 1g of active substance per kg of seed.

[0233] As used herein, the term "g ai / ha" refers to the application rate expressed in grams [g] of active ingredient [ai] per unit surface [ha]. The unit hectare (symbol ha) is the area of ​​100 mm sides (1 hm 2 ) square or 10,000 square meters. The hectare is a commonly used unit of area in the metric system.

[0234] When the combinations of the invention are used for seed treatment, an amount of 0.001 to 50 g of compound of formula (I) per kg of seed, preferably 0.01 to 10 g per kg of seed, will generally be sufficient.

[0235] Preferably, the compositions comprising compounds of formula (I) according to the invention are applied either prophylactically (meaning before the onset of the disease) or therapeutically (meaning after the onset of the disease).

[0236] The compositions of the present invention may be in any conventional form, such as, for example, two-part systems, dry seed treatment powders (DS), seed treatment emulsions (ES), seed treatment flowable concentrates (FS), seed treatment solutions (LS), seed treatment water dispersible powders (WS), seed treatment capsule suspensions (CF), seed treatment gels (GF), emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (WG), etc. (EG), emulsion, water-in-oil (EO), emulsion, oil-in-water (EW), microemulsion (ME), oil dispersion (OD), oil-miscible flowable (OF), oil-miscible liquid (OL), soluble concentrate (SL), ultra-low volume suspension (SU), ultra-low volume liquid (UL), technical concentrate (TK), dispersible concentrate (DC), wettable powder (WP), or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0237] Such compositions can be prepared in a conventional manner, for example, by mixing the active ingredient with suitable formulation inerts (diluents, solvents, fillers, and optionally other formulation ingredients such as surfactants, biocides, antifreeze agents, spreading agents, thickeners, and compounds providing auxiliary effects). Conventional sustained-release formulations can also be employed when long-lasting effectiveness is intended. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, can contain surfactants, such as wetting agents and dispersants, as well as other compounds providing auxiliary effects, such as condensation products of formaldehyde with naphthalenesulfonates, alkylarylsulfonates, ligninsulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0238] The seed dressing formulation is applied to seeds in a manner known per se, using the combination of the present invention and a diluent in a suitable seed dressing formulation form, such as an aqueous suspension or a dry powder form with good adhesion to the seeds. Such seed dressing formulations are known in the art. The seed dressing formulation may contain a single active ingredient or a combination of active ingredients in encapsulated form, for example, as slow-release capsules or microcapsules.

[0239] Generally, the formulations contain 0.01 to 90% by weight of active agent, 0 to 20% by weight of an agriculturally acceptable surfactant, and 10 to 99.99% by weight of a solid or liquid inert compound and adjuvant, where the active agent is composed of at least a compound of formula (I) according to the present invention, optionally together with other active agents, particularly microbicides, preservatives, etc. Concentrate forms of the composition generally contain about 2 to 80% by weight, preferably about 5 to 70% by weight, of the active agent. Application forms of the formulations can contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight, of the active agent. Commercially available products are preferably formulated as concentrates, but end users will usually use diluted formulations.

[0240] Commercially available products are preferably formulated as concentrates, although end users will typically utilize diluted formulations.

[0241] The application rates vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pests to be controlled, the prevailing weather conditions and other factors which depend on the method, time of application and target crop. As a general guideline, the compounds may be applied at a rate of 1 to 2000 l / ha, especially 10 to 1000 l / ha.

[0242] A preferred formulation may have the following composition (by weight): Emulsifiable concentrate: Active ingredient: 1-95%, preferably 60-90% Surfactant: 1 to 30%, preferably 5 to 20% Liquid carrier: 1 to 80%, preferably 1 to 35% Powder for dusting: Active ingredient: 0.1 to 10%, preferably 0.1 to 5% Solid carrier: 99.9 to 90%, preferably 99.9 to 99% Suspension concentrate: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surfactant: 1 to 40%, preferably 2 to 30% Wettable powder: Active ingredient: 0.5 to 90%, preferably 1 to 80% Surfactant: 0.5 to 20%, preferably 1 to 15% Solid carrier: 5 to 95%, preferably 15 to 90% Granules: Active ingredient: 0.1 to 30%, preferably 0.1 to 15% Solid carrier: 99.5 to 70%, preferably 97 to 85%

[0243] The disclosure in this application makes available any and all combinations of the embodiments disclosed herein.

[0244] The compounds according to the following Tables C-1 to C-21 can be prepared according to the above-mentioned methods. The following examples are intended to illustrate the present invention and to show preferred compounds of formula (I). In any of the following Tables C-1 to C-21, the possible presence of one or more asymmetric carbon atoms in the compound of formula (I) according to the present invention means that the compound can occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms.

[0245] The disclosure in this application makes available any and all combinations of the embodiments disclosed herein.

[0246] The compounds according to the following Tables C-1 to C-21 may be prepared according to the above methods. The following examples are intended to illustrate the invention and to show preferred compounds of formula (I).

[0247] Table A: This table shows the formula (I) [ka] wherein G is a group having the following formula as defined below: [ka] The present invention discloses the definition of 20 substituents G, which are:

[0248] [Table 1]

[0249] Table B: This table shows the formula (I) [ka] Disclose the definitions Q of the 14 substituents

[0250] [Table 2]

[0251] Tables C-1 to C21 disclose certain compounds of the invention of formula (I) where the Q and G substituents are as defined in Tables A and B. Table C-1: This table provides 20 compounds C-1.01 to C-1.20 of formula (I), in which R 2 , R 4 , R 5 and R 6 is H, Q is Q-1 as defined in Table B, and G is as defined in Table A. For example, compound C-1.01 has the following structure: [ka] It has. Table C-2: This table provides 20 compounds C-2.01 to C-2.20 of formula (I), in which R 2, R 5 , R 6 is H and R 4 is CH3, Q is Q-1 as defined in Table B, and G is as defined in Table A. For example, compound C-2.05 has the following structure: [ka] It has. Table C-3: This table provides 20 compounds C-3.01 to C-3.20 of formula (I), where R 2 , R 5 , R 6 is H and R 4 is CH3, Q is Q-2 as defined in Table B, and G is as defined in Table A. For example, compound C-3.11 has the following structure: [ka] It has. Table C-4: This table provides 20 compounds C-4.01 to C-4.20 of formula (I), where R 2 , R 5 , R 6 is H and R 4 is CH3, Q is Q-3 as defined in Table B, and G is as defined in Table A. Table C-5: This table provides 20 compounds C-5.01 to C-5.20 of formula (I), in which R 2 , R 5 , R 6 is H and R 4 is CH3, Q is Q-4 as defined in Table B, and G is as defined in Table A. Table C-6: This table provides 20 compounds C-6.01 to C-6.20 of formula (I), where R 2 , R 5 , R 6 is H and R 4 is CH3, Q is Q-5 as defined in Table B, and G is as defined in Table A. Table C-7: This table provides 20 compounds C-7.01 to C-7.20 of formula (I), where R 2 , R 5 , R 6 is H and R 4 is CH3, Q is Q-6 as defined in Table B, and G is as defined in Table A. Table C-8: This table provides 20 compounds C-8.01 to C-8.20 of formula (I), where R 2 , R 5 , R 6 is H and R 4 is CH3, Q is Q-7 as defined in Table B, and G is as defined in Table A. Table C-9: This table provides 12 compounds C-9.01 to C-9.20 of formula (I), where R 2 , R 5 , R 6 is H and R 4 is CH3, Q is Q-8 as defined in Table B, and G is as defined in Table A. For example, compound C-9.03 has the following structure: [ka] It has. Table C-10: This table provides 20 compounds C-10.01 to C-10.20 of formula (I), where R 2 , R 5 , R 6 is H and R 4 is CH3, Q is Q-9 as defined in Table B, and G is as defined in Table A. Table C-11: This table provides 20 compounds C-11.01 to C-11.20 of formula (I), where R 2 , R 5 , R 6 is H and R 4 is CH3, Q is Q-10 as defined in Table B, and G is as defined in Table A. Table C-12: This table provides 20 compounds C-12.01 to C-12.20 of formula (I), where R 2 , R5 , R 6 is H and R 4 is CH3, Q is Q-11 as defined in Table B, and G is as defined in Table A. Table C-13: This table provides 20 compounds C-13.01 to C-13.20 of formula (I), where R 2 , R 5 , R 6 is H and R 4 is CH3, Q is Q-12 as defined in Table B, and G is as defined in Table A. Table C-14: This table provides 20 compounds C-14.01 to C-14.20 of formula (I), where R 2 , R 5 , R 6 is H and R 4 is CH3, Q is Q-13 as defined in Table B, and G is as defined in Table A. Table C-15: This table provides 20 compounds C-15.01 to C-15.20 of formula (I), where R 2 , R 5 , R 6 is H and R 4 is CH3, Q is Q-14 as defined in Table B, and G is as defined in Table A. For example, compound C-15.12 has the following structure: [ka] It has. Table C-16: This table provides 20 compounds C-16.01 to C-16.20 of formula (I), where R 5 , R 6 is H and R 2 and R 4 is CH3, Q is Q-2 as defined in Table B, and G is as defined in Table A. Table C-17: This table provides 20 compounds C-17.01 to C-17.20 of formula (I), where R 5 , R 6 is H and R 2 and R 4is CH3, Q is Q-3 as defined in Table B, and G is as defined in Table A. Table C-18: This table provides 20 compounds C-18.01 to C-18.20 of formula (I), where R 5 , R 6 is H and R 2 and R 4 is CH3, Q is Q-5 as defined in Table B, and G is as defined in Table A. For example, compound C-18.01 has the following structure: Table C-19: This table provides 20 compounds C-19.01 to C-19.20 of formula (I), where R 5 , R 6 is H and R 2 is Cl and R 4 is CH3, Q is Q-2 as defined in Table B, and G is as defined in Table A. Table C-20: This table provides 20 compounds C-20.01 to C-20.20 of formula (I), wherein R 5 , R 6 is H and R 2 is Cl and R 4 is CH3, Q is Q-3 as defined in Table B, and G is as defined in Table A. Table C-21: This table provides 20 compounds C-21.01 to C-21.20 of formula (I), where R 5 , R 6 is H and R 2 is Cl and R 4 is CH3, Q is Q-5 as defined in Table B, and G is as defined in Table A. For example, compound C-21.01 has the following structure: [ka] It has. [Example]

[0252] The examples that follow are intended to illustrate the present invention and are not intended to limit it in any way.

[0253] The compounds of the present invention are distinguishable from known compounds by their high efficacy at low doses, which can be verified by one skilled in the art using the experimental procedures outlined in the Examples, and where necessary using low doses such as 60 ppm, 20 ppm or 2 ppm.

[0254] Compounds of formula (I) may have many benefits including, inter alia, advantageous levels of biological activity or excellent properties for use as agrochemical active ingredients (e.g., high biological activity, advantageous spectrum of activity, high safety profile (including improved crop tolerance), improved physicochemical properties or high biodegradability) for protecting plants against diseases caused by fungi.

[0255] Throughout this specification temperatures are given in degrees Celsius (°C) and "mp" means melting point. LC / MS or LC-MS or LCMS means liquid chromatography mass spectrometry, and a description of the equipment and methods follows.

[0256] 1 H NMR and 19 F NMR measurements were recorded on a Bruker 400 MHz spectrometer, and chemical shifts were expressed in terms of TMS ( 1 H) and CFCl3 ( 19 F) are shown in ppm relative to standard. Spectra were taken in deuterated solvents as indicated. Compounds were characterized using one of the following LCMS methods. Characteristic LCMS values ​​obtained for each compound are the retention time ("Rt", recorded in minutes) and the observed molecular ion (M+H). + or (MH) - It was.

[0257] LCMS Method A: Spectra were recorded on a Waters Corp. mass spectrometer (SQD, SQDII, or QDA single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive or negative ion, capillary: 0.8-3.00 kV, cone: 5-30 V, source temperature: 120-150 °C, desolvation temperature: 350-600 °C, cone gas flow: 50-150 l / h, desolvation gas flow: 650-1000 l / h, mass range: 50-900 Da), and a Waters Corporation Acquity UPLC: binary pump, heated column compartment, diode array detector, and ELSD. Column: Waters UPLC HSS. T3, 1.8 μm, 30 × 2.1 mm, temperature: 60 °C, DAD wavelength range (nm): 210–400, run time: 1.5 min; solvent: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH, flow rate (ml / min) 0.85, gradient: 10% B isocratic for 0.2 min, then 10–100% B for 1.0 min, 100% B isocratic for 0.2 min, 100–10% B for 0.05 min, 10% B isocratic for 0.05 min.

[0258] LCMS Method B: Spectra were recorded on a Waters Corp. mass spectrometer (SQD, SQDII or QDA single quadrupole mass spectrometer) equipped with an electrospray source. Optimal mass parameters: ionization method: electrospray (ESI), polarity: positive and negative polarity switch, scan type: full scan, capillary (kV): 0.8, cone voltage (V): 23, source temperature (℃): 120, desolvation gas flow rate (L / h): 1000, desolvation temperature: 600, cone gas flow rate (L / h): 50, mass range: 110–1200 Da; Gradient conditions: Solvent A: water with 0.1% formic acid:acetonitrile: 95:5 vol / vol, Solvent B: acetonitrile with 0.05% formic acid

[0259] [Table 3]

[0260] LCMS Method C: Spectra were recorded on a Waters Corp. mass spectrometer (SQD, SQDII or QDA single quadrupole mass spectrometer) equipped with an electrospray source. Optimal mass parameters: Ionization method: Electrospray (ESI); Polarity: Positive and negative polarity switch; Scan type: Full scan; Capillary (kV): 3.00; Cone voltage (V): 41.00; Source temperature (°C): 150; Desolvation gas flow rate (L / hr): 1000; Desolvation temperature (°C): 500; Cone gas flow rate (L / hr): 50; Mass range: 110-1000 Da Gradient conditions: Solvent A: water with 0.1% formic acid:acetonitrile: 95:5 vol / vol; Solvent B: acetonitrile with 0.05% formic acid

[0261] [Table 4]

[0262] LCMS Method D: Spectra were recorded on an Agilent Technologies 6410 triple quadrupole mass spectrometer (HPLC: Agilent 1200 Series HPLC). Optimal mass parameters: Ionization method: electrospray (ESI); polarity: positive and negative polarity switch; scan type: MS2 scan; capillary (kV): 4.00; fragmentor (V): 100.00; gas temperature (°C): 350; gas flow rate (L / min); 11; nebulizer gas (psi): 40; mass range: 110-1000 Da; detection (VWD): 254 nm. Gradient conditions: Solvent A: water with 0.1% formic acid:acetonitrile: 95:5 vol / vol; Solvent B: acetonitrile with 0.1% formic acid

[0263] [Table 5]

[0264] LCMS Method E: Spectra were recorded on a Waters mass spectrometer (Acquity QDa mass spectrometer) equipped with an electrospray source (polarity: positive and negative polarity switch), capillary voltage: 0.8 kV, cone range: 25 V, extractor voltage: V (no extraction voltage on the QDa detector), source temperature: 120 °C, desolvation temperature: 600 °C, cone gas flow: 50 L / h, desolvation gas flow: 1000 L / h, mass range: 110–850 Da), and a Waters Acquity UPLC: quaternary solvent manager, heated column compartment, diode array detector. Column: Acquity UPLC HSS T3 C18, 1.8 μm, 30 × 2.1 mm, temperature: 40 °C, DAD wavelength range (nm): 200–400, solvent gradient: A = water + 5% acetonitrile + 0.05% HCOOH, B = acetonitrile + 0.1% HCOOH. Gradient: 10% B for 0 min; 10–50% B for 0.–0.2 min; 50–100% B for 0.2–0.6 min; 100% B for 0.6–1.3 min; 100–10% B for 1.3–1.4 min; 10% B for 1.4–1.6 min; flow rate (mL / min) 0.6.

[0265] LCMS Method F: Spectra were recorded on a Waters Corporation ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive or negative ion, capillary: 3.0 kV, cone: 30 V, extractor: 3.00 V, source temperature: 150 °C, desolvation temperature: 400 °C, cone gas flow: 60 L / hr, desolvation gas flow: 700 L / hr, mass range: 140-800 Da) and a Waters Corporation ACQUITY UPLC equipped with a solvent degasser, binary pump, heated column compartment, and diode array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm; Temperature: 60 °C; DAD wavelength range (nm): 210–400; Solvent gradient: A = water / methanol 9:1 + 0.1% formic acid, B = acetonitrile + 0.1% formic acid; Gradient: 0–100% B in 3.0 min; Flow rate (ml / min) 0.75.

[0266] [Table 6]

[0267] This combination is thoroughly mixed with adjuvants and the mixture is thoroughly ground in a suitable mill to obtain a wettable powder, which is diluted with water to obtain a suspension of the desired concentration.

[0268] [Table 7]

[0269] This combination is thoroughly mixed with an adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a dust that can be used directly as a seed treatment.

[0270] emulsifiable concentrate Active ingredient 10% Octylphenol polyethylene glycol ether (4-5 mol ethylene oxide) 3% Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (35 mol ethylene oxide) 4% Cyclohexanone 30% Xylene mixture 50%

[0271] Emulsions of any desired dilution that can be used for plant protection are obtained from this concentrate by dilution with water.

[0272] [Table 8]

[0273] Ready-to-use dusts are obtained by combining and mixing with a carrier and grinding the mixture in a suitable mill. Such powders can also be used as dry fertilizers for seeds.

[0274] Extruded Granules Active ingredient 15% Sodium lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0275] This combination is mixed with an adjuvant, ground, and the mixture is wetted with water. The mixture is extruded and then dried in a stream of air.

[0276] Coated Granules Active ingredient 8% Polyethylene glycol (molecular weight 200) 3% Kaolin 89%

[0277] This micronized combination is applied uniformly in a mixer to kaolin wetted with polyethylene glycol, thus obtaining coated granules that do not generate dust.

[0278] Suspension concentrate Active ingredient 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (15 mol ethylene oxide) 6% Sodium lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%

[0279] The finely ground combination is thoroughly mixed with adjuvants to obtain a suspension concentrate, which can then be diluted with water to obtain a suspension of any desired dilution, and such dilutions can be used to treat and protect living plants and plant propagation material against microbial infestation by spraying, pouring, or dipping.

[0280] Flowable concentrate for seed treatment Active ingredient 40% Propylene glycol 5% Copolymer butanol PO / EO 2% Tristyrene phenol + 10-20 moles EO 2% 1,2-Benzisothiazolin-3-one (in the form of a 20% aqueous solution) 0.5% Monoazo dye calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%

[0281] The finely ground combination is thoroughly mixed with adjuvants to obtain a suspension concentrate, which can then be diluted with water to obtain a suspension of any desired dilution, and such dilutions can be used to treat and protect living plants and plant propagation material against microbial infestation by spraying, pouring, or dipping.

[0282] extended-release capsule suspension 28 parts of the combination are mixed with 2 parts aromatic solvent and 7 parts toluene diisocyanate / polymethylene-polyphenylisocyanate (8:1) mixture. This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts antifoaming agent, and 51.6 parts water until the desired particle size is achieved. To this emulsion, a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water is added. The mixture is stirred until the polymerization reaction is complete. The resulting capsule suspension is stabilized by adding 0.25 parts thickener and 3 parts dispersant. This capsule suspension formulation contains 28% active ingredient. The average capsule diameter is 8 to 15 microns. The resulting formulation is applied to seeds as an aqueous suspension in equipment suitable for this purpose.

[0283] Formulation types include emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (EG), emulsions, water-in-oil (EO), emulsions, oil-in-water (EW), microemulsions (ME), oil dispersions (OD), oil-miscible flowables (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), technical concentrates (TK), dispersible concentrates (DC), wettable powders (WP), soluble granules (SG) or any technically preferred formulation in combination with an agriculturally acceptable adjuvant.

[0284] Abbreviation CDCl3 deuterated chloroform Concentrated DABCO Triethylenediamine or TEDA, also known as 1,4-diazabicyclo[2.2.2]octane DCC dicyclohexylcarbodiimide DIPEA Diisopropylethylamine (N,N-diisopropylethylamine) DMF Dimethylformamide (N,N-dimethylformamide) DMSO dimethyl sulfoxide DMSO-d6 Deuterated dimethyl sulfoxide equiv. EtOAc ethyl acetate HATU 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate HCl Hydrochloric acid h / hrs time LCMS Liquid Chromatography Mass Spectrometry rh relative humidity rt room temperature RT retention time ssp. subspecies TBME Methyl tert-butyl ether or tert-butyl methyl ether THF tetrahydrofuran TLC thin layer chromatography TMS Tetramethylsilane T3P Propylphosphonic Anhydride, Reactive n-Propylphosphonic Cyclic Anhydride

[0285] Preparation example: Compounds of formula (I) according to the invention may be prepared using the synthetic techniques described both above and below.

[0286] "Mp" means melting point in °C (degrees Celsius). The free radical represents a methyl group.

[0287] 1 H NMR and 19 F NMR measurements were recorded on a Bruker 400 MHz spectrometer, and chemical shifts were referenced to TMS ( 1 H) and CFCl3 ( 19 F) are shown in ppm relative to standard. Spectra were taken in deuterated solvents as indicated. Compounds were characterized using one of the following LCMS methods. Characteristic LCMS values ​​obtained for each compound are retention time ("Rt", recorded in minutes) and observed molecular ion (M+H). + or (MH) - It was.

[0288] Example 1: Preparation of N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-1-(2,4-difluorophenyl)-triazole-4-carboxamide (Compound P-1, Table P) [ka] Step 1: Preparation of 2-(1-methylpyrazol-4-yl)propanenitrile [ka] 2-(1-Methyl-1h-pyrazol-4-yl)acetonitrile (10.00 g, 78.42 mmol) was dissolved in THF (314 mL) under argon, and the pale yellow solution was cooled to −78° C. To this solution, n-butyllithium (31 mL, 78.42 mmol) was added dropwise, and the resulting pale brown suspension was stirred at this temperature for 25 minutes. After this time, iodomethane (11.24 g, 4.93 mL, 78.42 mmol) was added dropwise. The resulting brown solution was stirred at −78° C. for 5 minutes, allowed to warm to room temperature (rt), and stirred at rt for 30 minutes under argon. The reaction mixture was poured into water and then extracted twice with EtOAc. The combined organic layers were washed once with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to provide 2-(1-methylpyrazol-4-yl)propanenitrile as a pale brown liquid. LC / MS (Method A); 136[M+H] + ;Retention times: 0.43 min, 0.44 min, 0.55 min. 1 H NMR(400MHz,CDCl3)δ ppm 1.64(d,J=6.90Hz,3H)3.86-3.93(m,4H)7.40(s,1H)7.46(s,1H).

[0289] Step 2: Preparation of 2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propanenitrile [ka] A sample of 2-(1-methylpyrazol-4-yl)propanenitrile (2.00 g, 14.80 mmol) was dissolved in THF (59.18 mL) under argon to give a pale yellow solution. The solution was cooled to −78° C. and then treated dropwise with n-butyllithium (5.90 mL, 14.80 mmol). The resulting pale brown suspension was stirred at this temperature for 10 minutes, after which 2,6-dichloropyridine (2.23 g, 14.80 mmol) was added in small portions. The resulting brown suspension was stirred at −78° C. for 5 minutes, allowed to reach room temperature, and stirred under argon for 30 minutes to give a pale brown solution. The reaction mixture was poured into water and extracted twice with ethyl acetate. The combined organic layers were washed once with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo at 60° C. to give 3.68 g of a dark brown liquid. The crude brown liquid was purified by flash chromatography with an eluent of ethyl acetate in cyclohexane to give 2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propanenitrile (2.71 g, 74.2% yield) as a pale yellow oil. LC / MS (Method A);247[M+H] + ;Retention time: 0.82 minutes. 1 H NMR(400MHz,CDCl3)δ ppm 2.12(s,3H)3.90(s,3H)7.27-7.32(m,1H)7.45(s,1H)7.46-7.54(m,2H)7.62-7.74(m,1H).

[0290] Step 3: Preparation of 2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propan-1-amine [ka] A solution of 2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propanenitrile (2.71 g, 11.0 mmol) in THF (33.0 mL) was treated dropwise with borane methyl sulfide complex (2.50 g, 3.13 mL, 33.0 mmol) at room temperature under argon, and the resulting pale yellow solution was stirred at 65°C for 4 hours. After the reaction mixture was cooled to 0°C, concentrated hydrochloric acid (HCl) (7.36 mL, 44.2 mmol) was added dropwise. The reaction mixture was stirred at 50°C for 1 hour. The reaction mixture was cooled to room temperature, and water was added. Aqueous sodium hydroxide solution (6 N NaOH) was added to the reaction mixture until the pH reached 12, and the resulting reaction mixture was extracted three times with ethyl acetate. The combined organic layers were washed once with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propan-1-amine as a pale yellow oil, which could be used in the next step without further purification. 1 H NMR(400MHz,DMSO d6)δ ppm 1.57(s,3H)2.98(d,J=12.72Hz,1H)3.16(d,J=12.72Hz,1H)3.77(s,3H)7.20-7.35(m,3H)7.50(s,1H)7.75(t,J=7.81Hz,1H).

[0291] Step 4: Preparation of methyl 1-(2,4-difluorophenyl)triazole-4-carboxylate [ka] A solution of 1-azido-2,4-difluorobenzene (0.30 g, 1.8 mmol) in methanol (3.6 mL) was treated successively with anhydrous copper(II) sulfate (0.053 g, 0.33 mmol), sodium ascorbate (0.46 g, 2.3 mmol) in water (3.6 mL), and then methyl prop-2-ynoate (0.14 g, 0.14 mL, 1.7 mmol). The reddish reaction mixture was stirred at rt for 2 days (monitored by LCMS). The reaction mixture was then concentrated in vacuo, and the residue was taken up in water and EtOAc. The organic layer was separated and washed with brine, and the separated organic layer was dried over MgSO, filtered, and concentrated in vacuo. The crude product was adsorbed onto ISOLUTE® and purified on a silica gel cartridge (Rf 200) eluting with cyclohexane / EtOAc to give the title compound as a white solid. LC / MS (Method A) m / z=240[M+H] + ;holding time=0.79 minutes; 1 H NMR(400MHz,CDCl3)δ ppm 4.02(s,3H)7.09-7.17(m,2H)7.96-8.05(m,1H)8.59(d,J=2.57Hz,1H)

[0292] Step 5: Preparation of 1-(2,4-difluorophenyl)triazole-4-carboxylic acid [ka] Methyl 1-(2,4-difluorophenyl)triazole-4-carboxylate (0.31 g, 1.3 mmol) was dissolved in THF (6.5 mL) and water (3.2 mL) under argon to give a light brown solution. To this solution was added LiOH.HO (0.047 g, 1.9 mmol), and the mixture was stirred at rt. After 3 h, LC / MS analysis (desired mass at rt = 0.63 min) indicated complete consumption of the starting material. The sample was concentrated in vacuo, the residue was taken up in water and EtOAc, and the resulting mixture was acidified with 2 N HCl. The organic layer was separated, dried over NaSO, filtered, and concentrated in vacuo to give the title compound as a white solid. LC / MS (Method A): m / z=226[M+H] + ;holding time=0.63 minutes; 1 H NMR(400MHz,DMSO)δ ppm 7.27-7.52(m,1H)7.73(ddd,J=11.10,8.71,2.57Hz,1H)7.95(td,J=8.80,5.87Hz,1H)9.15(d,J=1.47Hz,1H)13.26-13.60(m,1H)

[0293] Step 6: Preparation of N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-1-(2,4-difluorophenyl)triazole-4-carboxamide (Compound P-1, Table P) 1-(2,4-Difluorophenyl)triazole-4-carboxylic acid (0.225 g, 1.0 mmol) and 2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propan-1-amine (0.25 g, 1 mmol) were suspended in EtOAc (6 mL). To this mixture, diisopropylethylamine (DIPEA) (0.65 g, 5 mmol) and 1-propanephosphonic anhydride (T3P, 50% wt. in EtOAc, 2 mL) were added at 0°C, and the reaction mixture was stirred at rt for 2 h (LCMS analysis indicated completion of the reaction). The reaction mixture was diluted with water, and the resulting mixture was extracted with EtOAc (2 × 20 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The crude product was absorbed onto silica gel and purified by combiflash eluting with 0–80% cyclohexane / EtOAc to give the title compound as a white solid. 1H NMR(400MHz,CDCl3)δ ppm 8.50(d,J=2.57Hz,1H)8.05(br t,J=6.36Hz,1H)7.91(td,J=8.71,5.69Hz,1H)7.58(t,J=7.82Hz,1H)7.35(s,1H)7.29(s,1H)7.23(d,J=7.82H) z,1H)7.12(dd,J=8.86,8.01Hz,2H)7.06-7.10(m,1H)4.11(dd,J=16.75,6.60Hz,2H)3.88(s,3H)1.74(s,3H); LC / MS (Method B): m / z=458[M+H] + ;holding time=1.09 minutes

[0294] Example 2: Preparation of N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-1-(2,4-difluorophenyl)-1,2,4-triazole-3-carboxamide (Compound P-4, Table P) [ka] Step 1: Preparation of methyl 1-(2,4-difluorophenyl)-1,2,4-triazole-3-carboxylate [ka] Prepared similarly to that described in Org. Lett. 2018, 20, 6930-6933. Thus, a solution of 2,4-difluorobenzenediazonium tetrafluoroborate (prepared as described in J. Am. Chem. Soc. (1956), 78, 2593-6, 500 mg, 0.5 g, 2.1939 mmol) in THF (8.8 mL) was cooled to 0 °C, and lithium acetate dihydrate (0.44765 g, 4.3879 mmol), Cu(OAc) (0.10 equiv., 0.03985 g, 0.21939 mmol), and methyl 2-isocyanoacetate (1.20 equiv., 0.2609 g, 0.239 mL, 2.6327 mmol) were added at 0 °C. The mixture was stirred at this temperature for 4 h. LCMS analysis indicated the reaction was complete after this time. The reaction mixture was poured into water (25 mL), and the resulting mixture was extracted with EtOAc (2 x 20 mL). The combined organic layers were washed with brine, dried over NaSO, and concentrated in vacuo. The crude material was purified by column chromatography (24 g of SiO eluting with an EtOAc / cyclohexane gradient) to give the title compound as an oil. 1 H NMR(400MHz,CDCl3)δ ppm 8.68(d,J=2.81Hz,1H)7.93-8.00(m,1H)7.08-7.14(m,2H)4.08(s,3H)1.27(s,1H)

[0295] Step 2: Preparation of N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-1-(2,4-difluorophenyl)-1,2,4-triazole-3-carboxamide (Compound P-4, Table P) 2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propan-1-amine (0.031 g, 0.12 mmol) was added to a solution of methyl 1-(2,4-difluorophenyl)-1,2,4-triazole-3-carboxylate (0.025 g, 0.10 mmol) in toluene (0.75 mL) in a microwave vial. The reaction mixture was stirred under an argon atmosphere for 5 minutes, and then bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane adduct (0.041 g, 0.16 mmol) was added, and the resulting mixture was stirred in a microwave at 70 °C. After completion of the reaction, the reaction mixture was diluted with water, extracted with EtOAc, and the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The resulting crude residue was purified by chromatography on silica gel using a cyclohexane / ethyl acetate eluent system to give N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-1-(2,4-difluorophenyl)-1,2,4-triazole-3-carboxamide as gummy masses. LCMS (Method C): 458[M+H] + ;holding time=1.03 minutes; 1 H NMR(400MHz,CDCl3)δ ppm 8.52(d,1H),8.27(br t,1H),7.94(td,1H),7.51(t,1H),7.23-7.20(m,2H),7.14-7.18(m,1H),6.98-7.10(m,3H),4.01(dd,2H),3.80(s,3H),1.66(s,3H)

[0296] Example 3: Preparation of N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)triazole-5-carboxamide (Compound P-6, Table P) [ka] Step 1: Preparation of ethyl (2E)-2-(p-tolylsulfonylhydrazono)acetate [ka] A solution of 4-methylbenzenesulfonohydrazide (CAS [1576-35-8], 2 g, 10.73 mmol) in ethanol (40 mL) was treated with ethyl 2-oxoacetate (2.63 g, 12.88 mmol) at room temperature. The reaction mixture was stirred for 1 hour and concentrated in vacuo to remove ethanol. The resulting residue was diluted with water and extracted with EtOAc. The organic phase was separated and the solvent evaporated in vacuo to give ethyl (2E)-2-(p-tolylsulfonylhydrazono)acetate, which was used directly in the next step (Step 2). LCMS (Method C): 271[M+H] + ;holding time=1.04 minutes; 1 H NMR(400MHz,CDCl3)δ ppm 9.31(s,1H)7.85(d,J=8.31Hz,2H)7.34(d,J=8.07Hz,2H)7.23(s,1H)4.27(q,J =7.09Hz,2H)4.14(q,J=7.09Hz,1H)2.44(s,3H)2.07(s,2H)1.23-1.37(m,7H).

[0297] Step 2: Preparation of ethyl 2-(2,4-difluorophenyl)tetrazole-5-carboxylate [ka] 2,4-Difluoroaniline (1 g, 7.74 mmol) was solubilized in 6 M aqueous hydrochloric acid (deionized water) (6 mL, 36 mmol) and ethanol (5 mL) and cooled to 0° C. To the solution was added sodium nitrite (0.64 g, 9.29 mmol), and the resulting solution was stirred at 0° C. for 1 h and then added dropwise to a solution of ethyl (2E)-2-(p-tolylsulfonylhydrazono)acetate (2.3 g, 8.51 mmol) in pyridine (20 mL) at −20° C. The reaction mixture was allowed to warm slowly to room temperature and then stirred for 5 h. The resulting mixture was diluted with 1 N HCl, and the aqueous layer was extracted with EtOAc (3 × 20 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the crude product, which was purified by column chromatography eluting with 30% EtOAc in hexanes to give ethyl 2-(2,4-difluorophenyl)tetrazole-5-carboxylate as a reddish oil. LCMS (Method B): No [M+H+] detected; retention time = 1.10 min; 1 H NMR(400MHz,CDCl3δ ppm 7.86-7.94(m,1H)7.11-7.21(m,2H)4.60(q,J=7.21Hz,2H)2.03(s,1H)1.51(t,J=7.13Hz,3H)

[0298] Step 3: Preparation of 2-(2,4-difluorophenyl)tetrazole-5-carboxylic acid [ka] To a solution of methyl 5-methylisoxazole-3-carboxylate (300 mg, 1.18 mmol) in THF (3 mL) and water (1.5 mL) was added LiOH.HO (0.113 mg, 4.72) at rt, and the reaction mixture was stirred at room temperature for 30 min. The organic solvent was removed by concentration in vacuo, and the aqueous residue was diluted with 2 N HCl and then extracted with EtOAc (3 × 20 mL). The combined organic phases were dried over NaSO, filtered, and concentrated in vacuo to give 2-(2,4-difluorophenyl)tetrazole-5-carboxylic acid as a reddish solid. LCMS (Method C): 227[M+H] + ;Holding time=0.87~1.11 minutes; 1 H NMR(400MHz,DMSO-d6)δ ppm 8.10(td,J=8.69,5.75Hz,1H)7.73-7.88(m,1H)7.40-7.50(m,1H)3.36-3.63(m,3H)3.07-3.35(m,3H)1.99(s,1H)1.91(s,1H)1.24(s,1H)

[0299] Step 4: Preparation of N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)-5-carboxamide (compound P-6, Table X). A mixture of 2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propan-1-amine (6.37 g, 22.9 mmol, prepared as described above), 2-(2,4-difluorophenyl)tetrazole-5-carboxylic acid (6.32 g, 25.2 mmol), N,N-diisopropylethylamine (DIPEA) (9.33 g, 68.6 mmol), and T3P (50% by weight in EtOAc) (40 mL) was stirred in EtOAc (114 mL) at room temperature for 1 hour. LCMS then indicated the reaction was complete. The reaction mixture was diluted with water and EtOAc, the organic layer was separated, and the aqueous layer was back-extracted three times with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and evaporated in vacuo. The crude product was purified by column chromatography eluting with EtOAc / cyclohexane to give N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)-5-carboxamide as an off-white solid. LCMS (Method B): 459[M+H] + ;holding time=1.14 minutes; 1H NMR(400MHz,DMSO-d6)δ ppm 8.75(t,J=6.38Hz,1H),8.07(td,J=8.76,5.75Hz,1H),7.76-7.83(m,2H),7.62(s,1H),7.45(t,J=8.38Hz,1H),7.38(d,J=7.38Hz,1H),7 .35(d,J=0.75Hz,1H),7.29(d,J=7.25Hz,1H),4.08(dd,J=13.26,6.25Hz,1H),3.91(dd,J=13.32,6.57Hz,1H),3.78(s,3H),1.66(s,3H)

[0300] Example 4: Preparation of N-[2-(6-cyano-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)tetrazole-5-carboxamide (Compound P-5, Table P) [ka] N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)-5-carboxamide (2.40 g, 4.97 mmol, prepared as described in Example 3) and zinc cyanide (1.19 g, 9.94 mmol) were dissolved in N,N-dimethylformamide (25 mL) under a nitrogen atmosphere. The resulting reaction mixture was degassed under nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.58 g, 0.49 mmol) was then added, and the resulting light brown suspension was stirred at 120 °C in a microwave for 2 hours. The reaction progress was monitored by LCMS. After the reaction was complete, the reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by combi flash using EtOAc / cyclohexane as the eluent. The resulting compound was further purified by reverse phase column chromatography using acetonitrile in water as the eluent to give N-[2-(6-cyano-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)tetrazole-5-carboxamide as a white solid. LCMS (Method B): 450[M+H] + ;holding time=0.95 minutes; 1 H NMR(400MHz,DMSO-d6)δ ppm 8.80(t,J=6.30Hz,1H),8.07(td,J=8.74,5.75Hz,1H),7.90-7.99(m,2H),7.80(ddd,J=11.10,8.83,2.69Hz,1H),7.64(s,1H),7.63(d,J=8.34 Hz,1H),7.42-7.48(m,1H),7.36(d,J=0.73Hz,1H),4.13(dd,J=13.33,6.24Hz,1H),3.94(dd,J=13.39,6.66Hz,1H),3.78(s,3H),1.69(s,3H).

[0301] Example 5: Preparation of N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)triazole-4-carboxamide (Compound P-3, Table P) [ka] Step 1: Preparation of ethyl 2-[(2,4-difluorophenyl)hydrazono]-3-oxo-propanoate [ka] To a two-necked round-bottom flask equipped with a nitrogen inlet was added 2,4-difluoroaniline (4.00 g, 30.9 mmol) in water (32 mL) and concentrated HCl (12 mL, 35%) at room temperature. The reaction mixture was cooled to 0 °C, and a cold solution of sodium nitrite (2.56 g, 37.1 mmol) in water (32 mL) was added to the solution, and the resulting mixture was stirred at 0 °C for 5 minutes. In a separate round-bottom flask, a solution of ethyl 3-(dimethylamino)prop-2-enoate (12.0 g, 23.4 mmol) and potassium acetate (4.61 g, 46.4 mmol) in ethanol (40 mL) was stirred and cooled to 0 °C. To this was added the above diazotization solution dropwise at 0 °C, and the reaction mixture was allowed to warm to room temperature and stirred for 18 hours. LCMS indicated the formation of the desired product. The reaction was diluted with water and extracted with EtOAc (3 × 50 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give crude ethyl 2-[(2,4-difluorophenyl)hydrazono]-3-oxo-propanoate as a brown solid, which was used directly in the next step. LCMS (Method B): 257[M+H] + ;holding time=1.09 minutes

[0302] Step 2: Preparation of ethyl 2-[(2,4-difluorophenyl)hydrazono]-3-hydroxyimino-propanoate [ka] To a solution of 2-[(2,4-difluorophenyl)hydrazono]-3-oxopropanoate (3.00 g, 5.85 mmol) in ethanol (30 mL) was added potassium acetate (1.45 g, 14.6 mmol) and hydroxylamine hydrochloride (0.49 g, 7.02 mmol). The reaction mixture was stirred at 80° C. for 2 hours. LCMS showed complete conversion to the desired product. The reaction mixture was cooled to rt, diluted with water, and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over NaSO, and concentrated in vacuo to give the title compound as a brown solid, which was used directly in the next step. LCMS (Method B): 272[M+H]+ ;retention time=1.16 minutes;

[0303] Step 3: Preparation of ethyl 2-(2,4-difluorophenyl)triazole-4-carboxylate [ka] Ethyl 2-[(2,4-difluorophenyl)hydrazono]-3-hydroxyimino-propanoate (3.4 g, 6.3 mmol) was treated with acetic anhydride (34 mL, 10 mL / g) at room temperature. The reaction mixture was then stirred at 140° C. for 1 hour. The reaction was monitored by LC-MS. Upon completion, the reaction mixture was cooled and quenched with ice and cold brine. The reaction mixture was extracted with EtOAc (3×25 mL), and the combined organic layers were dried over NaSO and concentrated in vacuo to give the crude product. This was purified by combiflash using EtOAc / cyclohexane (5:95) as the eluent to give the title compound as a brown solid. LCMS (Method C): 254[M+H] + ;retention time=1.19 minutes

[0304] Step 4: Lithium; Preparation of 2-(2,4-difluorophenyl)triazole-4-carboxylate [ka] To a stirred solution of ethyl 2-(2,4-difluorophenyl)triazole-4-carboxylate (0.10 g, 0.31 mmol) in THF (0.4 mL) and water (0.1 mL) was added lithium hydroxide (11.0 mg, 0.47 mmol), and the reaction was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was concentrated in vacuo, and the residue was triturated with methyl tert-butyl methyl ether (TBME). This afforded lithium 2-(2,4-difluorophenyl)triazole-4-carboxylate, which was used directly in the next step. LCMS (Method B): 224[M+H] + ;holding time=0.29 minutes

[0305] Step 5: Preparation of N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)triazole-4-carboxamide (Compound P-3, Table P) Lithium; 2-(2,4-difluorophenyl)triazole-4-carboxylate (70.0 mg, 0.30 mmol), and 2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propan-1-amine (91.0 mg, 0.36 mmol) were suspended in ethyl acetate (5 mL) and treated with triethylamine (97.7 μL, 0.66 mmol) and T3P (50% by weight) in EtOAc (2 mL) at 0°C. The reaction was stirred at room temperature for 2 h, after which time TLC and LCMS indicated the reaction was complete. The reaction mixture was diluted with water and extracted with EtOAc (2 × 25 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by combiflash using 0–70% EtOAc / cyclohexane as the eluent to give the product as a yellow gummy mass. LCMS (Method C): 458[M+H] + ;holding time=1.19 minutes; 1 H NMR(400MHz,CDCl3)δ ppm 8.28(s,1H),8.13-8.23(m,1H),7.89-7.95(m,1H),7.58(t,J=7.82Hz,1H),7.32(s,1H) ,7.16-7.25(m,2H),6.97-7.10(m,3H),4.03(d,J=6.36Hz,2H),3.88(s,3H),1.72(s,3H)

[0306] Example 6: Preparation of N-[2-(6-cyano-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)triazole-4-carboxamide (Compound P-2, Table P) [ka] A solution of N-[2-(6-chloro-2-pyridyl)-2-(1-methylpyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)-5-carboxamide (0.1 g, 0.20 mmol) and zinc cyanide (0.049 g, 0.41 mmol) in anhydrous N,N-dimethylformamide (1 mL) was degassed under nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.024 g, 0.020 mmol) was then added, and the resulting light brown suspension was stirred in a microwave at 120 °C for 3 hours. After the reaction was complete, the reaction mixture was diluted with ice-cold water and extracted with EtOAc (2 × 25 mL). The combined organic layers were washed with brine, dried over Na SO , and concentrated in vacuo. The crude product was absorbed onto silica gel and purified by combiflash using 0-80% EtOAc / cyclohexane as the eluent to give the product as a white gummy solid. LCMS (Method B): 449[M+H] + ;holding time=1.07 minutes; 1 H NMR(400MHz,CDCl3)δ ppm 8.28(s,1H),8.07(brt,1H),7.90- 7.94(m,1H),7.76(t,J=7.29Hz,1H),7.62(d,J=7.46Hz,1H),7.43(d,J=8.07Hz,1H),7 .23-7.32(m,2H),7.02-7.11(m,2H),4.07(d,J=6.48Hz,2H),3.89(s,3H),1.74(s,3H)

[0307] Further examples of compounds of formula (I) that have been synthesized are shown in Table P.

[0308] [Table 9-1]

[0309] [Table 9-2]

[0310] Biological Examples Example B1: Alternaria solani / Tomato / Leaf disc (summer blight) Tomato leaf discs (cv. Baby) were placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The discs were inoculated with a fungal spore suspension two days after application. The inoculated discs were incubated in a climate cabinet under a 12 / 12 h (light / dark) photoperiod at 23°C / 21°C (day / night) and 80% relative humidity. Once an appropriate level of disease damage had developed on the untreated test discs (5-7 days after application), the efficacy of the compounds was evaluated as the percentage of disease control compared to the untreated controls. The following compounds provided at least 80% control of Alternaria solani at 200 ppm when compared to untreated controls that showed extensive disease development under identical conditions: P-1, P-3, P-5, P-6, P-7, P-8

[0311] Example B2: Botryotinia fuckeliana (Botrytis cinerea) / liquid culture (gray mold) Fungal conidia stored at low temperature are mixed directly into nutrient liquid medium (Vogels broth). A solution of the test compound (DMSO) is placed in a microtiter plate (96-well format), followed by the addition of nutrient broth containing fungal spores. Test plates are incubated at 24°C, and growth inhibition is measured photometrically 3-4 days after application. The following compounds provided at least 80% control of Botryotinia fuckeliana at 20 ppm compared to untreated controls, which showed significant disease development under identical conditions: P-1, P-5, P-6, P-7, P-8

[0312] Example B3: Glomerella lagenarium (Colletotrichum lagenarium) / liquid culture (anthrax) Fungal conidia from cold storage are mixed directly into nutrient broth (PDB potato dextrose broth). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format), followed by the nutrient broth containing the fungal spores. Test plates are incubated at 24°C, and growth inhibition is measured photometrically 3-4 days after application. The following compounds, at 20 ppm, provided at least 80% control of Glomerella lagenarium compared to untreated controls, which showed significant disease development under identical conditions: P-1, P-5, P-6, P-7, P-8

[0313] Example B4: Blumeria graminis f.sp. tritici (powdery mildew fungus (Erysiphe graminis f.sp. tritici)) / wheat / leaf disc preventative (powdery mildew in wheat) Wheat leaf discs (cv. Kanzler) were placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. One day after application, powdery mildew-infected plants were inoculated onto the leaf discs by shaking them over the test plate. The inoculated leaf discs were incubated in a climate chamber at 20°C and 60% relative humidity under a 24-hour dark followed by 12-hour light / 12-hour dark light regime. Once an appropriate level of disease damage had developed on the untreated test leaf discs (6-8 days after application), the efficacy of the compounds was evaluated as the percentage of disease control compared to the untreated control. The following compounds provided at least 80% control of Blumeria graminis f.sp. tritici at 200 ppm when compared to untreated controls that showed extensive disease development under identical conditions: P-1, P-2, P-5, P-6, P-7, P-8, P-9

[0314] Example B5: Fusarium culmorum / liquid culture (blight) Fungal conidia from cold storage are mixed directly into nutrient broth (PDB potato dextrose broth). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format), followed by the nutrient broth containing the fungal spores. Test plates are incubated at 24°C, and growth inhibition is measured photometrically 3-4 days after application. The following compounds provided at least 80% control of Fusarium culmorum at 20 ppm compared to untreated controls, which showed significant disease development under identical conditions: P-1, P-6, P-7, P-8

[0315] Example B6: Fusarium culmorum / wheat / spikelet preventive (fusarium head blight) Wheat spikelets (cv. Monsun) are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compounds diluted in water. One day after application, the spikelets are inoculated with a fungal spore suspension. The inoculated spikelets are incubated in a climate chamber under 72 hours of semi-darkness followed by a 12-hour light / 12-hour dark photoperiod at 20°C and 60% relative humidity. When an appropriate level of disease damage appears on untreated test spikelets (6-8 days after application), compound efficacy is evaluated as the percentage of disease control compared to the untreated control. The following compounds provided at least 80% control of Fusarium culmorum at 200 ppm when compared to untreated controls under the same conditions, which showed extensive disease development: P-6

[0316] Example B7: Wheat leaf spot fungus (Phaeosphaeria nodorum) (Septoria nodorum) / Wheat / Leaf disc preventative (leaf spot disease) Wheat leaf discs (cv. Kanzler) are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compounds diluted in water. The discs are inoculated with a fungal spore suspension two days after application. The inoculated test discs are incubated in a climate cabinet at 20°C and 75% relative humidity under a 12-hour light / 12-hour dark photoperiod. When an appropriate level of disease damage occurs on the untreated test discs (5-7 days after application), the efficacy of the compounds is evaluated as the percentage of disease control compared to the untreated ones. The following compounds, at 200 ppm, provided at least 80% control of wheat leaf blight (Phaeosphaeria nodorum) when compared to untreated controls that showed extensive disease development under identical conditions: P-1, P-5, P-6, P-7, P-8, P-9

[0317] Example B8: Monographella nivalis (Microdochium nivale) / Liquid culture (Root rot of cereals) Fungal conidia from cold storage are mixed directly into nutrient broth (PDB potato dextrose broth). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format), followed by the nutrient broth containing the fungal spores. Test plates are incubated at 24°C, and growth inhibition is measured photometrically 4-5 days after application. The following compounds provided at least 80% control of Monographella nivalis at 20 ppm compared to untreated controls, which showed significant disease development under identical conditions: P-1, P-5, P-6, P-7, P-8, P-9

[0318] Example B9: Mycosphaerella arachidis (Cercospora arachidicola) / liquid culture (early leaf spot) Fungal conidia from cold storage are mixed directly into nutrient broth (PDB potato dextrose broth). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format), followed by the addition of the nutrient broth containing the fungal spores. Test plates are incubated at 24°C, and growth inhibition is measured photometrically 4-5 days after application. The following compounds, at 20 ppm, provided at least 80% control of Mycosphaerella arachidis when compared to untreated controls, which showed widespread disease development under identical conditions: P-1, P-5, P-6, P-7, P-8

[0319] Example B10: Pyrenophora teres / barley / leaf disc preventative (net blotch) Barley leaf discs (cv. Hasso) are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compounds diluted in water. Two days after application, the leaf discs are inoculated with a fungal spore suspension. The inoculated leaf discs are incubated in a climate cabinet under a 12-hour light / 12-hour dark photoperiod at 20°C and 65% relative humidity. When an appropriate level of disease damage occurs on the untreated test discs (5-7 days after application), the efficacy of the compounds is evaluated as disease control compared to the untreated ones. The following compounds provided at least 80% control of Pyrenophora teres at 200 ppm when compared to untreated controls that showed extensive disease development under identical conditions: P-1, P-3, P-5, P-6, P-7, P-8, P-9

[0320] Example B11: Sclerotinia sclerotiorum / Liquid culture (sclerotinia rot) Mycelial fragments from freshly cultivated fungal liquid cultures are mixed directly into nutrient broth (PDB potato dextrose broth). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format), and the nutrient broth containing the fungal material is added. The test plate is incubated at 24°C, and growth inhibition is measured photometrically 3-4 days after application. The following compounds, at 20 ppm, provided at least 80% control of Sclerotinia sclerotiorum when compared to untreated controls that showed widespread disease development under identical conditions: P-5, P-6

[0321] Example B12: Wheat leaf blight fungus (Mycosphaerella graminicola) (Septoria tritici) / liquid culture (leaf blight) Fungal conidia from cold storage are mixed directly into nutrient broth (PDB potato dextrose broth). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format), followed by the nutrient broth containing the fungal spores. Test plates are incubated at 24°C, and growth inhibition is measured photometrically 4-5 days after application. The following compounds provided at least 80% control of Mycosphaerella graminicola at 20 ppm compared to untreated controls, which showed significant disease development under identical conditions: P-1, P-5, P-6, P-8, P-7, P-9

[0322] Example B13: Gibberella zeae (Fusarium graminearum) / wheat / spikelet preventive (Scab disease) Wheat spikelets (cv. Monsun) are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compounds diluted in water. The day after application, the spikelets are inoculated with a fungal spore suspension. The inoculated test leaf discs are incubated in a climate chamber under 72 hours of semi-darkness followed by a 12-hour light / 12-hour dark photoperiod at 20°C and 60% relative humidity. When an appropriate level of disease damage appears on untreated test spikelets (6-8 days after application), compound efficacy is evaluated as the percentage of disease control compared to the untreated control. The following compounds provided at least 80% control of Gibberella zeae at 200 ppm when compared to untreated controls under the same conditions, which showed extensive disease development: P-7

[0323] Example B14: Phytophthora infestans / Tomato / Leaf Slice Preventative (Late Blight) Tomato leaf discs placed on agar in multiwell plates (24-well format) are sprayed with the formulated test compounds diluted in water. One day after application, the discs are inoculated with a fungal spore suspension. The inoculated leaf discs are incubated in a climate cabinet under a 24-hour dark followed by a 12-hour light / 12-hour dark photoperiod at 16°C and 75% rh. Compound activity is evaluated as the percentage disease control compared to untreated when an appropriate level of disease damage appears on untreated test leaf discs (5-7 days after application). The following compounds provided at least 80% control of Phytophthora infestans at 200 ppm when compared to untreated controls under identical conditions that showed severe disease development: P-2

[0324] Example B15: Plasmopara viticola / grape / leaf blight preventative (late blight) Grapevine leaf discs are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compounds diluted in water. One day after application, the discs are inoculated with a fungal spore suspension. The inoculated leaf discs are incubated in a climate cabinet at 19°C and 80% rh under a 12-hour light / 12-hour dark photoperiod. Compound activity is assessed as percentage disease control compared to untreated when an appropriate level of disease damage appears on untreated test leaf discs (6-8 days after application). The following compounds, at 200 ppm, provided at least 80% control of Plasmopara viticola when compared to untreated controls that showed extensive disease development under identical conditions: P-1, P-2

[0325] Example B16: Magnaporthe grisea (Pyricularia oryzae) / liquid culture (rice blast) Fungal conidia from cold storage are mixed directly into nutrient broth (PDB potato dextrose broth). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format), followed by the addition of the nutrient broth containing the fungal spores. Test plates are incubated at 24°C, and growth inhibition is measured photometrically 3-4 days after application. The following compounds provided at least 80% control of Magnaporthe grisea at 20 ppm compared to untreated:

Claims

1. Compounds of formula (I): 【Chemical 1】 (In the formula, R 1 But hydrogen, C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, or C 3 ~C 6 cycloalkyl; R 2 But hydrogen, halogen, C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkylcarbonyl, N—C 1 ~C 4 Alkoxy-C-C 1 ~C 4 Alkyl-carbonimidoyl, N-hydroxy-C-C 1 ~C 4 Alkyl-carbonimidoyl, or C 1 ~C 4 alkoxycarbonyl; R 3 is hydrogen, halogen, or C 1 ~C 4 alkyl; R 4 But hydrogen, halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Alkylcarbonyl, C 1 ~C 4 Alkoxycarbonyl, C 1 ~C 4 alkylaminocarbonyl, or di(C 1 ~C 4 alkylamino)carbonyl; R 5 and R 6 is hydrogen or C 1 ~C 4 independently selected from alkyl; A 1 But, CR 7 or N, A 2 But, CR 8 or N; A 3 is CR 9 or N; R 7 , R 8 , and R 9 But hydrogen, C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, or C 1 ~C 4 independently selected from haloalkyl; Q is Q1, Q2, Q3, Q4, or Q5; 【Chemistry 2】 (In the formula, R 10 , R 11 , R 12 and R 13 But hydrogen, halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 2 ~C 4 Alkenyloxy, C 2 ~C 4 Alkynyloxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Alkoxy-C 1 ~C 4 Alkyl, N-C 1-4 Alkylamino, N,N-diC 1-4 Alkylamino, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 4 Alkylcarbonyl, N—C 1 ~C 4 Alkoxy-C 1 ~C 4 Alkyl-carbonimidoyl, N-hydroxy-C 1 ~C 4 alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, amino, phenyl, 5- or 6-membered heteroaryl, or C 3 ~C 6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S; said phenyl, 5- or 6-membered heteroaryl, and C 3 ~C 6 - any of the cycloalkyl is unsubstituted or is selected from halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, or C 1 ~C 4 substituted by 1, 2 or 3 substituents independently selected from alkoxy; Z 1 But C 1 ~C 4 alkyl, phenyl, 5- or 6-membered heteroaryl, or C 3 ~C 6 -cycloalkyl, wherein any of said 5- or 6-membered heteroaryl contains 1, 2, 3 or 4 heteroatoms individually selected from N, O or S, and said phenyl, 5- or 6-membered heteroaryl and C 3 ~C 6 - any of the cycloalkyl is unsubstituted or is selected from halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, or C 2 ~C 4 alkynyl); or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

2. A 1 is selected from CH or N; A 2 is selected from CH or N; A 3 is selected from CH or N; A 1 , A 2 and A 3 2. The compound of formula (I) according to claim 1, wherein at least two of are selected from N.

3. R 1 3. A compound of formula (I) according to claim 1 or 2, wherein is selected from methyl, ethyl or isopropyl.

4. R 2 A compound of formula (I) according to any one of claims 1 to 3, wherein is selected from hydrogen, fluorine, chlorine or methyl.

5. R 3 A compound of formula (I) according to any one of claims 1 to 4, wherein is selected from hydrogen or methyl.

6. R 4 A compound of formula (I) according to any one of claims 1 to 5, wherein is selected from hydrogen or methyl.

7. R 5 and R 6 A compound of formula (I) according to any one of claims 1 to 6, wherein is independently selected from hydrogen or methyl.

8. The compound of formula (I) according to any one of claims 1 to 7, wherein Q is selected from Q1, Q2, or Q3.

9. R 10 and R 11 are independently selected from hydrogen, chloro, bromo, methoxy, cyano, amino, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, (3-cyanopyrazol-1-yl), (4-cyanopyrazol-1-yl), (3,5-dimethylpyrazol-1-yl), (5-methylpyrazol-1-yl), (4-methylpyrazol-1-yl), (3-methylpyrazol-1-yl), pyrazol-1-yl, cyclopropyl, or 1-cyanocyclopropyl; R 12 and R 13 A compound of formula (I) according to any one of claims 1 to 8, wherein is hydrogen.

10. R 10 and R 11 10. The compound of formula (I) according to claim 9, wherein is independently selected from hydrogen, chloro, bromo, cyano, or amino.

11. Z 1 Examples of suitable fluorophenyls include 1-methylpyrazol-4-yl, 2,3,4-trifluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 2,4,6-trifluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3,5-difluoro-2-pyridyl, 5-fluoro-2-pyridyl, 3-fluoro-2-pyridyl, 2-fluoro-4-methoxy-phenyl, 2-fluoro-4-methylsulfonyl-phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 3,5-difluoro-2-furyl, 3-fluoro-2-furyl, 5 ...

11. The compound of formula (I) according to any one of claims 1 to 10, wherein the compound is selected from fluoro-2-furyl, 3,5-difluoro-2-thienyl, 3-fluoro-2-thienyl, 5-fluoro-2-thienyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-methoxyphenyl, 4-ethynyl-2-fluoro-phenyl, 4-fluoro-2-methoxy-phenyl, cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclohexyl, cyclopentyl, methyl, n-propyl, or phenyl.

12. Z 1 is selected from 1-methylpyrazol-4-yl, 2,4,6-trifluorophenyl, 3,5-difluoro-2-pyridyl, 2,4-difluorophenyl, 2-fluorophenyl, 2-furyl, 2-methylphenyl, 2-thienyl, 3,4-difluorophenyl, 3-chlorophenyl, 3-thienyl, 4-fluoro-2-methoxy-phenyl, 4-fluorophenyl, cyclobutyl, cyclohexyl, cyclopentyl, or phenyl.

13. An agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to any one of claims 1 to 12.

14. 13. A method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, comprising applying a fungicidally effective amount of a compound of formula (I) according to any one of claims 1 to 12, or a composition comprising said compound of formula (I), to said plant, a part thereof or its habitat.

15. Use of a compound according to any one of claims 1 to 12 as a fungicide.

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