Novel heteroaryl-triazole compounds as pesticides

Abstract

The present invention relates to compounds of general formula (I) 1 , R 2 , R 3 , R 4 and R 5 has the meaning given to it herein), formulations and compositions containing such compounds, and their use in controlling pests (which includes arthropods and insects) in plant protection and for controlling ectoparasites of animals. [Formula 1] TIFF2022552475000054.tif81141

Description

Technical Field

[0001] The present invention relates to novel heteroaryl - triazole compounds, formulations and compositions containing such compounds, and their use in the control of animal pests (which includes arthropods and insects) in plant protection and their use for controlling external parasites of animals.

Background Art

[0002] Certain heteroaryl - triazole compounds represented by formula (I) are disclosed in WO2017 / 192385 regarding their use in the control of external parasites of animals, and are also disclosed in WO2019 / 170626 and WO2019 / 215198 regarding their use in the control of pests (which includes arthropods and insects) in the field of plant protection. Further, patent applications WO2019 / 197468, WO2019 / 201835, WO2019 / 202077 and WO2019 / 206799 disclose certain heteroaryl - triazole compounds for use in the control of external parasites of animals and for controlling pests (which includes arthropods and insects) in the field of plant protection. WO2020 / 002563, WO2020 / 053364, WO2020 / 053365, WO2020 / 079198, WO2020 / 094363, EP3696175A1 describe azole - amide compounds, all of which are capable of being used as insecticides.

[0003] Modern crop protection products and veterinary ectoparasiticides have to meet numerous requirements, for example with regard to efficacy, persistence, spectrum and resistance breaking properties. Questions regarding toxicity, the possibility of combination with other active compounds or formulation auxiliaries play a role, in addition to the costs required for synthesizing the active compounds. Furthermore, resistance can also occur. For all these reasons, the search for novel crop protection compositions or veterinary ectoparasiticides cannot be considered complete, and there is an ongoing need for novel compounds which have improved properties at least with respect to individual aspects compared to known compounds.

Prior art documents

Patent documents

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Summary of the Invention

Problems to be Solved by the Invention

[0005] An object of the present invention was to provide a compound that expands the spectrum of pesticides in various aspects.

Means for Solving the Problems

[0006] Accordingly, the present invention provides a compound of general formula (I)

Chemical formula

[0007] 〔wherein (Constitution 1-1): X is O or S; Y is a direct bond or CH2; R 1 is hydrogen; C1-C6 alkyl [wherein the alkyl may be substituted with one substituent selected from -CN, -CONH2, -COOH, -NO2 and -Si(CH3)3]; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl; C3-C4 cycloalkyl-C1-C2 alkyl- [wherein the C3-C4 cycloalkyl may be substituted with one or two halogen atoms]; oxetan-3-yl-CH2-, or benzyl [wherein the benzyl may be substituted with a halogen atom or C1-C3 haloalkyl]; R 2is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, where the phenyl, pyridine, pyrimidine, pyrazine or pyridazine may be substituted with 1 to 3 substituents, provided that the substituents are not present on any carbon adjacent to the carbon to which the C=X-group is attached, and the substituents are each independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 haloalkylthio, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, -NO2, -SF5, -CN, -CONH2, -COOH and -C(S)NH2; R 3 is C1-C3 alkyl or C1-C3 haloalkyl; R 4 is pyridine, pyrimidine, pyrazine or pyridazine, where the pyridine, pyrimidine, pyrazine or pyridazine may be substituted with 1 substituent selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C3-C4 cycloalkyl, halogen or hydroxy; R 5 is halogen〕 provides a compound represented by.

[0008] The compound represented by formula (I) further includes all diastereomers or enantiomers and E / Z isomers present, as well as salts and N-oxides of the compound represented by formula (I), and also includes their use for controlling pests.

[0009] Regarding the preferred definitions of the radicals for the formulas specified above and below, they are described below.

Mode for Carrying Out the Invention

[0010] More preferably (Constitution 2-1), formula (I) [wherein, X is O or S; Y is a direct bond or CH2; R 1is hydrogen; C1-C3 alkyl [wherein the alkyl may be substituted with one substituent selected from -CN, -CONH2, -COOH, -NO2 and -Si(CH3)3]; C1-C3 haloalkyl; C2-C4 alkenyl; C2-C4 haloalkenyl; C2-C4 alkynyl; C2-C4 haloalkynyl; C3-C4 cycloalkyl-C1-C2 alkyl- [wherein the C3-C4 cycloalkyl may be substituted with one or two halogen atoms]; oxetan-3-yl-CH2-; or benzyl [wherein the benzyl may be substituted with a halogen atom or C1-C3 haloalkyl]; R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine may be substituted with 1 to 3 substituents, provided that the substituents are not present on any carbon adjacent to the carbon bonded to the C=X-group, and the substituents are each independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 haloalkylthio, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, -NO2, -SF5, -CN, -CONH2, -COOH and -C(S)NH2; R 3 is C1-C3 alkyl or C1-C3 haloalkyl; R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine may be substituted with one substituent selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C3-C4 cycloalkyl, halogen or hydroxy; R 5 is halogen〕 is a compound represented by.

[0011] Particularly preferably (Constitution 3-1), Formula (I) [wherein, X is O; Y is a direct bond; R 1is hydrogen; R 2 is phenyl or pyridine, where the phenyl or pyridine may be substituted with 1 to 3 substituents, provided that the substituents are not present on any carbon adjacent to the carbon bonded to the C=X group, and the substituents are each independently selected from the group consisting of fluorine, chlorine, bromine, -CN, -NO2, -SF5, methyl, difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, difluoromethylthio and trifluoromethylthio; R 3 is C1-C3 alkyl; R 4 is pyridine or pyrimidine, where the pyridine or pyrimidine may be substituted with 1 substituent selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy; R 5 is fluorine, chlorine, bromine or iodine〕 is a compound represented by.

[0012] Extremely particularly preferably (Constitution 4-1), Formula (I) [wherein, X is O; Y is a direct bond; R 1 is hydrogen; R 2 is 3-chloro-5-(trifluoromethyl)phenyl, 3-bromo-5-(trifluoromethyl)phenyl, 3-chloro-5-(trifluoromethoxy)phenyl, 3-bromo-5-(trifluoromethoxy)phenyl, 3-bromo-5-chlorophenyl, 3,5-dichlorophenyl, 3,5-dibromophenyl, 3,5-bis(trifluoromethyl)phenyl, 2,6-dichloro-pyridin-4-yl, 5-(trifluoromethyl)-pyridin-3-yl or 2-chloro-6-(trifluoromethyl)-pyridin-4-yl; R 3 is methyl; R 4is pyrimidin-2-yl or 5-chloro-pyridin-2-yl; R 5 is chlorine, bromine or iodine〕 is a compound represented by

[0013] In a further preferred embodiment, the present invention relates to a compound of formula (I’)

Chemical formula

[0014] wherein in the above formula, the structural elements Y, R 1 、R 2 、R 3 、R 4 and R 5 have the meanings given in configuration (1-1) or the meanings given in configuration (2-1) or the meanings given in configuration (3-1) or the meanings given in configuration (4-1).

[0015] In a further preferred embodiment, the present invention relates to a compound of formula (I’’)

Chemical formula

[0016] wherein in the above formula, R 3 is C1-C3 alkyl, particularly preferably methyl; and in the above formula, Y is a direct bond, and the structural elements R 1 、R 2 、R 4 and R 5 have the meanings given in configuration (1-1) or the meanings given in configuration (2-1) or the meanings given in configuration (3-1) or the meanings given in configuration (4-1).

[0017] In a further preferred embodiment, the present invention relates to a compound of formula (I’’’)

Chemical formula

[0018] relates to a compound represented by, wherein in the above formula, R 3 is C1-C3 alkyl, particularly preferably methyl; and in the above formula, Y is a direct bond, and the structural elements R 1 , R 2 , R 4 and R 5 have the meaning given in configuration (1-1) or the meaning given in configuration (2-1) or the meaning given in configuration (3-1) or the meaning given in configuration (4-1).

[0019] According to a further aspect, the present invention includes an intermediate compound useful for preparing the compound represented by the above general formula (I).

[0020] According to a further aspect, the present invention includes an intermediate compound useful for preparing the compound represented by the above general formula (I).

[0021] In particular, the present invention relates to a general formula (a)

Chemical formula

[0022] includes an intermediate compound represented by, wherein in the above general formula, R 1 is hydrogen, R 3 is methyl and Y is a direct bond, and R 4 and R 5 have the meaning given in configuration (3-1) or the meaning given in configuration (4-1).

[0023] In particular, the present invention includes intermediate compounds (INT-01 to INT-06) (see Table 2): INT-01: 1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine; R 4 = pyrimidin-2-yl, and R5 = Cl; INT-02: 1-(5-Bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine; R 4 = pyrimidin-2-yl, and, R 5 = Br; INT-03: 1-(5-Iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine; R 4 = pyrimidin-2-yl, and, R 5 = I; INT-04: (1S)-1-(5-Chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride; R 4 = pyrimidin-2-yl, and, R 5 = Cl; INT-05: (1S)-1-(5-Bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride; R 4 = pyrimidin-2-yl, and, R 5 = Br; INT-06: (1S)-1-(5-Iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride; R 4 = pyrimidin-2-yl, and, R 5 = I.

[0024] Depending on the type of its substituents, the compound represented by formula (I) may exist in the form of stereoisomers, i.e., in the form of geometric isomers and / or optical isomers or in the form of a mixture of isomers in various compositions. For example, even if generally only the compound represented by formula (I) is discussed in this specification, the present invention provides both pure stereoisomers and any desired mixture of these isomers.

[0025] However, according to the present invention, preferably, the optically active stereoisomeric form of the compound represented by formula (I) and its salts are used.

[0026] Accordingly, the present invention relates to both pure enantiomers and diastereomers and mixtures thereof for controlling pests (which include arthropods, and in particular, insects).

[0027] Where appropriate, the compounds represented by formula (I) can exist in various polymorphic forms or can exist as a mixture of various polymorphic forms. Both pure polymorphs and polymorph mixtures are provided by the present invention and can be used according to the present invention.

[0028] Definition Those skilled in the art know that when the expressions "a" or "an" are used in the present application, they can mean "1", "1 or more" or "at least 1" depending on the situation, even if not explicitly indicated.

[0029] For all structures described herein, such as ring systems and groups, adjacent atoms must not be -O-O- or -O-S-.

[0030] Structures having possible carbon atoms (C atoms) of variables are, for the purpose of more specifically specifying, in the present application, C 炭素原子の下限 -C 炭素原子の上限 Structure (C LL -C UL Structure) can be described. For example, an alkyl group can be composed of 3 to 10 carbon atoms, in which case it corresponds to C3-C 10 -alkyl. A ring structure composed of carbon atoms and heteroatoms can be described as an "LL~UL member" structure. One example of a 6-membered ring structure is toluene (a 6-membered ring structure substituted with a methyl group).

[0031] Collective terms for substituents, such as C LL -C UL -alkyl are complex substituents, such as C LL -C UL -cycloalkyl-C LL -C UL- When at the end of -alkyl, the first component of the complex substituent, e.g., C LL - C UL - cycloalkyl may be the same or different and, independently, be mono- or polysubstituted by the latter substituents, e.g., C LL - C UL - alkyl. All collective terms used in this application with respect to chemical groups, ring systems, and cyclic groups can be more specifically defined by adding " LL - C UL " or "LL~UL members".

[0032] In the definitions of the symbols given in the above formula, collective terms generally representing the following substituents were used.

[0033] Halogen relates to the elements of Group 7, preferably fluorine, chlorine, bromine, and iodine, more preferably fluorine, chlorine, and bromine, even more preferably fluorine and chlorine.

[0034] Examples of heteroatoms are N, O, S, P, B, Si. Preferably, the term "heteroatom" relates to N, S, and O.

[0035] According to the present invention, "alkyl", alone or as part of a chemical group, preferably represents a straight-chain or branched hydrocarbon having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylpropyl, 1,3-dimethylbutyl, 1,4-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl and 2-ethylbutyl. Alkyl having 1 to 4 carbon atoms, such as, in particular, methyl, ethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl, etc. is also preferred. The alkyl according to the present invention may be substituted with one or more identical or different radicals.

[0036] According to the present invention, "alkenyl", alone or as part of a chemical group, preferably represents a straight-chain or branched hydrocarbon having 2 to 6 carbon atoms and at least one double bond, such as vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl. Alkenyls having 2 to 4 carbon atoms, such as, in particular, 2-propenyl, 2-butenyl or 1-methyl-2-propenyl, etc., are also preferred. The alkenyl according to the present invention may be substituted with one or more identical or different radicals.

[0037] According to the present invention, "alkynyl", alone or as part of a chemical group, preferably represents a linear or branched hydrocarbon having 2 to 6 carbon atoms and at least one triple bond, such as 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl and 2,5-hexadiynyl. Alkynyl having 2 to 4 carbon atoms, such as, in particular, ethynyl, 2-propynyl or 2-butynyl-2-propenyl, etc. is also preferred. The alkynyl according to the present invention may be substituted with one or more identical or different radicals.

[0038] According to the present invention, "cycloalkyl", alone or as part of a chemical group, preferably represents a monocyclic, bicyclic or tricyclic hydrocarbon having 3 to 10 carbons, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl or adamantyl. Cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms, such as, in particular, cyclopropyl or cyclobutyl, etc. is also preferred. The cycloalkyl according to the present invention may be substituted with one or more identical or different radicals.

[0039] According to the present invention, "alkylcycloalkyl" preferably represents a monocyclic, bicyclic or tricyclic alkylcycloalkyl having 4 to 10 or 4 to 7 carbon atoms, such as methylcyclopropyl, ethylcyclopropyl, isopropylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. Alkylcycloalkyl having 4, 5 or 7 carbon atoms, such as, in particular, ethylcyclopropyl or 4-methylcyclohexyl, etc. are also preferred. The alkylcycloalkyl according to the present invention may be substituted with one or more identical or different radicals.

[0040] According to the present invention, "cycloalkylalkyl" preferably represents a monocyclic, bicyclic or tricyclic cycloalkylalkyl having 4 to 10 or 4 to 7 carbon atoms, such as cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl and cyclopentylethyl. Cycloalkylalkyl having 4, 5 or 7 carbon atoms, such as, in particular, cyclopropylmethyl or cyclobutylmethyl, etc. are also preferred. The cycloalkylalkyl according to the present invention may be substituted with one or more identical or different radicals.

[0041] According to the present invention, "hydroxyalkyl" preferably represents a straight-chain or branched-chain alcohol having 1 to 6 carbon atoms, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, s-butanol and t-butanol. A hydroxyalkyl group having 1 to 4 carbon atoms is also preferred. The hydroxyalkyl group according to the present invention may be substituted with one or more identical or different radicals.

[0042] According to the present invention, "alkoxy" preferably represents a linear or branched O-alkyl having 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, and t-butoxy. An alkoxy group having 1 to 4 carbon atoms is also preferred. The alkoxy group according to the present invention may be substituted with one or more identical or different radicals.

[0043] According to the present invention, "alkylthio" or "alkylsulfanyl" preferably represents a linear or branched S-alkyl having 1 to 6 carbon atoms, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, s-butylthio, and t-butylthio. An alkylthio group having 1 to 4 carbon atoms is also preferred. The alkylthio group according to the present invention may be substituted with one or more identical or different radicals.

[0044] According to the present invention, "alkylsulfinyl" preferably represents a linear or branched alkylsulfinyl having 1 to 6 carbon atoms, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, s-butylsulfinyl, and t-butylsulfinyl. An alkylsulfinyl group having 1 to 4 carbon atoms is also preferred. The alkylsulfinyl group according to the present invention can be substituted with one or more identical or different radicals and includes both enantiomers.

[0045] According to the present invention, "alkylsulfonyl" preferably represents a linear or branched alkylsulfonyl having 1 to 6 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, s-butylsulfonyl, and t-butylsulfonyl. An alkylsulfonyl group having 1 to 4 carbon atoms is also preferred. The alkylsulfonyl group according to the present invention may be substituted with one or more identical or different radicals.

[0046] According to the present invention, "cycloalkylthio" or "cycloalkylsulfanyl" preferably represents -S-cycloalkyl having 3 to 6 carbon atoms, such as cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio. A cycloalkylthio group having 3 to 5 carbon atoms is also preferred. The cycloalkylthio group according to the present invention may be substituted with one or more identical or different radicals.

[0047] According to the present invention, "cycloalkylsulfinyl" preferably represents -S(O)-cycloalkyl having 3 to 6 carbon atoms, such as cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl. A cycloalkylsulfinyl group having 3 to 5 carbon atoms is also preferred. The cycloalkylsulfinyl group according to the present invention can be substituted with one or more identical or different radicals, and includes both enantiomers.

[0048] According to the present invention, "cycloalkylsulfonyl" preferably represents -SO2-cycloalkyl having 3 to 6 carbon atoms, such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl. A cycloalkylsulfonyl group having 3 to 5 carbon atoms is also preferred. The cycloalkylsulfonyl group according to the present invention may be substituted with one or more identical or different radicals.

[0049] According to the present invention, "phenylthio" or "phenylsulfanyl" represents -S-phenyl, such as phenylthio. The phenylthio group according to the present invention may be substituted with one or more identical or different radicals.

[0050] According to the present invention, "phenylsulfinyl" represents -S(O)-phenyl, for example, phenylsulfinyl. The phenylsulfinyl group according to the present invention can be substituted with one or more identical or different radicals and includes both enantiomers.

[0051] According to the present invention, "phenylsulfonyl" represents -SO2-phenyl, for example, phenylsulfonyl. The phenylsulfonyl group according to the present invention can be substituted with one or more identical or different radicals.

[0052] According to the present invention, "alkylcarbonyl" represents a linear or branched alkyl-C(=O) having preferably 2 to 7 carbon atoms, such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, s-butylcarbonyl and t-butylcarbonyl. An alkylcarbonyl having 1 to 4 carbon atoms is also preferred. The alkylcarbonyl according to the present invention can be substituted with one or more identical or different radicals.

[0053] According to the present invention, "alkoxycarbonyl", alone or as a component of a chemical group, represents a linear or branched alkoxycarbonyl having preferably 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkoxy moiety, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl and t-butoxycarbonyl. The alkoxycarbonyl group according to the present invention can be substituted with one or more identical or different radicals.

[0054] According to the present invention, "alkylaminocarbonyl" represents a linear or branched alkylaminocarbonyl having preferably 1 to 6 or 1 to 4 carbon atoms in the alkyl moiety, such as methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, s-butylaminocarbonyl and t-butylaminocarbonyl. The alkylaminocarbonyl group according to the present invention may be substituted with one or more identical or different radicals.

[0055] According to the present invention, "N,N-dialkylaminocarbonyl" represents a linear or branched N,N-dialkylaminocarbonyl having preferably 1 to 6 or 1 to 4 carbon atoms in the alkyl moiety, such as N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-di(n-propylamino)carbonyl, N,N-di(isopropylamino)carbonyl and N,N-di-(s-butylamino)carbonyl. The N,N-dialkylaminocarbonyl group according to the present invention may be substituted with one or more identical or different radicals.

[0056] According to the present invention, "aryl" represents a monocyclic, bicyclic or polycyclic aromatic system having preferably 6 to 14, particularly 6 to 10 ring carbon atoms, such as phenyl, naphthyl, anthryl, phenanthrenyl, preferably phenyl. Further, aryl also represents a polycyclic system in which the bonding site is on the aromatic system, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenyl and the like. The aryl group according to the present invention may be substituted with one or more identical or different radicals.

[0057] An example of substituted aryl is arylalkyl, which may likewise be substituted with one or more identical or different radicals in the C1-C4-alkyl moiety and / or the C6-C 14 -aryl moiety. Examples of such arylalkyl include benzyl and phenyl-1-ethyl and the like.

[0058] According to the present invention, "heterocycle", "heterocyclic ring" or "heterocyclic ring system" represents a carbocyclic ring system having at least one ring in which at least one carbon atom is replaced by a heteroatom (preferably a heteroatom selected from the group consisting of N, O, S, P, B, Si, Se), and which is saturated, unsaturated or heteroaromatic (wherein the ring may or may not be substituted, and the bonding site is on a ring atom). Unless otherwise defined differently, the heterocyclic ring preferably has 3 to 9 ring atoms (in particular, 3 to 6 ring atoms) and one or more (preferably 1 to 4, in particular 1, 2 or 3) heteroatoms (preferably heteroatoms selected from the group consisting of N, O and S) in the heterocyclic ring, provided that two oxygen atoms must not be directly adjacent. The heterocyclic ring usually contains 4 or fewer nitrogen atoms and / or 2 or fewer oxygen atoms and / or 2 or fewer sulfur atoms. When the heterocyclyl radical or heterocyclic ring may be substituted, the heterocyclyl radical or heterocyclic ring may be condensed with another carbocyclic ring or heterocyclic ring. In the case of a heterocyclyl which may be substituted, the present invention also includes polycyclic systems such as 8-azabicyclo[3.2.1]octanyl or 1-azabicyclo[2.2.1]heptyl. In the case of a heterocyclyl which may be substituted, the present invention also includes spirocyclic systems such as 1-oxa-5-azaspiro[2.3]hexyl.

[0059] The heterocyclyl group according to the present invention is, for example, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, pyrrolinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, thiazolidinyl, oxazolidinyl, dioxolanyl, dioxolyl, pyrazolidinyl, tetrahydrofuranyl, dihydrofuranyl, oxetanyl, oxiranyl, azetidinyl, aziridinyl, oxazetidinyl, oxaziridinyl, oxazepanyl, oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl, oxomorpholinyl, oxopiperazinyl and oxazepanyl.

[0060] Particularly important is heteroaryl, i.e., heteroaromatic. According to the present invention, the term "heteroaryl" represents a heteroaromatic compound, i.e., a completely unsaturated aromatic heterocyclic compound included in the above definition of a heterocycle. Preferred is a 5- to 7-membered ring having 1 to 3 (preferably 1 or 2) identical or different heteroatoms selected from the above group. The heteroaryl according to the present invention is, for example, furyl, thienyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl and 1,2,4-triazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl and 1,2,5-oxadiazolyl, azepinyl, pyrrolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl and 1,2,3-triazinyl, 1,2,4-oxazinyl, 1,3,2-oxazinyl, 1,3,6-oxazinyl and 1,2,6-oxazinyl, oxepinyl, thiepinyl, 1,2,4-triazolonyl, and 1,2,4-diazepinyl. The heteroaryl group according to the present invention may also be substituted with one or more identical or different radicals.

[0061] The term "(optionally) substituted" group / substituent, such as a substituted alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical, etc., means a substituted radical derived from an unsubstituted basic structure, where the substituent (e.g., 1 substituent, or a plurality of substituents, preferably 1, 2, 3, 4, 5, 6 or 7 substituents) is amino, hydroxyl, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, C1-C4-carboxyl, carboxamide, SF5, aminosulfonyl, C1-C4-alkyl, C1-C4-haloalkyl, C3-C4-cycloalkyl, C2-C4-alkenyl, C5-C6-cycloalkenyl, C2-C4-alkynyl, N-mono-C1-C4-alkylamino, N,N-di-C1-C4-alkylamino, N-C1-C4-alkanoylamino, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, C3-C4-cycloalkoxy, C5-C6-cycloalkenyloxy, C1-C4-alkoxycarbonyl, C2-C4-alkenyloxycarbonyl, C2-C4-alkynyloxycarbonyl, C6-aryloxycarbonyl, C 10 -aryloxycarbonyl, C 14 -aryloxycarbonyl, C1-C4-alkanoyl, C2-C4-alkenylcarbonyl, C2-C4-alkynylcarbonyl, C6-arylcarbonyl, C 10 -arylcarbonyl, C 14-arylcarbonyl, C1-C4-alkylthio, C1-C4-haloalkylthio, C3-C4-cycloalkylthio, C2-C4-alkenylthio, C5-C6-cycloalkenylthio, C2-C4-alkynylthio, C1-C4-alkylsulfinyl (wherein both enantiomers of the C1-C4-alkylsulfinyl group are included), C1-C4-haloalkylsulfinyl (wherein both enantiomers of the C1-C4-haloalkylsulfinyl group are included), C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, N-mono-C1-C4-alkylaminosulfonyl, N,N-di-C1-C4-alkylaminosulfonyl, C1-C4-alkylphosphinyl, C1-C4-alkylphosphonyl (wherein both enantiomers of the C1-C4-alkylphosphinyl and C1-C4-alkylphosphonyl are included), N-C1-C4-alkylaminocarbonyl, N,N-di-C1-C4-alkylaminocarbonyl, N-C1-C4-alkanoylaminocarbonyl, N-C1-C4-alkanoyl-N-C1-C4-alkylaminocarbonyl, C6-aryl, C 10 -aryl, C 14 -aryl, C6-aryloxy, C 10 -aryloxy, C 14 -aryloxy, benzyl, benzyloxy, benzylthio, C6-arylthio, C 10 -arylthio, C 14 -arylthio, C6-arylamino, C 10 -arylamino, C 14-Aryl amino, benzyl amino, heterocyclyl and trialkylsilyl, substituents bonded via a double bond (e.g., C1-C4-alkylidene (e.g., methylidene or ethylidene), oxo group, imino group and substituted imino group) are selected from the group consisting of. When two or more radicals form one or more rings, these can be carbocyclic, heterocyclic, saturated, partially saturated, unsaturated (including, for example, aromatic rings), and may be further substituted. The substituents (the "first substituent level") listed above as examples, when they contain a hydrocarbonaceous component, may have therein further substituents (the "second substituent level"), for example, one or more of the substituents independently selected from halogen, hydroxyl, amino, nitro, cyano, isocyano, azide, acylamino, oxo group and imino group. The term "substituted (optionally substituted)" group preferably includes only one or two substituent levels.

[0062] A chemical group substituted with a halogen or a halogenated group (e.g., alkyl or alkoxy) according to the present invention is mono-substituted with a halogen or multi-substituted with a halogen up to the maximum possible number of substituents. Such a group is also referred to as a halo group (e.g., haloalkyl). When multi-substituted with a halogen, the halogen atoms may be the same or different, and all may be bonded to one carbon atom or to a plurality of carbon atoms. The halogen is, in particular, fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, and more preferably fluorine. More specifically, the group substituted with a halogen is a monohalocycloalkyl, e.g., 1-fluorocyclopropyl, 2-fluorocyclopropyl or 1-fluorocyclobutyl, a monohaloalkyl, e.g., 2-chloroethyl, 2-fluoroethyl, 1-chloroethyl, 1-fluoroethyl, chloromethyl or fluoromethyl, a perhaloalkyl, e.g., trichloromethyl or trifluoromethyl or CF2CF3, a polyhaloalkyl, e.g., difluoromethyl, 2-fluoro-2-chloroethyl, dichloromethyl, 1,1,2,2-tetrafluoroethyl or 2,2,2-trifluoroethyl. Further examples of haloalkyl are trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, chloromethyl, bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, pentafluoroethyl, 3,3,3-trifluoropropyl and pentafluoro-t-butyl. Preferred is a haloalkyl having 1 to 4 carbon atoms and 1 to 9 (preferably 1 to 5) identical or different halogen atoms selected from fluorine, chlorine and bromine. Particularly preferred is a haloalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms selected from fluorine and chlorine (e.g., in particular, difluoromethyl, trifluoromethyl or 2,2-difluoroethyl).Further examples of compounds substituted with halogen are haloalkoxy such as OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3, OCH2CHF2 and OCH2CH2Cl, haloalkylsulfanyl such as difluoromethylthio, trifluoromethylthio, trichloromethylthio, chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2,2,2-trifluoroethylthio or 2-chloro-1,1,2-trifluoroethylthio, haloalkylsulfinyl such as difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, chlorodifluoromethylsulfinyl, 1-fluoroethylsulfinyl, 2-fluoroethylsulfinyl, 2,2-difluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl and 2-chloro-1,1,2-trifluoroethylsulfinyl, haloalkylsulfonyl groups such as difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, chlorodifluoromethylsulfonyl, 1-fluoroethylsulfonyl, 2-fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl and 2-chloro-1,1,2-trifluoroethylsulfonyl.

[0063] In the case of a radical having a carbon atom, those having 1 to 4 carbon atoms (particularly 1 or 2 carbon atoms) are preferred. Generally, substituents selected from the group consisting of halogen (e.g., fluorine and chlorine), (C1-C4)alkyl (preferably methyl or ethyl), (C1-C4)haloalkyl (preferably trifluoromethyl), (C1-C4)alkoxy (preferably methoxy or ethoxy), (C1-C4)haloalkoxy, nitro and cyano are preferred. Here, particularly preferred are the substituents methyl, methoxy, fluorine and chlorine.

[0064] The substituted amino (e.g., mono-substituted amino or di-substituted amino) means a radical selected from the group of N-substituted substituted amino radicals by 1 or 2 identical or different radicals selected from the group consisting of alkyl, hydroxy, amino, alkoxy, acyl and aryl; preferably N-monoalkylamino and N,N-dialkylamino (e.g., methylamino, ethylamino, N,N-dimethylamino, N,N-diethylamino, N,N-di-n-propylamino, N,N-diisopropylamino or N,N-dibutylamino), N-monoalkoxyalkylamino or N,N-dialkoxyalkylamino groups (e.g., N-methoxymethylamino, N-methoxyethylamino, N,N-di(methoxymethyl)amino or N,N-di(methoxyethyl)amino), N-monoarylamino and N,N-diarylamino, e.g., optionally substituted aniline, acylamino, N,N-diacylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino and, further, saturated N-heterocycle; here, preferred is an alkyl radical having 1 to 4 carbon atoms; here, aryl is preferably phenyl or substituted phenyl; for acyl, the definition further given below applies, preferably (C1-C4)-alkanoyl. The same also applies to the substituted hydroxylamino or hydrazino.

[0065] The replaced amino also includes a quaternary ammonium compound (salt) having four organic substituents on the nitrogen atom.

[0066] Optionally substituted phenyl is preferably unsubstituted phenyl or phenyl monosubstituted or polysubstituted (preferably up to trisubstituted) with the same or different radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl, cyano, isocyano and nitro, for example, o-tolyl, m-tolyl and p-tolyl, dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl and 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl and 4-fluorophenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl and 4-trifluoromethylphenyl, and 4-trichloromethylphenyl, 2,4-dichlorophenyl, 3,5-dichlorophenyl, 2,5-dichlorophenyl and 2,3-dichlorophenyl, o-methoxyphenyl, m-methoxyphenyl and p-methoxyphenyl, 4-heptafluorophenyl.

[0067] The cycloalkyl which may be substituted is preferably unsubstituted cycloalkyl or cycloalkyl mono- or polysubstituted (preferably up to trisubstituted) with identical or different radicals selected from the group consisting of halogen, cyano, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkyl and (C1-C4)-haloalkoxy, in particular cycloalkyl substituted with one or two (C1-C4)-alkyl radicals.

[0068] The compounds of the present invention may exist in preferred embodiments. The individual embodiments described herein can be combined with one another. Combinations that are contrary to the laws of nature and thus would be excluded by a person skilled in the art based on their expertise are not included. For example, ring structures having three or more adjacent oxygen atoms are excluded.

[0069] Isomer The compounds represented by formula (I) can exist in the form of geometric isomers, and / or in the form of optically active isomers, or in the form of corresponding isomer mixtures in various compositions, depending on the type of their substituents. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the present invention encompasses both pure stereoisomers and any mixtures of these isomers.

[0070] Method and use The present invention also relates to a method for controlling pests, wherein in the method, a compound represented by formula (I) is allowed to act on the pests and / or their habitat. The control of pests is preferably carried out in agriculture and forestry, and in the protection of materials. Preferably, surgical or therapeutic treatment methods for the human or animal body and diagnostic methods carried out on the human or animal body are excluded from the above method.

[0071] The present invention further relates to the use of a compound of formula (I) as a pesticide, in particular as a crop protection agent.

[0072] In connection with this application, the term "pesticide" always includes, in any case, the term "crop protection agent".

[0073] The compound of formula (I), in which the plants show good tolerance, the toxicity to warm-blooded animals is at a desirable level, and which shows good environmental compatibility, is suitable for protecting plants and plant organs against biotic and abiotic stress factors, for increasing the yield, for improving the quality of the harvest, and also for controlling pests encountered in agriculture, horticulture, animal husbandry, hydroponics, in forests, in gardens and leisure facilities, in the protection of stored products and materials, and in the field of hygiene, in particular insects, arachnids, helminths, in particular nematodes, and molluscs.

[0074] In connection with this patent application, the term "hygiene" is understood to mean any and all means, methods and practices aimed at preventing diseases (in particular infectious diseases), and any and all means, methods and practices useful for protecting the health of humans and animals and / or for protecting the environment and / or for maintaining cleanliness. According to the present invention, this includes, in particular, means for cleaning, disinfecting and sterilizing, for example, means for cleaning, disinfecting and sterilizing fibrous or hard surfaces (in particular glass, wood, concrete, porcelain, ceramic, plastic surfaces, or even surfaces made of metal(s)), and means for ensuring that these are maintained in a state free from hygienic pests and / or their excrement. In this connection, preferably, surgical or therapeutic treatment methods that can be applied to the human or animal body, and diagnostic methods performed on the human or animal body, are excluded from the scope of protection according to the present invention.

[0075] The term "field of hygiene" thus encompasses all areas, technical fields and industrial applications in which such hygienic means, methods and practices are important, for example, all areas, technical fields and industrial applications related to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, hospitals, livestock sheds, the livestock industry, etc.

[0076] Thus, the term "hygiene pest" is understood to mean one or more pests whose presence is a problem in the field of hygiene, in particular with regard to health reasons. Thus, the main objective is, in the field of hygiene, to avoid or minimize the presence of hygiene pests and / or to avoid or minimize contact with hygiene pests. This can be achieved, in particular, by applying pesticides that can be used both for prevention of occurrence and for dealing with existing occurrences. It is also possible to use preparations that avoid or reduce contact with pests. Examples of hygiene pests can include, for example, the organisms described below.

[0077] Thus, the term "hygienic protection" encompasses all actions that maintain and / or improve such hygienic means, methods and practices.

[0078] The compounds represented by formula (I) can preferably be used as pesticides. They are effective against normal susceptible species and resistant species and are active against all or some developmental stages. Examples of the above pests can include the following: Pests of the phylum Arthropoda, particularly of the class Arachnida, such as species of the genus Acarus, such as Acarus siro, Aceria kuko, Aceria sheldoni, species of the genus Aculops, species of the genus Aculus, such as Aculus fockeui, Aculus schlechtendali, species of the genus Amblyomma, Amphitetranychus viennensis, species of the genus Argas, species of the genus Boophilus, species of the genus Brevipalpus, such as Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, species of the genus Centruroides, species of the genus Chorioptes, Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, species of the genus Dermacentor, species of the genus Eotetranychus, such as Eotetranychus hicoriae, Epitrimerus pyri, species of the genus Eutetranychus, such as Eutetranychus banksi, species of the genus Eriophyes) For example, Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., such as Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., such as Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp.) For example, Panonychus citri (= Metatetranychus citri), Panonychus ulmi (= Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., for example, Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., for example, Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici;. Of the class Chilopoda, for example, Geophilus spp., Scutigera spp.; Of the order Collembola or class Collembola, for example, Onychiurus armatus; Sminthurus viridis; Of the class Diplopoda, for example, Blaniulus guttulatus; Of the class Insecta, for example, of the order Blattodea, for example, Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., for example, Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; Coleoptera, such as Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agrilus spp., such as Agrilus planipennis, Agrilus coxalis, Agrilus bilineatus, Agrilus anxius, Agriotes spp., such as Agriotes linneatus, Agriotes mancus, Agriotes obscurus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anomala dubia, Anoplophora spp., such as Anoplophora glabripennis, Anthonomus spp., such as Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Athous haemorrhoidales, Atomaria spp., such as Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp.) For example, Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., for example, Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., for example, Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., for example, Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., for example, Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp.) Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dendroctonus spp., e.g., Dendroctonus ponderosae, Dermestes spp., Diabrotica spp., e.g., Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., e.g., Epilachna borealis, Epilachna varivestis, Epitrix spp., e.g., Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp.) Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hoplia argentea, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., for example, Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., for example, Leucoptera coffeella, Limonius ectypus, Lissorhoptrus oryzophilus, Listronotus spp. (= Hyperodes spp.), Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp.) For example, Megacyllene robiniae, Megascelis spp., Melanotus spp., such as Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., such as Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., such as Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., such as Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp.) For example, Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., for example, Psylliodes affinis. ) Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Scolytus spp., e.g., Scolytus multistriatus, Sinoxylon perforans, Sitophilus spp., e.g., Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., e.g., Sternechus paludatus, Symphyletes spp., Tanymecus spp., e.g., Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp.) For example, Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., for example, Zabrus tenebrioides;. Of the order Dermaptera, for example, Anisolabis maritime, Forficula auricularia, Labidura riparia; Diptera, such as species of the genus Aedes, e.g., Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, species of the genus Agromyza, e.g., Agromyza frontella, Agromyza parvicornis, species of the genus Anastrepha, species of the genus Anopheles, e.g., Anopheles quadrimaculatus, Anopheles gambiae, species of the genus Asphondylia, species of the genus Bactrocera, e.g., Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, species of the genus Chironomus, species of the genus Chrysomya, species of the genus Chrysops, Chrysozona pluvialis, species of the genus Cochliomya, species of the genus Contarinia) For example, Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., such as Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., such as Dasineura brassicae, Delia spp., such as Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., such as Drosophila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp.)、Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., for example, Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., for example, Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., for example, Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya or Pegomyia spp., for example, Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp.) For example, Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., for example, Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., for example, Tipula paludosa, Tipula simplex, Toxotrypana curvicauda;. Insects of the order Hemiptera, such as Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., such as Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., such as Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., such as Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp.) For example, Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., for example, Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., for example, Cacopsylla pyricola, Calligypona marginata, Capulinia spp.)、Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., for example, Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp.) For example, Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., such as Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., such as Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., such as Icerya purchasi, Idiocerus spp., Idioscopus spp.) Laodelphax striatellus, Lecanium spp., e.g., Lecanium corni (= Parthenolecanium corni), Lepidosaphes spp., e.g., Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., e.g., Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., e.g., Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp.) For example, Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., for example, Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., for example, Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., for example, Phenacoccus... Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., e.g., Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., e.g., Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., e.g., Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., e.g., Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp.) For example, Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., for example, Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., for example, Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp.) Toxoptera spp., such as Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., such as Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;. Among the Heteroptera, for example, species of the genus Aelia, Anasa tristis, species of the genus Antestiopsis, species of the genus Boisea, species of the genus Blissus, species of the genus Calocoris, Campylomma livida, species of the genus Cavelerius, species of the genus Cimex, for example, Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, species of the genus Collaria, Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, species of the genus Dysdercus, species of the genus Euschistus, for example, Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, species of the genus Eurydema, species of the genus Eurygaster, Halyomorpha halys, species of the genus Heliopeltis, Horcias nobilellus, species of the genus Leptocorisa)、Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., such as Lygocoris pabulinus, Lygus spp., such as Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., such as Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., such as Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.;. Of the order Hymenoptera, for example, species of Acromyrmex spp., Athalia spp., such as Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., such as Diprion similis, Hoplocampa spp., such as Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monommium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., such as Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., such as Vespa crabro, Wasmannia auropunctata, Xeris spp.; Of the order Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber; Termites of the order Isoptera, such as species of the genus Coptotermes, such as Coptotermes formosanus, Cornitermes cumulans, species of the genus Cryptotermes, species of the genus Incisitermes, species of the genus Kalotermes, Microtermes obesi, species of the genus Nasutitermes, species of the genus Odontotermes, species of the genus Porotermes, species of the genus Reticulitermes, such as Reticulitermes flavipes, Reticulitermes hesperus; Lepidoptera, such as Achroia grisella, Acronicta major, Adoxophyes spp., such as Adoxophyes orana, Aedia leucomelas, Agrotis spp., such as Agrotis segetum, Agrotis ipsilon, Alabama spp., such as Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., such as Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp.) For example, Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., for example, Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., for example, Dioryctria zimmermani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., for example, Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp.) Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., for example, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., for example, Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., for example, Helicoverpa armigera, Helicoverpa zea, Heliothis spp., for example, Heliothis virescens, Hepialus spp., for example, Hepialus humuli, Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp.) For example, Leucoptera coffeella, Lithocolletis spp., such as Lithocolletis blancardella, Lithophane antennata, Lobesia spp., such as Lobesia botrana, Loxagrotis albicosta, Lymantria spp., such as Lymantria dispar, Lyonetia spp., such as Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., such as Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp., such as Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp.) For example, Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., such as Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., such as Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (= Plutella maculipennis), Podesia spp., such as Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., such as Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., such as Schoenobius bipunctifer, Scirpophaga spp., such as Scirpophaga innotata, Scotia segetum, Sesamia spp., such as Sesamia inferens, Sparganothis spp., Spodoptera spp.) For example, Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., for example, Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.; Of the order Orthoptera or Saltatoria, for example, Acheta domesticus, Dichroplus spp., Gryllotalpa spp., for example, Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., for example, Locusta migratoria, Melanoplus spp., for example, Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; Of the order Phthiraptera, for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.; Of the order Psocoptera, for example, Lepinotus spp., Liposcelis spp.; Of the order Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp., for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; Thrips of the order Thysanoptera, such as Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., such as Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., such as Thrips palmi, Thrips tabaci; Zygentoma ( = Thysanura) of the order Thysanura, such as Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; Pests of Symphyla, such as species of Scutigerella, such as Scutigerella immaculata; Pests of the phylum Mollusca, such as those of the class Bivalvia, such as species of Dreissena; and, further, those of the class Gastropoda, such as species of Arion, such as Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., such as Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.; Plant pests of the phylum Nematoda (i.e., plant-parasitic nematodes), in particular, species of the genus Aglenchus, such as Aglenchus agricola, species of the genus Anguina, such as Anguina tritici, species of the genus Aphelenchoides, such as Aphelenchoides arachidis, Aphelenchoides fragariae, species of the genus Belonolaimus, such as Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, species of the genus Bursaphelenchus, such as Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, species of the genus Cacopaurus, such as Cacopaurus pestis, species of the genus Criconemella, such as Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), species of the genus Criconemoides) For example, Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., such as Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., such as Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., such as Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., such as Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp., Hoplolaimus spp., Longidorus spp., such as Longidorus africanus, Meloidogyne spp., such as Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp.) Paraphelenchus spp., Paratrichodorus spp., for example, Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., for example, Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., for example, Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., for example, Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., for example, Tylenchorhynchus annulatus, Tylenchulus spp., for example, Tylenchulus semipenetrans, Xiphinema spp., for example, Xiphinema index.

[0079] The compound represented by formula (I) may optionally be used, at a specific concentration or specific application rate, as a herbicide, phytotoxicity reducing agent, growth regulator or agent for improving plant characteristics, or as a microbicide or gametocide, for example, as a fungicide, antimycotic, bactericide or virucide (which also includes agents against viroids), or as an agent against MLO (mycoplasma-like organisms) and RLO (rickettsia-like organisms). Where appropriate, they can also be used as intermediates or precursors for synthesizing other active compounds.

[0080] Formulation / usage form The present invention further relates to formulations, in particular formulations for controlling unwanted animal pests. The formulations can be applied to animal pests and / or their habitats.

[0081] The formulations of the present invention can be provided to the end user in a "ready-for-use" form, i.e., the formulations can be applied directly to plants or seeds by means of a suitable device such as a spraying device or a dusting device. Alternatively, the formulations can be provided to the end user in the form of a concentrate that needs to be diluted, preferably with water, before use. Thus, unless otherwise indicated, the expression "formulation" means such a concentrate, while the expression "form" means the end user in the form of a "ready-for-use" solution, i.e., usually such a diluted formulation.

[0082] The formulations of the present invention can be prepared in a conventional manner, for example, by mixing the compounds of the present invention with one or more suitable auxiliaries such as those disclosed herein.

[0083] The formulation contains at least one compound of the present invention and at least one agriculturally suitable auxiliary (for example, a carrier(s) and / or a surfactant(s)).

[0084] The carrier is a solid or liquid natural or synthetic organic or inorganic substance that is generally inert. Such carriers generally improve the application of the compound, for example, to plants, plant parts or seeds. Examples of suitable solid carriers include, but are not limited to, ammonium salts, especially ammonium sulfate, ammonium phosphate and ammonium nitrate, natural rock powders such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, silica gel, and synthetic rock powders such as micronized silica, alumina and silicates. Examples of solid carriers typically useful for preparing granules include, but are not limited to, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, synthetic granules composed of inorganic and organic powders, and granules composed of organic materials such as paper, sawdust, coconut shells, corn cobs and tobacco stalks. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents and combinations thereof.Examples of suitable solvents include polar and non-polar organic chemical liquids such as those selected from the following types: aromatic and non-aromatic hydrocarbons (e.g., cyclohexane, paraffins, alkylbenzenes, xylene, toluene, tetrahydronaphthalene, alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons, e.g., chlorobenzenes, chloroethylenes or methylene chloride), alcohols and polyols (which may optionally be substituted, etherified and / or esterified, e.g., ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or glycol), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone or cyclohexanone), esters (which include fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (e.g., dimethylformamide or fatty acid amides) and their esters, lactams (e.g., N-alkylpyrrolidones, particularly N-methylpyrrolidone) and lactones, sulfones and sulfoxides (e.g., dimethyl sulfoxide), oils of plant or animal origin, nitriles (alkyl nitriles, e.g., acetonitrile, propionitrile, butyronitrile, or aromatic nitriles, e.g., benzonitrile), carbonates (cyclic carbonates, e.g., ethylene carbonate, propylene carbonate, butylene carbonate, or dialkyl carbonates, e.g., dimethyl carbonate, diethyl carbonate, dipropyl carbonate, dibutyl carbonate, dioctyl carbonate). The carrier can also be a liquefied gas extender, i.e., a liquid that is a gas at standard temperature and pressure, such as an aerosol propellant, e.g., halocarbons, butane, propane, nitrogen and carbon dioxide, etc.

[0085] Preferred solid carriers are selected from clay, talc and silica.

[0086] Preferred liquid carriers are selected from water, fatty acid amides and their esters, aromatic and non-aromatic hydrocarbons, lactams, lactones, carbonates, ketones, (poly)ethers.

[0087] The amount of the carrier is typically in the range of 1 to 99.99% by weight, preferably in the range of 5 to 99.9% by weight, more preferably in the range of 10 to 99.5% by weight, and most preferably in the range of 20 to 99% by weight of the formulation.

[0088] The liquid carrier is typically present in the range of 20 to 90% by weight, for example, in the range of 30 to 80% by weight of the formulation.

[0089] The solid carrier is typically present in the range of 0 to 50% by weight, preferably in the range of 5 to 45% by weight, for example, in the range of 10 to 30% by weight of the formulation.

[0090] When the formulation contains two or more carriers, its approximate range means the total amount of the carriers.

[0091] The surfactant can be an ionic (cationic or anionic), zwitterionic or non-ionic surfactant, for example, an ionic or non-ionic emulsifier, foaming agent, dispersant, wetting agent, penetration enhancer and any mixture thereof. Examples of suitable surfactants include, but are not limited to, the following: salts of polyacrylic acid, ethoxylated poly(α-substituted) acrylate derivatives, salts of lignosulfonic acid (e.g., sodium lignosulfonate), salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide and / or propylene oxide with or without alcohol or fatty acid or fatty amine (polyoxyethylene fatty acid esters, e.g., castor oil ethoxylate, polyoxyethylene fatty alcohol ethers, e.g., alkylaryl polyglycol ethers), substituted phenols (preferably, alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably, alkyl taurates), phosphate esters of polyethoxylated alcohol or polyethoxylated phenol, fatty esters of polyols (e.g., fatty acid esters of glycerol or sorbitol or sucrose), sulfates (e.g., alkyl sulfates and alkyl ether sulfates), sulfonates (e.g., alkyl sulfonates, aryl sulfonates and alkylbenzene sulfonates), sulfonated polymers of naphthalene / formaldehyde, phosphate esters, protein hydrolysates, lignosulfite waste liquor and methyl cellulose. References to salts in this paragraph preferably indicate the respective alkali salts, alkaline earth metal salts and ammonium salts.

[0092] Preferred surfactants are selected from ethoxylated poly(α-substituted) acrylate derivatives, polycondensates of ethylene oxide and / or propylene oxide containing alcohol, polyoxyethylene fatty acid esters, alkylbenzene sulfonates, sulfonated polymers of naphthalene / formaldehyde, polyoxyethylene fatty acid esters such as castor oil ethoxylate, sodium lignosulfonate and arylphenol ethoxylate.

[0093] The amount of surfactant is typically in the range of 5 to 40% by weight, for example in the range of 10 to 20% by weight, of the formulation.

[0094] Further examples of suitable auxiliaries are, inter alia: water repellents, desiccants, binders (adhesives, tackifiers, fixing agents, for example carboxymethyl cellulose, and natural and synthetic polymers in the form of powders or granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids, polyvinylpyrrolidone and tyrosin), thickeners and second thickeners (for example cellulose ethers, acrylic acid derivatives, xanthan gum, modified clays, such as products available under the name Bentone, and micronized silica), stabilizers (for example cryostabilizers, preservatives (for example dichlorophen, benzyl alcohol hemi formal, 1,2-benzisothiazolin-3-one, 2-methyl-4-isothiazolin-3-one), antioxidants, light stabilizers, in particular ultraviolet stabilizers, or another agent which improves chemical and / or physical stability), dyes or pigments (for example inorganic pigments, such as iron oxide, titanium oxide and Prussian Blue; organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes), defoamers (for example silicone defoamers and magnesium stearate), antifreezes, fixing agents, gibberellins, and processing aids, mineral and vegetable oils, fragrances, waxes, nutrients (which include micronutrients such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts), protective colloids, thixotropic substances, penetrants, sequestering agents, and complex formers).

[0095] The choice of the auxiliaries depends on the intended method of application of the compounds of the invention and / or on the physical properties of those compounds. Furthermore, the auxiliaries can also be chosen in order to impart special properties (technical, physical and / or biological properties) to the formulation or to the use forms prepared from that formulation. By choosing the auxiliaries, the formulation can be customized to specific needs.

[0096] The formulation contains an insecticidal / acaricidal / nematicidal effective amount of the compound(s) of the present invention. The term "effective amount" represents an amount sufficient to control harmful insects / mites / nematodes on cultivated plants or in the protection of materials and that does not cause substantial damage to the treated plants. Such amounts can vary within a wide range and depend on various factors, such as the species of the insects / mites / nematodes to be controlled, the cultivated plants or materials treated, the climatic conditions, and the specific compound of the present invention used. Usually, the formulation according to the present invention contains from 0.01 to 99% by weight, preferably from 0.05 to 98% by weight, more preferably from 0.1 to 95% by weight, even more preferably from 0.5 to 90% by weight, and most preferably from 1 to 80% by weight of the compound of the present invention. The formulation can contain two or more compounds of the present invention. In such cases, the approximate range indicates the total amount of the compounds of the present invention.

[0097] The formulations of the present invention can be of any conventional formulation type, such as solutions (e.g., aqueous solutions), emulsions, aqueous and oily suspensions, powders (e.g., wettable powders, soluble powders), dusts, pastes, granules (e.g., soluble granules, broadcast granules), suspoemulsion formulations, natural or synthetic products impregnated with the compounds of the present invention, fertilizers, and furthermore, those microencapsulated in polymeric substances. The compounds of the present invention can be present in a suspended form, an emulsified form or a dissolved form. Examples of certain suitable formulation types are solutions, water-soluble concentrates (e.g., SL, LS), dispersible concentrates (DC), suspensions and suspension formulations (e.g., SC, OD, OF, FS), emulsions (e.g., EC), emulsion concentrates (e.g., EW, EO, ES, ME, SE), capsule suspensions (e.g., CS, ZC), pastes, pastilles, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), pressing formulations (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), pesticidal products (e.g., LN), and gel formulations (e.g., GW, GF) for treating plant propagation materials (e.g., seeds). These formulation types and further formulation types are defined by the Food and Agriculture Organization of the United Nations (FAO). An overview is given in ““Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6th Ed. May 2008, Croplife International”.

[0098] Preferably, the formulations of the present invention are in the form of one of the following types: EC, SC, FS, SE, OD, WG, WP, CS, and more preferably, EC, SC, OD, WG, CS.

[0099] Examples of the types of formulations and further details regarding their preparation are provided below. When two or more compounds of the present invention are present, the approximate amounts of the compounds of the present invention indicate the total amount of the compounds of the present invention. This also applies mutatis mutandis to such components when two or more representative ones among any further components of the formulation (e.g., wetting agents, binders) are present.

[0100] (i) Water-soluble thickener (SL, LS) 10 to 60% by weight of at least one compound of the present invention and 5 to 15% by weight of a surfactant (e.g., a polycondensate of ethylene oxide and / or propylene oxide containing alcohol) are dissolved in an amount of water and / or a water-soluble solvent (e.g., alcohols such as propylene glycol, or carbonates such as propylene carbonate) such that the total amount is 100% by weight. Before application, the concentrate is diluted with water.

[0101] (ii) Dispersible thickener (DC) 5 to 25% by weight of at least one compound of the present invention and 1 to 10% by weight of a surfactant and / or binder (e.g., polyvinylpyrrolidone) are dissolved in an amount of an organic solvent (e.g., cyclohexanone) such that the total amount is 100% by weight. A dispersion is obtained by diluting with water.

[0102] (iii) Emulsion (EC) 15 to 70% by weight of at least one compound of the present invention and 5 to 10% by weight of a surfactant (e.g., a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in an amount of a water-insoluble organic solvent (e.g., aromatic hydrocarbon or fatty acid amide) and, if necessary, an additional water-soluble solvent such that the total amount is 100% by weight. An emulsion is obtained by diluting with water.

[0103] (iv) Emulsifying agent (EW, EO, ES) 5 to 40% by weight of at least one compound of the present invention and 1 to 10% by weight of a surfactant (for example, a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate, or a polycondensate of ethylene oxide and / or propylene oxide with or without alcohol) are dissolved in 20 to 40% by weight of a water-insoluble organic solvent (for example, an aromatic hydrocarbon). This mixture is added to water in an amount such that the total amount is 100% by weight using an emulsifier. The resulting formulation is a homogeneous emulsion. Before application, the emulsion can be further diluted with water.

[0104] (v) Suspension agent and suspension formulation (v-1) Aqueous (SC, FS) In a suitable grinding device (for example, a stirred ball mill), 20 to 60% by weight of at least one compound of the present invention is finely ground by adding 2 to 10% by weight of a surfactant (for example, sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1 to 2% by weight of a thickener (for example, xanthan gum) and water, and a fine active substance suspension is obtained. Water is added in an amount such that the total amount is 100% by weight. By diluting with water, a stable suspension of the active substance is obtained. In the FS type formulation, a binder (for example, polyvinyl alcohol) up to 40% by weight is added.

[0105] (v-2) Oil-based (OD, OF) In a suitable grinding device (for example, a stirred ball mill), 20 to 60% by weight of at least one compound of the present invention is finely ground by adding 2 to 10% by weight of a surfactant (for example, sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1 to 2% by weight of a thickener (for example, modified clay, especially Bentone, or silica) and an organic carrier, and a fine active substance oil suspension is obtained. The organic carrier is added in an amount such that the total amount is 100% by weight. By diluting with water, a stable dispersion of the active substance is obtained.

[0106] (vi) Granular wettable powder and water-soluble granule (WG, SG) 1 to 90% by weight (preferably 20 to 80% by weight, most preferably 50 to 80% by weight) of at least one compound of the present invention is micronized by adding a surfactant (for example, sodium lignosulfonate and sodium alkylnaphthylsulfonate) and optionally a carrier substance, and converted into a granular wettable powder or a water-soluble granule using typical technical equipment (for example, extrusion granulation, spray drying granulation, fluidized bed granulation). The surfactant and the carrier substance are used in amounts such that the total amount is 100% by weight. By diluting with water, a stable dispersion or solution of the active substance can be obtained.

[0107] (vii) Wettable powder and water-soluble powder W (WP, SP, WS) 50 to 80% by weight of at least one compound of the present invention is ground in a rotor-stator mill by adding 1 to 20% by weight of a surfactant (for example, sodium lignosulfonate, sodium alkylnaphthylsulfonate) and a solid carrier (for example, silica gel) in an amount such that the total amount is 100% by weight. By diluting with water, a stable dispersion or solution of the active substance can be obtained.

[0108] (viii) Gel agent (GW, GF) In a stirred ball mill, 5 to 25% by weight of at least one compound of the present invention is micronized by adding 3 to 10% by weight of a surfactant (for example, sodium lignosulfonate), 1 to 5% by weight of a binder (for example, carboxymethyl cellulose) and water in an amount such that the total amount is 100% by weight. Thereby, a fine suspension of the active substance can be obtained. By diluting with water, a stable suspension of the active substance can be obtained.

[0109] (ix) Microemulsion agent (ME) 5 to 20% by weight of at least one compound of the present invention is added to 5 to 30% by weight of an organic solvent blend (for example, fatty acid dimethylamide and cyclohexanone), 10 to 25% by weight of a surfactant blend (for example, polyoxyethylene fatty alcohol ether and arylphenol ethoxylate) and water in an amount such that the total amount is 100% by weight. The mixture is stirred for 1 hour to spontaneously generate a thermodynamically stable microemulsion.

[0110] (x) Microcapsule (CS) An oil phase containing 5 to 50% by weight of at least one compound of the present invention, 0 to 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and 2 to 15% by weight of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, and di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Poly(meth)acrylate microcapsules are formed by radical polymerization initiated by a radical initiator. Alternatively, an oil phase containing 5 to 50% by weight of at least one compound of the present invention, 0 to 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethane-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol), thereby forming polyurea microcapsules. Optionally, a polyamine (e.g., hexamethylenediamine) may be added to form polyurea microcapsules. The monomers account for 1 to 10% of the total weight of the CS formulation.

[0111] (xi) Dustable powders (DP, DS) At least one compound of the present invention in an amount of 1 to 10% by weight is pulverized and intimately mixed with a solid carrier (e.g., pulverized kaolin) in an amount such that the total amount is 100% by weight.

[0112] (xii) Granule (GR, FG) At least one compound of the present invention in an amount of 0.5 to 30% by weight is pulverized and combined with a solid carrier (e.g., silicate) in an amount such that the total amount is 100% by weight.

[0113] (xiii) Ultra-low volume liquids (UL) At least one compound of the present invention in an amount of 1 to 50% by weight is dissolved in an organic solvent (e.g., aromatic hydrocarbon) in an amount such that the total amount is 100% by weight.

[0114] Formulations (i) to (xiii) may optionally further contain additional adjuvants, for example, 0.1 to 1% by weight of a preservative, 0.1 to 1% by weight of an antifoaming agent, 0.1 to 1% by weight of a dye and / or pigment, and 5 to 10% by weight of an antifreeze, etc.

[0115] Mixture The compound represented by formula (I) can be used, for example, in combination with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficial species, herbicides, fertilizers, bird repellents, phytotonics, sterilants, phytotoxicity reducing agents, semiochemicals and / or plant growth regulators in order to broaden the spectrum of action, to increase the duration of action, to increase the rate of action, to prevent repulsion, or to prevent the development of resistance. Furthermore, such combinations of active compounds can improve plant growth and / or can improve the tolerance to abiotic factors (such as high or low temperatures), tolerance to waterlogging or the tolerance to an increase in water content or soil salt concentration. Furthermore, it is also possible to improve the flowering and fruiting performance, to optimize the germination ability and root development, to facilitate harvesting, to increase the yield, to influence ripening, to improve the quality and / or nutritional value of the harvested product, to increase the shelf life of the harvested product, and / or to improve the processability of the harvested product.

[0116] Furthermore, the compound represented by formula (I) can also be present in a mixture with another active compound or semiochemical (such as an attractant, and / or a bird repellent, and / or a plant activator, and / or a growth regulator, and / or a fertilizer). Similarly, the compound represented by formula (I) can also be used to improve plant characteristics (such as growth, yield and quality of the harvest).

[0117] In certain embodiments according to the present invention, the compound represented by formula (I) is present in a formulation or in a form of use prepared from such a formulation, in admixture with a further compound (preferably a compound described below).

[0118] If one of the compounds described below can exist in various tautomeric forms, those forms are likewise included in each case, even if not expressly mentioned. Furthermore, all the co-formulants named can, where possible by virtue of their functional groups, also form salts with suitable bases or acids in some cases.

[0119] Insecticide / acaricide / nematicide The active compounds identified herein by their “common names” are known and are described, for example, in the Pesticide Handbook (“The Pesticide Manual” 16th Ed., British Crop Protection Council 2012) or can be found on the Internet (for example, “http: / / www.alanwood.net / pesticides”). Their classification is based on the then current “IRAC Mode of Action Classification Scheme” at the time of filing of this patent application.

[0120] (1) Acetylcholinesterase (AChE) inhibitors, preferably carbamates, which are selected from aldicarb, aldicarb sulfoxide, aldicarb sulfone, benfuracarb, benomyl, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, methiocarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or Organophosphates, which are selected from acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, kasugamycin, chlorethoxyfos, chlorfenvinphos, chloromethiophos, chlorpyrifos-methyl, coumaphos, cyanophos, dimethoate-S-methyl, diazinon, dichlorvos / DDVP, dichlorvos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, etoprophos, famphur, fenamiphos, fenitrothion, fenthion, fostiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl)salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pyrimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotepp, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and bamidothion.

[0121] (2) GABA-regulated chloride channel blockers, preferably Cyclodiene-organochlorines, which are selected from chlordane and endosulfan; or Phenylpyrazoles (fiproles), which are selected from ethiprole and fipronil.

[0122] (3) Sodium channel modulators, preferably Pyrethroids, which are selected from acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans-isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, monofluoroethrin, permethrin, phenothrin [(1R)-trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin and transfluthrin; or, DDT; or, methoxychlor.

[0123] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, preferably, Neonicotinoids, which are selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or, Nicotine; or, Sulfoximines, which are selected from sulfoxaflor; or, Butenolides, which are selected from flupyradifurone; or, Mesions, which are selected from triflumizopyrim.

[0124] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators (site I), preferably, Spinosyns, which are selected from spinetoram and spinosad.

[0125] (6) Glutamate-gated chloride channel (GluCl) allosteric modulators, preferably avermectin / milbemycin compounds, which are selected from abamectin, emamectin benzoate, lepimectin, and milbemycin.

[0126] (7) Juvenile hormone mimics, preferably juvenile hormone analogs, which are selected from hydroprene, kinoprene, and methoprene; or phenoxycarb; or pyriproxyfen.

[0127] (8) Various unspecified (multi-site) inhibitors, preferably alkyl halides, which are selected from methyl bromide and other alkyl halides; or chloropicrin; or sulfuryl fluoride; or borax; or tartar emetic; or methyl isocyanate products, which are selected from dazomet and metam.

[0128] (9) Chordotonal organ TRPV channel modulators, preferably pyridine azomethanes, which are selected from pimetrozine and pyrifluquinazone; or pyropenes, which are selected from afidopyropene.

[0129] (10) Mite growth inhibitors that act on CHS1, which are selected from clofentezine, hexythiazox, diflovidazin, and etoxazole.

[0130] (11) A microbial disruptor of the insect midgut, which is selected from Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and Bt plant proteins (which are selected from Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, and Cry34Ab1 / 35Ab1).

[0131] (12) An inhibitor of mitochondrial ATP synthase, preferably, An ATP disruptor, which is selected from diafenthiuron; or, An organotin compound, which is selected from azocyclotin, cyhexatin, and fenbutatin oxide; or, Propargite; or tetradifon.

[0132] (13) An uncoupler of oxidative phosphorylation by disrupting the proton gradient, which is selected from chlorfenapyr, DNOC, and sulfluramid.

[0133] (14) A nicotinic acetylcholine receptor channel blocker, which is selected from bensultap, cartap hydrochloride, thiocylam, and thiosultap-sodium.

[0134] (15) An inhibitor of chitin biosynthesis acting on CHS1, preferably, Benzoyl ureas, which are selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0135] (16) Chitin biosynthesis inhibitors (type 1), which are selected from buprofezin.

[0136] (17) Molting disruptors (especially for Diptera, i.e., dipterans), which are selected from cyromazine.

[0137] (18) Ecdysone receptor agonists, preferably Diacylhydrazines, which are selected from chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0138] (19) Octopamine receptor agonists, which are selected from amitraz.

[0139] (20) Mitochondrial complex III electron transport inhibitors, which are selected from hydramethylnon, acequinocyl, fluacrypyrim and bifenazate.

[0140] (21) Mitochondrial complex I electron transport inhibitors, preferably METI acaricides and insecticides, which are selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad; or Rotenone (Derris).

[0141] (22) Voltage-dependent sodium channel blockers, preferably Oxadiazines, which are selected from indoxacarb; or Semicarbazones, which are selected from metaflumizone.

[0142] (23) Inhibitors of acetyl-CoA carboxylase, preferably, Tetronic acid derivatives and tetramic acid derivatives, which are selected from spirodiclofen, spirodiclofen, spirodiclofen, spirotetramat.

[0143] (24) Inhibitors of mitochondrial complex IV electron transport, preferably, Phosphide-based, which are selected from aluminum phosphide, calcium phosphide, phosphine and zinc phosphide; or, Cyanides, which are selected from calcium cyanide, potassium cyanide and sodium cyanide.

[0144] (25) Inhibitors of mitochondrial complex II electron transport, preferably, β-Ketonitrile derivatives, which are selected from cyenopyrafen and cyflumetofen; or, Carboxyanilide-based, which is selected from piflubumide.

[0145] (28) Ryanodine receptor modulators, preferably, Diamide-based, which are selected from chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide and tetraliniprole.

[0146] (29) Chordotonal organ modulators (target site not defined), which is selected from flonicamid.

[0147] (30) GABA-regulated chloride channel allosteric modulators, preferably, Meta-diamide-based, which is selected from broflanilide; or, Isoxazole-based, which is selected from fluxametamide.

[0148] (31) Baculoviruses, preferably, Granulosis viruses (GVs), which are selected from Cydia pomonella GV and Thaumatotibia leucotreta (GV); or, Nucleopolyhedroviruses (NPVs), which are selected from Anticarsia gemmatalis MNPV and Helicoverpa armigera NPV.

[0149] (32) Nicotinic acetylcholine receptor allosteric modulators (site II), which are selected from GS-omega / kappa HXTX-Hv1a peptides.

[0150] (33) Further active ingredients selected from the following: acinonapil, afoxolaner, azadirachtin, benclothiaz, benzoximate, benzpyrioxime, bromopropylate, chinomethionat, chloroprallethrin, cryolite, Cyclobutrifluram, cycloxaprid, Cyetpyrafen, cyhalodiamide, Cyproflanilide (CAS 2375110-88-4), dichloromethothiaz, dicofol, dimpropyridaz, ε-methofluthrin, epsilon-momfluthrin, flometokine, fluazaindoline, Flucypyriprole (CAS 1771741-86-6), fluenesulfone, flufenoxuron, flufenoxystrobin, flufiprole, flufexaflone, fluopyram, flupyrimidine, fluralaner, fufenozide, Flupentiofenox, guazipyr, heptafluthrin, imidaclothiz, iprodione, isocycloseram, κ-bifenthrin, κ-tefluthrin, lotilaner, meperfluthrin, Nicofluprole (CAS 1771741-86-6), oxathiazosulfyl, paichongding, pyridalyl, pyrifluquinazone, pyriminostrobin, sarolaner, Spidoxamat, spirobudiclofen, tetramethylfluthrin, tetrachlorantraniliprole, tigolaner, thioxazafen, thiofluoximate, Tyclopyrazoflor, iodomethane; furthermore, preparations based on Bacillus firmus (I-1582, Votivo) and azadirachtin (BioNeem), and furthermore, the following compound: 1-{2-fluoro-4-methyl-5-[(2,2,(2-Trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO2006 / 043635) (CAS 885026-50-6), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]deca-3-en-2-one (known from WO2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]deca-3-en-4-yl ethyl carbonate (known from EP2647626) (CAS 1440516-42-6), PF1364 (known from JP2010 / 018586) (CAS 1204776-60-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoro-propan-2-one (known from WO2013 / 144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxide-3-thietanyl)benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxide-3-thietanyl)benzamide and 4-[(5S)-5-(3,5-(dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxide-3-thietanyl)benzamide (known from WO2013 / 050317A1) (CAS 1332628-83-7), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide and (-)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide (known from WO2013 / 162715A2, WO2013 / 162716A2, US2014 / 0213448A1) (CAS 1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile (known from CN101337937A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thiomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, known from CN103109816A) (CAS 1232543-85-9); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO2012 / 034403A1) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from WO2011 / 085575A1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN101337940A) (CAS 1108184-52-6); (2E)- and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide (known from CN101715774A) (CAS 1232543-85-9); 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropanecarboxylic acid ester (known from CN103524422A) (CAS 1542271-46-4); (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from CN102391261A) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2,4-di-O-methyl-,1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,[[4-Triazol-3-yl]phenyl]carbamate]-α-L-mannopyranose (known from US2014 / 0275503A1) (CAS 1181213-14-8); 8-(2-Cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 1253850-56-4), (8-anti)-8-(2-Cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 933798-27-7), (8-syn)-8-(2-Cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (known from WO2007040280A1, WO2007040282A1) (CAS 934001-66-8), N-[4-(Aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from CN103265527A) (CAS 1452877-50-7), 3-(4-Chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decan-2,4-dione (known from WO2014 / 187846A1) (CAS 1638765-58-8), 3-(4-Chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]deca-3-en-4-yl-carboxylic acid ethyl ester (known from WO2010 / 066780A1, WO2011151146A1) (CAS 1229023-00-0), N-[1-(2,6-Difluorophenyl)-1H-pyrazol-3-yl]-2-(trifluoromethyl)benzamide (known from WO2014 / 053450A1) (CAS 1594624-87-9), N-[2-(2,6-Difluorophenyl)-2H-1,2,[[3-Triazol-4-yl]-2-(trifluoromethyl)benzamide (known from WO2014 / 053450A1) (CAS 1594637-65-6), N-[1-(3,5-difluoro-2-pyridinyl)-1H-pyrazol-3-yl]-2-(trifluoromethyl)benzamide (known from WO2014 / 053450A1) (CAS 1594626-19-3), (3R)-3-(2-chloro-5-thiazolyl)-2,3-dihydro-8-methyl-5,7-dioxo-6-phenyl-5H-thiazolo[3,2-a]pyrimidinium inner salt (known from WO2018 / 177970A1) (CAS 2246757-58-2); 3-(2-chloro-5-thiazolyl)-2,3-dihydro-8-methyl-5,7-dioxo-6-phenyl-5H-thiazolo[3,2-a]pyrimidinium inner salt (known from WO2018 / 177970A1) (CAS 2246757-56-0); N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-2-(methylsulfonyl)-propanamide (known from WO2019 / 236274A1) (CAS 2396747-83-2), N-[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-2-fluoro-3-[(4-fluorobenzoyl)amino]-benzamide (known from WO2019059412A1) (CAS 1207977-87-4).

[0151] Fungicide The active ingredients specified herein by "common name" are known and are described, for example, in "The Pesticide Manual (16th Ed. British Crop Protection Council)" or can be searched on the Internet (e.g., www.alanwood.net / pesticides ).

[0152] All bactericidal co - agents named in classes (1) - (15) can, if possible by their functional groups, also form salts with suitable bases or acids in some cases. All co - agents named in classes (1) - (15) can, where appropriate, include tautomeric forms.

[0153] (1) Inhibitors of ergosterol biosynthesis, for example, (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropimorph, (1.006) fenpropidin, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016) procymidone, (1.017) propiconazole, (1.018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025) triticonazole, (1.026) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.027) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.028) (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.029) (2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030) (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.031) (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.(2S)-2-(1-Chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.033)(2S)-2-[4-(4-Chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034)(R)-[3-(4-Chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035)(S)-[3-(4-Chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036)[3-(4-Chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037)1-({(2R,4S)-2-[2-Chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.038)1-({(2S,4S)-2-[2-Chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.039)1-{[3-(2-Chlorophenyl)-2-(2,4-difluorophenyl)oxolan-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.040)1-{[rel(2R,3R)-3-(2-Chlorophenyl)-2-(2,4-difluorophenyl)oxolan-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.041)1-{[rel(2R,3S)-3-(2-Chlorophenyl)-2-(2,4-difluorophenyl)oxolan-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.042)2-[(2R,4R,5R)-1-(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.044) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.045) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.048) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) mefenoxazole, (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.060) 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.063) N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidohydroxamic acid amide, (1.064) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidohydroxamic acid amide, (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidohydroxamic acid amide, (1.066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidohydroxamic acid amide, (1.067) N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidohydroxamic acid amide, (1.068) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidohydroxamic acid amide, (1.069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidohydroxamic acid amide, (1.070) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidohydroxamic acid amide, (1.071) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidohydroxamic acid amide, (1.072) N'-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidohydroxamic acid amide, (1.073) N'-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidohydroxamic acid amide, (1.074) N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidohydroxamic acid amide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidohydroxamic acid amide, (1.076) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidohydroxamic acid amide, (1.077) N’-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidohydroxamic acid, (1.078) N’-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidohydroxamic acid, (1.079) N’-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidohydroxamic acid, (1.080) N’-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidohydroxamic acid, (1.081) ipfentrifluconazole, (1.082) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.083) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.084) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.085) 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, and, (1.086) 4-[[6-[rac-(2R)-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile.

[0154] (2) Inhibitors of the respiratory chain in Complex I or Complex II, such as, (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) flutriafol, (2.009) isofetamid, (2.010) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (2.013) isopyrazam (syn-epimeric racemate (1RS,4SR,9RS) and anti-epimeric racemate (1RS,4SR,9SR) mixture), (2.014) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.015) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pidiflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027) 3-(Difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.028) Imidacloprid, (2.029) 3-(Difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) Fluindapyr, (2.031) 3-(Difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3-(Difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.033) 5,8-Difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.034) N-(2-Cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N-(2-tert-Butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N-(2-tert-Butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-(5-Chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) N-(5-Chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.039) N-[(1R,4S)-9-(Dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042) N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide, (2.049) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.(2.051) N-Cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.052) N-Cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-Cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-Cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-Cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-Cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.057) Pyrapropion.

[0155] (3) Inhibitors of the respiratory chain in complex III, for example, (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) cumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018) pyra-metostrobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.023) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) fenpicoxamid, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}methylcarbamate, (3.030) methyltetraprole, (3.031) Florilpicoxamide.

[0156] (4) Inhibitors of mitosis and cell division, for example, (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) penthiopyrad, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.017) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.018) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.020) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.021) 4-(2-Chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.022) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.025) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine.

[0157] (5) Compounds that can act on multiple sites, for example, (5.001) Bordeaux mixture, (5.002) captan, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) basic copper chloride, (5.009) copper(II) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinc, (5.017) copper oxine, (5.018) propineb, (5.019) sulfur and sulfur agents, for example, calcium polysulfide, (5.020) thiram, (5.021) dinneb, (5.022) dithiram, (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3’,4’:5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

[0158] (6) Compounds that can induce the host's defense, for example, (6.001) acibenzolar-S-methyl, (6.002) isothianyl, (6.003) probenazole, (6.004) thiazinyl.

[0159] (7) Inhibitors of the biosynthesis of amino acids and / or proteins, for example, (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

[0160] (8) Inhibitors of ATP production, for example, (8.001) silthiopham.

[0161] (9) Inhibitors of cell wall synthesis, for example, (9.001) benalaxyl, (9.002) dimethomorph, (9.003) fluomorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

[0162] (10) Inhibitors of lipid and membrane synthesis, for example, (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

[0163] (11) Inhibitors of melanin biosynthesis, for example, (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl {3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

[0164] (12) Inhibitors of nucleic acid synthesis, for example, (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[0165] (13) Inhibitors of signal transduction, for example, (13.001) Fluazinam, (13.002) Iprodione, (13.003) Procymidone, (13.004) Proquinazid, (13.005) Quinoxyphen, (13.006) Vinclozolin.

[0166] (14) Compounds that can act as uncoupling agents, for example, (14.001) Fluazinam, (14.002) Mepyldinocap.

[0167] (15) A further bactericide selected from the group consisting of the following: (15.001) abscisic acid, (15.002) benzothiazole, (15.003) benthiavalicarb, (15.004) capsimycin, (15.005) carvone, (15.006) quinomethionate, (15.007) kresoxim-methyl, (15.008) cyflufenamid, (15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) fosetyl-aluminum, (15.013) fosetyl-calcium, (15.014) fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenone, (15.017) mildiomycin, (15.018) natamycin, (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) oxathiapiprolin, (15.023) oxyfenthiin, (15.024) pentachlorophenol and salts thereof, (15.025) phosphorous acid and its salts, (15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone), (15.028) tebufloquin, (15.029) tecnazene, (15.030) tolfenpyrad, (15.031) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.032) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034) diphenamid, (15.035) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.036) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.037) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.038) 2-[6-(3-fluorophenyl)-5-methylpyridin-2-yl]quinazoline, (15.039) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.040) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.041) ipfufenoquin, (15.042) 2-{2-fluoro-6-[(8-fluoromethylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043) fluoxapiprolin, (15.044) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate, (15.045) 2-Phenylphenol and salts, (15.046) 3-(4,4,5-Trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.047) Quinofumelin, (15.048) 4-Amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-Amino-5-fluoropyrimidin-2(1H)-one), (15.049) 4-Oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.050) 5-Amino-1,3,4-thiadiazole-2-thiol, (15.051) 5-Chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene 2-sulfonohydrazide, (15.052) 5-Fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053) 5-Fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-Fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine, (15.055) But-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.056) (2Z)-3-Amino-2-cyano-3-phenylacrylic acid ethyl ester, (15.057) Phenazine-1-carboxylic acid, (15.058) Propyl 3,4,5-trihydroxybenzoate, (15.059) Quinolin-8-ol, (15.060) Quinolin-8-ol sulfate (2:1), (15.061) {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamic acid tert-butyl, (15.062) 5-Fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one, (15.063) Aminopyrifen, (15.064) (N'-[2-Chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidohydroformamide), (15.065) (N'-(2-Chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylimidohydroformamide), (15.(066)(2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol), (15.067)(5-bromo-1-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline), (15.068)(3-(4,4-difluoro-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7-yl)quinoline), (15.069)(1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline), (15.070)8-fluoro-3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15.071)8-fluoro-3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15.072)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-8-fluoroquinoline, (15.073)(N-methyl-N-phenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide), (15.074)(methyl {4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamate), (15.075)(N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}cyclopropanecarboxamide), (15.076)N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.077)N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.078)N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.079)N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclopropanecarboxamide, (15.080)N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.081) 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, (15.082) N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]acetamide, (15.083) N-[(E)-N-methoxy-C-methyl-carboximidoyl]-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-benzamide, (15.084) N-[(Z)-N-methoxy-C-methyl-carboximidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.085) N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-methyl]propanamide, (15.086) 4,4-Dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.087) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, (15.088) 5-Methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.089) N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide, (15.090) 1-Methoxy-1-methyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.091) 1,1-Diethyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.092) N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.093) N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15.094) 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.095) N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl)cyclopropanecarboxamide, (15.096) N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]f. Phenyl]methyl]propanamide, (15.097) N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]propanamide, (15.098) 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.099) 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.100) 3-Ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.101) 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.102) 4,4-Dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.103) 5,5-Dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.104) 3,3-Dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.105) 1-[[3-Fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-phenyl]methyl]azepan-2-one, (15.106) 4,4-Dimethyl-2-[[4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-phenyl]methyl]isoxazolidin-3-one, (15.107) 5,5-Dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.108) Ethyl (1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazol-4-yl)acetate, (15.109) N,N-dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-1,2,4-triazol-3-amine, and, (15.110) N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butanamide.

[0168] Biological pest control agent as a mixing component The compound represented by formula (I) can be combined with a biological pest control agent.

[0169] Biological pest control agents particularly include bacteria, fungi, yeasts, plant extracts, and products formed by microorganisms (for example, proteins and secondary metabolites).

[0170] Biological pest control agents include bacteria, for example, spore-forming bacteria, bacteria that colonize roots, and bacteria that act as biological insecticides, fungicides, or nematicides.

[0171] Examples of the above bacteria that are used or can be used as biological pest control agents are as follows: Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular, Bacillus cereus strain CNCM I-1562, or Bacillus firmus strain I-1582 (deposit number CNCM I-1582), or Bacillus pumilus, in particular, strain GB34 (deposit number ATCC 700814) and strain QST2808 (deposit number NRRL B-30087), or Bacillus subtilis, in particular, strain GB03 (deposit number ATCC SD-1397), or Bacillus subtilis strain QST713 (deposit number NRRL B-21661), or Bacillus subtilis strain OST 30002 (deposit number NRRL B-50421), Bacillus thuringiensis, in particular, Bacillus thuringiensis subspecies israelensis (serotype H-14) strain AM65-52 (deposit number ATCC 1276), or Bacillus thuringiensis subsp. aizawai, in particular, strain ABTS-1857 (SD-1372), or Bacillus thuringiensis subsp. kurstaki strain HD-1, or Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.)(Rotylenchulus reniformis nematode)-PR3 (Accession No. ATCC SD-5834), Streptomyces microflavus strain AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (Accession No. NRRL 30232).

[0172] Examples of fungi and yeasts that are being used or can be used as biological pest control agents are as follows: Beauveria bassiana, in particular strain ATCC 74040, Coniothyrium minitans, in particular strain CON / M / 91-8 (deposit number DSM-9660), Lecanicillium spp., in particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (currently: Isaria fumosorosea), in particular strain IFPC 200613 or strain Apopka 97 (deposit number ATCC 20874), Paecilomyces lilacinus, in particular Paecilomyces lilacinus strain 251 (AGAL 89 / 030550), Talaromyces flavus, in particular strain V117b, Trichoderma atroviride, in particular strain SC1 (deposit number CBS 122089), Trichoderma harzianum, in particular Trichoderma harzianum rifai T39 (deposit number CNCM I-952).

[0173] Examples of viruses that are being used or can be used as biological pesticides against pests are as follows: Apple leafroller (Adoxophyes orana) granulosis virus (GV), codling moth (Cydia pomonella) granulosis virus (GV), cotton bollworm (Helicoverpa armigera) nuclear polyhedrosis virus (NPV), beet armyworm (Spodoptera exigua) mNPV, fall armyworm (Spodoptera frugiperda) mNPV, African cotton leafworm (Spodoptera littoralis) NPV.

[0174] Bacteria and fungi that are added as "inoculum sources" to plants or parts of plants or organs of plants and that enhance plant growth and plant health by virtue of their specific properties are likewise included. Examples that can be cited are the following: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp. or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.

[0175] Examples of products formed by plant extracts and microorganisms (which include proteins and secondary metabolites) that are being used or can be used as biological pest control agents are the following: Garlic (Allium sativum), Wormwood (Artemisia absinthium), Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, (「Requiem TM Insecticide」), Rotenone, Ryania / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract, in particular, rapeseed powder or mustard powder, and bio-insecticidal / acaricidal active substances obtained from olive oil, in particular, for example, in products having the trade name FLiPPER (registered trademark), contained as active ingredients, carbon chain length C 16 -C 20 unsaturated fats / carboxylic acids having.

[0176] Agent for reducing phytotoxicity as a mixing component The compound represented by formula (I) can be combined with phytotoxicity reducing agents such as benoxacor, cloquintocet (-mexyl), cymetrinil, cyprosulfamide, dichloramide, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4), etc.

[0177] Plants and plant parts According to the present invention, all plants and parts of plants can be treated. Here, plants include all plants and parts of plants such as desirable and undesirable wild plants or crop plants (including naturally occurring crop plants), for example, cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peppers, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, kidney beans, Brassica oleracea plants (e.g., cabbages) and other vegetable species, cotton, tobacco, rapeseed, and further, fruit plants (those having fruits, apple trees, pear trees, citrus fruit trees and grapevines), etc. Crop plants can be plants obtained by conventional breeding methods and optimization methods, or plants obtained by biotechnological methods and genetic engineering methods, or plants that can be obtained by a combination of the above methods. Such crop plants include transgenic plants, and also plant varieties that can be protected by variety rights or plant varieties that cannot be protected. Plants should be understood to mean all growth stages, for example, from seeds, seedlings, and young plants (immature plants) to mature plants. Parts of plants should be understood to mean all parts and organs of the above-ground and underground parts of plants such as shoots, leaves, flowers and roots, and examples include leaves, needles, stems, trunks, flowers, fruiting bodies, fruits and seeds, and further, tubers, roots and rhizomes, etc. Harvested plants or harvested parts of plants, and vegetative propagation materials and generative propagation materials, for example, seedlings, tubers, rhizomes, cuttings and seeds, etc. are also included in the parts of plants.

[0178] The treatment according to the invention of plants and parts of plants with the compounds of formula (I) can be carried out directly by customary treatment methods, for example by dipping, spraying, vaporizing, fogging, scattering, coating, injecting, etc., or by allowing the compounds to act on the surroundings of the plants and parts of plants, the environment or the storage space, and in the case of propagation material, in particular seeds, also by applying one or more coatings.

[0179] As already mentioned above, according to the invention, all plants and their parts can be treated. In a preferred embodiment, wild plant species and plant varieties, or plant species and plant varieties obtained by customary biological breeding methods such as crossing or protoplast fusion, and furthermore their parts are treated. In a further particularly preferred embodiment, transgenic plants and plant varieties (genetically modified organisms) obtained by genetic engineering methods, where appropriate in combination with customary methods, and their parts are treated. The terms "parts", "parts of plants" or "plant parts" have already been explained above. The invention is particularly preferably used for treating plants of customary varieties which are commercially available or in use. A plant variety is understood to mean a plant having new properties ("traits") obtained by customary breeding or mutagenesis or recombinant DNA techniques. They can be varieties, variants, biotypes or genotypes.

[0180] Transgenic plants, seed treatment and integration events According to the present invention, the compound represented by formula (I) can advantageously be used for treating those plants, plant varieties or parts of plants which have received genetic material conferring advantageous and / or useful properties (traits) on transgenic plants, plant varieties or parts of plants. Thus, the present invention is contemplated to be combinable with one or more recombinant traits or transgenic events or combinations thereof. For the purposes of the present application, a transgenic event is created by inserting a specific recombinant DNA molecule at a specific location (locus) on a chromosome of the plant genome. This insertion results in the formation of a novel DNA sequence, referred to as an "event", which is characterized by the inserted recombinant DNA molecule and a certain amount of genomic DNA flanking / adjacent to both ends of the inserted DNA. Such traits or transgenic events include, but are not limited to, pest resistance, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production and herbicide tolerance, where the trait is measured in comparison to a plant lacking such a trait or transgenic event. Specific examples of such advantageous and / or useful properties (traits) are improved plant growth, vigor, stress tolerance, standability, lodging tolerance, nutrient uptake, plant nutrition and / or yield, in particular improved growth, improved tolerance to high or low temperatures, improved tolerance to drought or water or soil salinity levels, enhanced flowering performance, improved ease of harvesting, accelerated maturation, increased yield, improved quality and / or nutritional value of the harvested product, improved shelf life and / or processability of the harvested product, and improved resistance or tolerance to harmful animals and harmful microorganisms (e.g., insects, arachnids, nematodes, mites, slugs and snails).

[0181] Among the DNA sequences encoding proteins conferring resistance or tolerance properties against such pests and harmful microorganisms (especially insects), in particular, there is mentioned the genetic material derived from Bacillus thuringiensis encoding Bt proteins, which are widely described in the literature and well known to those skilled in the art. Furthermore, proteins extracted from bacteria such as Photorhabdus are also mentioned (WO97 / 17432 and WO98 / 08932).In particular, the following are included: Bt Cry proteins or VIP proteins (which include CrylA, CryIAb, CryIAc, CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF proteins) or fragments thereof that exhibit toxicity, and furthermore, hybrids or combinations thereof, in particular, CrylF proteins or hybrids derived from CrylF proteins (e.g., hybrid CrylA-CrylF proteins or fragments thereof that exhibit toxicity), CrylA type proteins or fragments thereof that exhibit toxicity, preferably, CrylAc proteins or hybrids derived from CrylAc proteins (e.g., hybrid CrylAb-CrylAc proteins), or, CrylAb or Bt2 proteins or fragments thereof that exhibit toxicity, Cry2Ae, Cry2Af or Cry2Ag proteins or fragments thereof that exhibit toxicity, CrylA.105 proteins or fragments thereof that exhibit toxicity, VIP3Aa19 proteins, VIP3Aa20 proteins, VIP3A proteins produced in the COT202 or COT203 cotton events, VIP3Aa proteins or fragments thereof that exhibit toxicity described in "Estruch et al. (1996), Proc Natl Acad Sci US A. 28;93(11):5389-94", Cry proteins described in WO2001 / 47952, insecticidal proteins derived from Xenorhabdus (described in WO98 / 50427), insecticidal proteins derived from Serratia (in particular, insecticidal proteins derived from Serratia entomophila), or, insecticidal proteins derived from various species of the genus Photorhabdus, for example, Tc-proteins derived from Photorhabdus described in WO98 / 08932.Furthermore, any variant or mutant of those proteins that differ by several amino acids (1 to 10, preferably 1 to 5) from the sequences listed above (in particular, the sequences of those fragments that exhibit toxicity), or any variant or mutant of those proteins that are fused to a signal peptide (e.g., a plastid signal peptide) or another protein or peptide, are also included herein.

[0182] Another particularly important example of such a property is being imparted with resistance to one or more herbicides (e.g., imidazolinones, sulfonylureas, glyphosate or phosphinothricin). Among the DNA sequences encoding proteins that impart the property of resistance to a specific herbicide to transformed plant cells and plants, in particular, the following can be mentioned: the bar gene or PAT gene described in WO2009 / 152359 that imparts resistance to glufosinate herbicides or the Streptomyces coelicolor gene, an appropriate EPSPS ( 5-Enolpyruvylshikimate-3-phosphate synthase ) encoding a gene that imparts resistance to herbicides targeting EPSPS (in particular, herbicides such as glyphosate and its salts), a gene encoding glyphosate - n - acetyltransferase, or a gene encoding glyphosate oxidoreductase. Further appropriate herbicide - resistant traits include, among others: at least one ALS (acetolactate synthase) inhibitor (e.g., WO2007 / 024782), a mutant Arabidopsis ALS / AHAS gene (e.g., U.S. Patent No. 6,855,533), a gene encoding 2,4 - D - monooxygenase that imparts resistance to 2,4 - D (2,4 - dichlorophenoxyacetic acid), and a gene encoding dicamba monooxygenase that imparts resistance to dicamba (3,6 - dichloro - 2 - methoxybenzoic acid).

[0183] Yet another particularly important example of such properties is, for example, the improved resistance to phytopathogenic fungi, bacteria and / or viruses by, for example, systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and furthermore resistance genes and the proteins and toxins expressed thereby.

[0184] Particularly useful transgenic events in transgenic plants or plant varieties that can preferably be processed according to the present invention include the following: Event 531 / PV-GHBK04 (cotton, insect control, described in WO2002 / 040677), Event 1143-14A (cotton, insect control, not deposited, described in WO2006 / 128569); Event 1143-51B (cotton, insect control, not deposited, described in WO2006 / 128570); Event 1445 (cotton, herbicide tolerance, not deposited, described in US-A2002-120964 or WO2002 / 034946); Event 17053 (rice, herbicide tolerance, deposited as PTA-9843, described in WO2010 / 117737); Event 17314 (rice, herbicide tolerance, deposited as PTA-9844, described in WO2010 / 117735); Event 281-24-236 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in WO2005 / 103266 or US-A2005-216969); Event 3006-210-23 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in US-A2007-143876 or WO2005 / 103266); Event 3272 (maize, quality-related trait, deposited as PTA-9972, described in WO2006 / 098952 or US-A2006-230473); Event 33391 (wheat, herbicide tolerance, deposited as PTA-2347, described in WO2002 / 027004), Event 40416 (maize, insect control - herbicide tolerance, deposited as ATCC PTA-11508, described in WO11 / 075593); Event 43A47 (maize, insect control - herbicide tolerance, deposited as ATCC PTA-11509, described in WO2011 / 075595); Event 5307 (maize, insect control, deposited as ATCC PTA-9561, described in WO2010 / 077816);Event ASR-368 (bentgrass, herbicide tolerance, deposited as ATCC PTA-4816, described in US-A2006-162007 or WO2004 / 053062); Event B16 (maize, herbicide tolerance, not deposited, described in US-A2003-126634); Event BPS-CV127-9 (soybean, herbicide tolerance, deposited as NCIMB No.41603, described in WO2010 / 080829); Event BLR1 (rape, restoration of male sterility, deposited as NCIMB 41193, described in WO2005 / 074671), Event CE43-67B (cotton, insect control, deposited as DSM ACC2724, described in US-A2009-217423 or WO2006 / 128573); Event CE44-69D (cotton, insect control, not deposited, described in US-A2010-0024077); Event CE44-69D (cotton, insect control, not deposited, described in WO2006 / 128571); Event CE46-02A (cotton, insect control, not deposited, described in WO2006 / 128572); Event COT102 (cotton, insect control, not deposited, described in US-A2006-130175 or WO2004 / 039986); Event COT202 (cotton, insect control, not deposited, described in US-A2007-067868 or WO2005 / 054479); Event COT203 (cotton, insect control, not deposited, described in WO2005 / 054480);); Event DAS21606-3 / 1606 (soybean, herbicide tolerance, deposited as PTA-11028, described in WO2012 / 033794), Event DAS40278 (maize, herbicide tolerance, deposited as ATCC PTA-10244, described in WO2011 / 022469);Event DAS-44406-6 / pDAB8264.44.06.l (soybean, herbicide tolerance, deposited as PTA-11336, described in WO2012 / 075426), Event DAS-14536-7 / pDAB8291.45.36.2 (soybean, herbicide tolerance, deposited as PTA-11335, described in WO2012 / 075429), Event DAS-59122-7 (maize, insect control-herbicide tolerance, deposited as ATCC PTA 11384, described in US-A2006-070139); Event DAS-59132 (maize, insect control-herbicide tolerance, not deposited, described in WO2009 / 100188); Event DAS68416 (soybean, herbicide tolerance, deposited as ATCC PTA-10442, described in WO2011 / 066384 or WO2011 / 066360); Event DP-098140-6 (maize, herbicide tolerance, deposited as ATCC PTA-8296, described in US-A2009-137395 or WO08 / 112019); Event DP-305423-1 (soybean, quality-related trait, not deposited, described in US-A2008-312082 or WO2008 / 054747); Event DP-32138-1 (maize, hybridization system, deposited as ATCC PTA-9158, described in US-A2009-0210970 or WO2009 / 103049); Event DP-356043-5 (soybean, herbicide tolerance, deposited as ATCC PTA-8287, described in US-A2010-0184079 or WO2008 / 002872); Event EE-I (eggplant, insect control, not deposited, described in WO07 / 091277); Event Fil 17 (maize, herbicide tolerance, deposited as ATCC 209031, described in US-A2006-059581 or WO98 / 044140);Event FG72 (soybean, herbicide tolerance, deposited as PTA-11041, described in WO2011 / 063413); Event GA21 (maize, herbicide tolerance, deposited as ATCC 209033, described in US-A2005-086719 or WO98 / 044140); Event GG25 (maize, herbicide tolerance, deposited as ATCC 209032, described in US-A2005-188434 or WO98 / 044140); Event GHB119 (cotton, insect control-herbicide tolerance, deposited as ATCC PTA-8398, described in WO2008 / 151780); Event GHB614 (cotton, herbicide tolerance, deposited as ATCC PTA-6878, described in US-A2010-050282 or W02007 / 017186); Event GJ11 (maize, herbicide tolerance, deposited as ATCC 209030, described in US-A2005-188434 or WO98 / 044140); Event GMRZ13 (sugar beet, virus resistance, deposited as NCIMB-41601, described in WO2010 / 076212); Event H7-1 (sugar beet, herbicide tolerance, deposited as NCIMB 41158 or NCIMB 41159, described in US-A2004-172669 or WO2004 / 074492); Event JOPLIN1 (wheat, disease resistance, not deposited, described in US-A2008-064032); Event LL27 (soybean, herbicide tolerance, deposited as NCIMB41658, described in WO2006 / 108674 or US-A2008-320616); Event LL55 (soybean, herbicide tolerance, deposited as NCIMB 41660, described in WO2006 / 108675 or US-A2008-196127); Event LLcotton25 (cotton, herbicide tolerance, deposited as ATCC PTA-3343, described in WO2003 / 013224 or US A2003-097687);Event LLRICE06 (rice, herbicide tolerance, deposited as ATCC 203353, described in US 6,468,747 or WO2000 / 026345); Event LLRice62 (rice, herbicide tolerance, deposited as ATCC 203352, described in WO2000 / 026345), Event LLRICE601 (rice, herbicide tolerance, deposited as ATCC PTA-2600, described in US-A2008-2289060 or WO2000 / 026356); Event LY038 (maize, quality-related trait, deposited as ATCC PTA-5623, described in US-A2007-028322 or WO2005 / 061720); Event MIR162 (maize, insect control, deposited as PTA-8166, described in US-A2009-300784 or WO2007 / 142840); Event MIR604 (maize, insect control, not deposited, described in US-A2008-167456 or WO2005 / 103301); Event MON15985 (cotton, insect control, deposited as ATCC PTA-2516, described in US-A2004-250317 or WO2002 / 100163); Event MON810 (maize, insect control, not deposited, described in US-A2002-102582); Event MON863 (maize, insect control, deposited as ATCC PTA-2605, described in WO2004 / 011601 or US-A2006-095986); Event MON87427 (maize, pollination control, deposited as ATCC PTA-7899, described in WO2011 / 062904); Event MON87460 (maize, stress tolerance, deposited as ATCC PTA-8910, described in WO2009 / 111263 or US-A2011-0138504); Event MON87701 (soybean, insect control, deposited as ATCC PTA-8194, described in US-A2009-130071 or WO2009 / 064652);Event MON87705 (soybean, trait related to quality - herbicide tolerance, deposited as ATCC PTA-9241, described in US-A2010-0080887 or WO2010 / 037016); Event MON87708 (soybean, herbicide tolerance, deposited as ATCC PTA-9670, described in WO2011 / 034704); Event MON87712 (soybean, yield, deposited as PTA-10296, described in WO2012 / 051199), Event MON87754 (soybean, trait related to quality, deposited as ATCC PTA-9385, described in WO2010 / 024976); Event MON87769 (soybean, trait related to quality, deposited as ATCC PTA-8911, described in US-A2011-0067141 or WO2009 / 102873); Event MON88017 (maize, insect control - herbicide tolerance, deposited as ATCC PTA-5582, described in US-A2008-028482 or WO2005 / 059103); Event MON88; 913 (cotton, herbicide tolerance, deposited as ATCC PTA - 4854, described in WO2004 / 072235 or US - A2006 - 059590); event MON88302 (rape, herbicide tolerance, deposited as PTA - 10955, described in WO2011 / 153186), event MON88701 (cotton, herbicide tolerance, deposited as PTA - 11754, described in WO2012 / 134808), event MON89034 (maize, insect control, deposited as ATCC PTA - 7455, described in WO07 / 140256 or US - A2008 - 260932); event MON89788 (soybean, herbicide tolerance, deposited as ATCC PTA - 6708, described in US - A2006 - 282915 or WO2006 / 130436); event MSl1 (rape, pollination control - herbicide tolerance, deposited as ATCC PTA - 850 or PTA - 2485, described in WO2001 / 031042); event MS8 (rape, pollination control - herbicide tolerance, deposited as ATCC PTA - 730, described in WO2001 / 041558 or US - A2003 - 188347); event NK603 (maize, herbicide tolerance, deposited as ATCC PTA - 2478, described in US - A2007 - 292854); event PE - 7 (rice, insect control, not deposited, described in WO2008 / 114282); event RF3 (rape, pollination control - herbicide tolerance, deposited as ATCC PTA - 730, described in WO2001 / 041558 or US - A2003 - 188347); event RT73 (rape, herbicide tolerance, not deposited, described in WO2002 / 036831 or US - A2008 - 070260); event SYHT0H2 / SYN - 000H2 - 5 (soybean, herbicide tolerance, deposited as PTA - 11226, described in WO2012 / 082548), event T227 - 1 (sugar beet, herbicide tolerance, not deposited, described in WO2002 / 44407 or US - A2009 - 265817); event T25 (maize, herbicide tolerance,not deposited; described in US-A2001-029014 or WO2001 / 051654); event T304-40 (cotton, insect control-herbicide tolerance, deposited as ATCC PTA-8171, described in US-A2010-077501 or WO2008 / 122406); event T342-142 (cotton, insect control, not deposited, described in WO2006 / 128568); event TC1507 (maize, insect control-herbicide tolerance, not deposited, described in US-A2005-039226 or WO2004 / 099447); event VIP1034 (maize, insect control-herbicide tolerance, deposited as ATCC PTA-3925, described in WO2003 / 052073), event 32316 (maize, insect control-herbicide tolerance, deposited as PTA-11507, described in WO2011 / 084632), event 4114 (maize, insect control-herbicide tolerance, deposited as PTA-11506, described in W02011 / 084621), event EE-GM3 / FG72 (soybean, herbicide tolerance, ATCC accession number PTA-11041) [which may optionally be stacked with event EE-GM1 / LL27 or event EE-GM2 / LL55] (WO2011 / 063413A2), event DAS-68416-4 (soybean, herbicide tolerance, ATCC accession number PTA-10442, WO2011 / 066360Al), event DAS-68416-4 (soybean, herbicide tolerance, ATCC accession number PTA-10442, WO2011 / 066384Al), event DP-040416-8 (maize, insect control, ATCC accession number PTA-11508, WO2011 / 075593Al), event DP-043A47-3 (maize, insect control, ATCC accession number PTA-11509, WO2011 / 075595Al), event DP-004114-3 (maize, insect control, ATCC accession number PTA-11506, WO2011 / 084621Al), event DP-032316-8 (maize, insect control, ATCC accession number PTA-11507, WO2011 / 084632Al), event MON-88302-9 (rape,Herbicide tolerance, ATCC Deposit No. PTA-10955, WO2011 / 153186Al), Event DAS-21606-3 (soybean, herbicide tolerance, ATCC Deposit No. PTA-11028, WO2012 / 033794A2), Event MON-87712-4 (soybean, traits related to quality, ATCC Deposit No. PTA-10296, WO2012 / 051199A2), Event DAS-44406-6 (soybean, stacked herbicide tolerance, ATCC Deposit No. PTA-11336, WO2012 / 075426Al), Event DAS-14536-7 (soybean, stacked herbicide tolerance, ATCC Deposit No. PTA-11335, WO2012 / 075429Al), Event SYN-000H2-5 (soybean, herbicide tolerance, ATCC Deposit No. PTA-11226, WO2012 / 082548A2), Event DP-061061-7 (rape, herbicide tolerance, deposit number not available, WO2012071039Al), Event DP-073496-4 (rape, herbicide tolerance, deposit number not available, US2012131692), Event 8264.44.06.1 (soybean, stacked herbicide tolerance, deposit number PTA-11336, WO2012075426A2), Event 8291.45.36.2 (soybean, stacked herbicide tolerance, deposit number PTA-11335, WO2012075429A2), Event SYHT0H2 (soybean, ATCC Deposit No. PTA-11226, WO2012 / 082548A2), Event MON88701 (cotton, ATCC Deposit No. PTA-11754, WO2012 / 134808Al), Event KK179-2 (alfalfa, ATCC Deposit No. PTA-11833, WO2013 / 003558Al), Event pDAB8264.42.32.1 (soybean, stacked herbicide tolerance, ATCC Deposit No. PTA-11993, WO2013 / 010094Al), Event MZDT09Y (maize, ATCC Deposit No. PTA-13025, WO2013 / 012775Al).

[0185] Furthermore, a list of such transgenic events is provided by the United States Department of Agriculture (USDA), Animal and Plant Health Inspection Service (APHIS), and can be found on their websites on the World Wide Web at " aphis.usda.gov ". For the purposes of this application, the status of the list as it exists / existed on the filing date of this application is relevant.

[0186] Genes / events conferring the desired trait can also be present in combination with each other in transgenic plants. Examples of transgenic plants that can be mentioned include important crop plants such as cereals (wheat, rice, triticale, barley, rye, oats), maize, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other types of vegetables, cotton, tobacco, rapeseed, and furthermore, fruit plants (those having fruits, apples, pears, citrus fruits and grapes), etc. Maize, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed are particularly important. Particularly important traits are the improved resistance of plants to insects, arachnids, nematodes as well as slugs and snails, and the improved resistance of plants to one or more herbicides.

[0187] Commercially available examples of such plants, plant parts or plant seeds that can preferably be treated according to the invention include commercially available products (e.g., plant seeds) sold or being sold under the following trade names: GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY®, VT DOUBLE PRO®, VT TRIPLE PRO®, BOLLGARD II®, ROUNDUP READY 2 YIELD®, YIELDGARD®, ROUNDUP READY 2® XTEN DTM , INTACTA RR2 PRO®, VISTIVE GOLD®, and / or XTENDFLEXTM .

[0188] Crop protection - type of treatment The treatment of plants and parts of plants using the compound represented by formula (I) is carried out directly by using conventional treatment methods, for example, by dipping, spraying, atomizing, irrigation, vaporization, dusting, smoking, scattering, foaming, coating, spreading-on, injection, drenching, drip irrigation, etc., or by allowing the compound to act on the surroundings, habitat or storage space of the plants and parts of plants. Further, in the case of propagation material, especially in the case of seeds, it is also treated by coating, such as coating with one or more coatings, as a powder for dry seed treatment, a solution for liquid seed treatment, or a water-soluble powder for slurry treatment. Furthermore, it is also possible to apply the compound represented by formula (I) by the ultra-low volume method, or to inject the application form or the compound itself represented by formula (I) into the soil.

[0189] A preferred direct treatment of plants is foliar application (i.e., applying the compound represented by formula (I) to the foliage), in which case the treatment frequency and application rate should be adapted according to the level of occurrence of the pest.

[0190] In the case of systemic active compounds, the compounds of formula (I) also reach the plants via the root system. In that case, the plants are treated by applying the compounds of formula (I) to their habitat. This can be done, for example, by drenching, or by mixing with soil or nutrient solution [i.e., impregnating the liquid form of the compounds of formula (I) into the plant growth location (e.g., soil, or hydroponic system)], or by soil application [i.e., introducing the compounds of formula (I) according to the invention in solid form (e.g., in granular form) into the plant growth location], or by drip application (often also referred to as "chemigation") [i.e., liquid application from the ground surface or underground drip line over a specific period of time at a defined location near the plant, together with varying amounts of water, of the compounds of formula (I) according to the invention]. In the case of rice crops, this can also be done by metering the compounds of formula (I) in solid application form (e.g., as granules) and supplying them to flooded paddy fields.

[0191] Digital technology The compounds of the invention can be used in combination with models, for example, in combination with models incorporated into computer programs for site-specific crop management, satellite farming, precision farming or precision agriculture. Such models support site-specific management of agricultural fields using data from various sources such as soil, climate, crops (e.g., type, growth stage, plant health), weeds (e.g., type, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, yield, etc. in order to optimize profitability, sustainability and environmental protection. In particular, such models are useful for optimizing agronomic decisions, controlling the accuracy of pesticide application, and recording the operations performed.

[0192] As an example, if a certain model calculates that a pest infestation has been modeled and has reached a threshold at which it is recommended to apply the compound of the present invention to a crop plant, the compound of the present invention can be applied to the crop plant according to an appropriate dosing schedule.

[0193] Examples of commercially available systems that include an agronomic model are, for example, FieldScripts by The Climate Corporation TM , Xarvio by BASF TM , AGLogic by John Deere TM and others.

[0194] The compounds of the present invention can also be used in combination with computerized spraying devices, such as spot spraying devices or precision spraying devices, attached to or housed within a farm vehicle (e.g., a tractor, robot, helicopter, airplane, unmanned aerial vehicle (UAV), e.g., a drone, etc.). Such devices typically include an input sensor (e.g., a camera, etc.) and a processing device (which is configured to analyze the input data and, based on the analysis of the input data, provide a determination to apply the compound of the present invention to a crop plant (each, a weed) in a specific and accurate manner). The use of such computerized spraying devices typically also requires a positioning system (e.g., a GPS receiver) for localizing the recorded data and guiding or controlling the farm vehicle, a geographic information system (GIS) for presenting the information on an understandable map, and an appropriate farm vehicle for performing the necessary farming operations, such as spraying.

[0195] As an example, pests can be detected from an image acquired by a camera. As an example, the pests can be identified and / or classified based on the image. In such identification and / or classification, an image processing algorithm can be used. Such an image processing algorithm can utilize a machine learning algorithm, for example, a trained neutral network, a decision tree, etc., and can utilize an artificial intelligence algorithm. In this way, the compounds described in this specification can be applied only where necessary.

[0196] Seed treatment The control of pests by treating plant seeds has been known for a long time and has been continuously improved. However, seed treatment is accompanied by a series of problems that cannot necessarily be solved satisfactorily. Thus, it is desirable to develop a method for protecting seeds and plants during germination that eliminates or at least significantly reduces the need for additional application of pesticides during plant storage, after sowing, or after germination. Furthermore, it is also desirable to optimize the amount of active compound used so that the seeds and plants during germination are optimally protected from pest attacks without causing damage to the plants themselves by the active compound used. In particular, in the method of treating seeds, in order to achieve optimal protection of the seeds using the minimum amount of pesticide and, furthermore, to achieve optimal protection of the plants during germination, the endogenous insecticidal or nematicidal properties of pest-resistant transgenic plants or pest-tolerant transgenic plants should also be taken into account.

[0197] Accordingly, the present invention also relates in particular to a method for protecting seeds and germinating plants from attack by pests, wherein the method comprises treating said seeds with one of the compounds of formula (I). The method according to the invention for protecting seeds and germinating plants from attack by pests further encompasses methods in which the seeds are treated simultaneously or sequentially in one operation with a compound of formula (I) and a mixing component. It also further encompasses methods in which the seeds are treated at different times with a compound of formula (I) and a mixing component.

[0198] The present invention further relates to the use of a compound of formula (I) for treating seeds in order to protect the seeds and the plants resulting from said seeds against pests.

[0199] Furthermore, the present invention relates to seeds treated with a compound of formula (I) according to the invention so as to be protected against pests. The present invention further relates to seeds treated simultaneously with a compound of formula (I) and a mixing component. The present invention further relates to seeds treated at different times with a compound of formula (I) and a mixing component. In the case of seeds treated at different times with a compound of formula (I) and a mixing component, the individual substances may be present in different layers on the surface of the seeds. In this case, the layer containing the compound of formula (I) and the mixing component can optionally be separated by an intermediate layer. The present invention also further relates to seeds on which a compound of formula (I) and a mixing component are applied as components of a coating or as an additional one or more layers applied to the coating.

[0200] Furthermore, the present invention relates to seeds subjected to a film coating process in order to prevent abrasion of the seeds by dust after being treated with a compound of formula (I).

[0201] One of the advantages in the case of the penetration-transferring compound represented by formula (I) is the fact that by treating the seeds, not only the seeds themselves are protected against pests, but also the plants emerging from those seeds are protected after germination. In this way, it is possible to save the effort of directly treating the crop at the time of sowing or shortly after sowing.

[0202] It should also be regarded as a further advantage that the germination and emergence of the treated seeds can be enhanced by treating the seeds with the compound represented by formula (I).

[0203] It is also considered advantageous that the compound represented by formula (I) can be used, in particular, also for transgenic seeds.

[0204] Furthermore, the compound represented by formula (I) can also be used in combination with compositions or compounds of signal transduction technology, whereby the colonization by symbiotic organisms (e.g., rhizobia, mycorrhizal fungi and / or endophytic bacteria or fungi) is improved and / or nitrogen fixation is optimized.

[0205] The compound represented by formula (I) is suitable for protecting the seeds of all plant varieties used in agriculture, in greenhouses, in forests or in horticulture. In particular, these are seeds of cereals (e.g., wheat, barley, rye, oats and millet), maize, cotton, soybeans, rice, potatoes, sunflowers, coffee, tobacco, canola, rapeseed, beets (e.g., sugar beets and fodder beets), peanuts, vegetables (e.g., tomatoes, cucumbers, kidney beans, cruciferous vegetables, onions and lettuce), fruit plants, lawns and ornamental plants. It is particularly important to treat the seeds of cereals (e.g., wheat, barley, rye and millet), maize, soybeans, cotton, canola, rapeseed, vegetables and rice.

[0206] As already described above, the treatment of transgenic seeds with the compounds of formula (I) is also of particular importance. This is especially the case for seeds of plants generally containing at least one heterologous gene that controls the expression of a polypeptide having insecticidal and / or nematicidal properties. These heterologous genes in transgenic seeds can be derived from microorganisms such as Bacillus species, Rhizobium species, Pseudomonas species, Serratia species, Trichoderma species, Clavibacter species, Glomus species or Gliocladium species. The present invention is particularly suitable for treating transgenic seeds containing at least one heterologous gene derived from a Bacillus sp. It is particularly preferably a heterologous gene derived from Bacillus thuringiensis.

[0207] In connection with the present invention, the compounds of formula (I) are applied to the seeds. Preferably, the seeds are treated in a state that is sufficiently stable to avoid damage during the treatment. Generally, the seeds can be treated at any point in time between harvesting and sowing. Commonly used seeds are separated from the plant and have the ear axis, husk, petiole, outer skin, hairs or pulp removed. For example, seeds that have been harvested, had impurities removed, and dried to a water content that allows storage can be used. Alternatively, seeds that have been treated with, for example, water after drying and then dried again (e.g., priming) can also be used. In the case of rice seeds, it is also possible to use seeds that have been immersed, for example, in water until a specific stage (pigeon breast stage) of the rice embryo is reached, thereby stimulating germination and making emergence more uniform.

[0208] When treating seeds, care must generally be taken to select the amount of the compound of formula (I) and / or the amount of further additives to be applied to the seeds so that the germination of the seeds is not adversely affected or the resulting plants are not damaged. This must be ensured especially in the case of active compounds which may exhibit phytotoxic effects at certain application rates.

[0209] Generally, the compound of formula (I) is applied to the seeds in a suitable formulation. Suitable formulations and methods for treating seeds are known to those skilled in the art.

[0210] The compound of formula (I) can be converted into customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seeds, and furthermore also into ULV formulations.

[0211] These formulations are prepared in a known manner by mixing the compound of formula (I) with customary additives, such as customary extenders, and furthermore with a solvent or diluent, colorants, wetting agents, dispersants, emulsifiers, defoamers, preservatives, a second thickener, adhesives, gibberellins and the like, and furthermore with water.

[0212] Colorants which can be incorporated into the seed dressing formulations which can be used according to the invention are all colorants customary for such purposes. Pigments which are not very soluble in water or dyes which are soluble in water can be used. Examples thereof include colorants known under the names "Rhodamin B", "C.I.Pigment Red 112" and "C.I.Solvent Red 1".

[0213] Useful wetting agents that can be incorporated into the seed coating formulations that can be used according to the present invention are all substances that promote wetting and are customarily used in formulations of pesticidal active compounds. Preferably, alkylnaphthalenesulfonates such as diisopropylnaphthalenesulfonate or diisobutylnaphthalenesulfonate are used.

[0214] Useful dispersants and / or emulsifiers that can be incorporated into the seed coating formulations that can be used according to the present invention are all nonionic, anionic and cationic dispersants that are customarily used in formulations of pesticidal active ingredients. Preferably, nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants are used. Suitable nonionic dispersants include, in particular, ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, and their phosphorylated or sulfated derivatives. Suitable anionic dispersants are, in particular, lignosulfonates, polyacrylates and arylsulfonate / formaldehyde condensates.

[0215] Antifoaming agents that can be incorporated into the seed coating formulations that can be used according to the present invention are all foam-suppressing substances that are customarily used in formulations of pesticidal active ingredients. Preferably, silicone antifoaming agents and magnesium stearate are used.

[0216] Preservatives that can be incorporated into the seed coating formulations that can be used according to the present invention are all substances that can be used for this purpose in pesticidal compositions. Examples include dichlorophene and benzyl alcohol hemi formal.

[0217] The second thickener that can be incorporated into the seed coating formulation that can be used according to the present invention is all substances that can be used for this purpose in the agrochemical composition. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clay and micronized silica are preferred.

[0218] The adhesive that can be incorporated into the seed coating formulation that can be used according to the present invention is all customary binders that can be used in seed coating products. Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tyrosin can be mentioned as preferred.

[0219] The gibberellins that can be incorporated into the seed coating formulation that can be used according to the present invention are preferably gibberellin A1, gibberellin A3 (= gibberellic acid), gibberellin A4 and gibberellin A7; particularly preferably, gibberellic acid is used. The gibberellins are known (cf. R. Wegler “Chemie der Pflanzenschutz- and Schadlingsbekampfungsmittel”, vol.2, Springer Verlag, 1970, pp.401-412).

[0220] The seed coating formulation that can be used according to the present invention can be used directly or, after dilution with water in advance, to treat a wide range of different types of seeds. For example, a concentrate or a preparation obtainable from the concentrate by dilution with water can be used to coat the seeds of cereals such as wheat, barley, rye, oats and triticale, and also, furthermore, the seeds of maize, rice, rapeseed, pea, kidney bean, cotton, sunflower, soybean and beet, or can be used to coat the seeds of a wide range of different vegetable seeds. The seed coating formulation that can be used according to the present invention or their diluted use forms can also be used to coat the seeds of transgenic plants.

[0221] When treating seeds using a seed coating formulation that can be used in accordance with the present invention or a form prepared by adding water to the seed coating formulation, all mixing devices that can be customarily used for seed coating are useful. Specifically, the procedure for seed coating involves placing the seeds into a mixer (which can be operated batchwise or continuously), adding the desired specific amount of the seed coating formulation either as is or after diluting it with water in advance, and mixing everything until the formulation is homogeneously distributed on the surface of the seeds. When appropriate, a drying step is subsequently performed.

[0222] The application rate of the seed coating formulation that can be used in accordance with the present invention can be varied within a relatively wide range. It depends on the specific content of the compound represented by formula (I) in the formulation and the seeds. The application rate of the compound represented by formula (I) is generally from 0.001 to 50 g per kg of seeds, preferably from 0.01 to 15 g per kg of seeds.

[0223] Animal health In the field of animal health, i.e., in the field of veterinary medicine, the compound represented by formula (I) exhibits activity against animal parasites, particularly against external parasites or internal parasites. The term "internal parasite" particularly includes helminths and protozoa (e.g., coccidia). External parasites are typically and preferably arthropods, particularly insects or mites.

[0224] In the field of veterinary medicine, the compound represented by formula (I), which has a preferably low toxicity to warm-blooded animals, is suitable for controlling parasites that occur in livestock animals, breeding animals, zoo animals, laboratory animals, experimental animals, and domestic animals in animal breeding and livestock industries. They are active against all or specific developmental stages of the parasites.

[0225] Examples of livestock for agricultural use include, for example, the following: mammals such as sheep, goats, horses, donkeys, camels, pigs, rabbits, reindeer, roe deer, and in particular, cows and pigs; or poultry such as turkeys, ducks, geese, and in particular, chickens; or fish or crustacean animals such as fish or crustacean animals in aquaculture; or optionally, insects such as bees.

[0226] Examples of domestic animals include, for example, the following: mammals such as hamsters, chinchillas, rats, mice, chinchillas, ferrets, and in particular, dogs and cats; cage birds; reptiles; amphibians, or aquarium fish.

[0227] In certain embodiments, the compound represented by formula (I) is administered to a mammal.

[0228] In certain other embodiments, the compound represented by formula (I) is administered to birds, i.e., cage birds, or in particular, poultry.

[0229] By using the compound represented by formula (I) to control animal parasites, it is intended to reduce or prevent the diseases and deaths of the above animals, and to reduce or prevent a decrease in productivity (in the case of meat, milk, wool, leather, eggs, honey, etc.), as a result, more economical and easier animal breeding becomes possible, and a better health state of the animals can be achieved.

[0230] The terms "control" or "controlling", as used herein in the context of the field of animal health, mean that the compound of formula (I) is effective in reducing the incidence of individual parasites in an animal infected with the parasite to a non-harmful level. More specifically, "control", as used in the present invention, means that the compound of formula (I) is effective in killing individual parasites, inhibiting their growth, or inhibiting their proliferation.

[0231] Representative arthropods include, but are not limited to, the following: Of the order Anoplurida, for example, species of the genus Haematopinus, Linognathus, Pediculus, Phtirus, Solenopotes; Of the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example, species of the genus Bovicola, Damalina, Felicola; Lepikentron, Menopon, Trichodectes, Trimenopon, Trinoton, Werneckiella; Diptera and Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.; Of the order Siphonapterida, for example, species of Ceratophyllus, Ctenocephalides, Pulex, Tunga, Xenopsylla; Of the order Heteropterida, for example, species of Cimex, Panstrongylus, Rhodnius, Triatoma; and harmful and sanitary pests of the order Blattarida.

[0232] Furthermore, among the arthropods, but not limited to, the following mites can also be mentioned as examples: Acari (Acarina) and Metastigmata, for example, of the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp.; of the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (formerly belonging to multi-host ticks); Mesostigmata, such as Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Sternostoma spp., Tropilaelaps spp., Varroa spp.; Actinedida (Prostigmata), such as Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Ornithocheyletia spp., Psorergates spp., Trombicula spp.; and Acaridida (Astigmata), such as Acarus spp., Caloglyphus spp., Chorioptes spp.) Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp..

[0233] Representative parasitic protozoa include, but are not limited to, the following: Mastigophora (Flagellata), for example: Metamonada: of the order Diplomonadida, for example, Giardia spp., Spironucleus spp.; Parabasala: of the order Trichomonadida, for example, Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp; Euglenozoa: of the order Trypanosomatida, for example, Leishmania spp., Trypanosoma spp.; Sarcomastigophora (Rhizopoda), for example, Entamoebidae, for example, Entamoeba spp., Centramoebidae, for example, Acanthamoeba sp., Euamoebidae, for example, Hartmanella sp.; Alveolata, for example, Apicomplexa (Sporozoa), for example, Cryptosporidium spp.; Eimeriida, for example, Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp.; Adeleida, for example, Hepatozoon spp., Klossiella spp.; Haemosporida, for example, Leucocytozoon spp., Plasmodium spp.; Piroplasmida, for example, Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp.; Vesibuliferida, for example, Balantidium spp., Buxtonella spp.; Microspora, for example, species of the genus Encephalitozoon, Enterocytozoon, Globidium, Nosema, and, further, for example, Myxozoa spp.

[0234] Examples of pathogenic helminths for humans or animals include, for example, Acanthocephala, Nemathelminthes, Pentastomida, and Platyhelminthes [e.g., Monogenea, Cestodes, and Trematodes].

[0235] Representative helminths include, but are not limited to, the following: Monogenea: For example: species of the genus Dactylogyrus, Gyrodactylus, Microbothrium, Polystoma, Troglocephalus; Cestodes: of the order Pseudophyllidea, for example: species of the genus Bothridium, Diphyllobothrium, Diplogonoporus, Ichthyobothrium, Ligula, Schistocephalus, Spirometra; Order Cyclophyllida, for example: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.; Trematodes: of the subclass Digenea, for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp., Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp.) Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.;. Nematodes: of the order Trichinellida, for example: Capillaria spp., Eucoleus spp., Paracapillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.; of the order Tylenchida, for example: Micronema spp., Parastrongyloides spp., Strongyloides spp.; Order Rhabditina, for example: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp.) Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.; Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp.;. Order Spirurida, for example: species of Acanthocheilonema spp., Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp., Stephanofilaria spp., Strongyluris spp.) Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp.;. Phylum Acanthocephala: For example, Macracanthorhynchus spp. and Prosthenorchis spp. of the order Oligacanthorhynchida; for example, Moniliformis spp. of the order Moniliformida; For example, Filicollis spp. of the order Polymorphida; for example, Acanthocephalus spp., Echinorhynchus spp., and Leptorhynchoides spp. of the order Echinorhynchida; Phylum Pentastoma: For example, Linguatula spp. of the order Porocephalida.

[0236] In the field of veterinary medicine and in animal husbandry, the administration of the compound represented by formula (I) is carried out by methods generally known in the art, for example, enterally, parenterally, transdermally or nasally, in the form of a suitable preparation. The administration can be carried out prophylactically, methaphylactically or therapeutically.

[0237] Thus, one embodiment of the present invention relates to a compound represented by formula (I) for use as a drug.

[0238] Another aspect relates to a compound represented by formula (I) for use as an antiendoparasitical agent.

[0239] Another specific aspect relates to a compound represented by formula (I) for use as an anthelmintic agent, and more particularly for use as a nematicide, a platyhelminthicidal agent, an acanthocephalicidal agent or a pentastomicidal agent.

[0240] Another specific aspect relates to a compound represented by formula (I) for use as an antiprotozoal agent.

[0241] Another aspect relates to a compound represented by formula (I) for use as an antiectoparasitical agent, particularly for use as an arthropodicidal agent, and more particularly for use as an insecticide or an acaricide.

[0242] A further aspect of the invention is a veterinary formulation comprising an effective amount of at least one compound represented by formula (I) and at least one of the following: a pharmaceutically acceptable excipient (e.g., a solid diluent or a liquid diluent), a pharmaceutically acceptable adjuvant (e.g., a surfactant), particularly a pharmaceutically acceptable excipient customarily used in veterinary formulations, and / or a pharmaceutically acceptable adjuvant customarily used in veterinary formulations.

[0243] Related aspects of the present invention are methods of preparing veterinary formulations described herein, where the method comprises mixing at least one compound represented by formula (I) with pharmaceutically acceptable excipients and / or adjuvants (in particular, pharmaceutically acceptable excipients customarily used in veterinary formulations, and / or pharmaceutically acceptable adjuvants customarily used in veterinary formulations).

[0244] Another specific aspect of the present invention is a veterinary formulation selected from the group of ectoparasiticidal formulations and endoparasiticidal formulations according to the above aspect, more specifically, a veterinary formulation selected from the group of anthelmintic formulations, antiprotozoal formulations and arthropodicidal formulations, even more specifically, a veterinary formulation selected from the group of nematocidal formulations, platyhelminthicidal formulations, acanthocephalicidal formulations, pentastomicidal formulations, insecticidal formulations and acaricidal formulations, and a method for preparing the same.

[0245] Another aspect relates to a method of treating a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites described herein, where the method comprises administering to an animal (in particular a non-human animal) in need of such treatment an effective amount of a compound represented by formula (I).

[0246] Another aspect relates to a method of treating a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites described herein, where the method comprises administering to an animal (in particular a non-human animal) in need of such treatment a veterinary formulation as defined herein.

[0247] Another aspect relates to the use of a compound of formula (I) in the treatment of parasitic infections in animals (especially non - human animals), particularly infections by parasites selected from the group of ectoparasites and endoparasites described herein.

[0248] In the context of animal health or veterinary medicine, the term "treatment" encompasses prophylactic treatment, metaphylactic treatment after infection or therapeutic treatment.

[0249] In certain embodiments, for the field of veterinary medicine, a mixture of at least one compound of formula (I) and another active ingredient (especially endoparasiticides and ectoparasiticides) is provided.

[0250] In the field of animal health, a "mixture" not only means that two (or more) different active ingredients are formulated into a common formulation and thereby administered together, but also means a product that contains separate formulations for each active compound. Thus, when administering three or more active compounds, all the active compounds can be formulated into a common formulation, or all the active compounds can be formulated into separate formulations; similarly, a mixed form where some of the active compounds are formulated together and some of the active compounds are formulated separately is also possible. In separate formulations, the plurality of active compounds can be administered separately or consecutively.

[0251] The active compounds identified herein by "common name" are known and are described, for example, in the "Pesticide Manual" (see above) or can be searched for on the Internet (e.g., "http: / / www.alanwood.net / pesticides").

[0252] Typical active ingredients selected from the group of said pesticides against external parasites as the mixed partner agent include, but are not limited to, the insecticides and acaricides described in detail above. Regarding further active ingredients that can be used, according to the above classification based on the current "IRAC Mode of Action Classification Scheme", they are described below: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-regulated chloride channel blockers; (3) sodium channel modulators; (4) nicotinic acetylcholine receptor (nAChR) competitive modulators; (5) nicotinic acetylcholine receptor (nAChR) allosteric modulators; (6) glutamate-regulated chloride channel (GluCl) allosteric modulators; (7) juvenile hormone mimics; (8) various unspecified (multi-site) inhibitors; (9) modulators of chordotonal organs; (10) acarid growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, for example, ATP disruptors; (13) uncouplers of oxidative phosphorylation by disrupting the proton gradient; (14) nicotinic acetylcholine receptor channel blockers; (15) inhibitors of chitin biosynthesis (type 0); (16) inhibitors of chitin biosynthesis (type 1); (17) molting disruptors (especially for Diptera (i.e., flies)); (18) ecdysone receptor agonists; (19) octopamine receptor agonists; (21) mitochondrial complex I electron transport inhibitors; (25) mitochondrial complex II electron transport inhibitors; (20) mitochondrial complex III electron transport inhibitors; (22) voltage-dependent sodium channel blockers; (23) inhibitors of acetyl-CoA carboxylase; (28) ryanodine receptor modulators; (30) GABA-regulated chloride channel allosteric modulators.

[0253] Active compounds whose mechanism of action is unknown or not specified, such as, fentrifanil, phenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenimin, diclany, amidoflumet, quinomethionate, triarathene, crothiazoben, tetrasul, potassium oleate, petroleum, methoxadiazone, gossypol, flutenzin, bromopropylate, cryolite; Another class of compounds, such as, butacarb, dimethilan, chloethocarb, phosphocarb, pirimiphos (-ethyl), parathion (-ethyl), methacrifos, isopropyl o -salicylate, trichlorfon, tigolaner, sulprofos, propaphos, sebufos, pyridathion, protopate, dichlofenthion, dimethon -S -methylsulfone, isazophos, cyanofenphos, dialifos, carbophenothion, outathion, aromufenvinphos (-methyl), azinphos (-ethyl), chlorpyrifos (-ethyl), phosmet, iodofenphos, dioxabenzofos, formothion, honohos, flupyrazophos, fensulphothion, ethirimfos; Organochlorine compounds, such as, camphechlor, lindane, heptachlor; or, phenylpyrazole - based, such as, acetoprole, pyrafluprole, pyriprole, vaniliprole, fipronil; or, isoxazoline - based, such as, sarolaner, afoxolaner, lotilaner, fluralaner; Pyrethroid - based, such as, (cis -, trans -) metofluthrin, profluthrin, flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protripermbut, pyresmethrin, RU15525, terallethrin, cis -resmethrin, heptafluthrin, bioethanomethrin, biopermethrin, fenpyrithrin, cis -cyphenothrin, cis -permethrin, cyfluthrin, cyhalothrin (lambda -), crotoxyphos, or, halogenated hydrocarbons (HCHs); Neonicotinoid - based, such as, nithiazine; Dicloromezotiaz, triflumezopyrim; Macrocyclic lactones, for example, nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin oxime; triprene, epofenonan, diofenolan; Biological agents, hormones, or pheromones, for example, natural products, for example, thuringiensin, codlemone, or neem components; Dinitrophenol-based, for example, dinocap, dinobuton, binapacryl; Benzoylurea-based, for example, fluazuron, penfluron; Amidine derivatives, for example, chlormebuform, simiazole, demiditraz; Bee hive varroa acaricides, for example, organic acids, for example, formic acid, oxalic acid.

[0254] Typical active ingredients selected from the group of the endoparasite-killing drugs as the mixed partner drugs include, but are not limited to, anthelmintic active compounds and antiprotozoal active compounds, etc.

[0255] Examples of the anthelmintic active compounds include, but are not limited to, the following nematicidal active compounds, trematocidal active compounds and / or cestocidal active compounds, etc.: Of the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemycin, ivermectin, emamectin, milbemycin; Benzimidazoles and probenzimidazoles classes, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimin, fenbendazole, febantel, thiabendazole, cyclobenzendazole, cambendazole, albendazole-sulfoxide, albendazole, flubendazole; Depsipeptides class, preferably cyclic depsipeptides class, especially 24-membered cyclic depsipeptides class, for example: emodepside, PF1022A; Tetrahydropyrimidines class, for example: morantel, pyrantel, oxantel; Imidazothiazoles class, for example: butamisole, levamisole, tetramisole; Aminophenylamidines class, for example: amidantel, deacylated amidantel (dAMD), tribendimidine; Aminoacetonitriles class, for example: monepantel; Paraherquamides class, for example: paraherquamide, derquantel; Salicylanilides class, for example: tribromsalan, bromoxanide, brotianide, clioxanide, closantel, niclosamide, oxyclozanide, rafoxanide; Substituted phenols class, for example: nitroxynil, bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan; Organophosphates class, for example: trichlorfon, naphthalofos, dichlorvos / DDVP, crufomate, coumaphos, haloxon; Of the class of piperazinones / quinolines, for example: praziquantel, epsiprantel; Of the class of piperazines, for example: piperazine, hydroxyzine; Of the class of tetracyclines, for example: tetracycline, chlortetracycline, doxycycline, oxytetracycline, rolitetracycline; Of various other classes, for example: bunamidine, niridazole, resorantel, omphalotin, oriptraz, nitros canate, nitroxynil, oxamniquine, mirasan, miracil, lucanthone, hycanthone, hetolin, emetine, diethylcarbamazine, dichlorophene, diamphenethide, clonazepam, bephenium, amoscanate, chlorthrion.

[0256] Antiprotozoal active compounds include, but are not limited to, the following active compounds: Of the class of triazines, for example: diclazuril, ponazuril, retrazuril, toltrazuril; Of the class of polyether ionophores, for example: monensin, salinomycin, maduramycin, narasin; Of the class of macrolide lactones, for example: milbemycin, erythromycin; Of the class of quinolones, for example: enrofloxacin, pradofloxacin; Of the class of quinine, for example: chloroquine; Of the class of pyrimidines, for example: pyrimethamine; Of the class of sulfonamides, for example: sulfaquinoxaline, trimethoprim, sulfachloropyridazine; Of the class of thiamines, for example: amprolium; Of the class of lincosamides, for example: clindamycin; Of the class of carbanylides, for example: imidocarb; Of the class of nitrofurans, for example: nifurtimox; Compounds of the class of quinazolinone alkaloids, for example: halofuginone; Compounds of various other classes, for example: oxamniquine, paromomycin; Compounds of the class of vaccines or microbial antigens, for example: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus.

[0257] All the named co-formulants can, if possible by virtue of their functional groups, optionally form salts with suitable bases or acids.

[0258] Vector control The compounds represented by formula (I) can also be used in the control of vectors. For the purposes of the present invention, a vector is an arthropod (in particular an insect or an arachnid) capable of transporting pathogens (for example, viruses, worms, unicellular organisms and bacteria) from a pathogen-carrying host (plant, animal, human, etc.) to a host. The pathogen can be transported mechanically to the host (for example, trachoma by non-biting flies), or can be transported by injection into the host (for example, malaria parasites by mosquitoes).

[0259] Examples of vectors and the diseases or pathogens transported by vectors are as follows: (1) Mosquitoes · Anopheles: Malaria, filariasis; · Culex: Japanese encephalitis, other viral diseases, filariasis, transport of other helminths; · Aedes: Yellow fever, dengue fever, other viral diseases, filariasis; · Simuliidae: Transport of helminths (especially Onchocerca volvulus); · Psychodidae: Transmission of leishmaniasis; (2) Lice: Skin infections, epidemic typhus; (3) Fleas: Infectious diseases, spotted fever, tapeworms; (4) Flies: Sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases; (5) Ticks: Acariosis, epidemic typhus, rickettsialpox, tularemia, St. Louis encephalitis, tick-borne encephalitis (TBE), Crimean-Congo hemorrhagic fever, borreliosis; (6) Mites: Borrellioses, for example, Borrelia burgdorferi sensu lato, Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), babesioses (Babesia canis canis), ehrlichiosis.

[0260] In the context of the present invention, examples of vectors are insects capable of transporting plant viruses to plants, such as aphids, flies, leafhoppers or thrips. Other vectors capable of transporting plant viruses are mites, lice, beetles and nematodes.

[0261] In the context of the present invention, further examples of vectors are insects and arachnids capable of transporting pathogens to animals and / or humans, such as mosquitoes [in particular, mosquitoes of the genus Aedes, Anopheles mosquitoes, such as Anopheles gambiae, Anopheles arabiensis, Anopheles funestus, Anopheles dirus (malaria), and Culex mosquitoes], psychodids, such as Phlebotomus, Lutzomyia, lice, fleas, flies, mites and ticks.

[0262] When the compound represented by formula (I) is resistance-breaking, control of the vector is likewise possible.

[0263] The compound represented by formula (I) is suitable for use in the prevention of diseases and / or the prevention of pathogens carried by vectors. Thus, a further aspect of the present invention is the use of the compound represented by formula (I) for controlling vectors, for example, in agriculture, in horticulture, in gardens and leisure facilities, and further, in the protection of material substances and stored products.

[0264] Protection of industrial materials The compound represented by formula (I) is suitable for protecting industrial materials against attack or destruction by insects [such as insects of the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma].

[0265] In the context of the present invention, industrial materials are understood to mean abiotic materials, for example, preferably plastics, adhesives, sizes, paper and cardboard, leather, wood, processed wood products and paints, etc. The present invention is particularly preferably used for protecting wood.

[0266] In a further embodiment, the compound represented by formula (I) is used together with at least one further insecticide and / or at least one fungicide.

[0267] In a further embodiment, the compound represented by formula (I) is present as a ready-to-use pesticidal agent. That is, they can be applied to the material substance without further modification. Suitable further insecticides or fungicides are, in particular, those mentioned above.

[0268] Surprisingly, it has also been found that the compound represented by formula (I) can be used to protect objects in contact with seawater or brackish water, in particular hulls, screens, nets, buildings, mooring facilities and signalling systems, etc. from fouling. Similarly, the compound represented by formula (I) can be used as a biocide, either alone or in combination with another active compound.

[0269] Pest control in the sanitary field The compound represented by formula (I) is suitable for controlling pests in the hygiene field. In particular, the present invention can be applied to control insects, arachnids, ticks and mites encountered in the domestic field, in the hygiene field and in the protection of stored products, in particular in enclosed spaces (such as dwellings, factory aisles, offices, passenger compartments of vehicles, livestock farming). To control pests, the compound represented by formula (I) is used alone or in combination with another active compound and / or adjuvant. They are preferably included in household insecticide products. The compound represented by formula (I) is effective against susceptible and resistant species and is further effective against all stages of development.

[0270] These pests include, for example, pests of the order Scorpiones, Araneae, and Opiliones of the class Arachnida, pests of the classes Chilopoda and Diplopoda, pests of the order Blattodea, Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera, and Zygentoma of the class Insecta, and pests of the order Isopoda of the class Malacostraca, etc.

[0271] They are used, for example, in aerosol, non-pressurized spray products such as pump sprays and mist sprays, automatic fogging systems, foggers, foams, gels, evaporator products having cellulose or plastic evaporator tablets, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free or passive evaporation systems, moth papers, moth bags, and moth gels, or are used as granules or powders, incorporated into baits for spreading, or used in bait stations.

Table 1

[0272] Description regarding preparation method and intermediate The compound represented by formula (I’) can be prepared as exemplified in Scheme 1 below, where R 1 , R 2 , R3 , R 4 , R 5 And Y are as already defined, and X represents OH or Cl.

[0273] Scheme 1 [Chemical formula]

[0274] X = OH : The triazole compound represented by formula (a) is reacted with the carboxylic acid represented by formula (b) (X = OH) to produce the compound represented by formula (I'). For example, a mixture of the triazole represented by formula (a), the carboxylic acid represented by formula (b) (X = OH), a suitable coupling reagent (e.g., T3P (registered trademark), HATU, DCC or HOBt), and a suitable base (e.g., triethylamine or DIPEA) in a suitable solvent (e.g., ethyl acetate or DMF) is mixed at a temperature in the range of about 0 to 100 °C to produce the compound represented by formula (I'). This compound can then be isolated and, if necessary, purified using techniques well known in the art such as chromatography.

[0275] X = Cl : The triazole compound represented by formula (a) is reacted with the carboxylic acid chloride represented by formula (b) (X = Cl) to produce the compound represented by formula (I'). For example, a mixture of the triazole represented by formula (a), the carboxylic acid chloride represented by formula (b) (X = Cl), and a suitable base (e.g., triethylamine or DIPEA) in a suitable solvent (e.g., dichloromethane or THF) is mixed at a temperature in the range of 0 to 100 °C to produce the compound represented by formula (I'). This compound can then be isolated and, if necessary, purified using techniques well known in the art such as chromatography.

[0276] The carboxylic acid represented by formula (b) (X = OH) and the carboxylic acid chloride represented by formula (b) (X = Cl) are commercially available or can be synthesized by methods known to those skilled in the art. The required triazole compound represented by formula (a) can be prepared as illustrated in Scheme 2 below, where R 1 、R 3 、R 4 、R 5 and Y are as already described and LG is a suitable leaving group (see also WO2017192385 and WO2019 / 170626A1).

[0277] Scheme 2

Chemical formula

[0278] The amine represented by formula (c) is reacted with the substituted triazole represented by formula (d) to produce the compound represented by formula (a). For example, a mixture of the triazole represented by formula (d) and the amine represented by formula (c) in a suitable solvent (e.g., acetonitrile or DMF) and a suitable base (e.g., K2CO3, NaH or DIPEA) is mixed at a temperature in the range of about 20 to 120 °C to produce the compound represented by formula (a). This compound can then be isolated and, if necessary, purified using techniques well known in the art such as chromatography.

[0279] Alternatively, the substituted triazole represented by formula (d) is reacted with ammonia to produce a compound represented by formula (e). For example, a solution of ammonia dissolved in a suitable solvent (e.g., methanol) and the substituted triazole represented by formula (d) are mixed in a sealed tube at a temperature within the range of about 0 to 25 °C to produce a compound represented by formula (e). This compound can then be isolated and, if necessary, purified using techniques well known in the art such as grinding. The substituted triazole represented by formula (e) and the compound represented by formula (f) in a suitable solvent (e.g., acetonitrile or DMF) and a suitable base (e.g., K2CO3 or DIPEA) are mixed at a temperature within the range of about 20 to 120 °C to produce a compound represented by formula (a). This compound can then be isolated and, if necessary, purified using techniques well known in the art such as chromatography.

[0280] Scheme 3 illustrates the preparation of 3-halotriazole-containing amine (n) used, for example, in the synthesis of Example I-001. R 1 is hydrogen, R 3 is methyl, X is oxygen, Y is a direct bond, R 5 is a halogen such as fluorine, chlorine, bromine or iodine, and also R 2 and R 4 have the meanings given in formula (I).

[0281] Scheme 3

Chemical formula

[0282] In the first step, (αS)-1,3-dihydro-α-methyl-1,3-dioxo-2H-isoindole-2-acetic acid (g) (Pht-Ala-OH; purchased from ABCR) is reacted with 1-N-Boc-2-methyl-isothiourea (h) (purchased from ABCR) in the presence of a base and the coupling reagent HATU to produce N-acylated 1-N-Boc-2-methyl-isothiourea (i). In the second step, as described in WO2014009425A1, it is cyclized using an R 4 -substituted hydrazine (j) in the presence of a base (e.g., pyridine) to produce a 1,2,4-triazole represented by formula (k) [wherein R 5 is an NH-Boc group]. In the third step, after N-Boc-deprotection under acidic conditions (e.g., HCl in dioxane), 3-amino-1,2,4-triazole hydrochloride (l) (R 5 =NH2) is produced, which can first be treated with tert-butyl nitrite in the fourth step and then with a copper halide as a salt, e.g., CuCl2 (R 5 =Cl) [described in "N. Desroy et al., J. Med. Chem. 2013, 56, 1418-1430"], CuBr2 (R 5 =Br) [described in "JP-Pat.2010070503A"], a CuI / I2 mixture (R 5 =I) [described in "K. Pchalek and M. P. Hay J. Org. Chem. 2006, 71, 6530-6535"], or diiodomethane (R 5 =I) [described in "N. R. Norcross et al. J. Med. Chem., 2016, 59(13), 6101-6120"] to produce a 3-halogen-substituted 1,2,4-triazole (m). Alternatively, HF can be used instead of the copper halide as described, for example, in "V. Krchnak and Z. Arnold Coll. Czech. Chem. Commun., 1975, 40(5), 1390-1395" to produce fluorine (R 5=(F) can be introduced. In the first step, as described in WO2018086605, react with hydrazine hydrate in a suitable solvent (e.g., ethanol) to remove the phthalimide protecting group in (m). In the final step, react the resulting amine (n) with carboxylic acid (b) to produce the compound of the example, for example, (I''a), for example, Example I-001 described in Scheme 1.

[0283] Scheme 4 illustrates, for example, the preparation of 3-amino-substituted 1,2,4-triazole (q) used as a starting compound for synthesizing Examples I-017 to I-019. R 1 is hydrogen, R 3 is methyl, X is oxygen, Y is a direct bond, and R 5 is a halogen such as fluorine, chlorine, bromine or iodine, and R 2 and R 4 have the meanings given in formula (I).

[0284] Scheme 4

Chemical formula

[0285] In the first step, as described in WO2018086605, react with hydrazine hydrate in a suitable solvent (e.g., ethanol) to remove the phthalimide protecting group from 1,2,4-triazole (see Scheme 3) represented by formula (k) [wherein R 5 is an NH-Boc group]. Then, in the second step, react the resulting N-Boc-protected amine (o) with carboxylic acid (b) to produce compound (p). In the third step, after N-Boc-deprotection under acidic conditions (e.g., HCl in dioxane), 3-amino-1,2,4-triazole (q) (R 5=NH2) is generated, which can be first treated with tert-butyl nitrite in the final fourth step and then with a copper halide as a salt, for example, CuCl2 (R 5 =Cl) [described in "N. Desroy et al., J. Med. Chem. 2013, 56, 1418-1430"], CuBr2 (R 5 =Br) [described in "JP-Pat.2010070503A"], a CuI / I2 mixture (R 5 =I) [described in "K. Pchalek and M. P. Hay J. Org. Chem. 2006, 71, 6530-6535"], or diiodomethane (R 5 =I) [described in "N. R. Norcross et al. J. Med. Chem., 2016, 59(13), 6101-6120"] can be treated, thereby generating 3-halogen-substituted 1,2,4-triazoles (I''a), for example, Examples I-017 to I-019.

[0286] For example, as described in "V. Krchnak and Z. Arnold Coll. Czech. Chem. Commun., 1975, 40(5), 1390-1395", by using HF instead of copper halide (see Scheme 4), or by subjecting 3-diazo-3H-[1,2,4]triazole to a photoreaction in concentrated tetrafluoroboric acid (EP1208321, 1987), or by replacing bromine at 120 °C in dimethyl sulfoxide as described in "A. Zumbrunn Synthesis 1357-1361, 1998", fluorine (R 5 =F) can be introduced.

[0287] Furthermore, chlorine in the intermediate (ma) protected with phthalyl (R 5By replacing =Cl) with fluorine, a fluorinated intermediate (mb) can be obtained, and by removing the protecting group, the corresponding 3-fluorine-substituted 1,2,4-triazoleamine (na) can be obtained.

[0288] Scheme 5

Chemical formula

[0289] Scheme 6 illustrates the preparation of a 3-amino-substituted 1,2,4-triazole (q) enriched in the (S)-enantiomer, which is used, for example, as a starting compound for the synthesis of Example I-027. R 1 is hydrogen, R 3 is methyl, X is oxygen, Y is a direct bond, and R 5 is a halogen such as fluorine, chlorine, bromine or iodine, and R 2 and R 4 have the meanings given in formula (I).

[0290] Scheme 6

Chemical formula

[0291] In the first step, N-Boc-alanine (r) is reacted with 1-N-Boc-2-methylisothiourea (h) (purchased from ABCR) (see Scheme 5) in the presence of a base and a coupling reagent (e.g., HATU) to produce tert-butyl N-[(1S)-2-[[(tert-butoxycarbonylamino)-methylsulfanyl-methylene]amino]-1-methyl-2-oxo-ethyl]carbamate (s), which can be used without purification. In the second step, (s) is cyclized using an R 4 -substituted hydrazine (j) in the presence of an acid (e.g., acetic acid) to give a compound of formula (t) [wherein R 5The (S)-enantiomer-enriched NH-Boc-protected 1,2,4-triazole represented by 〕 is produced. In the third step, both N-Boc protecting groups are removed from the 1,2,4-triazole represented by formula (t) 〔wherein R 5 is NH-Boc〕 to produce a 3-amino-1,2,4-triazole-containing amine (u) or a related hydrochloride. Then, in the fourth step, the obtained 1,2,4-triazoleamine represented by formula (u) is reacted with a carboxylic acid (b) to produce a compound (q). In the final fifth step, the compound (q) is first reacted with tert-butyl nitrite and then with a copper halide as a salt, for example, CuCl2 (R 5 = Cl) 〔described in "N. Desroy et al., J. Med. Chem. 2013, 56, 1418-1430"〕, CuBr2 (R 5 = Br) 〔described in "JP-Pat.2010070503A"〕, or diiodomethane (R 5 = I) 〔described in "N. R. Norcross et al. J. Med. Chem., 2016, 59(13), 6101-6120"〕, thereby producing a 3-halogen-substituted 1,2,4-triazole (I''a) enriched in the (S)-enantiomer, as shown by Example Compound I-027.

[0292] 1-N-Boc-2-methyl-isothiourea is commercially available: see "ABCR GmbH Product List: AB528361".

[0293] Scheme 7 illustrates the preparation of a 3-halotriazole-containing amine intermediate (na) enriched in the (S)-enantiomer, where R 1 is hydrogen, R 3 is methyl, Y is a direct bond, and R 5 is a halogen such as fluorine, chlorine, bromine or iodine, and R 4has the meaning given in formula (I).

[0294] Scheme 7

Chemical formula

[0295] In the first step, N-Boc-alanine (r) is reacted with 1-N-Z-2-methyl-isothiourea (ha) (purchased from Chemieliva Pharmaceutical Product List) (see Scheme 6) in the presence of a base and a coupling reagent (e.g., HATU) to produce tert-butyl N-[(1S)-2-[[(benzyloxycarbonylamino)-methylsulfanyl-methylene]amino]-1-methyl-2-oxo-ethyl]carbamate (sa), which can be used without purification. In the second step, (sa) is cyclized using an R 4 -substituted hydrazine (j) in the presence of an acid (e.g., acetic acid) to produce an (S)-enantiomer-enriched NH-Z, NH-Boc-protected 1,2,4-triazole represented by formula (ta) [wherein R 5 is NH-Z]. In the third step, the N-Z protecting group is removed from the 1,2,4-triazole represented by formula (ta) [wherein R 5 is NH-Z] by hydrogenation (autoclave, 5 bar) in the presence of 10% palladium / carbon to produce 3-amino-1,2,4-triazole (ua) protected with NH-Boc. Then, in the fourth step, the obtained NH-Boc-protected 3-amino-1,2,4-triazole represented by formula (ua) is first reacted with tert-butyl nitrite, and then with a copper halide as a salt, e.g., CuCl2 (R 5 =Cl) [described in "N. Desroy et al., J. Med. Chem. 2013, 56, 1418-1430"], CuBr2 (R 5 =Br) [described in "JP-Pat.2010070503A"], or diiodomethane (R 5 =Br)5 =I) React with 〔described in "N. R. Norcross et al. J. Med. Chem., 2016, 59(13), 6101 - 6120"〕, thereby generating an NH - Boc - protected 3 - halogen - substituted 1,2,4 - triazole intermediate (v) enriched in the (S) - enantiomer. In the final fifth step, intermediate (v) is treated with 4N HCl in dioxane to generate a 3 - halogen - 1,2,4 - triazole - containing amine (na), which can be coupled with carboxylic acid (b) to generate compound (I''a) enriched in the (S) - enantiomer.

[0296] 1 - N - Z - 2 - methyl - isothiourea is commercially available: (See Chemieliva Pharmaceutical Product List; Order number: CA1251032); Z = benzyloxycarbonyl.

[0297] The present invention is illustrated by the following preparation examples and use examples, but these examples do not limit the present invention.

Example

[0298] Preparation example Synthesis of 3-chloro-N-[1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethoxy)benzamide (Example I-001)

Chemical formula

[0299] Step 1 tert-Butyl N-[N-[2-(1,3-dioxoisoindolin-2-yl)propanoyl]-C-methylsulfanyl-carboximidoyl]carbamate

Chemical formula

[0300] 1.09 g (5.0 mmol) of (αS)-1,3-dihydro-α-methyl-1,3-dioxo-2H-isoindole-2-acetic acid (Pht-Ala-OH; purchased from ABCR) and 0.95 g (5.0 mmol) of 1-N-Boc-2-methyl-isothiourea (purchased from ABCR) in THF (30 mL) were added with triethylamine (2.1 mL) and HATU, and the reaction mixture was stirred at a temperature of 80 °C and further stirred at the same temperature for 2 h. Then, water was added and the mixture was extracted with sodium bicarbonate solution and dichloromethane. After dehydration, the solvent was evaporated. The remaining solid residue was subjected to chromatography using a cyclohexane / acetone gradient on silica gel to give 1.40 g (purity: 97.0%; yield: 70%) of the racemic title compound.

[0301] Formula: C 18 H 21 N3O5S Molecular weight: 391.44 g / mol UPLC-MS (acid) [m / z]: 392.2 [M+H] + 11H-NMR peak list (400 MHz, DMSO-d6, ppm): δ = 11.8958 (0.5); 11.4353 (0.9); 7.9299 (0.5); 7.9221 (1.0); 7.9152 (1.2); 7.9102 (1.0); 7.9063 (1.2); 7.9000 (2.1); 7.8930 (1.1); 7.8847 (2.6); 7.8785 (1.3); 7.8744 (1.2); 7.8627 (0.8); 4.9976 (0.8); 4.9794 (0.8); 3.3230 (9.5); 2.5251 (0.4); 2.5204 (0.6); 2.5117 (8.2); 2.5072 (16.6); 2.5027 (21.9); 2.4981 (15.8); 2.4936 (7.6); 2.2949 (2.4); 1.9720 (6.0); 1.6029 (2.9); 1.5848 (3.0); 1.5719 (1.3); 1.5540 (1.1); 1.4430 (16.0); 1.3971 (11.0); 1.2665 (6.6); -0.0002 (0.5). Step 2 tert-Butyl N-[5-[1-(1,3-dioxoisoindolin-2-yl)ethyl]-1-pyrimidin-2-yl-1,2,4-triazol-3-yl]carbamate

Chem.

[0302] A solution of 1.0 g (2.55 mmol) of tert-butyl N-[N-[2-(1,3-dioxoisoindolin-2-yl)propanoyl]-C-methylsulfanyl-carboximidoyl]carbamate in pyridine (50 mL) was added to 337.5 mg (3.06 mmol) of 2-hydrazinopyrimidine, and the reaction mixture was stirred at room temperature at 80 °C for 2 hours. Then, the solvent was evaporated under reduced pressure, and the crude product was subjected to chromatography using a cyclohexane / acetone gradient on silica gel to give 780 mg (purity: 95.9%; yield: 67%) of the racemic title compound.

[0303] Formula: C 21 H21 Molecular weight of N7O4: 435.43 g / mol UPLC-MS (acid) [m / z]: 436.3 [M+H] + 1 H-NMR peak list (600 MHz, DMSO-d6, ppm): δ = 9.9739 (1.2); 8.7635 (2.7); 8.7554 (2.7); 7.8169 (0.6); 7.8126 (0.8); 7.8097 (2.9); 7.8052 (3.0); 7.8020 (0.9); 7.7979 (0.6); 7.4395 (0.7); 7.4315 (1.4); 7.4234 (0.7); 6.0850 (0.8); 6.0732 (0.8); 5.7533 (0.3); 3.3088 (9.2); 2.5080 (3.8); 2.5050 (8.0); 2.5020 (11.1); 2.4989 (8.1); 2.4960 (3.8); 1.9448 (0.4); 1.9123 (0.4); 1.8008 (2.4); 1.7890 (2.4); 1.4365 (16.0); 1.3974 (6.1); -0.0001 (1.9). Step 3 2-[1-(5-Amino-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]isoindoline-1,3-dione hydrochloride

Chem.

[0304] 8.8 g (17.1 mmol) of tert-butyl N-[5-[1-(1,3-dioxoisoindolin-2-yl)ethyl]-1-pyrimidin-2-yl-1,2,4-triazol-3-yl]carbamate was treated with a solution of 4N HCl in dioxane (150 mL), and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was then concentrated, and the racemic solid residue was used in halogen introduction (step 4) without purification.

[0305] Formula: C 16 H 14 Molecular weight of ClN7O2: 371.78 g / mol HPLC-MS (ESI positive) [m / z]: 336.2 [M-HCl] + Step 4 2-[1-(5-Chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]isoindoline-1,3-dione

Chem.

[0306] To 300.0 mg (0.89 mmol) of 2-[1-(5-amino-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]isoindoline-1,3-dione hydrochloride in acetonitrile (20 mL), 204.5 mg (1.52 mmol) of Cu(II) chloride was added, and then the reaction mixture was treated dropwise with 129.1 mg (1.25 mmol) of tert-butyl nitrite at room temperature. The reaction mixture was then stirred at 70 °C for 1 hour. The reaction mixture was treated with ethyl acetate and then extracted with saturated NaHCO3 solution and water. The organic phase was separated, dried, and the solvent was evaporated to give 178 mg (purity: 77%; yield: 56%) of the racemic title compound. This was used in the coupling reaction (step 5) without purification.

[0307] Formula: C 16 H 11 ClN6O2 Molecular weight: 354.75 g / mol UPLC-MS (acid) [m / z]: 355.3 [M+H] + Step 5 1-(5-Chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine (INT-01)

Chem.

[0308] To 499.0 mg (2.5 mmol) of 2-[1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]isoindoline-1,3-dione in ethanol (20 mL) was added 320.0 mg (3.51 mmol) of hydrazine hydrate, and the reaction mixture was heated with reflux. After 30 minutes, a colorless precipitate formed. The reaction mixture was stirred and heated with reflux for an additional 2 hours, acetone (2 mL) was added, and heating was continued for an additional 30 minutes. The reaction mixture was concentrated, and the solid residue was treated with ethanol. After filtration, the filtrate was evaporated under reduced pressure to give 310.0 mg (purity: 70 - 80%, yield: 98%) of racemic intermediate INT-01. This was used in Step 6 without purification.

[0309] Formula: C8H9ClN6 Molecular weight: 224.65 g / mol UPLC-MS (neutral) [m / z]: 225.1 [M+H] + Step 6 3-Chloro-N-[1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethoxy)benzamide To 150.0 mg (0.66 mmol) of 1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine, 164.0 mg (0.66 mmol) of 3-chloro-5-(trifluoromethoxy)-benzoic acid, 120 mg (0.92 mmol) of DIPEA in DMF (3 mL) was added 310.0 mg (0.81 mmol) of HATU, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, the solid residue was treated with dichloromethane, and then extracted with saturated aqueous NaHCO3 and water. The organic phase was separated, dried over Na2SO4, and the solvent was evaporated under reduced pressure. The remaining solid residue was purified by HPLC using a water / acetonitrile neutral gradient to give 122.0 mg (purity: 98.8%; yield: 41%) of the racemic title compound.

[0310] Formula: C 18 H 11 BrN6O2 Molecular weight: 447.20 g / mol HPLC-MS Neutral (ESI Positive) [m / z]: 447.1 [M+H] + The compounds represented by Formula (I-002) to Formula (I-008) described in Table 1 below can be prepared in the same manner.

[0311] Synthesis of 3-bromo-N-[1-(5-bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide (Example I-009)

Chemical formula

[0312] Step 1 2-[1-(5-Bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]isoindoline-1,3-dione

Chemical formula

[0313] To 300.0 mg (0.89 mmol) of 2-[1-(5-amino-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]isoindoline-1,3-dione hydrochloride (synthesized according to Step 1-3 of Example I-001) in acetonitrile (20 mL) was added 350.0 mg (1.56 mmol) of Cu(II) bromide, and then the reaction mixture was treated dropwise with 150 mg (1.45 mmol) of tert-butyl nitrite at room temperature. The reaction mixture was then stirred at 70 °C for 1 hour. The reaction mixture was treated with ethyl acetate and then extracted with saturated NaHCO3 solution and water. The organic phase was separated, dried over Na2SO4, and the solvent was evaporated under reduced pressure. The remaining solid residue was purified by HPLC using a water / MeCN neutral gradient to obtain 234.0 mg (purity: 96.8%; yield: 66%) of the racemic title compound.

[0314] Formula: C 16 H 11 BrN6O2 Molecular weight: 398.01 g / mol HPLC-MS (ESI Positive) [m / z]: 399.2 [M+H] + Step 2 1-(5-Bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine (INT-02) [Chemical formula]

[0315] 678.8 mg (7.45 mmol) of hydrazine hydrate was added to 1.16 g (2.9 mmol) of 2-[1-(5-bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]isoindoline-1,3-dione 2 in ethanol (30 mL), and the reaction mixture was heated while refluxing. After 30 minutes had elapsed, a colorless precipitate formed. The reaction mixture was stirred and further heated while refluxing for 2 hours, acetone (20 mL) was added, and heating was continued for an additional 30 minutes. The reaction mixture was concentrated, and the solid residue was treated with ethanol. After filtration, the filtrate was evaporated under reduced pressure to obtain 900 mg (purity: 50 - 60%) of racemic intermediate INT-02. This was used in Step 6 without purification.

[0316] Formula: C8H9BrN6 Molecular weight: 269.11 g / mol UPLC-MS (neutral): 271.1 [M+H] + Step 3 3-Bromo-N-[1-(5-bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide 122.6 mg (0.45 mmol) of 1-(5-bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine, 125.0 mg (0.45 mmol) of 3-bromo-5-(trifluoromethyl)-benzoic acid (purity: 97%), 81.7 mg (0.63 mmol) of DIPEA in 3.76 g (51.5 mmol) of DMF were added to 205.6 mg (0.54 mmol) of HATU, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, the solid residue was treated with dichloromethane, and then extracted with saturated aqueous NaHCO3 and water. The organic phase was separated, dried over Na2SO4, and the solvent was evaporated under reduced pressure. The remaining solid residue was purified by HPLC using a water / MeCN neutral gradient to give 29.0 mg (purity: 100%; yield: 12%) of the racemic title compound.

[0317] Formula: C 16 H 11 Br2F3N6O Molecular weight: 520.11 g / mol HPLC-MS acid (ESI positive) [m / z]: 521.0 [M+H] + The compounds represented by the formulas (I-010) to (I-016) described in Table 1 below can be prepared in the same manner.

[0318] Synthesis of 3-chloro-N-[1-[5-chloro-2-(5-chloro-2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-5-(trifluoromethyl)benzamide (Example I-017)

Chemical formula

[0319] Step 1 tert-Butyl N-[1-(5-chloro-2-pyridyl)-5-[1-(1,3-dioxoisoindolin-2-yl)ethyl]-1,2,4-triazol-3-yl]carbamate

Chemical formula

[0320] 16.4 g (41.9 mmol) of tert-butyl N-[N-[2-(1,3-dioxoisoindolin-2-yl)propanoyl]-C-methylsulfanyl-carboximidoyl]carbamate (synthesized according to Step 1 of Example I-001) was added to a solution of 7.2 g (50.3 mmol) of 5-chloro-2-hydrazinyl-pyridine in pyridine (200 mL), and the reaction mixture was stirred at 80 °C for 2.5 hours. Thereafter, the solvent was evaporated under reduced pressure, and the crude product was subjected to chromatography on silica gel using a cyclohexane / acetone gradient to give 17.9 g (purity: 99.1%; yield: 90.6%) of the racemic title compound.

[0321] Formula: C 22 H 21 ClN6O4 Molecular weight: 468.90 g / mol HPLC-MS (ESI positive) [m / z]: 269.1 (M+H] + Step 2 tert-Butyl N-[5-(1-aminoethyl)-1-(5-chloro-2-pyridyl)-1,2,4-triazol-3-yl]carbamate

Chemical formula

[0322] 7.2 g (79.9 mmol) of hydrazine hydrate was added to 15.0 g (31.9 mmol) of tert-butyl N-[1-(5-chloro-2-pyridyl)-5-[1-(1,3-dioxoisoindolin-2-yl)ethyl]-1,2,4-triazol-3-yl]carbamate in ethanol (300 mL), and the reaction mixture was heated under reflux. After 30 minutes, a colorless precipitate formed. The reaction mixture was stirred and heated under reflux for an additional 2 hours, acetone was added, and heating was continued for an additional 30 minutes. The reaction mixture was concentrated, and the solid residue was treated with ethanol. After filtration, the filtrate was evaporated under reduced pressure to give 10.8 g (yield: 100%) of the racemic title compound. This was used in Step 3 without purification.

[0323] Formula: C14 H 19 ClN6O2 Molecular weight: 338.80 g / mol HPLC-MS acid (ESI positive) [m / z]: 339.1 [M+H] + Step 3 tert-Butyl N-[1-(5-chloro-2-pyridyl)-5-[1-[[3-chloro-5-(trifluoromethyl)benzoyl]amino]ethyl]-1,2,4-triazol-3-yl]carbamate

Chem.

[0324] 9.4 g (27.8 mmol) of tert-butyl N-[5-(1-aminoethyl)-1-(5-chloro-2-pyridyl)-1,2,4-triazol-3-yl]carbamate, 6.4 g (27.8 mmol) of 3-chloro-5-(trifluoromethyl)-benzoic acid (purity: 97%), and 4.6 g (36.2 mmol) of DIPEA in DMF (300 mL) were added to 12.7 g (33.4 mmol) of HATU, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the solid residue was treated with dichloromethane and then extracted with saturated aqueous NaHCO3 and water. The organic phase was separated, dried over Na2SO4, and the solvent was evaporated under reduced pressure. The remaining solid residue was first purified by MPLC using a cyclohexane / acetone gradient (purity: 50.1%) and then by HPLC using a water / MeCN neutral gradient to give 4.3 g (purity: 100%; yield: 29%) of the racemic title compound.

[0325] Formula: C 22 H 21 Cl2F3N6O3 Molecular weight: 545.35 g / mol HPLC-MS acid (ESI positive) [m / z]: 545.3 [M+H] + Step 4 N-[1-[5-Amino-2-(5-chloro-2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3-chloro-5-(trifluoromethyl)benzamide

Chem.

[0326] 4.2 g (7.8 mmol) of tert-butyl N-[1-(5-chloro-2-pyridyl)-5-[1-[[3-chloro-5-(trifluoromethyl)benzoyl]amino]ethyl]-1,2,4-triazol-3-yl]carbamate was treated with a solution of 4N HCl in dioxane (403 mL), and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was then concentrated, and the racemic solid residue was used in the halogen introduction (step 5) without purification.

[0327] Formula: C 17 H 13 Cl2F3N6O Molecular weight: 445.23 g / mol HPLC-MS acid (ESI positive) [m / z]: 446.1 [M+H] + Step 5 3-Chloro-N-[1-[5-chloro-2-(5-chloro-2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-5-(trifluoromethyl)benzamide 154.0 mg (1.14 mmol) of copper(II) chloride was added to 300.0 mg (0.67 mmol) of N-[1-[5-amino-2-(5-chloro-2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3-chloro-5-(trifluoromethyl)benzamide in acetonitrile (15 mL), and the reaction mixture was then treated dropwise with 97.2 mg (0.94 mmol) of tert-butyl nitrite at room temperature. The reaction mixture was then stirred at a temperature of 70 °C for 1 h. The reaction mixture was treated with ethyl acetate and then extracted with saturated NaCl solution. The solvent was then evaporated under reduced pressure, and the crude product was subjected to chromatography on silica gel using a cyclohexane / acetone gradient to give 78.8 mg (purity: 100%; yield: 25%) of the racemic title compound.

[0328] Formula: C 17 H 11 Cl3F3N5O Molecular weight: 464.66 g / mol HPLC-MS acid (ESI positive) [m / z]: 465.1 [M+H] + 11H-NMR Peak List (600 MHz, DMSO-d6, ppm): δ = 9.4153 (2.5); 9.4039 (2.5); 8.6405 (4.4); 8.6397 (4.4); 8.6363 (4.6); 8.6354 (4.4); 8.2234 (3.8); 8.2191 (3.7); 8.2089 (4.1); 8.2045 (4.1); 8.1234 (4.3); 8.1208 (2.9); 8.0758 (3.9); 8.0629 (4.2); 7.8635 (5.1); 7.8627 (5.0); 7.8490 (4.7); 7.8482 (4.6); 5.9368 (0.4); 5.9252 (2.1); 5.9137 (3.3); 5.9022 (2.2); 5.8906 (0.4); 3.3194 (43.3); 2.6183 (0.3); 2.6152 (0.5); 2.6122 (0.3); 2.5243 (1.0); 2.5212 (1.2); 2.5180 (1.2); 2.5093 (25.1); 2.5062 (54.5); 2.5031 (77.0); 2.5001 (56.8); 2.4971 (26.3); 2.3902 (0.3); 2.3871 (0.5); 2.3840 (0.3); 1.6404 (11.4); 1.6287 (11.5); 1.3975 (16.0); -0.0001 (4.0). Synthesis of N-[1-[5-bromo-2-(5-chloro-2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3-chloro-5-(trifluoromethyl)benzamide (Example I-018)

Chem.

[0329] 200.0 mg (0.44 mmol) of N-[1-[5-amino-2-(5-chloro-2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3-chloro-5-(trifluoromethyl)benzamide (synthesized according to the procedure of Step 4 of Example I-017) in MeCN (10 mL) was added to 170.5 mg (0.76 mmol) of Cu(II) bromide, and then the reaction mixture was treated dropwise with 64.8 mg (0.62 mmol) of tert-butyl nitrite at room temperature. Subsequently, the reaction mixture was stirred at a temperature of 70 °C for 1 hour. The reaction mixture was treated with ethyl acetate and then extracted with saturated NaCl solution. Thereafter, the solvent was evaporated under reduced pressure, and the crude product was subjected to chromatography using a cyclohexane / acetone gradient on silica gel to give 93.8 mg (purity: 99.3%; yield: 41%) of the racemic title compound.

[0330] Formula: C 17 H 11 BrCl2F3N5O Molecular weight: 509.12 g / mol HPLC-MS acid (ESI positiv) [m / z]: 510.0 [M+H] + 11H-NMR peak list (600 MHz, DMSO-d6, ppm): δ = 9.4115 (2.6); 9.4001 (2.7); 8.6396 (0.4); 8.6349 (4.7); 8.6311 (4.5); 8.6307 (4.4); 8.2163 (3.4); 8.2120 (3.3); 8.2089 (0.4); 8.2018 (3.6); 8.1975 (3.6); 8.1214 (4.6); 8.0745 (4.3); 8.0615 (4.7); 7.8651 (5.0); 7.8506 (4.6); 5.9417 (0.4); 5.9302 (2.0); 5.9253 (0.4); 5.9186 (3.2); 5.9139 (0.5); 5.9071 (2.1); 5.8955 (0.4); 3.3216 (92.2); 2.6184 (0.4); 2.6154 (0.5); 2.6124 (0.4); 2.5244 (1.1); 2.5214 (1.4); 2.5182 (1.5); 2.5094 (26.3); 2.5064 (55.2); 2.5033 (76.9); 2.5003 (57.3); 2.4973 (27.2); 2.3904 (0.4); 2.3873 (0.5); 2.3843 (0.3); 1.6353 (11.1); 1.6285 (2.0); 1.6237 (11.1); 1.3974 (16.0); -0.0001 (2.7). Synthesis of 3-chloro-N-[1-[2-(5-chloro-2-pyridyl)-5-iodo-1,2,4-triazol-3-yl]ethyl]-5-(trifluoromethyl)benzamide (Example I-019)

Chem.

[0331] Method A: 300.0 mg (0.67 mmol) of N-[1-[5-amino-2-(5-chloro-2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3-chloro-5-(trifluoromethyl)benzamide (synthesized according to Step 4 of Example I-017) in tetrahydrofuran (15 mL) was added with 12.8 mg (0.06 mmol) of Cu(I) iodide and 171.0 (0.67 mmol) of iodine (under argon atmosphere), and then the reaction mixture was treated dropwise with 64.8 mg (0.62 mmol) of tert-butyl nitrite at room temperature. Then, the reaction mixture was stirred at a temperature of 70 °C for 1 hour. The reaction mixture was treated with ethyl acetate and then extracted with saturated NaCl solution. Thereafter, the solvent was evaporated under reduced pressure, and the crude product was subjected to chromatography using a cyclohexane / acetone gradient on silica gel to obtain 22.0 mg (purity: 99.0%; yield: 6%) of the racemic title compound and 136.0 mg (purity: 97.0%; yield: 46%) of racemic 3-chloro-N-[1-[2-(5-chloro-2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-5-(trifluoromethyl)benzamide as a by-product.

[0332] Method B: 9.3 mg (34.7 mmol) of diiodomethane was added to 300.0 mg (0.67 mmol) of N-[1-[5-amino-2-(5-chloro-2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-3-chloro-5-(trifluoromethyl)benzamide (synthesized according to Step 4 of Example I-017) in MeCN (10 mL) (under argon atmosphere), and then the reaction mixture was treated dropwise with 319.6 mg (3.10 mmol) of tert-butyl nitrite at room temperature. Then, the reaction mixture was stirred at a temperature of 80 °C for 3 hours. The reaction mixture was treated with ethyl acetate and then extracted with saturated NaCl solution. Thereafter, the solvent was evaporated under reduced pressure, and the crude product was subjected to chromatography using a cyclohexane / acetone gradient on silica gel to obtain 268.1 mg (purity: 100.0%; yield: 72%) of the racemic title compound.

[0333] Formula: C 17 H 11 BrCl2FIN5O Molecular weight: 556.11 g / mol HPLC-MS acid (ESI positiv) [m / z]: 556.0 [M+H] + 1 1H-NMR peak list (600 MHz, DMSO-d6, ppm): δ = 9.3946 (1.4); 9.3829 (1.5); 8.6199 (2.4); 8.6191 (2.4); 8.6157 (2.5); 8.6148 (2.4); 8.1956 (2.0); 8.1913 (1.9); 8.1811 (2.2); 8.1768 (2.2); 8.1195 (2.3); 8.1170 (1.6); 8.0712 (2.1); 8.0689 (1.5); 8.0609 (2.3); 7.8528 (2.7); 7.8520 (2.7); 7.8383 (2.5); 7.8374 (2.5); 5.9340 (1.1); 5.9224 (1.8); 5.9107 (1.1); 3.3185 (30.0); 3.2880 (0.3); 2.6146 (0.4); 2.5236 (0.7); 2.5206 (0.9); 2.5174 (0.9); 2.5087 (17.6); 2.5056 (38.0); 2.5025 (53.6); 2.4995 (39.5); 2.4965 (18.2); 2.3865 (0.3); 1.6176 (5.8); 1.6060 (5.8); 1.3975 (16.0); 1.2507 (1.1); -0.0001 (2.9). Synthesis of 3-bromo-N-[1-(5-iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethoxy)benzamide (Example I-020)

Chem.

[0334] Step 1 2-[1-(5-iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]isoindoline-1,3-dione

Chem.

[0335] To 11.22 g (30.17 mmol) of 2-[1-(5-amino-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]isoindoline-1,3-dione hydrochloride (synthesized according to the procedure of Step 1-3 of Example I-001) in acetonitrile (448 mL) was added 180.95 g (675.64 mmol) of diiodomethane (under an argon atmosphere), and then the reaction mixture was treated dropwise with 14.31 g (138.82 mmol) of tert-butyl nitrite at room temperature. The reaction mixture was then stirred at 80 °C for 3 hours. The reaction mixture was treated with ethyl acetate and then extracted with saturated NaCl solution. Thereafter, the solvent was evaporated under reduced pressure, and the crude product was subjected to chromatography using a cyclohexane / acetone gradient on silica gel to give 8.1 g (purity: 99.1%; yield: 60.2%) of the racemic title compound.

[0336] Formula: C 16 H 11 IN6O2 Molecular weight: 446.20 g / mol HPLC-MS acid (ESI positive): 447.0 [M+H] + Step 2 1-(5-iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine (INT-03)

Chemical Structure

[0337] To 3.07 g (6.89 mmol) of 2-[1-(5-iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]isoindoline-1,3-dione in ethanol (100 mL) was added 1.56 g (17.2 mmol) of hydrazine hydrate, and the reaction mixture was heated under reflux. After 30 minutes, a colorless precipitate formed. The reaction mixture was stirred and heated under reflux for an additional 2 hours, acetone (2 mL) was added, and heating was continued for an additional 30 minutes. The reaction mixture was concentrated, and the solid residue was treated with ethanol. After filtration, the filtrate was evaporated under reduced pressure to give racemic intermediate INT-003. This was used in Step 3 without purification.

[0338] Formula: C8H9IN6 Molecular Weight: 316.10 g / mol HPLC-MS Acid (ESI-Positive) [m / z]: 316.9, 317.0 [M+H] + Step 3 3-bromo-N-[1-(5-iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethoxy)benzamide To 132.9 mg (0.37 mmol) of (αS)-methyl-1-[3-iodo-1-pyrimidinyl-1H-1,2,4-triazol]-5-methanamine, 121.4 mg (0.41 mmol) of 3-bromo-5-(trifluoromethoxy)-benzoic acid (purity: 97%), 75.0 mg (0.58 mmol) of DIPEA in DMF (3.65 g, 50.0 mmol) was added 193.7 mg (0.51 mmol) of HATU, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, the solid residue was treated with dichloromethane, and then extracted with saturated aqueous NaHCO3 and water. The organic phase was separated, dried over Na2SO4, and the solvent was evaporated under reduced pressure. The remaining solid residue was purified by HPLC using a water / acetonitrile neutral gradient to give 91.6 mg (purity: 100%; yield: 38.0%) of the racemic title compound.

[0339] Formula: C 16 H 11 BrF3IN6O2 Molecular Weight: 583.11 g / mol HPLC-MS Neutral (ESI-Positive) [m / z]: 584.9 [M+H] + The compounds represented by Formula (I-021) to Formula (I-025) described in Table 1 below can be prepared in the same manner.

[0340] Synthesis of N-[(1S)-1-(5-iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide (Example I-027)

Chemical Structure

[0341] Step 1 N-[5-[(1S)-1-(tert-butoxycarbonylamino)ethyl]-1-pyrimidin-2-yl-1,2,4-triazol-3-yl]carbamic acid tert-butyl

Chemical Structure

[0342] 6.1 g (32.2 mmol) of N-Boc-alanine (Boc-Ala-OH; purchased from Sigma-Aldrich) and 6.1 g (32.0 mmol) of tert-butyl N-methyl-N-(methylsulfanyl-carbonimidoyl)carbamate (ABCR GmbH Product List: AB528361) in dioxane (20 mL) were added with 9.7 g (96.6 mmol) of DIPEA and 17.2 g (45.4 mmol) of HATU, and the reaction mixture was stirred at room temperature for 3 hours. Then, 5.0 g (45.4 mmol) of pyrimidin-2-ylhydrazine was added to the tert-butyl N-[N-[(2S)-2-(tert-butoxycarbonylamino)propanoyl]-C-methylsulfanyl-carbonimidoyl]-N-methyl-carbamate acetate formed in situ, and the reaction mixture was stirred at a temperature of 50 °C for 2 hours. Thereafter, the reaction mixture was treated with ethyl acetate and then extracted with saturated NaCl aqueous solution and water. The organic phase was separated, dehydrated with Na2SO4, and the solvent was evaporated under reduced pressure. The remaining crude product was subjected to chromatography using a cyclohexane / acetone gradient on silica gel to obtain 4.1 g (purity: 90%; yield: 23%) of the title compound. The enantiomeric excess of the chiral title compound was measured: ee-value = 100%; R t = 9.26 min.

[0343] Formula: C 18 H 27 N7O4 Molecular weight: 405.46 g / mol HPLC-MS neutral [m / z]: 406.2 [M+H] + 11H-NMR peak list (400.2 MHz, d6-DMSO, ppm): δ = 9.9069 (0.8); 8.9590 (1.5); 8.9469 (1.5); 8.7705 (0.7); 8.7670 (0.8); 8.7595 (0.8); 8.7560 (0.8); 8.5468 (0.9); 8.5433 (0.9); 8.5258 (1.0); 8.5223 (0.9); 7.6020 (0.9); 7.5899 (1.8); 7.5777 (0.9); 7.5330 (1.0); 7.5220 (1.0); 7.5120 (1.0); 7.5010 (0.9); 3.3288 (11.8); 2.8918 (1.3); 2.7332 (1.0); 2.7319 (1.1); 2.6904 (0.5); 2.5258 (0.4); 2.5210 (0.6); 2.5124 (9.4); 2.5078 (19.4); 2.5032 (25.9); 2.4986 (18.5); 2.4940 (8.7); 1.4523 (16.0); 1.4394 (1.3); 1.4219 (1.2); 1.4180 (1.2); 1.3977 (5.5); 1.3818 (0.3); 1.2936 (4.8); 1.2769 (0.4); 0.0080 (0.9); -0.0002 (28.6); -0.0086 (0.9). Step 2 5-[(1S)-1-aminoethyl]-1-pyrimidin-2-yl-1,2,4-triazol-3-amine hydrochloride

Chem.

[0344] 7.2 g (17.7 mmol) of tert-butyl N-[5-[(1S)-1-(tert-butoxycarbonylamino)ethyl]-1-pyrimidin-2-yl-1,2,4-triazol-3-yl]carbamate was dissolved in 4N HCl-dioxane solution (150 mL), and the mixture was stirred at room temperature for 18 h. Then, the solvent was evaporated under reduced pressure to obtain the title compound, which can be used in the coupling reaction in Step 3.

[0345] Formula: C8H 11 N7HCl Molecular weight: 241.68 g / mol HPLC-MS acid (ESI-positive) [m / z]: 206.2 [M-HCl] + Step 3 N-[(1S)-1-(5-amino-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide [Chem.]

[0346] 400 mg (1.55 mmol) of bis-3,5-(trifluoromethyl)-benzoic acid and 260 mg (2.0 mmol) of DIPEA in acetonitrile (17.3 mL) were added to 650 mg (1.7 mmol) of HATU, and the reaction mixture was stirred for 10 minutes. Then, 375 mg (1.55 mmol) of 5-[(1S)-1-aminoethyl]-1-pyrimidin-2-yl-1,2,4-triazole-3-amine-hydrochloride was added together with triethylamine (1.0 mL), and the reaction mixture was stirred overnight at room temperature. The reaction mixture was treated with water and then extracted with dichloromethane. The separated organic phase was dehydrated with MgSO4 and concentrated under reduced pressure. The remaining crude product was subjected to preparative HPLC chromatography to obtain 150 mg (purity: 93.5%; yield: 22%) of the title compound.

[0347] Formula: C 17 H 13 F6N7O Molecular weight: 445.33 g / mol HPLC-MS neutral (ESI-positive) [m / z]: 446.1 [M+H] + Step 4 N-[(1S)-1-(5-iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide To 220 mg (0.49 mmol) of N-[(1S)-1-(5-amino-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide in acetonitrile (20 mL) was added 270 mg (1.0 mmol) of diiodomethane (argon atmosphere), and then the reaction mixture was treated dropwise with 75 mg (0.72 mmol) of tert-butyl nitrite at room temperature. The reaction mixture was then stirred at 70 °C for 2 hours. The reaction mixture was treated with ethyl acetate and then extracted with saturated NaCl solution. The solvent was then evaporated under reduced pressure, and the crude product was subjected to chromatography by HPLC to give 125 mg (purity: 93.5%; yield: 42.5%) of the title compound. The enantiomeric excess of the chiral title compound was measured using chiral HPLC: Chiralcel OD-RH column (4.6 mm × 150 mm × 5 μm), room temperature, elution with 0.1% phosphoric acid (A) and acetonitrile (B), gradient A:B 95 / 5 to 10 / 90, detection at 210 nm: ee-value = 97% (R t = 10.98 min).

[0348] Formula: C 17 H 11 F6IN6O Molecular weight: 556.21 g / mol HPLC-MS acid (ESI positive): 557.0 [M+H] + Synthesis of (1S)-1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride Step 1 tert-Butyl N-[(1S)-1-[5-(benzyloxycarbonylamino)-2-pyrimidin-2-yl-1,2,4-triazol-3-yl]ethyl]carbamate

Chemical formula

[0349] 200 mg (1.05 mmol) of N-Boc-alanine (Boc-Ala-OH; purchased from Sigma-Aldrich) and 240 mg (1.07 mmol) of phenylmethyl N-[imino(methylthio)methyl]carbamate (Chemieliva Pharmaceutical Product List; Order number: CA1251032) in N,N-dimethylformamide (5 mL) were added with 320 mg (3.16 mmol) of DIPEA and 600 mg (1.57 mmol) of HATU, and the reaction mixture was stirred at room temperature for 3 h. Then, 140 mg (1.27 mmol) of pyrimidin-2-ylhydrazine and acetic acid (0.25 mL) were added to the N-[(1S)-2-[[benzyloxycarbonylamino(methylsulfanyl)methylene]amino]-1-methyl-2-oxo-ethyl]carbamate formed in situ, and the reaction mixture was stirred at a temperature of 50 °C for 1 h. Thereafter, the reaction mixture was treated with ethyl acetate and then extracted with saturated NaCl aqueous solution and water. The organic phase was separated, dehydrated with Na2SO4, and the solvent was evaporated under reduced pressure. The remaining crude product was subjected to chromatography using a cyclohexane / acetone gradient on silica gel to obtain 239 mg (purity: 96.5%; yield: 47%) of the title compound.

[0350] Formula: C 21 H 25 N7O4 Molecular weight: 439.47 g / mol LC-MS neutral [m / z]: 440.2 [M+H] + 11H-NMR peak list (600.1 MHz, d6-DMSO, ppm): δ = 10.3936 (2.8); 8.9644 (3.7); 8.9564 (3.5); 7.6071 (2.6); 7.5990 (4.9); 7.5909 (2.5); 7.4600 (0.9); 7.4473 (1.0); 7.4405 (2.0); 7.4383 (2.6); 7.4265 (4.3); 7.4031 (2.7); 7.4000 (0.8); 7.3910 (4.7); 7.3782 (2.2); 7.3456 (1.5); 7.3370 (0.6); 7.3336 (1.9); 7.3215 (0.6); 5.5211 (0.5); 5.5092 (0.8); 5.4974 (0.6); 5.1592 (8.4); 3.3174 (105.4); 2.6190 (0.4); 2.6161 (0.7); 2.6130 (1.0); 2.6100 (0.7); 2.6071 (0.4); 2.5221 (2.2); 2.5190 (2.7); 2.5159 (2.8); 2.5070 (50.7); 2.5041 (106.9); 2.5010 (147.1); 2.4980 (108.0); 2.4950 (50.4); 2.3879 (0.6); 2.3849 (0.8); 2.3819 (0.6); 1.4435 (3.6); 1.4320 (3.3); 1.2872 (16.0); 1.0400 (0.9); -0.0001 (2.9) Step 2 tert-Butyl N-[(1S)-1-(5-amino-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]carbamate

Chem.

[0351] 560 mg (1.27 mmol) of tert-butyl N-[(1S)-1-[5-(benzyloxycarbonylamino)-2-pyrimidin-2-yl-1,2,4-triazol-3-yl]ethyl]carbamate was hydrogenated in ethanol (10 mL) at room temperature (5 bar, 16 h) in the presence of 50 g (46.9 mmol) of 10% palladium / carbon (Aldrich) catalyst. The remaining crude product was filtered through silica gel to give 160 mg (purity: 79%; yield: 32%) of the title compound.

[0352] Formula: C 13 H 19 N7O2 Molecular weight: 305.34 g / mol HPLC-MS neutral [m / z]: 306.1 [M+H] + Step 3 tert-Butyl N-[(1S)-1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]carbamate

Chem.

[0353] 130.0 mg (0.96 mmol) of copper(II) chloride was added to 160.0 mg (0.52 mmol) of tert-butyl N-[(1S)-1-(5-amino-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]carbamate in acetonitrile (10 mL), and then the reaction mixture was treated dropwise with 80.0 mg (0.77 mmol) of tert-butyl nitrite at room temperature. The reaction mixture was then stirred at 70 °C for 2 h. The reaction mixture was treated with ethyl acetate and then extracted with saturated NaCl solution. The solvent was then evaporated under reduced pressure, and the crude product was subjected to chromatography by preparative HPLC to give 47.0 mg (yield: 28%) of the title compound. The enantiomeric excess of the chiral title compound was measured by Chiralcel OD_RH (acid): ee-value = 80%; R t = 9.37 min.

[0354] Formula: C 13 H17 Molecular weight of ClN6O2: 324.77 g / mol 1 1H-NMR peak list (600.4 MHz, d7-DMF): δ = 9.0802 (3.6); 9.0725 (3.5); 8.0234 (40.3); 7.7498 (1.4); 7.7418 (2.7); 7.7338 (1.4); 7.4383 (0.8); 7.4266 (0.8); 5.6675 (0.6); 5.6561 (0.8); 5.6450 (0.6); 3.4532 (93.6); 2.9512 (0.8); 2.9207 (13.3); 2.9177 (27.1); 2.9146 (37.5); 2.9115 (27.7); 2.9086 (14.0); 2.7834 (0.8); 2.7503 (13.9); 2.7471 (28.0); 2.7440 (39.2); 2.7408 (28.5); 2.7376 (14.6); 1.5839 (5.6); 1.5725 (5.4); 1.3118 (16.0); 1.1391 (0.6); 0.0053 (2.3); -0.0001 (69.1); -0.0056 (2.8) Step 4 (1S)-1-(5-Chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride [Chem.]

[0355] 337 mg (1.03 mmol) of tert-butyl N-[(1S)-1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]carbamate was dissolved in 4N HCl-dioxane solution (10 mL), and the mixture was stirred at room temperature for 18 hours. Then, the solvent was evaporated under reduced pressure to obtain the title compound, which could be used for the coupling reaction. Thereafter, the solvent was evaporated to obtain 260.0 mg (yield: 96%) of the title compound. The enantiomeric excess of the chiral title compound was measured by Chiralcel OD_RH (acid): ee-value = 100%; R t = 1.39 min.

[0356] Formula: C8H9ClN6HCl Molecular weight: 261.11 g / mol HPLC-MS acid (ESI-positive) [m / z]: 225.0 [M-HCl] + Synthesis of (1S)-1-(5-bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride Step 1 tert-Butyl N-[(1S)-1-(5-bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]carbamate

Chem.

[0357] To 500.0 mg (1.63 mmol) of tert-butyl N-[(1S)-1-(5-amino-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]carbamate in acetonitrile (20 mL) was added 690.0 mg (3.08 mmol) of copper(II) bromide, and then the reaction mixture was treated dropwise with 250.0 mg (2.42 mmol) of tert-butyl nitrite at room temperature. The reaction mixture was then stirred at 70 °C for 2 hours. The reaction mixture was treated with ethyl acetate and then extracted with saturated NaCl solution. Thereafter, the solvent was evaporated under reduced pressure and the crude product was subjected to chromatography using a cyclohexane / acetone gradient on silica gel to give 333.0 mg (purity: 100%; yield: 55%) of the title compound. The enantiomeric excess of the chiral title compound was measured by Chiralcel OD_RH (acid): ee-value = 100%; R t = 9.63 minutes.

[0358] Formula: C 13 H 17 BrN6O2 Molecular weight: 369.22 g / mol HPLC-MS neutral [m / z]: 369.0 [M+H] + Step 2 (1S)-1-(5-Bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride

Chem.

[0359] 330 mg (0.89 mmol) of tert-butyl N-[(1S)-1-(5-bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]carbamate was dissolved in 4N HCl-dioxane solution (10 mL), and the mixture was stirred at room temperature for 18 h. The solvent was then evaporated under reduced pressure to give 250 mg (yield: 91.5%) of the title compound, which can be used in the coupling reaction.

[0360] Formula: C8H9BrN6HCl Molecular weight: 305.57 g / mol HPLC-MS acid (ESI-positive) [m / z]: 270.9 [M-HCl] + Synthesis of (1S)-1-(5-iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride Step 1 tert-Butyl N-[(1S)-1-(5-iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]carbamate

Chemical Structure

[0361] 816.7 mg (3.04 mmol) of diiodomethane was added to 500.0 mg (1.63 mmol) of tert-butyl N-[(1S)-1-(5-amino-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]carbamate in acetonitrile (20 mL), and then the reaction mixture was treated dropwise with 250.0 mg (2.42 mmol) of tert-butyl nitrite at room temperature. The reaction mixture was then stirred at 70 °C for 2 h. The reaction mixture was treated with ethyl acetate and then extracted with saturated NaCl solution. The solvent was then evaporated under reduced pressure, and the crude product was subjected to chromatography by preparative HPLC to give 294.0 mg (purity: 100%; yield: 43%) of the title compound.

[0362] Formula: C 13 H 17Molecular weight of IN6O2: 416.22 g / mol HPLC-MS neutral [m / z]: 417.0 [M+H] + Step 2 (1S)-1-(5-Iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride

Chem.

[0363] 290 mg (0.69 mmol) of tert-butyl N-[(1S)-1-(5-iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]carbamate was dissolved in 4N HCl-dioxane solution (10 mL), and the mixture was stirred at room temperature for 18 h. Then the solvent was evaporated under reduced pressure to give the title compound, which can be used in the coupling reaction. The enantiomeric excess of the chiral title compound was measured by Chiralcel OD_RH (acid): ee-value = 100%; R t = 1.41 min.

[0364] Formula: C8H9IN6HCl Molecular weight: 352.56 g / mol HPLC-MS acid (ESI-positive) [m / z]: 317.0 [M-HCl] + Analytical data of the compound Measurement of [M+H] + or M - by LC-MS under acidic chromatography conditions was carried out using 1 mL of formic acid per liter of acetonitrile and 0.9 mL of formic acid per liter of Millipore water as the eluent. Column "Zorbax Eclipse Plus C18 50 mm×2.1 mm" was used. The temperature of the column oven was 55 °C.

[0365] Intermediate compound N-[5-[(1S)-1-(tert-butoxycarbonylamino)ethyl]-1-pyrimidin-2-yl-1,2,4-triazol-3-yl]carbamic acid tert-butyl, N-[(1S)-1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]carbamic acid tert-butyl, (1S)-1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride [INT-04], N-[(1S)-1-(5-bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]carbamic acid tert-butyl, (1S)-1-(5-iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride [INT-06], and the enantiomeric excess of Example I-027 was measured using chiral HPLC: Chiralcel OD-RH column (4.6 mm × 150 mm × 5 μm), room temperature, elution with 0.1% phosphoric acid (A) and acetonitrile (B), gradient A:B from 95 / 5 to 10 / 90, detection at 210 nm.

[0366] 1 The measurement of 1H NMR data was carried out using a "Bruker Avance III 400 MHz" equipped with a 1.7 mm TCI cryoprobe, a "Bruker Avance III 600 MHz" equipped with a 5 mm multinuclear cryoprobe, or a "Bruker Avance NEO 600 MHz" equipped with a 5 mm TCI cryoprobe, using tetramethylsilane as the reference standard (0.0) and the solvents CD3CN, CDCl3 or D6-DMSO.

[0367] The NMR data of the selected examples are described in the customary form (δ values, multiplicity splitting, number of hydrogen atoms) or as an NMR peak list.

[0368] NMR peak list method The 1 1H NMR data of the selected examples are 1It is shown in the form of an \(^1H\) NMR peak list. For each signal peak, the \(\delta\) value (ppm) is first described, and then, within parentheses, the signal intensity is described. Pairs of \(\delta\) value - signal intensity numbers for various signal peaks are described separated from each other by semicolons.

[0369] Therefore, the peak list for one example takes the following form: \(\delta_1\) (intensity 1); \(\delta_2\) (intensity 2);...; \(\delta\) i (intensity i );...; \(\delta\) n (intensity n ).

[0370] The intensity of a sharp signal correlates with the height (cm) of the signal in the printed example of the NMR spectrum and indicates the true ratio of the signal intensities. In the case of a broad signal, several peaks or the center of the signal and their relative intensities can be shown in comparison to the strongest signal in the spectrum.

[0371] 1 To calibrate the chemical shift of the \(^1H\) NMR spectrum, tetramethylsilane is used and / or, especially when the spectrum is measured in DMSO, the chemical shift of the solvent is used. Therefore, in the NMR peak list, the peak of tetramethylsilane may be present but does not necessarily have to be present.

[0372] 1 The list of \(^1H\) NMR peaks is similar to a conventional 1 printout of \(^1H\) NMR and thus usually includes all the peaks described in the customary interpretation of NMR.

[0373] Furthermore, like a conventional 1 printout of \(^1H\) NMR, they can also show the signal of the solvent, the signal of the stereoisomers of the target compound (which are also provided by the present invention) and / or the signal of the peaks of impurities.

[0374] In recording the compound signals within the delta range of the solvent and / or water, 1 The list by the inventors of the H NMR peaks shows the peaks of standard solvents, such as the peak of DMSO in DMSO-D6 and the peak of water (which usually have relatively high intensities on average).

[0375] The peaks of the stereoisomers and / or impurities of the target compound usually have lower intensities on average than the peaks of the target compound (for example, the target compound having a purity exceeding 90%).

[0376] Such stereoisomers and / or impurities may be specific to a particular preparation method. Therefore, their peaks can help confirm the reproducibility of the inventors' preparation method in terms of "by-product fingerprints".

[0377] Those skilled in the art who calculate the peaks of the target compound by known methods (MestreC, ACD simulations, and further using empirically evaluated expected values) can, if necessary, use additional intensity filters to separate the peaks of the target compound as appropriate. This separation will 1 be similar to the picking of such peaks in the conventional interpretation of H NMR.

[0378] 1 For further details regarding the H NMR peak list, it can be found in "Research Disclosure Database Number 564025".

[0379] The compounds of the present invention described in Table 1 below are likewise preferred compounds of the formula (I) of the present invention [wherein R 1 is hydrogen, R 3 is methyl, X is oxygen, Y is a direct bond, and R 5 is halogen], which are obtained according to or in a similar manner to the preparation examples described above.

Table 2

[0380] TIFF0007695237000046.tif241170

[0381] TIFF0007695237000047.tif254166

[0382] TIFF0007695237000048.tif241170

[0383] TIFF0007695237000049.tif238170

Table 3

[0384] Biological examples Rhipicephalus (Boophilus) microplus - in vitro contact test Larval Rhipicephalus (Boophilus) microplus (Parkhurst strain showing resistance to synthetic pyrethroids) Dissolve 9 mg of the compound in 1 mL of acetone and dilute with acetone to the desired concentration. Put 250 μL of the test solution into a 25 mL glass test tube and distribute it uniformly on its inner wall by rotating and tilting (at 30 rpm for 2 hours) on a shaker. With a compound concentration of 900 ppm, an inner surface of 44.7 cm 2 and uniform distribution, a drug dose of 5 μg / cm 2 is achieved.

[0385] After the solvent has evaporated, place 20 - 50 larvae of the cattle tick (Rhipicephalus microplus) into each test tube, close it with a perforated lid, and incubate it horizontally in an incubator at 85% relative humidity and 27°C. After 48 hours, determine the efficacy. Tap the test tube gently to let the larvae fall to the bottom and record the negative geotactic behavior. Larvae that climb up to the upper part of the vial like the untreated control larvae are recorded as surviving, larvae that do not climb up like the untreated control larvae but have jerky movements or only spasming legs are recorded as near death, and tick larvae remaining at the bottom and not moving at all are counted as dead.

[0386] When at least 80% efficacy is monitored at a compound concentration of 5 μg / cm 2 the compound shows good efficacy against the cattle tick (Rhipicephalus microplus). 100% efficacy means that all cattle tick larvae are dead or near death; 0% means that there are no dead or near - death cattle tick larvae.

[0387] In this test, for example, the following compounds of the preparation examples showed 100% good activity at an application rate of 5 μg / cm 2 (= 500 g / ha): I - 002, I - 003, I - 004, I - 006, I - 007, I - 008, I - 009, I - 010, I - 012, I - 015, I - 017, I - 020, I - 021, I - 022, I - 024.

[0388] In this test, for example, the following compounds of the preparation examples showed 90% good activity at an application rate of 5 μg / cm 2 (= 500 g / ha): I - 013, I - 019.

[0389] In this test, for example, the following compounds of the preparation examples showed 80% good activity at an application rate of 5 μg / cm 2 (= 500 g / ha): I - 016, I - 018.

[0390] Rhipicephalus (Boophilus) microplus - dipping test Test animals: Cattle tick (Rhipicephalus microplus) strain Parhurst (SP-resistant) Solvent: Dimethyl sulfoxide To prepare a suitable preparation of the active compound, 10 mg of the active compound is dissolved in 0.5 mL of the solvent, and the resulting concentrate is diluted with water to the desired concentration.

[0391] This compound solution is pipetted into a tube. 8 - 10 adult female cattle ticks (Rhipicephalus microplus) that are engorged are placed into a tube with holes. The tubes are immersed in the aqueous solution of the compound until the ticks are completely wet. After the liquid has drained, the ticks are transferred to filter paper in a plastic tray and stored in an artificial climate chamber.

[0392] After 7 days have passed, monitor for egg laying of fertilized eggs. Eggs that are not clearly fertilized are stored in an artificial climate chamber until they hatch, which is about 42 days later. 100% efficacy means that all eggs are unfertilized; 0% means that all eggs are fertilized.

[0393] In this test, for example, the following compound of the preparation example showed good activity of 80% at an application rate of 100 ppm: I-002.

[0394] Rhipicephalus (Boophilus) microplus - injection test Solvent: Dimethyl sulfoxide To prepare a suitable preparation of the active compound, 10 mg of the active compound is dissolved in 0.5 mL of the solvent, and the resulting concentrate is diluted with the solvent to the desired concentration.

[0395] Inject 1 μL of the compound solution into the abdomen of 5 engorged adult female cattle ticks (Rhipicephalus microplus). Transfer the ticks to a replica plate and incubate them in an artificial climate chamber.

[0396] After 7 days have passed, monitor the spawning of fertilized eggs. Eggs that are not clearly fertilized are stored in an artificial climate chamber until they hatch, which is about 42 days later. 100% efficacy means that all eggs are unfertilized eggs; 0% means that all eggs are fertilized.

[0397] In this test, for example, the following compounds of the preparation examples showed 100% good activity at a dosage of 20 μg per animal: I-002, I-003, I-004, I-005, I-017, I-018, I-019.

[0398] In this test, for example, the following compounds of the preparation examples showed 100% good activity at a dosage of 4 μg per animal: I-002, I-003, I-004, I-005, I-007, I-008, I-009, I-010, I-013, I-014, I-015, I-016, I-017, I-019.

[0399] In this test, for example, the following compounds of the preparation examples showed 80% good activity at a dosage of 4 μg per animal: I-006, I-012, I-018.

[0400] Ctenocephalides felis - in vitro contact test Adult Ctenocephalides felis Dissolve 9 mg of the compound in 1 mL of acetone and dilute with acetone to the desired concentration. Put 250 μL of the test solution into a 25-mL glass test tube and distribute it evenly on its inner wall by rotating and tilting on a shaker (2 hours at 30 rpm). With a compound concentration of 900 ppm, an inner surface of 44.7 cm 2 and uniform distribution, a dosage of 5 μg / cm 2 is achieved.

[0401] After the solvent has evaporated, place 5 - 10 adult cat fleas (Ctenocephalides felis) into each test tube, close it with a perforated lid, and incubate it in a horizontal position at room temperature and indoor relative humidity. After 48 hours, determine the efficacy. Tap the test tube gently to drop the fleas to the bottom and incubate them on a heating plate at 45 - 50 °C for a maximum of 5 minutes. Fleas that remain immobile or move jerkily and cannot avoid the heat by crawling up are recorded as dead or dying.

[0402] When at least 80% efficacy is monitored at a compound concentration of 5 μg / cm 2 the compound shows good efficacy against cat fleas (Ctenocephalides felis). 100% efficacy means that all fleas are dead or dying; 0% means that there are no dead or dying fleas.

[0403] In this test, for example, the following compounds of the preparation examples showed 100% good activity at an application rate of 5 μg / cm 2 (= 500 g / ha): I - 006, I - 020, I - 021.

[0404] In this test, for example, the following compounds of the preparation examples showed 90% good activity at an application rate of 5 μg / cm 2 (= 500 g / ha): I - 008, I - 013, I - 024.

[0405] In this test, for example, the following compounds of the preparation examples showed 80% good activity at an application rate of 5 μg / cm 2 (= 500 g / ha): I - 009, I - 010.

[0406] In this test, for example, the following compounds of the preparation examples showed 100% good activity at an application rate of 1 μg / cm 2 (= 100 g / ha): I - 002, I - 020, I - 021.

[0407] In this test, for example, the following compounds of the preparation examples showed good activity of 90% at an application rate of 1 μg / cm 2 (= 100 g / ha): I-008, I-013.

[0408] In this test, for example, the following compounds of the preparation examples showed good activity of 80% at an application rate of 1 μg / cm 2 (= 100 g / ha): I-014, I-024.

[0409] Ctenocephalides felis - oral test Solvent: dimethyl sulfoxide To prepare a suitable preparation of the active compound, 10 mg of the active compound is dissolved in 0.5 mL of the solvent, and the resulting concentrate is diluted with bovine blood to the desired concentration.

[0410] About 20 adult cat fleas (Ctenocephalides felis) without food are placed in a flea chamber. A bovine blood containing the compound solution is supplied to a blood chamber whose bottom is sealed with parafilm, and the chamber is placed on top of the top of the flea chamber covered with gauze, whereby the fleas can suck the blood. The blood chamber is heated to 37 °C, and the flea chamber is maintained at room temperature.

[0411] After 2 days, the mortality rate (%) is determined. 100% means that all the fleas are dead; 0% means that no fleas are dead.

[0412] In this test, for example, the following compounds of the preparation examples showed good activity of 100% at an application rate of 100 ppm: I-002, I-003, I-005, I-006, I-007, I-008, I-009, I-010, I-012, I-013, I-014, I-015, I-016, I-020, I-021, I-023.

[0413] In this test, for example, the following compounds of the preparation examples showed good activity of 90% at an application rate of 100 ppm: I-004, I-022.

[0414] Rhipicephalus sanguineus - In vitro contact test using adult Rhipicephalus sanguineus Dissolve 9 mg of the compound in 1 mL of acetone and dilute with acetone to the desired concentration. Put 250 μL of the test solution into a 25 mL glass test tube and distribute it uniformly on its inner wall by rotating and tilting on a shaker (30 rpm for 2 hours). With a compound concentration of 900 ppm, an inner surface of 44.7 cm 2 and uniform distribution, a dosage of 5 μg / cm 2 is achieved.

[0415] After the solvent has evaporated, place 5 - 10 adult Rhipicephalus sanguineus in each test tube, close it with a perforated lid, and incubate it in a horizontal position at room temperature and indoor relative humidity. After 48 hours, determine the efficacy. Tap the test tube gently to drop the Rhipicephalus sanguineus to the bottom and incubate it on a heating plate at 45 - 50 °C for a maximum of 5 minutes. Record as dead or dying any Rhipicephalus sanguineus that remains immobile or moves jerkily and cannot avoid the heat by crawling upwards.

[0416] When at least 80% efficacy is monitored for a compound at a compound concentration of 5 μg / cm 2 that compound shows good efficacy against Rhipicephalus sanguineus. 100% efficacy means that all Rhipicephalus sanguineus are dead or dying; 0% means that there are no dead or dying Rhipicephalus sanguineus.

[0417] In this test, for example, the following compounds of the preparation examples are at 5 μg / cm 2At an application rate of (= 500 g / ha), the following showed 100% good activity: I-003, I-004, I-005, I-007, I-008, I-009, I-010, I-012, I-014, I-020.

[0418] In this test, for example, the following compounds of the preparation examples showed 80% good activity at an application rate of 5 μg / cm 2 (= 500 g / ha): I-002, I-006, I-013, I-021, I-022, I-024.

[0419] Diabrotica balteata - Spray test Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: alkylaryl polyglycol ether To produce a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the above amounts of solvent, and the resulting concentrate is diluted with water containing an emulsifier at a concentration of 1000 ppm to the desired concentration. Further test concentrations are prepared by diluting with water containing an emulsifier.

[0420] The soaked wheat (Triticum aestivum) seeds are placed in a multiwell plate filled with agar and a small amount of water and incubated for 1 day to germinate (5 seeds per well). The germinated wheat seeds are sprayed with a test solution containing the active ingredient at the desired concentration. Then, 10 - 20 larvae of Diabrotica balteata are parasitized per unit.

[0421] After 7 days, the efficacy (%) is determined. 100% means that all wheat seedlings grew as in the untreated and unparasitized control; 0% means that there were no growing wheat seedlings.

[0422] In this test, for example, the following compounds of the preparation examples showed good activity of 100% at an application rate of 100 g / ha (= 32 μg / well): I-001, I-002, I-003, I-004, I-005, I-006, I-009, I-013, I-014, I-016, I-017, I-018, I-019, I-020, I-021, I-022, I-024.

[0423] In this test, for example, the following compounds of the preparation examples showed good activity of 80% at an application rate of 100 g / ha (= 32 μg / well): I-008, I-010, I-015.

[0424] Myzus persicae - Oral test Solvent: 100 parts by weight of acetone To produce a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the above amount of solvent, and the resulting concentrate is diluted with water to the desired concentration.

[0425] 50 μL of the compound solution is placed in a microtiter plate, and 150 μL of IPL41 insect medium (33% + 15% sugar) is added to make a total volume of 200 μL / well. Then, the plate is sealed with parafilm, and through the parafilm, a mixed population of the green peach aphid (Myzus persicae) can absorb the compound preparation.

[0426] After 5 days, the mortality rate (%) is determined. 100% means that all the green peach aphids are dead, and 0% means that there are no dead green peach aphids.

[0427] In this test, for example, the following compounds of the preparation examples showed good activity of 100% at an application rate of 4 ppm: I-001, I-002, I-003, I-004, I-009, I-010, I-013, I-016, I-020, I-021, I-022.

[0428] In this test, for example, the following compounds of the preparation examples showed good activity of 90% at an application rate of 4 ppm: I-006, I-007.

[0429] Myzus persicae - Spray test Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: alkylaryl polyglycol ether To produce a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the above amounts of the solvent and diluted with water containing an emulsifier at a concentration of 1000 ppm to the desired concentration. Further test concentrations are prepared by diluting with water containing an emulsifier.

[0430] Disks of leaves of Chinese cabbage (Brassica pekinensis) infested with Myzus persicae of all ages are sprayed with a preparation of the active ingredient at the desired concentration.

[0431] After 5 days, the mortality rate (%) is determined. 100% means that all Myzus persicae have died, and 0% means that no Myzus persicae have died.

[0432] In this test, for example, the following compounds of the preparation examples showed good activity of 90% at an application rate of 100 g / ha: I-001, I-006, I-007, I-010, I-020, I-021.

[0433] In this test, for example, the following compound of the preparation example showed good activity of 70% at an application rate of 100 g / ha: I-009.

[0434] Nezara viridula - Spray test Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: alkylaryl polyglycol ether To produce a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the above amount of solvent, and the resulting concentrate is diluted with water containing an emulsifier at a concentration of 1000 ppm to the desired concentration. Further test concentrations are prepared by dilution with water containing an emulsifier.

[0435] Spray a test solution containing the active ingredient at the desired concentration onto barley (Hordeum vulgare) plants infested with larvae of the southern green stink bug (Nezara viridula).

[0436] After 4 days, determine the percentage of dead insects. 100% means that all southern green stink bugs are dead; 0% means that no southern green stink bugs are dead.

[0437] In this test, for example, the following compounds of the preparation examples showed good activity of 100% at an application rate of 100 g / ha: I-008, I-024.

[0438] In this test, for example, the following compound of the preparation example showed good activity of 90% at an application rate of 100 g / ha: I-007.

[0439] Spodoptera frugiperda - Spray test Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: alkylaryl polyglycol ether To produce a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the above amount of solvent and diluted with water containing an emulsifier at a concentration of 1000 ppm to the desired concentration. Further test concentrations are prepared by dilution with water containing an emulsifier.

[0440] Spray a preparation of the active ingredient at the desired concentration onto sections of leaves of maize (Zea mays). After drying, infest the sections of the leaves with larvae of the fall armyworm (Spodoptera frugiperda).

[0441] After 7 days have passed, the mortality rate (%) of the insects is determined. 100% means that all the Spodoptera litura larvae have died, and 0% means that no Spodoptera litura larvae have died.

[0442] In this test, for example, the following compounds of the preparation examples showed good activity of 100% at an application rate of 100 g / ha: I-001, I-002, I-003, I-004, I-005, I-010, I-013, I-016, I-019, I-020, I-021, I-022.

[0443] In this test, for example, the following compounds of the preparation examples showed good activity of 83% at an application rate of 100 g / ha: I-017, I-018.

[0444] In this test, for example, the following compound of the preparation example showed good activity of 67% at an application rate of 100 g / ha: I-009.

[0445] Aedes aegypti test (AEDSAE surface treatment and contact assay) Solvent: Acetone + 2000 ppm rapeseed methyl ester (RME) To produce a sufficient solution containing the active ingredient, it is necessary to dissolve the test compound in a solvent mixture (acetone 2 mg / mL / RME 2000 ppm). This solution is transferred onto a shiny tile with a pipette, and after the acetone has evaporated, adult mosquitoes of the Aedes aegypti strain MONHEIM are placed on its dried surface. The exposure time is 30 minutes. After 24 hours have passed since the insects were brought into contact with the treated surface, the mortality rate (%) of the insects is determined. A mortality rate of 100% means that all the test insects have died, and 0% means that no insects have died.

[0446] In the following examples, in this test, 20 mg / m 2showed 80 - 100% efficacy at the surface concentration of: I-001, I-002, I-003, I-004, I-007, I-010, I-013, I-016, I-018, I-021.

[0447] The following examples showed 80 - 100% efficacy at the surface concentration of 4 mg / m 2 : I-001, I-002, I-004, I-007, I-008, I-012, I-021.

[0448] Anopheles funestus test (ANPHFU surface treatment and contact assay) Solvent: Acetone + 2000 ppm rapeseed oil methyl ester (RME) To produce a sufficient solution containing the active ingredient, it is necessary to dissolve the test compound in a solvent mixture (acetone 2 mg / mL / RME 2000 ppm). This solution is transferred onto a shiny tile with a pipette. After the acetone has evaporated, adult mosquitoes of the Anopheles funestus strain FUMOZ-R (Hunt et al., Med. Vet. Entomol. 2005 Sep; 19(3): 271 - 275) are placed on the dried surface. The exposure time is 30 minutes. After 24 hours have elapsed since the insects were brought into contact with the treated surface, the mortality rate (%) is determined. A 100% mortality rate means that all the test insects have died, and 0% means that no insects have died.

[0449] The following examples showed 80 - 100% efficacy at the surface concentration of 20 mg / m 2 : I-001, I-007, I-013, I-016, I-018.

[0450] Musca domestica test (MUSCDO surface treatment and contact assay) Solvent: Acetone + 2000 ppm rapeseed oil methyl ester (RME) To produce a sufficient active ingredient-containing solution, it is necessary to dissolve the test compound in a solvent mixture (acetone 2 mg / mL / RME 2000 ppm). This solution is transferred onto a shiny tile with a pipette, and after the acetone has evaporated, adult flies of the WHO-N strain of the Musca domestica species are placed on its dried surface. The exposure time is 30 minutes. After 24 hours have elapsed since the insects were brought into contact with the treated surface, the percentage of dead insects is determined. A 100% dead insect rate means that all the tested insects have died, and 0% means that no insects have died. The following examples showed an efficacy of 80 - 100% at a surface concentration of 20 mg / m 2 : I-001, I-002, I-003, I-010, I-013, I-019, I-021.

[0451] The following examples showed an efficacy of 80 - 100% at a surface concentration of 4 mg / m 2 : I-001, I-003, I-021.

[0452] Blattella germanica test (BLTTGE surface treatment and contact assay) Solvent: Acetone + 2000 ppm rapeseed methyl ester (RME) To produce a sufficient active ingredient-containing solution, it is necessary to dissolve the test compound in a solvent mixture (acetone 2 mg / mL / RME 2000 ppm). This solution is transferred onto a shiny tile with a pipette, and after the acetone has evaporated, adult animals of the PAULINIA strain of the Blattella germanica species are placed on its dried surface. The exposure time is 30 minutes. After 24 hours have elapsed since the insects were brought into contact with the treated surface, the percentage of dead insects is determined. A 100% dead insect rate means that all the tested insects have died, and 0% means that no insects have died. The following examples showed an efficacy of 80 - 100% at a surface concentration of 20 mg / m 2 : I-002, I-003, I-016, I-021. In one aspect, the present invention provides the following. (Item 1) Formula (I)

Chem.

Chem.

Claims

1. Formula (I) 【Chemical 1】 [In the formula,[[]] X is O or S; Y is a direct bond or CH ２ ; R １ is hydrogen; C １ -C ６ alkyl [wherein the alkyl may be substituted with one substituent selected from -CN, -CONH ２ , -COOH, -NO ２ and -Si(CH ３ ) ３ ; C １ -C ６ haloalkyl; C ２ -C ６ alkenyl; C ２ -C ６ haloalkenyl; C ２ -C ６ alkynyl; C ２ -C ６ haloalkynyl; C ３ -C ４ cycloalkyl-C １ -C ２ alkyl-[wherein the C ３ -C ４ cycloalkyl may be substituted with one or two halogen atoms]; oxetan-3-yl-CH ２ -, or benzyl [wherein the benzyl may be substituted with a halogen atom or C １ -C ３ haloalkyl]; R ２ is 3-bromo-5-(trifluoromethoxy)phenyl, 3-bromo-5-chlorophenyl, 3,5-dichlorophenyl, 3,5-dibromophenyl, 2,6-dichloro-pyridin-4-yl, 5-(trifluoromethyl)-pyridin-3-yl or 2-chloro-6-(trifluoromethyl)-pyridin-4-yl; R ３ is C １ -C ３ alkyl or C １ -C ３ is haloalkyl; R ４ is pyridine, pyrimidine, pyrazine or pyridazine, where the pyridine, pyrimidine, pyrazine or pyridazine is C １ -C ３ alkyl, C １ -C ３ haloalkyl, C １ -C ３ alkoxy, C ３ -C ４ cycloalkyl, halogen or hydroxy; R ５ is halogen]] A compound represented by Claim 2 X is O or S; Y is a direct bond or CH ２ ; R １ is hydrogen; C １ -C ３ alkyl [where the alkyl may be substituted with one substituent selected from -CN, -CONH ２ , -COOH, -NO ２ and -Si(CH ３ ) ３ ; C １ -C ３ haloalkyl; C ２ -C ４ alkenyl; C ２ -C ４ haloalkenyl; C ２ -C ４ alkynyl; C ２ -C ４ haloalkynyl; C ３ -C ４ cycloalkyl-C １ -C ２ alkyl - [where the C ３ -C ４ cycloalkyl may be substituted with one or two halogen atoms]; oxetan-3-yl-CH ２—; or benzyl [wherein the benzyl may be substituted with a halogen atom or C １ —C ３ haloalkyl]; R ３ is C １ —C ３ alkyl or C １ —C ３ haloalkyl; R ４ is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine may be substituted with one substituent selected from the group consisting of C １ —C ３ alkyl, C １ —C ３ haloalkyl, C １ —C ３ alkoxy, C ３ —C ４ cycloalkyl, halogen or hydroxy; R ５ is halogen; The compound according to claim 1.

3. X is O; Y is a direct bond; R １ is hydrogen; R ３ is C １ —C ３ alkyl; R ４ is pyridine or pyrimidine, wherein the pyridine or pyrimidine may be substituted with one substituent selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy; R ５ is fluorine, chlorine, bromine or iodine; The compound according to claim 1 or 2.

4. X is O; Y is a direct bond; R １is hydrogen; R ３ is methyl; R ４ is pyrimidin-2-yl or 5-chloro-pyrimidin-2-yl; R ５ is chlorine, bromine or iodine; The compound according to any one of claims 1 to 3.

5. Formula (a) 【Chemical formula 2】 〔In the formula, R １ is hydrogen, R ３ is methyl and Y is a direct bond, R ４ is pyridine or pyrimidine, where the pyridine or pyrimidine may be substituted with one substituent selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, and ethoxy; R ５ is fluorine, chlorine or iodine〕 The compound represented by.

6. Compounds 1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine, 1-(5-iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine, (1S)-1-(5-chloro-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride, (1S)-1-(5-bromo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride, and (1S)-1-(5-iodo-2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine hydrochloride.

7. A preparation comprising at least one compound represented by formula (I) according to any one of claims 1 to 4.

8. Further, a preparation according to claim 7, which contains at least one bulking agent and / or at least one surfactant.

9. A preparation according to claim 7 or 8, characterized in that the compound represented by formula (I) is mixed with at least one further active compound.

10. A method for controlling pests, which comprises applying the compound represented by formula (I) according to any one of claims 1 to 4 or the preparation according to claim 7 or 8 to the pests and / or their habitat, provided that methods of treating the human or animal body by surgery or therapy and diagnostic methods carried out on the human or animal body are excluded.

11. The method according to claim 10, characterized in that the pests are pests and include insects, arachnids or nematodes, or the pests are insects, arachnids or nematodes, provided that methods of treating the human or animal body by surgery or therapy and diagnostic methods carried out on the human or animal body are excluded.

12. Use of the compound represented by formula (I) according to any one of claims 1 to 4 or the preparation according to claim 7 or 8 for controlling pests, provided that use in methods of treating the human or animal body by surgery or therapy and use in diagnostic methods carried out on the human or animal body are excluded.

13. The use according to claim 12, characterized in that the pests include insects, arachnids or nematodes, or the pests are insects, arachnids or nematodes, provided that use in methods of treating the human or animal body by surgery or therapy and use in diagnostic methods carried out on the human or animal body are excluded.

14. Use according to claim 12 or 13 in crop protection.

15. Use according to claim 12 or 13 in the field of animal health, provided that the use in methods of treating the human or animal body by surgery or therapy and the use in diagnostic methods carried out on the human or animal body are excluded.

16. A method for protecting seeds or germinating plants from pests, comprising the method step of contacting the seeds with a compound represented by the formula (I) according to any one of claims 1 to 4 or a formulation according to claim 7 or 8.

17. Seeds obtained by the method according to claim 16.

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