Aryltetrahydropyridine compound and pest control agent

Abstract

The present invention relates to an aryl tetrahydropyridine compound represented by formula (1) or a salt thereof. In formula (1), Q represents Q-1 or the like, J represents J-1 or the like, G represents G-1 or the like, R1 represents a halogenated (C1-C6) alkyl group or the like, R2 represents a hydrogen atom or the like, R3 represents a hydrogen atom or the like, X represents an oxygen atom or the like, Y represents an oxygen atom or the like, and A1 represents a nitrogen atom or the like. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to novel aryltetrahydropyridine compounds and their salts, their production intermediates, and pest control agents, agricultural chemicals, pest control agents, insecticides or miticides, seed treatment agents and soil treatment agents containing the compounds and / or their salts as active ingredients. Background Art

[0002] It is known that certain aryltetrahydropyridine compounds exhibit pest control activity (for example, Patent Documents 1 and 2).

[0003] Prior art literature

[0004] Patent Literature

[0005] Patent Document 1: International Publication No. 2021 / 261562

[0006] Patent Document 2: International Publication No. 2023 / 127806 Summary of the invention

[0007] Problems to be solved by the invention

[0008] However, the long-term use of pesticides has led to the emergence of pests and harmful organisms that have acquired resistance to existing pesticides. Therefore, people often expect to develop a new pesticide with excellent pest control effect.

[0009] Technical means to solve problems

[0010] The inventors of the present invention have conducted intensive studies with the goal of solving the above problems and have found that the novel aryltetrahydropyridine compound represented by the following formula (1) according to the present invention exhibits excellent pest control activity, particularly excellent insecticidal and acaricidal activity, thereby completing the present invention.

[0011] That is, the present invention relates to an aryltetrahydropyridine compound represented by the following formula (1) or a salt thereof.

[0012]

[0013] [wherein, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, Q-26, Q-27, Q-28, Q-29, Q-30, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-48, Q-49, Q-50, Q-51, Q-52, Q-53, Q-54, Q-55 or Q-56,

[0014]

[0015]

[0016] Z 1represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo(C1-C6)alkyl group, a halo(C2-C6)alkenyl group, a halo(C2-C6)alkynyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C2-C6 alkoxy(C1-C6)alkoxy group, a C2-C6 alkenyloxy group, a halo(C2-C6)alkenyloxy group, a C2-C6 alkynyloxy group, a halo(C2-C6)alkynyloxy group, a C1-C6 Alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated (C1-C6) alkylthio, halogenated (C1-C6) alkylsulfinyl, halogenated (C1-C6) alkylsulfonyl, C2-C6 alkenylthio, C2-C6 alkenylsulfinyl, C2-C6 alkenylsulfonyl, halogenated (C2-C6) alkenylthio, halogenated (C2-C6) alkenylsulfinyl, halogenated (C2-C6) alkenylsulfonyl, C2-C6 alkynylthio, C2-C6 C2-C6 alkynylsulfinyl, C2-C6 alkynylsulfonyl, halo (C2-C6) alkynylthio, halo (C2-C6) alkynylsulfinyl, halo (C2-C6) alkynylsulfonyl, -NH2, C1-C6 alkylamino, di (C1-C6) alkylamino, halo (C1-C6) alkylamino, dihalo (C1-C6) alkylamino, formyl, carboxyl, C1-C6 alkylcarbonyl, halo (C1-C6) alkylcarbonyl, C1-C6 alkoxy alkylcarbonyl, halogenated (C1-C6) alkoxycarbonyl, C1-C6 alkylaminocarbonyl, halogenated (C1-C6) alkylaminocarbonyl, di(C1-C6) alkylaminocarbonyl, hydroxy, C1-C6 alkylcarbonyloxy, C1-C6 alkoxycarbonyloxy, C1-C6 alkylsulfonyloxy, halogenated (C1-C6) alkylsulfonyloxy, -SO3H, C1-C6 alkylaminosulfonyl, di(C1-C6) alkylaminosulfonyl, -C(=NOR 12 )R 13 , cyano or nitro,

[0017] R 12 represents a hydrogen atom or a C1-C6 alkyl group,

[0018] R 13 represents a hydrogen atom or a C1-C6 alkyl group,

[0019] Z 3 represents a hydrogen atom or a C1-C6 alkyl group,

[0020] J stands for J-1 or J-2,

[0021]

[0022] A 1 represents a nitrogen atom or CH,

[0023] G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G-32, G-33, G-34, G-35, G-36, G-37, G-38, G-39, G-40, G-41, G-42, G-43, G-44, G-45, G-46, G-47, G-48, G-49, G-50, G-51, G-52, G-53, G-54, G-55, G-56, G-57, G-58, G-59, G-60 or G-61,

[0024]

[0025] Z 2represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo(C1-C6)alkyl group, a halo(C2-C6)alkenyl group, a halo(C2-C6)alkynyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkoxy(C1-C6)alkoxy group, a C2-C6 alkenyloxy group, a halo(C2-C6)alkenyloxy group, a C2-C6 alkynyloxy group, a halo(C2-C6)alkynyloxy group, a C1-C6 Alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated (C1-C6) alkylthio, halogenated (C1-C6) alkylsulfinyl, halogenated (C1-C6) alkylsulfonyl, C2-C6 alkenylthio, C2-C6 alkenylsulfinyl, C2-C6 alkenylsulfonyl, halogenated (C2-C6) alkenylthio, halogenated (C2-C6) alkenylsulfinyl, halogenated (C2-C6) alkenylsulfonyl, C2-C6 alkynylthio, C2-C6 C2-C6 alkynylsulfinyl, C2-C6 alkynylsulfonyl, halo (C2-C6) alkynylthio, halo (C2-C6) alkynylsulfinyl, halo (C2-C6) alkynylsulfonyl, -NH2, C1-C6 alkylamino, di (C1-C6) alkylamino, halo (C1-C6) alkylamino, dihalo (C1-C6) alkylamino, formyl, carboxyl, C1-C6 alkylcarbonyl, halo (C1-C6) alkylcarbonyl, C1-C6 alkoxy alkylcarbonyl, halogenated (C1-C6) alkoxycarbonyl, C1-C6 alkylaminocarbonyl, halogenated (C1-C6) alkylaminocarbonyl, di(C1-C6) alkylaminocarbonyl, hydroxy, C1-C6 alkylcarbonyloxy, C1-C6 alkoxycarbonyloxy, C1-C6 alkylsulfonyloxy, halogenated (C1-C6) alkylsulfonyloxy, -SO3H, C1-C6 alkylaminosulfonyl, di(C1-C6) alkylaminosulfonyl, -C(=NOR 14 )R 15 , nitro or cyano,

[0026] R 14 represents a hydrogen atom or a C1-C6 alkyl group,

[0027] R 15 represents a hydrogen atom or a C1-C6 alkyl group,

[0028] Z 4 represents a C1-C6 alkyl group,

[0029] R 1 represents a hydrogen atom, a halogen atom, a halogenated (C1-C6) alkyl group, a C1-C6 alkyl group or a cyano group,

[0030] R 2represents a hydrogen atom, a C1-C6 alkyl group, a halogenated (C1-C6) alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, -C(O)R 4 、-C(O)OR 5 , D-1, D-2 or D-3,

[0031]

[0032] R 4 represents a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylcarbonyl group, a di(C1-C6)alkylamino group, or is replaced by R 6 Substituted (C1-C6) alkyl,

[0033] R 6 represents a halogen atom, a C1-C6 alkoxy group, a cyano group, a nitro group, a phenyl group, or a 8 Substituted phenyl,

[0034] Z 5 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a cyano group or a nitro group,

[0035] R 8 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a cyano group or a nitro group,

[0036] R 5 represents a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, 9 Substituted (C1-C6) alkyl, phenyl or R 10 Substituted phenyl,

[0037] R 9 represents a halogen atom, a C1-C6 alkoxy group, a cyano group, a nitro group, a phenyl group, or a 11 Substituted phenyl,

[0038] R 10 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a cyano group or a nitro group,

[0039] R 11 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a cyano group or a nitro group,

[0040] R 3 represents a hydrogen atom, a C1-C6 alkyl group, a halogenated (C1-C6) alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group or a C1-C6 alkylcarbonyl group,

[0041] X represents an oxygen atom or a sulfur atom,

[0042] Y represents an oxygen atom or a sulfur atom,

[0043] t1 represents an integer of 0 or 1,

[0044] t2 represents an integer of 0, 1 or 2,

[0045] t3 represents an integer of 0, 1, 2 or 3,

[0046] t4 represents an integer of 0, 1, 2, 3 or 4,

[0047] t5 represents an integer of 0, 1, 2, 3, 4 or 5,

[0048] t8 represents an integer of 0, 1, 2, 3 or 4.]

[0049] Effects of the Invention

[0050] The compound represented by formula (1) according to the present invention exhibits excellent insecticidal and acaricidal activity against many agricultural pests, spider mites, and internal or external parasites of mammals or birds. Therefore, the present invention can provide a novel aryltetrahydropyridine compound or a salt thereof which is useful as a pest control agent, particularly an insecticide. DETAILED DESCRIPTION

[0051] In the compound of the present invention represented by formula (1) (hereinafter also referred to as "the compound of the present invention"), it is considered that there are tautomers represented by the following formulas, and the compound of the present invention represented by formula (1) includes all tautomers or a mixture of tautomers contained in any ratio.

[0052]

[0053] The compounds of the present invention may have E-isomers and Z-isomers in geometrical isomers depending on the types of substituents. The compounds of the present invention include these E-isomers, Z-isomers, or mixtures containing the E-isomers and Z-isomers in any ratio.

[0054] In addition, the compound of the present invention has optically active forms due to the presence of one or two or more asymmetric carbon atoms or asymmetric sulfur atoms, and the compound of the present invention includes all optically active forms or racemic forms.

[0055] In addition, the compounds of the present invention may exist in tautomers depending on the types of substituents, and the compounds of the present invention include all tautomers or mixtures of tautomers in any ratio.

[0056] In addition, since bond rotation is restricted due to steric hindrance between substituents, the compounds of the present invention may exist in the form of one or more rotational isomers. The compounds of the present invention include all rotational isomers or mixtures of diastereomers in any ratio.

[0057] Among the compounds of the present invention, the compounds that can form salts according to conventional methods can be formed into, for example: salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydroiodic acid; salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, and perchloric acid; salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid; salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, and citric acid; salts of amino acids such as glutamic acid and aspartic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium, barium, and magnesium; aluminum salts; and quaternary ammonium salts such as tetramethylammonium salts, tetrabutylammonium salts, and benzyltrimethylammonium salts.

[0058] Next, specific examples of each substituent shown in the present specification are shown below: Here, n- represents normal, i- represents iso, s- represents secondary, and tert- represents tertiary.

[0059] Examples of the "halogen atom" in the present specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. It should be noted that the term "halogeno" in the present specification also refers to these halogen atoms.

[0060] In this manual, “C a ~C b The expression "alkyl" means a straight-chain or branched hydrocarbon group having a to b carbon atoms, and specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, n-hexyl, etc., and the group can be selected within the range of the number of carbon atoms specified for each.

[0061] In this specification, the term "halogenated (C a ~C bThe expression "alkyl" means a linear or branched hydrocarbon group having a to b carbon atoms in which hydrogen atoms bonded to carbon atoms are arbitrarily replaced by halogen atoms. In this case, when the alkyl group is substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. Specific examples include fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl, 2-bromo-2,2-difluoroethyl, 1,1,2,2 The following examples include tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-chloro-1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 2,2-difluoropropyl, 3,3,3-trifluoropropyl, 3-bromo-3,3-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 2,2,2-trifluoro-1-(methyl)ethyl, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, and nonafluorobutyl, and the like can be selected within the range of the number of carbon atoms specified in each.

[0062] In this manual, “C a ~C b The expression "alkenyl" means a linear or branched unsaturated hydrocarbon group having a to b carbon atoms and having one or more double bonds in the molecule. Specific examples include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 2-butenyl, 2-methyl-2-propenyl, 3-methyl-2-butenyl, 1,1-dimethyl-2-propenyl, etc., and the group can be selected within the range of the number of carbon atoms specified by each.

[0063] In this specification, the term "halogenated (C a ~C bThe expression "alkenyl" means an unsaturated hydrocarbon group having a to b carbon atoms, in which the hydrogen atoms bonded to the carbon atoms are arbitrarily replaced by halogen atoms, and having one or more double bonds in the molecule. In this case, when the alkenyl group is substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. Specific examples include: 2,2-dichlorovinyl, 2-fluoro-2-propenyl, 2-chloro-2-propenyl, 3-chloro -2-propenyl, 2-bromo-2-propenyl, 3,3-difluoro-2-propenyl, 2,3-dichloro-2-propenyl, 3,3-dichloro-2-propenyl, 2,3,3-trifluoro-2-propenyl, 2,3,3-trichloro-2-propenyl, 1-(trifluoromethyl)vinyl, 4,4-difluoro-3-butenyl, 3,4,4-trifluoro-3-butenyl, 3-chloro-4,4,4-trifluoro-2-butenyl, etc. can be selected within the range of the number of carbon atoms specified in each.

[0064] In this manual, “C a ~C b The expression "alkynyl" means a linear or branched unsaturated hydrocarbon group having a to b carbon atoms and having one or more triple bonds in the molecule. Specific examples include ethynyl, propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-hexynyl, etc., and the group can be selected within the range of the number of carbon atoms specified by each.

[0065] In this specification, the term "halogenated (C a ~C b The expression "alkynyl" means an unsaturated hydrocarbon group having a to b carbon atoms, in which the hydrogen atoms bonded to the carbon atoms are arbitrarily replaced by halogen atoms, which is a straight-chain or branched unsaturated hydrocarbon group and has one or more triple bonds in the molecule. In this case, when the alkynyl group is substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. Specific examples include 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 3-iodo-2-propynyl, etc., which can be selected within the range of the number of carbon atoms specified by each.

[0066] In this manual, “C a ~C b The expression "alkoxy" means an alkyl-O-group having the above-mentioned carbon number of a to b, and specific examples thereof include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, 2-ethylhexyloxy, etc., and the group can be selected within the range of the number of carbon atoms specified for each.

[0067] In this specification, "halogenated C a ~C bThe expression "alkoxy" means a haloalkyl-O-group having the above-mentioned meaning and having a carbon number of a to b. Specific examples thereof include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, and 1,1,2,3,3,3-hexafluoropropoxy, and the like can be selected within the range of the carbon number specified by each.

[0068] In this manual, “C a ~C b Alkoxy (C d ~C e The expression "alkoxy" means that the hydrogen atoms bonded to the carbon atoms are replaced by any C a ~C b Specific examples of the alkoxy group having the above meaning and having d to e carbon atoms, which is optionally substituted by an alkoxy group, include methoxymethoxy and 2-methoxyethoxy, and the group can be selected within the range of the number of carbon atoms specified for each.

[0069] In this manual, “C a ~C b The expression "alkenyloxy" means an alkenyl-O-group having the above meaning and having a to b carbon atoms, and specific examples thereof include 2-propenyloxy, 2-butenyloxy, 2-methyl-2-propenyloxy, 3-methyl-2-butenyloxy, etc., and the group can be selected within the range of the number of carbon atoms specified for each.

[0070] In this specification, the term "halogenated (C a ~C b The expression "alkenyloxy" means a haloalkenyl-O-group having a to b carbon atoms, and specific examples thereof include 3,3-difluoroallyloxy and 3,3-dichloroallyloxy, and the like, which can be selected within the range of the number of carbon atoms specified for each.

[0071] In this manual, “C a ~C b The expression "alkynyloxy" means an alkynyl-O- group having the above meaning and having a to b carbon atoms, and specific examples thereof include ethynyloxy, propynyloxy, 2-butynyloxy, 1-pentynyloxy, 1-hexynyloxy, etc., and the group can be selected within the range of the number of carbon atoms specified for each.

[0072] In this specification, the term "halogenated (C a ~C bThe expression "alkynyloxy" means a haloalkynyl-O-group having the above-mentioned carbon number of a to b, and specific examples thereof include 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy, 3-iodo-2-propynyloxy, etc., which can be selected within the range of the carbon number specified by each.

[0073] In this manual, “C a ~C b The expression "alkylthio" means an alkyl-S- group having the above meaning and having a to b carbon atoms, and specific examples thereof include methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, etc., and the group can be selected within the range of the number of carbon atoms specified for each.

[0074] In this specification, the term "halogenated (C a ~C b The expression "alkylthio" means a haloalkyl-S- group having the above-mentioned meaning and having a carbon number of a to b. Specific examples thereof include difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, pentafluoroethylthio, 1,1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylthio, nonafluorobutylthio and the like, and the group can be selected within the range of the carbon number specified by each.

[0075] In this manual, “C a ~C b The expression "alkenylthio" means an alkenyl-S-group having the above meaning and having a to b carbon atoms, and specific examples thereof include 2-propylenethio, 2-butylenethio, 2-methyl-2-propylenethio, 3-methyl-2-butylenethio, etc., and the group can be selected within the range of the number of carbon atoms specified for each.

[0076] In this specification, the term "halogenated (C a ~C b The expression "alkenylthio" means a haloalkenyl-S- group having the above-mentioned meaning and having a to b carbon atoms, and specific examples thereof include 2-fluoro-2-propylenethio, 2-chloro-2-propylenethio, 3,3-difluoro-2-propylenethio, 3,3-dichloro-2-propylenethio, 2,3,3-trifluoro-2-propylenethio, 4,4-difluoro-3-butylenethio, 3,4,4-trifluoro-3-butylenethio, and the like, and the group can be selected within the range of the number of carbon atoms specified by each.

[0077] In this manual, “C a ~C bThe expression "alkynylthio" means an alkynyl-S- group having the above meaning and having a to b carbon atoms, and specific examples thereof include propynylthio, butynylthio, pentynylthio, hexynylthio, etc., and the group can be selected within the range of the number of carbon atoms specified for each.

[0078] In this specification, the term "halogenated (C a ~C b The expression "alkynylthio" means a haloalkynyl-S- group having the above meaning and having a carbon number of a to b. Specific examples thereof include 3-chloro-2-propynylthio, 3-bromo-2-propynylthio, 3-iodo-2-propynylthio, etc., which can be selected within the range of the carbon number specified by each.

[0079] In this manual, “C a ~C b The expression "alkylsulfinyl" means an alkyl-S(O)- group having the above meaning and having a to b carbon atoms. Specific examples thereof include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl and the like, and the group can be selected within the range of the number of carbon atoms specified by each.

[0080] In this specification, the term "halogenated (C a ~C b The expression "haloalkyl-S(O)- group" means a haloalkyl-S(O)- group having the above-mentioned carbon number of a to b, and specific examples thereof include difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylsulfinyl, nonafluorobutylsulfinyl and the like, and the group can be selected within the range of the number of carbon atoms specified by each.

[0081] In this manual, “C a ~C b The expression "alkenylsulfinyl" means an alkenyl-S(O)- group having the above meaning and having a to b carbon atoms. Specific examples thereof include 2-propenylsulfinyl, 2-butenylsulfinyl, 2-methyl-2-propenylsulfinyl, 3-methyl-2-butenylsulfinyl, etc., and the group can be selected within the range of the number of carbon atoms specified by each.

[0082] In this specification, the term "halogenated (C a ~C bThe expression "haloalkenyl-S(O)- group" means a haloalkenyl-S(O)- group having the above-mentioned carbon number of a to b. Specific examples thereof include 2-fluoro-2-propenylsulfinyl, 2-chloro-2-propenylsulfinyl, 3,3-difluoro-2-propenylsulfinyl, 3,3-dichloro-2-propenylsulfinyl, 4,4-difluoro-3-butenylsulfinyl and 3,4,4-trifluoro-3-butenylsulfinyl, and the like, and the group can be selected within the range of the number of carbon atoms specified by each.

[0083] In this manual, “C a ~C b The expression "alkynylsulfinyl" means an alkynyl-S(O)- group having the above meaning and having a to b carbon atoms. Specific examples thereof include 2-propynylsulfinyl and 2-butynylsulfinyl, and the group can be selected within the range of the number of carbon atoms specified for each.

[0084] In this specification, the term "halogenated (C a ~C b The expression "halogenated alkynyl-S(O)- group" means a haloalkynyl-S(O)- group having the above-mentioned carbon number of a to b, and specific examples thereof include 3-chloro-2-propynylsulfinyl, 3-bromo-2-propynylsulfinyl, 3-iodo-2-propynylsulfinyl, etc., which can be selected within the range of the number of carbon atoms specified by each.

[0085] In this manual, “C a ~C b The expression "alkylsulfonyl" means an alkyl-SO2- group having the above meaning and having a to b carbon atoms. Specific examples thereof include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, etc., and the group can be selected within the range of the number of carbon atoms specified by each.

[0086] In this specification, the term "halogenated (C a ~C b The expression "alkylsulfonyl" means a halogenated alkyl-SO2- group having the above-mentioned carbon number of a to b. Specific examples thereof include difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl and 2-chloro-1,1,2-trifluoroethylsulfonyl. The groups can be selected within the range of the carbon number specified by each.

[0087] In this manual, “C a ~C bThe expression "alkenylsulfonyl" means an alkenyl-SO2- group having the above meaning and having a to b carbon atoms. Specific examples thereof include 2-propenylsulfonyl, 2-butenylsulfonyl, 2-methyl-2-propenylsulfonyl, 3-methyl-2-butenylsulfonyl, etc., and the group can be selected within the range of the number of carbon atoms specified for each.

[0088] In this specification, the term "halogenated (C a ~C b The expression "alkenylsulfonyl" means a haloalkenyl-SO2- group having the above-mentioned meaning and having a to b carbon atoms. Specific examples thereof include 2-fluoro-2-propenylsulfonyl, 2-chloro-2-propenylsulfonyl, 3,3-difluoro-2-propenylsulfonyl, 3,3-dichloro-2-propenylsulfonyl, 4,4-difluoro-3-butenylsulfonyl and 3,4,4-trifluoro-3-butenylsulfonyl, and the like, and the group can be selected within the range of the number of carbon atoms specified by each.

[0089] In this manual, “C a ~C b The expression "alkynylsulfonyl" means an alkynyl-SO2- group having the above meaning and having a to b carbon atoms. Specific examples thereof include 2-propynylsulfonyl and 2-butynylsulfonyl, and the group can be selected within the range of the number of carbon atoms specified for each.

[0090] In this specification, the term "halogenated (C a ~C b The expression "alkynylsulfonyl" means a haloalkynyl-SO2- group having the above-mentioned meaning and having a to b carbon atoms. Specific examples thereof include 3-chloro-2-propynylsulfonyl, 3-bromo-2-propynylsulfonyl, 3-iodo-2-propynylsulfonyl, etc., and the group can be selected within the range of the number of carbon atoms specified by each.

[0091] In this manual, “C a ~C b The expression "alkylamino" means an amino group in which one hydrogen atom is substituted by an alkyl group having the above-mentioned meaning and having a to b carbon atoms. Specific examples thereof include methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, tert-butylamino, etc., and the group can be selected within the range of the number of carbon atoms specified for each.

[0092] In this specification, the term "halogenated (C a ~C bThe expression "alkylamino" means an amino group in which one hydrogen atom is substituted by a haloalkyl group having the above-mentioned meaning and having a to b carbon atoms. Specific examples thereof include 2,2,2-trifluoroethylamino, 2-chloro-2,2-difluoroethylamino, 3,3,3-trifluoropropylamino, etc., and the group can be selected within the range of the number of carbon atoms specified by each.

[0093] In this specification, “two (C a ~C b The expression "(1)alkylamino" means an amino group in which both hydrogen atoms are substituted by an alkyl group having the above-mentioned meaning and having a to b carbon atoms. The alkyl groups may be the same as or different from each other. Specific examples include dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, isopropyl(methyl)amino, di(n-propyl)amino, di(n-butyl)amino, etc., and the group may be selected within the range of the number of carbon atoms specified by each.

[0094] In this specification, the term "dihalogenated (C a ~C b The expression "(2,2,2-trifluoroethyl)amino" means an amino group in which both hydrogen atoms are substituted by a haloalkyl group having the above-mentioned meaning and having a to b carbon atoms. The alkyl groups may be the same as or different from each other. Specific examples thereof include bis(2,2,2-trifluoroethyl)amino, and the like. The groups may be selected within the range of the number of carbon atoms specified for each group.

[0095] In this manual, “C a ~C b The expression "cycloalkyl" means a cyclic saturated hydrocarbon group having a to b carbon atoms, which can form a single ring or a compound ring structure of 3 to 10 members. In addition, each ring can be arbitrarily substituted by an alkyl group within the range of the specified number of carbon atoms. Specific examples include: cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., which can be selected within the range of the specified number of carbon atoms.

[0096] In this manual, “C a ~C b The expression "alkylcarbonyl" means an alkyl-C(O)- group having the above meaning and having a to b carbon atoms. Specific examples thereof include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutyryl, pivaloyl, hexanoyl, heptanoyl and the like, and the group can be selected within the range of the number of carbon atoms specified for each.

[0097] In this specification, the term "halogenated (C a ~C bThe expression "haloalkyl-C(O)- group" means a haloalkyl-C(O)- group having the above-mentioned carbon number of a to b, and specific examples thereof include fluoroacetyl, chloroacetyl, difluoroacetyl, dichloroacetyl, trifluoroacetyl, chlorodifluoroacetyl, bromodifluoroacetyl, trichloroacetyl, pentafluoropropionyl, heptafluorobutyryl, 3-chloro-2,2-dimethylpropionyl, etc., and the group can be selected within the range of the number of carbon atoms specified by each.

[0098] In this manual, “C a ~C b The expression "alkoxycarbonyl" means an alkyl-OC(O)- group having the above meaning and having a to b carbon atoms, and specific examples thereof include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, 2-ethylhexyloxycarbonyl, etc., and the group can be selected within the range of the number of carbon atoms specified by each.

[0099] In this specification, the term "halogenated (C a ~C b The expression "halogenated alkyl-OC(O)- group" means a haloalkyl-OC(O)- group having a to b carbon atoms, and specific examples thereof include chloromethoxycarbonyl, 2-chloroethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, etc., and the group can be selected within the range of the number of carbon atoms specified by each.

[0100] In this manual, “C a ~C b The expression "alkylaminocarbonyl" means a carbamoyl group in which one hydrogen atom is substituted by an alkyl group having the above-mentioned meaning and having a to b carbon atoms. Specific examples thereof include methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, isopropylcarbamoyl, n-butylcarbamoyl, isobutylcarbamoyl, sec-butylcarbamoyl and tert-butylcarbamoyl, and the like can be selected within the range of the number of carbon atoms specified by each.

[0101] In this specification, the term "halogenated (C a ~C b The expression "alkylaminocarbonyl" means a carbamoyl group in which one hydrogen atom is substituted by a haloalkyl group having the above-mentioned meaning and having a carbon number of a to b. Specific examples thereof include 2-fluoroethylcarbamoyl, 2-chloroethylcarbamoyl, 2,2-difluoroethylcarbamoyl, 2,2,2-trifluoroethylcarbamoyl, etc., and the group can be selected within the range of the number of carbon atoms specified by each.

[0102] In this specification, “two (C a ~C bThe expression "(1)alkylaminocarbonyl" means a carbamoyl group in which both hydrogen atoms are substituted by an alkyl group having the above meaning and having a to b carbon atoms, and the alkyl groups may be the same as or different from each other. Specific examples include N,N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N,N-di(n-propyl)carbamoyl, N,N-di(n-butyl)carbamoyl, etc., which can be selected within the range of the number of carbon atoms specified by each.

[0103] In this manual, “C a ~C b The expression "alkylcarbonyloxy" means an alkyl-C(O)-O- group having the above meaning and having a to b carbon atoms. Specific examples include acetoxy, propionyloxy, butyryloxy, isobutyryloxy, etc., and the group can be selected within the range of the number of carbon atoms specified for each.

[0104] In this manual, “C a ~C b The expression "alkoxycarbonyloxy" means an alkoxy-C(O)-O- group having the above meaning and having a to b carbon atoms, and specific examples thereof include methoxycarbonyloxy, ethoxycarbonyloxy, isobutoxycarbonyloxy, tert-butoxycarbonyloxy, etc., and the group can be selected within the range of the number of carbon atoms specified by each.

[0105] In this manual, “C a ~C b The expression "alkylsulfonyloxy" means an alkylsulfonyl-O-group having the above meaning and having a to b carbon atoms. Specific examples thereof include methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, isopropylsulfonyloxy, etc., and the group can be selected within the range of the number of carbon atoms specified by each group.

[0106] In this specification, the term "halogenated (C a ~C b The expression "alkylsulfonyloxy" means a halogenated alkylsulfonyl-O-group having the above-mentioned carbon number of a to b, and specific examples thereof include difluoromethylsulfonyloxy, trifluoromethylsulfonyloxy, chlorodifluoromethylsulfonyloxy, bromodifluoromethylsulfonyloxy, etc., and the group can be selected within the range of the number of carbon atoms specified by each.

[0107] In this manual, “C a ~C bThe expression "alkylaminosulfonyl" means an aminosulfonyl group in which one hydrogen atom is substituted by an alkyl group having the above meaning and having a to b carbon atoms. Specific examples thereof include methylaminosulfonyl, ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl, n-butylaminosulfonyl, isobutylaminosulfonyl, sec-butylaminosulfonyl and tert-butylaminosulfonyl, and the like can be selected within the range of the number of carbon atoms specified by each.

[0108] In this specification, “two (C a ~C b The expression "(1)alkylaminosulfonyl" means an aminosulfonyl group in which both hydrogen atoms are substituted by an alkyl group having the above meaning and having a to b carbon atoms, wherein the alkyl groups may be the same as or different from each other, and specific examples thereof include N,N-dimethylaminosulfonyl, N-ethyl-N-methylaminosulfonyl, N,N-diethylaminosulfonyl, N,N-di(n-propyl)aminosulfonyl, and N,N-di(n-butyl)aminosulfonyl, and the like, and the groups may be selected within the range of the number of carbon atoms specified by each group.

[0109] In this manual, “C a ~C b The expression "cycloalkylcarbonyl" means a cycloalkyl-C(O)- group having the above meaning and having a to b carbon atoms. Specific examples thereof include cyclopropylcarbonyl, 2-methylcyclopropylcarbonyl, cyclobutylcarbonyl, etc., and the group can be selected within the range of the number of carbon atoms specified for each.

[0110] In this specification, the term "halogenated (C a ~C b The expression "cycloalkylcarbonyl" means a halogenated cycloalkyl-C(O)- group having the above-mentioned carbon number of a to b, and specific examples thereof include 2,2-dichlorocyclopropylcarbonyl and 2,2-dichloro-1-methylcyclopropylcarbonyl, which can be selected within the range of the carbon number specified for each.

[0111] In this manual, “ 6 Replaced (C a ~C b The expression "alkyl" means that any hydrogen atom bonded to a carbon atom is replaced by one or more substituents R 6 The alkyl group having a to b carbon atoms which is partially or fully substituted can be selected within the range of the number of carbon atoms specified. 6 When there are two or more substituents, 6 They may be the same as or different from each other.

[0112] In this manual, “ 8The expression "substituted phenyl" means that any hydrogen atom bonded to a carbon atom is replaced by one or more substituents R 8 In this case, the substituent R 8 When there are two or more substituents, 8 They may be the same as or different from each other.

[0113] In this manual, “ 9 Replaced (C a ~C b The expression "alkyl" means that any hydrogen atom bonded to a carbon atom is replaced by one or more substituents R 9 The alkyl group having a to b carbon atoms which is partially or fully substituted can be selected within the range of the number of carbon atoms specified. 9 When there are two or more substituents, 9 They may be the same as or different from each other.

[0114] In this manual, “ 10 The expression "substituted phenyl" means that any hydrogen atom bonded to a carbon atom is replaced by one or more substituents R 10 In this case, the substituent R 10 When there are two or more substituents, 10 They may be the same as or different from each other.

[0115] In this manual, “ 11 The expression "substituted phenyl" means that any hydrogen atom bonded to a carbon atom is replaced by one or more substituents R 11 In this case, the substituent R 11 When there are two or more substituents, 11 They may be the same as or different from each other.

[0116] Next, the method for producing the compound of the present invention represented by formula (1) is described as follows. The compound of the present invention can be produced, for example, by the following method. It should be noted that the following description is only for illustration, and the compound of the present invention represented by formula (1) can also be produced by other methods. Hereinafter, "the compound of the present invention represented by formula (1)" is also recorded as "the compound of the present invention (1)", and in addition, "the compound represented by formula (2)" is also recorded as "compound (2)". Other compounds are also recorded in the same manner.

[0117] [Manufacturing method 1]

[0118] The compound (1) of the present invention can be produced by reacting the compound (2) with the compound (3).

[0119]

[0120] (wherein, Ja represents Ja-1 or Ja-2,

[0121]

[0122] J, Q, G, X, Y, A 1 , R 1 , R 2 and R 3 represents the same meaning as above, Ga represents a halogen atom, etc., and Gb represents B(OH)2, etc.)

[0123] The compound (1) of the present invention can be produced by reacting the compound (2) with the compound (3) in a solvent or in the absence of a solvent.

[0124] When a solvent is used, the solvent used may be any solvent that is inactive in the reaction, and examples thereof include: alcohol solvents such as water, methanol, and ethanol; ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane; aromatic hydrocarbon solvents such as benzene, xylene, and toluene; aliphatic hydrocarbon solvents such as pentane, hexane, and cyclohexane; halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1,2-dichloroethane; nitrile solvents such as acetonitrile and propionitrile; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and N,N'-dimethylimidazolidinone; dimethyl sulfoxide or a mixed solvent thereof, etc.

[0125] This reaction can also be carried out using a base. Examples of the base that can be used include organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), and 1,5-diazabicyclo[4.3.0]-5-nonene (DBN); inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate, cesium carbonate, and potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. The amount (equivalent) of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2).

[0126] The reaction can be carried out in the presence of a palladium catalyst. Examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (2valent) dichloromethane adduct. The amount of the palladium catalyst used can be 0.005 to 20 equivalents relative to 1 equivalent of compound (2).

[0127] This reaction can be carried out in the presence of a ligand. Examples of the ligand include 1,1'-bis(diphenylphosphino)ferrocene, etc. The ligand can be used in an amount of 0.005 to 20 equivalents based on 1 equivalent of the compound (2).

[0128] The reaction temperature can be set to any temperature from -78°C to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, and can generally be set to any time within the range of 5 minutes to 100 hours.

[0129] Compound (2) can be produced according to a known method known in the literature, for example, a method described in International Publication No. 2021 / 261562.

[0130] Some of the compounds (3) are known compounds, and some are commercially available. Other compounds can be produced by synthetic methods of known compounds.

[0131] [Manufacturing method 2]

[0132] The compound (1) of the present invention can be produced by reacting the compound (4) with the compound (5).

[0133]

[0134] (In the formula, J, Q, X, Y, R 2 and R 3 represents the same meaning as above, and Qa represents a C1-C6 alkoxy group. )

[0135] The compound (1) of the present invention can be produced by reacting the compound (4) with the compound (5) in a solvent or without a solvent.

[0136] When a solvent is used, the solvent used may be inert in the reaction, and examples thereof include the solvents exemplified in Production Method 1.

[0137] This reaction can also be carried out using a base. Examples of the base that can be used include the bases exemplified in Production Method 1. The base can be used in an amount (equivalent) of 0.1 to 100 equivalents based on 1 equivalent of Compound (4).

[0138] The reaction temperature can be set to any temperature from -78°C to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, and can generally be set to any time within the range of 5 minutes to 100 hours.

[0139] Compound (4) can be produced according to a known method known in the literature, for example, a method described in International Publication No. 2021 / 261562.

[0140] Some of the compounds (5) are known compounds, and some are commercially available. Other compounds can be produced by synthetic methods of known compounds.

[0141] [Manufacturing method 3]

[0142] Among the compounds (1) of the present invention, a compound (1a) wherein J represents J-2 can be produced by reacting a compound (6).

[0143]

[0144] (In the formula, Q, G, X, Y, R 2 and R 3 Means the same as above.)

[0145] Compound (1a) can be produced by reacting Compound (6) in a solvent or without a solvent.

[0146] When a solvent is used, the solvent used may be inactive in the reaction, and examples thereof include the solvents exemplified in Production Method 1.

[0147] This reaction can also be carried out using a base. Examples of the base that can be used include the bases exemplified in Production Method 1. The base can be used in an amount (equivalent) of 0.1 to 100 equivalents based on 1 equivalent of Compound (6).

[0148] The reaction temperature can be set to any temperature from -78°C to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, and can generally be set to any time within the range of 5 minutes to 100 hours.

[0149] The compound (6) used in the production method 3 can be produced according to the following reaction formula.

[0150]

[0151] (In the formula, Q, G, X, Y, R 2 and R 3 represents the same meaning as above, and Jb represents a C1-C6 alkyl group. )

[0152] [Manufacturing process 1]

[0153] Compound (8) can be produced by reacting Compound (9) with Compound (5) according to a known method known in the literature, for example, the method described in International Publication No. 2016 / 118611.

[0154] Some of the compounds (9) are known compounds, and some are commercially available. Other compounds can be prepared by known methods described in literature, for example, the method described in The Journal of Organic Chemistry, 2004, Vol. 69, Items 130-141.

[0155] [Manufacturing process 2]

[0156] Compound (7) can be produced by reacting Compound (8) according to a known method known in the literature, for example, the method described in The Journal of Organic Chemistry, 2006, Vol. 24, Items 9045 to 9050.

[0157] [Manufacturing process 3]

[0158] Compound (6) can be produced by reacting Compound (7) with Compound (10) according to a known method known in the literature, for example, the method described in Synthetic Communications, 2006, Vol. 36, Items 729-741.

[0159] Some of the compounds (10) are known compounds, and some of them can be obtained as commercial products. In addition, the other substances can be prepared according to known methods recorded in the literature, for example, the method described in Bioorganic & Medicinal Chemistry, 2018, Vol. 26, Items 1713-1726.

[0160] In the reactions of manufacturing methods 1 to 3 and reaction formula 1, the reaction mixture after the reaction is completed is directly concentrated, or dissolved in an organic solvent and concentrated after washing, or put into ice water and concentrated after organic solvent extraction, etc., to obtain the target compound of the present invention. In addition, when purification is required, it can be separated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography, liquid chromatography fractionation, etc.

[0161] Examples of the production intermediates of the compounds of the present invention that can be produced by these methods include the compounds shown in Tables 1 to 6.

[0162] In addition, the descriptions of Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, Q-10 and Q-12a in the table represent the following structures.

[0163]

[0164] In addition, G-1, G-2, G-3 and G-7 in the table respectively represent the following structures.

[0165]

[0166] It should be noted that the numbers in the above structural formula represent substituents (Z 1 ) t2 ,(Z 1 ) t3 ,(Z 1 ) t4 ,(Z 1 ) t5 ,(Z 2 ) t4 or (Z 2 ) t5 The number of the substitution position, for example, in the table, "Q-1(4-F)" represents "4-fluorophenyl" and "Q-1" represents "phenyl".

[0167] [Table 1]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174] [Table 2]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181] [Table 3]

[0182]

[0183]

[0184] [Table 4]

[0185]

[0186] [Table 5]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193] [Table 6]

[0194]

[0195]

[0196]

[0197] The pest control agent in the present invention refers to a pest control agent targeting harmful arthropods in the agricultural and horticultural fields or the livestock and health fields (targeting internal and external parasites of mammals or birds as livestock and pets, household and commercial sanitary pests, and annoying pests).

[0198] In addition, the agricultural chemicals in the present invention refer to insecticides, acaricides, nematicides, herbicides, fungicides, and the like in the agricultural and horticultural fields.

[0199] The sanitary pests in this specification refer to: harmful invertebrates that cause allergic symptoms such as severe pain, swelling, and itching by biting the target animal, and may cause fatal anaphylactic shock in some cases, or may spread serious diseases and may cause death in some cases by sucking blood; invertebrates that may contaminate food in the form of pathogens such as viruses, bacteria, and parasites by contacting with food; invertebrates whose living bodies, corpses, molted shells, feces, etc. become allergens and cause allergic diseases such as bronchial asthma, rhinitis, conjunctivitis, and atopic dermatitis; invertebrates that cause economic losses by pests on food, clothing, and housing; and invertebrates that cause disgust by being generated and invaded in the living environment of people although they do not cause direct harm. More specifically, they refer to ants that bite with large jaws, wasps that bite with poisonous stingers, mosquitoes and assassin bugs that suck blood from the skin, and termites that are omnivorous and harm buildings such as houses.

[0200] The disgusting pests in this specification refer to pests that do not cause direct harm to humans in the human living environment, but their appearance and form make people feel disgusted and cause psychological harm.

[0201] Specific examples of insects, mites, crustaceans, mollusks, nematodes, ectoparasites, and endoparasites that can be controlled using the compound of the present invention include the following organisms, but the present invention is not limited thereto.

[0202] Examples of the pests include: Lepidoptera: Allium leafminer (Acrolepiopsis sapporensis), Yam leafminer (Acrolepiopsis suzukiella), Smaller tea tortrix (Adoxophyes honmai), Summer fruittortrix (Adoxophyes orana fasciata), Fruit-piercing moth (Adristyrannus), Sweet potato leaf worm (Aedia leucomelas), Blackcutworm (Agrotis ipsilon), Turnip moth (Agrotis segetum), Cotton leafworm (Alabama argillacea), Asiatic leafroller (Archips breviplicanus), Apple tortrix (Archips fuscocupreanus), Orientaltussock moth (Artaxa subflava), Bamboo zygaenid (Artona martini), Japanese giant looper (Ascotis selenaria), Asiatic common looper (Autographa nigrisigna), Pear leaf miner (Bucculatrix pyrivorella), Tea leafroller (Caloptilia theivora), Peach fruitmoth (Carposina sasakii), Rice stem borer (Chilo suppressalis), Rice leafroller (Cnaphalocrocis medinalis), Yellow peach moth (Conogethes punctiferalis), Carpenter moth (Cossus insularis), Threespotted plusia (Ctenoplusiaagnata), Codling moth (Cydiapomonella), Pine moth (Dendrolimus spectabilis), Jananesehemlock caterpillar (Dendrolimus superans), Cucumber moth (Diaphaniaindica), Sugarcane borer (Diatraea saccharalis), Eilemafuscodorsalis (Eilema fuscodorsalis), Eilema laevis (Eilema laevis), Lesser corn stalk borer (Elasmopalpus lignosellus), Grapeberry moth (Endopiza viteana), Limabean pod borer (Etiella zinckenella), Euproctis piperita (Euproctis piperita), Tea caterpillar tussock moth(Euproctispseudoconspersa), Japanese bamboo lappet moth(Euthrix albomaculata), Drinker moth(Euthrix potatoria), Oriental lappet(Gastropacha orientalis), Mulberry pyralid(Glyphodes pyloalis), Plum fruit moth(Grapholita dimorpha), Oriental fruit moth(Grapholita molesta), Sweet potato leaffolder(Helcystogrammatriannulella), Cotton bollworm(Helicoverpa armigera), Oriental tobacco budworm(Helicoverpa assulta), Corn earworm(Helicoverpa zea), Tobacco budworm(Heliothisvirescens), Cabbage webworm (Hellulaundalis), Oriental tea tortrix (Homona magnanima), Fall webwormmoth (Hyphantria cunea), Pearlleaf worm (Illiberis pruni), Prunusbud moth (Illiberis rotundata), Quercus lasiocampid (Kunugiaundans), Quercus lasiocampid (Kunugia yamadai), Soybean pod borer (Leguminivora glycinivorella), Mulberry tiger moth (Lemyraimparilis), Gypsy moth (Lymantria dispar), Peach leafminer (Lyonetia clerkella), Silver-striped shallow leaf moth (Lyonetia prunifoliella malinella), Cabbage armyworm (Mamestra brassicae), Tomato hornworm (Manduca quinquemaculata), Tobacco hornworm (Manduca sexta), Soybean podworm (Matsumuraeses phaseoli), Oriental moth (Monema flavescens), Rice green caterpillar (Naranga aenescens), White-spotted tussock moth (Orgyia thyellina), Asian corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Adzuki bean borer (Ostrinia scapulalis), Dark fruit-tree tortrix (Pandemis heparana), Bluegrasswebworm (Parapediasia teterrella), Green cochlid (Parasa consocia), Parasa lepida (Parasa lepida), Chinese cochlid (Parasa sinica), Straight swift (Parnara guttata), Pink bollworm (Pectinophora gossypiella), Citrus leafminer (Phyllocnistiscitrella), Apple leafminer (Phyllonorycter ringoniella), Large white (Pieris brassicae), Cabbage white butterfly (Pieris rapaecrucivora), Diamondback moth (Plutella xylostella), Oriental armyworm (Pseudaletia separata), Soybean armyworm looper(Pseudoplusiaincludens)、Swan moth(Sphrageidus similis)、Lawn grasscutworm(Spodoptera depravata)、Southern armyworm(Spodopteraeridania)、Beet armyworm(Spodoptera exigua)、Fall armyworm(Spodoptera frugiperda)、Cotton leafworm(Spodoptera littoralis)、Common cutworm(Spodoptera litura)、Persimmon fruit moth(Stathmopoda masinissa)、Peach tree borer(Synanthedon exitiosa)、Cherry tree borer(Synanthedon hector)、Toleria romanovi(Toleria romanovi)、Cabbage looperlooper (Trichoplusia ni), etc.

[0203] Coleoptera: Common bean weevil (Acanthoscelidesobtectus), Cupreous chafer (Anomala cuprea), Soybean beetle (Anomala rufocuprea), Asian long-horn beetle (Anoplophora glabripennis), White-spotted longicorn beetle (Anoplophora malasiaca), Boll weevil (Anthonomus grandis), Cucurbit leaf beetle (Aulacophora femoralis), Adzuki bean beetle (Callosobruchus chinensis), Beet flea beetle (Chaetocnema concinna), Sweetpotato weevil (Cylas formicarius), Reaf beetle (Demotina fasciculata), Northern corn rootworm (Diabrotica barberi), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm (Diabroticavirgifera), Rice plant weevil (Echinocnemus squameus), Mexican bean beetle (Epilachna varivestis), Large twenty-eight-spotted ladybird (Epilachna vigintioctomaculata), Twenty-eight-spotted ladybird (Epilachna vigintioctopunctata), Epuraea domina (Epuraeadomina), West Indian sweet potato weevil (Euscepes postfasciatus), Citrusflower chafer (Gametis jucunda), White-fringed beetle (Graphognatus leucoloma), Yellowish elongate chafer (Heptophylla picea), Alfalfa weevil (Hypera postica), Tobacco beetle (Lasioderma serricorne), Colorado potato beetle (Leptinotarsa ​​decemlineata), Rice water weevil (Lissohoptrusoryzophilus), Sweetpotato wireworm (Melanotus fortnumi), Sugarcane wireworm (Melanotus tamsuyensis), Pollen beetle (Meligethesaeneus), Japanese pine sawyer (Monochamus alternatus), Blackvine weevil weevil(Otiorhynchus sulcatus), Rice leaf beetle(Oulema oryzae), Rove beetle(Paederus fuscipes), Mustard leaf beetle(Phaedon cochleariae), Striped flea beetle(Phyllotreta striolata), Japanese beetle(Popillia japonica), Yellow-spotted longicornbeetle(Psacothea hilaris), Solanum flea beetle(Psylliodesangusticollis), Peach curculio(Rhynchites heros), Granary weevil(Sitophilus granarius), Maize weevil(Sitophilus zeamais), Huntingbillbug(Sphenophorusvenatus vestitus), Yellow mealworm (Tenebriomolitor), Red flour beetle (Tribolium castaneum), Grape borer (Xylotrechus pyrrhoderus), etc.

[0204] Hymenoptera: Chestnut sawfly (Apethymus kuri), Large rose sawfly (Arge pagana), Cabbage sawfly (Athalia infumata), Turnip sawfly (Athalia rosae), Japanese carpenter ant (Camponotus japonicus), Chestnut gall wasp (Dryocosmus kuriphilus), Army ant (Eciton burchellii, E.schmitti), Argentine ant (Linepithemahumile), Pharaoh ant (Monomorium pharaonis), Bulldog ant (Myrmeciaspp.), European pine sawfly (Neodiprion sertifer), Fire ant (Solenopsis spp.), Asian giant hornet (Vespa mandarinia), Japanese yellow hornet (Vespa simillima), etc.

[0205] Diptera: Yellow fever mosquito (Aedes aegypti), Asian tiger mosquito (Aedes albopictus), Aedes spp., Aedes niorhynchus, Rice leaf miner (Agromyza oryzae), Mexican fruit fly (Anastrepha ludens), African malaria mosquito (Anopheles gambiae), African malaria mosquito (Anopheles hyrcanus sinensis), Anopheles koreicus (Anopheles koreicus), Anopheles lesteri (Anopheles lesteri), Anopheles maculipennis, Anopheles spp., Soybean pod gall midge (Asphondylia yushimai), Atylotus spp., Melon fly (Bactrocera cucurbitae), Oriental fruit fly (Bactrocera dorsalis), Queensland fruit fly (Bactrocera tryoni), Japanese orange fly (Bactrocera tsuneonis), Red-headed gnat (Boophthora erythrocephala), Braula coeca, Braula spp., Red-headed blowfly (Calliphora erythrocephala), Calliphora lata (Calliphora lata), Calliphora spp.), Bottle fly (Calliphora vicina), Mediterranean fruit fly (Ceratitis capitata), Pea leaf miner (Chromatomyia horticola), Old World screw-worm fly (Chrysomyabezziana), Blow fly (Chrysomya chloropyga), Oriental latrine fly (Chrysomya megacephala), Chrysomya spp., Splayed deerfly (Chrysopscaecutiens), Chrysops relictus, Chrysops spp., Deerfly (Chrysops suavis), Chrysozona pluvialis, New World screw-worm fly (Cochliomyia hominivorax), House mosquito (Culex pipiensmolestus), House mosquito (Culex pipiens pallens), Culex quinquefasciatus, Culex tarsalis, Culex tritaeniorhynchus (Culex tritaeniorhynchus), Culex spp., Biting midge (Culicoidesarakawae), Culicoides spp., Bot flies (Cuterebra spp.), Onion fly (Delia antiqua), Seed corn maggot (Delia platura), Human botfly (Dermatobia hominis), Japanese fruit fly (Drosophila suzukii), Eusimulium spp.), Lesser house fly (Fannia canicularis), Toilet fly (Fannia spp.)、Red-tailed stomach fly Horse nose bot fly (Gasterophilus haemorrhoidalis), Naked stomach fly (Gasterophilus inermis), Intestinal stomach fly Horse bot fly (Gasterophilus intestinalis), Throat bot fly (Gasterophilus nasalis), Black-horned stomach fly (Gasterophilus nigricornis), Black-bellied stomach fly (Gasterophilus pecorum), Gasterophilus spp., Tsetse fly (Glossina morsitans, G.palpalis), Glossina spp., Western horn fly (Haematobia irritans), Oriental horn fly (Haematobia irritans exigua), Horn fly (Haematobia spp.), Haematobia stimulans, Italian fly Haematopota italic (Haematopota italic), Common horse fly(Haematopota pluvialis), Haematopota spp., Forest fly(Hippobosca equina), Hippobosca spp., Hippobosca variegate(Hippobosca variegate), Hybomitra ciurea, Hybomitra spp., Smaller rice leaf miner(Hydrellia griseola), Hydrotaea albipuncta, Sheep headfly(Hydrotaea irritans), Hydrotaea spp., Warble fly(Hypoderma bovis), Common cattle grub(Hypoderma lineatum), Hypoderma spp.), Black gnat (Leptoconopsnipponensis), Lipoptena capreoli (Lipoptena capreoli), Lipoptena cervi, Lipoptena spp., Cabbage leafminer (Liriomyza brassicae), Tomato leaf miner (Liriomyza bryoniae), Stone leek leafminer (Liriomyza chinensis), Pea leafminer (Liriomyzahuidobrensis), Tomato leafminer (Liriomyza sativae), Serpentine leafminer (Liriomyza trifolii), Australian sheep blowfly (Lucilia cuprina), Green bottle fly (Lucilia illustris), Commongreen bottle fly (Lucilia sericata), Lucilia spp., Lutzomyia spp., Hessian fly (Mayetiola destructor), Sheep ked (Melophagus ovinus), Melophagus spp., Sweat fly (Morellia simplex), Morellia spp., Face fly (Musca autumnalis), Housefly (Musca domestica), Musca spp., Australian bush fly (Muscavetus tissima), Odagmia ornate, Odagmia spp., Sheep nasalbot fly (Oestrus ovis), Oestrus spp., Beet leaf miner (Pegomya cunicularia), Philipomyia spp.)、Long whiskered sandfly(Phlebotomuslongipalpis)、Still feeding sandfly(Phlebotomus papatasi)、Sandfly(Phlebotomus spp.)、Black blow fly(Phormia regina)、Prosimulium yezoensis(Prosimuliumyezoensis)、Northern blowfly(Protophormia terraenovae)、Przhevalskiana silenus(Przhevalskiana silenus)、Apple maggot(Rhagoletis pomonella)、Rhinoestrus spp.)、Flesh fly(Sarcophagacarnaria)、Flesh fly(Sarcophaga peregrina)、Sarcophaga spp.)、Black fly(Simulium ochraceum)、Climbing gnat(Simulium reptans), Simulium spp., Orange wheat blossom midge (Sitodiplosis mosellana), Stable fly (Stomoxys calcitrans), Stomoxys spp., Tabanus atratus, Tabanus bromius, Greenhead horse fly (Tabanus nigrovittatus), Tabanus spodopterus, Tabanus spp., Tabanus sudeticus, Horse fly (Tabanus trigonus), Moth fly (Telmatoscopus albipunctatus), Tipula paludosa, Tipula spp., Wilhelmia equine, Wilhelmia spodopterus spp.), Wohlfahrtia spp., etc.

[0206] Hemiptera: green stink bug (Acrosternum hilare), Peaaphid (Acyrthosiphon pisum), Camellia spiny whitefly (Aleurocanthuscamelliae), Orange spiny whitefly (Aleurocanthus spiniferus), Indiancotton leafhopper (Amrasca devastans), California red scale (Aonidiellaaurantii), Cowpea aphid (Aphis craccivora), Black bean aphid (Aphisfabae), Soybean aphid (Aphis glycines), Cotton aphid (Aphis gossypii), Green apple aphid (Aphis pomi), Spiraea aphid (Aphis spiraecola), Pale greenplant bug(Apolygus spinolae), Grape Leafhopper(Arboridia apicalis), Foxglove aphid(Aulacorthum solani), Beardsley leafhopper(Balclutha saltuella), Silverleaf whitefly(Bemisia argentifolii), Sweetpotato whitefly(Bemisia tabaci), Truechinch bug(Blissus leucopterus), Leafcurl plum aphid(Brachycaudushelichrysi), Cabbage aphid(Brevicoryne brassicae), Orientalchinch bug(Cavelerius saccharivorus), Indian wax scale(Ceroplastes ceriferus), Red wax scale(Ceroplastesrubens), Walnut aphid (Chromaphis juglandicola), Bed bug (Cimex lectularius), Rice stink bug (Cletus punctiger), Citricola scale (Coccus pseudomagnoliarum), San jose scale (Comstockaspis perniciosa), Citrus whitefly (Dialeurodes citri), Asian citrus psyllid (Diaphorina citri), Green stink bug (Dichelops furcatus), Russian wheat aphid (Diuraphis noxia), Sloebug (Dolycoris baccarum), Giant margarodid scale (Drosicha corpulenta), Rosy apple aphid (Dysaphis plantaginea), Red cotton bug(Dysdercus cingulatus), Potato Leafhopper(Empoasca fabae), Empoasca nipponica(Empoasca nipponica), Tea green leafhopper(Empoasca onukii), Bean's smaller green leafhopper(Empoascasakaii), Grape Leafhopper(Epiacanthus stramineus), Woolyapple aphid(Eriosoma lanigerum), Cabbage bug(Eurydema rugosa), Brown stink bug(Euschistus servus), Whitespotted spined bug(Eysarcorisaeneus), Eysarcoris lewisi(Eysarcoris lewisi), White-spotted stink bug (Eysarcorisventralis), Tea scale (Fiorinia theae), Sheildbug (Glaucias subpunctatus), Island fleahopper (Halticus insularis), Brown marmorated stink bug (Halyomorpha halys), Mealy plum aphid (Hyalopterus pruni), Cottony cushion scale (Icerya purchasi), Smallbrown planthopper (Laodelphax striatellus), Rice bug (Leptocorisachinensis), Turnip aphid (Lipaphis erysimi), Western tarnishedplant bug (Lygus hesperus), Tarnished plant bug (Lygus lineolaris), Potato aphid (Macrosiphum euphorbiae), Aster leafhopper (Macrosteles fascifrons), Grape Leafhopper (Macrostelesstriifrons), Sugarcane spittlebug (Mahanarva fimbriolata), Blackmargined aphid (Monellia caryella), Green peach aphid (Myzus persicae), Lettuce aphid (Nasonovia ribisnigri), Onion aphid (Neotoxoptera formosana), Green rice leafhopper (Nephotettixcincticeps), Eastern green stink bug (Nezara antennata), Southern green stink bug (Nezara viridula), Brown rice planthopper (Nilaparvatalugens), Squash bug (Paradasynus spinosus), Cotton mealy bug (Phenacoccus solani), Redbanded stink bug (Piezodorusguildinii), Redbanded shield bug (Piezodorus hybneri), Citrusmealybug (Planococcus citri), Japanese mealybug (Planococcuskraunhiae), Brown-winged green bug (Plautia crossota), Peony scale (Pseudaonidia paeoniae), Cotton fleahopper (Pseudatomoscelis seriatus), Mulberry scale (Pseudaulacaspis pentagona), White peach scale (Pseudaulacaspis prunicola), Comstock mealybug (Pseudococcuscomstocki), Grape mealybug (Pseudococcus maritimus), Pear sucker (Psylla pyrisuga), Blood-sucking bug (Rhodnius prolixus), Birdcherry-oat aphid (Rhopalosiphum padi), Rice root aphid (Rhopalosiphumrufiabdominalis), Rhopalid bug (Rhopalus maculatus), Bean bug (Riptortus clavatus), Greenbug (Schizaphis graminum), Japanese black rice bug (Scotinophora lurida), Corn leaf aphid (Sitobionakebiae), English grain aphid aphid (Sitobion avenae), White-backed riceplanthopper(Sogatella furcifera), Rice stink bug(Stenodemasibiricum), Sorghum plant bug(Stenotus rubrovittatus), Azalea lace bug(Stephanitis pyrioides), Seed bug(Togo hemipterus), Black citrus aphid(Toxoptera aurantii), Brown citrus aphid(Toxoptera citricida), Greenhouse whitefly(Trialeurodesvaporariorum), Kissing bug(Triatoma dimidiata), Kissing bug(Triatoma infestans), Rice leaf bug(Trigonotylus caelestialium), Citrus snow scale(Unaspis citri), Euonymus scale (Unaspiseuonymi), Arrowhead scale (Unaspis yanonensis), Grapephylloxera (Viteus vitifolii), etc.

[0207] Thysanoptera: Flower thrips (Frankliniella intonsa), Western flower thrips (Frankliniella occidentalis), Greenhouse thrips (Heliothrips haemorrhoidalis), Japanese gall-forming thrips (Ponticulothrips diospyrosi), Yellow tea thrips (Scirtothripsdorsalis), Melon thrips (Thrips palmi), Onion thrips (Thripstabaci), etc.

[0208] Orthoptera: Australian plague locust (Chortoice testerminifera), Oriental mole cricket (Gryllotalpa orientalis), Migratory locust (Locusta migratoria), Lesser paddy grasshopper (Oxya japonica), Rice grasshopper (Oxya yezoensis), Desert locust (Schistocerca gregaria), Emma field cricket (Teleogryllus emma), etc.

[0209] Dictyoptera: German cockroach (Blattella germanica), Formosan subterranean termite (Coptotermes formosanus), Daikoku dry-wood termite (Cryptotermes domesticus), Western dry-wood termite (Incisitermes minor), Black-winged subterranean termite (Odontotermes formosanus), American cockroach (Periplaneta americana), Smoky-brown cockroach (Periplaneta fuliginosa), Japanese cockroach (Periplaneta japonica), Japanese subterranean termite (Reticulitermes speratus), etc.

[0210] Isoptera: Formosan termite Coptotermes formosanus (Coptotermesformosanus), yellow-breasted termite Reticulitermes speratus (Reticulitermes speratus), black-winged termite Odontotermes formosanus (Odontotermes formosanus), etc.

[0211] Acari: Cyclamen mite (Phytonemus pallidus), Broad mite (Polyphagotarsonemus latus), Tarsonemus bilobatus (Tarsonemus bilobatus), Penthaleus erythrocephalus (Penthaleus erythrocephalus), Winter grain mite (Penthaleus major), Rice spider mite (Oligonychus shinkajii), Citrus red mite (Panonychus citri), Panonychus mori (Panonychus mori), European red mite (Panonychus ulmi), Kanzawa spider mite (Tetranychus kanzawai), Two-spotted spider mite mite(Tetranychus urticae), Acaphylla theavagrans(Acaphylla theavagrans), Dry bulb mite(Aceria tulipae), Tomato erineum mite(Aculops lycopersici), Pink citrus rust mite(Aculops pelekassi), Apple rust mite(Aculusschlechtendali), Eriophyes chibaensis(Eriophyes chibaensis), Phyllocoptruta oleivora(Phyllocoptruta oleivora), Bulb mite(Rhizoglyphus robini), Mold mite(Tyrophagus putrescentiae), Tyrophagus similis(Tyrophagus similis), Acarapis spp.)、Honey bee tracheal mite(Acarapis woodi)、Acarus spp.)、Lone startick(Amblyomma americanum)、Cayenne tick(Amblyomma cajennense)、South African bont tick(Amblyomma hebraeum)、Gulf coast tick(Amblyomma maculatum)、Amblyomma spp.)、Tropical bont tick(Amblyomma variegatum)、Fowl tick(Argas persicus)、Pigeon tick(Argas reflexus)、Argas spp.)、Blue cattle tick(Boophilus annulatus)、Boophilus calceratus)、African blue tick(Boophilus decoloratus), Tropical cattle tick (Boophilus microplus), Ixodes species (Boophilus spp.), Caloglyphus spp., Chelacaropsis moorei, Cheyletiella blakei, Rabbit furmite (Cheyletiella parasitovorax), Cheyletiella spp., Cheyletiella yasguri, Cheyletus eruditus, Cheyletus malaccensis, Chorioptic mange mite (Chorioptes bovis), Chorioptes spp., Cytodites spp.), Cattle follicle mite (Demodex bovis), Demodex caballi (Demodex caballi), Dog follicle mite (Demodex canis), Goat follicle mite (Demodex caprae), Cat follicle mite (Demodex cati), Horse follicle mite (Demodex equi), Face mite (Demodex folliculorum), Sheep follicle mite (Demodexovis), Demodex spp., Sarcoptes suis mite (Demodex suis), Winter tick (Dermacentor albipictus), Rocky Mountain wood tick (Dermacentor andersoni), Ornate sheep tick (Dermacentor marginatus), Meadow tick (Dermacentor pictus), Ornate dog tick tick(Dermacentorreticulatus), Dermacentor spp., American dog tick(Dermacentorvariabilis), Poultry red mite(Dermanyssus gallinae), Dermanyssus spp.)、American house dust mite(Dermatophagoides farina)、House dust mite(Dermatophagoides pteronyssinus)、Eutrombiculawichmanni)、Storage mite(Glycyphagus destructor)、House itchmite(Glycyphagus domesticus)、Haemaphysalis cinnabarina)、Common rodent tick(Haemaphysalis concinna)、Yellow dog tick(Haemaphysalis leachi)、Bush tick(Haemaphysalis longicornis)、Haemaphysalis otophila)、Red sheep tick(Haemaphysalis punctate)、Haemophysalis spp.)、Haplochthonius simplex)、Trombiculid mite (Helenicula miyagawai), Tortoise tick (Hyalommaaegyptium), Small Hyalomma anatolicum, Bont-legged tick (Hyalomma marginatum), Hyalomma mauritanicus, Hyalomma spp., Hyalomma transiens (Small smooth bont-legged tick, Hyalomma transiens), Hypodectes spp.)、Dog tick(Ixodes canisuga)、Hedgehog tick(Ixodes hexagonus)、Australian paralysis tick(Ixodes holocyclus)、Western black-legged tick(Ixodes pilosus)、Castor bean tick(Ixodes ricinus)、Karoo paralysis tick(Ixodes rubicundus)、Deertick(Ixodes scapularis)、Ixodes spp.)、Knemidocoptes spp.)、Laminosioptes spp.)、Leptotrombidium akamushi)、Leptotrombidium pallida)、Tsutsugamushi mite(Leptotrombidiumscutellare), Listrophorus spp., Feather mite(Megninia cubitalis), Myobia spp., Neoschoengastia xerothermobia, Harvest mite(Neotrombicula autumnalis), Neotrombicula desaleri(Neotrombiculadesaleri), Cat mange mite(Notoedres cati), Notoedres spp., Ornithocheyletia spp., Soft tick(Ornithodorus moubata), Ornithodorus spp., Tropical fowl mite(Ornithonyssus bursa), Ornithonyssus spp., Northern fowl mite Mite (Ornithonyssus sylviarum), Spinose ear tick (Otobius megnini), Otobius spp.)、Dogear mite(Otodectes cynotis)、Otodectes spp.)、Canine nasal mite(Pneumonyssoides caninum)、Pneumonyssoides mange(Pneumonyssoides mange)、Pneumonyssus spp.)、Pneumonyssus spp.)、Psorergates spp.)、Psoroptic mite(Psoroptes communis)、Rabbit ear mite(Psoroptescuniculi)、Psoroptes equi)、Sheep scab mite(Psoroptes ovis)、Psoroptes spp.)、Feather mite(Pterolichus obtusus)、Pterolichus spp.), Raillietia spp., Brownear tick (Rhipicephalus appendiculatus), Brown ear tick (Rhipicephalus bursa), Cape rhipicephalus (Rhipicephalus capensis), Asian blue tick (Rhipicephalus evertsi), Kennel tick (Rhipicephalus sanguineus), Rhipicephalus spp., Rhipicephalus turanicus, Zambian rhipicephalus (Rhipicephalus zambeziensis), Sarcoptes bovis, Sarcoptes equi, Sarcoptes ovis, Sarcoptes sanguineus rupicaprae (=S.caprae)), Itchmite (Sarcoptes scabiei), Sarcoptes spp., Sarcoptes suis, Itch mite (Sarcoptes canis), Sternostoma spp.), Trombicula akamushi, Trombicula spp., Cheese mite (Tyrophagus putrescentiae), Tyrophagus spp., Varroa mite (Varroa jacobsoni), Varroa spp., etc.;.

[0212] Anoplurida: Short-nosed cattle louse (Haematopinus urysternus), Tail switch louse (Haematopinus quadripertusus), Haematopinus spp., Large pig louse (Haematopinus suis), Buffalo louse (Haematopinus tuberculatus), Rabbit louse (Haemodipsus ventricosus), Dog sucking louse (Linognathus setosus), Linognathus spp., Long-nosed cattle louse (Linognathus vituri), Head louse (Pediculus humanus), Pediculus spp., Mouse louse (Polyplax serratus), Crab louse (Pthirus pubis), Pthirus spp., Little blue cattlelouse (Solenopotes capillatus), Solenopotes spp., etc.

[0213] Mallophaga: Goat biting louse (Bovicola caprae), Angora goat feather louse (Bovicola limbata), Sheep body louse (Bovicola ovis), Bovicola spp., Chicken head louse (Cuclotogaster heterographa), Cattle chewing louse (Damalinia bovis), Felicola spp., Catlouse (Felicola subrostrata), Brown chicken louse (Goniodes dissmilis), Fluff louse (Goniodes gallinae), Large hen louse (Goniodes gigas), Lepikentron ovis, Lepikentron spp., Wing louse (Lipeurus caponis), Body louse (Menacanthus cornutus), Small body louse(Menacanthuspallidulus), feather louse(Menacanthus spp.), chicken body louse(Menacanthusstramineus), chicken shaft louse(Menopon gallinae), fowl louse(Menopon spp.), dog biting louse(Trichodectes canis), Trichodectes spp.), Werneckiella equi(Werneckiella equi), Werneckiella spp., etc.;

[0214] Siphonaptera: Hen flea (Ceratophyllus gallinae), Dog flea (Ctenocephalides canis), Cat flea (Ctenocephalides felis), Sticktight flea (Echidnophaga gallinacean), Human flea (Pulex irritans), Chigoe flea (Tunga penetrans), Oriental rat flea (Xenopsyllacheopis), etc.

[0215] Other parasites include: Monogenea; Benedenia epinepheli, Benedenia hoshinai, Benedenia sekii, Benedenia seriolae, Bivagina tai, Sea louse (Caligus curtus), Caligus elongates, Caligus labaracis (Caliguslabaracis), Caligus longipedis, Caligus orientalis, Caligus teres, Dactylogyrus spp., Gyrodactylus spp., Heteraxine heterocerca, Heterobothrium okamotoi, Lamellodiscus spp.), (Lepeophtheirus cuneifer(Lepeophtheirus cuneifer), Lepeophtheirus hippoglossi(Lepeophtheirus hippoglossi), Lepeophtheirus spectoralis(Lepeophtheirus pectoralis), salmon louse(Lepeophtheirussalmonis), Microcotyle sebastis, Microcotylesebastisci, Neobenedenia, Neobenedenia congeri, Neobenedenia girellae, Neoheterobthrium hirame, Polystoma spp., Pseudocaligus fugu, Zeuxaptajaponica, etc.;

[0216] Cestoda: Andyra spp., Anoplocephalas spp., Avitellina spp., Bertiella spp., Bothridium spp., Cittataenia spp., Davainea spp., Diorchis spp., Manson's tapeworm (Diphyllobothrium erinacei), fish tapeworm (Diphyllobothrium latum), Diphyllobothrium spp., Diphyllogonoporus spp. spp.), Diplopylidium spp., dog tapeworm (Dipylidium caninum), Dipylidium spp., dog tapeworm (Echinococcus granulosus), fox tapeworm (Echinococcus multilocularis), Echinococcus spp., Echinocotyle spp., Echinolepsis spp., Hydatigera spp., Hymenolepis diminuta, Hymenolepis spp., Joyeuxiella spp., Ligura spp. spp.), Mesocestoides spp., Moniezia benedeni, Moniezia spp., Paranoplocephala spp., Raillietina spp., Schistocephalus spp., Spirometra spp., Stilesia spp.), beef tapeworm (Taenia saginata), pork tapeworm (Taeniasolium), Taenia spp., cat tapeworm (Taenia taeniaeformis), Thysaniezia spp., Thysanosomsa spp., etc.;.

[0217] Trematoda: Austrobilharzia spp., Brachylaema spp., Calicophoron spp., Catatropis spp., Chinese river fluke (Clonorchis sinensis), Clonorchis spp., Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp.), Eurytrema coelomaticum, pancreasfluke(Eurytrema pancreaticum), Eurytrema spp., liver fluke(Fasciola gigantica), sheep liver fluke(Fasciola hepatica), Fasciola spp., Fasciolides spp., large intestinalfluke(Fasciolopsis bruski), 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., Orientallung fluke (Paragonimus westermani), Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma haematobium, Schistosoma japonicum, Schistosoma mansoni, Schistosoma spp., Trichobilharzia spp., Troglotrema spp., etc.; Nematoda: Aelurostrongylus spp.), Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Anisakis spp., Ascaridia galli, Ascaridia spp., Ascaris spp., Ascaris suum, Aspiculuris spp., Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp., Cooperia oncophora, Cooperia spp., Crenosoma spp.), Cyathostoma spp., Cyclococercus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Dirofilaria immitis, Dirofilaria spp.), Dracunculus spp., Draschia spp., Elaphostrongylus spp., Enoplida, Enterobius spp., Filaroides spp., Filicollis spp., Globocephalus spp., Gnathostoma spp., Gongylonema spp., Gyalocephalus spp., Habronema spp., Barber's pole worm (Haemonchus contortus), Haemonchus spp., Heterakis spp.), Hyostrongylus spp., Litomosoides spp., Loa spp., Macracanthorhynchus spp., Marshallagia spp., Metastrongylus spp., Micronema spp., Moniliformis spp., Muellerius spp., Nematodirus spp., Neostrongylus spp., Obeliscoides spp., Oeophagostomum dentatum, Oesophagodontus spp., Oesophagostomum radiatum radiatum), Oesophagostomum spp., Ollulanus spp., Onchocerca gibsoni, Onchocerca spp., Brown stomach worm (Ostertagia ostertagi), Ostertagia spp., Oxyuris spp., Parabronema spp., Paracrenosoma spp.), Parafilaria spp., Parafilaroides spp., Parascaris spp., Parelaphostrongylus spp., Passalurus spp., Physaloptera spp., Pneumostrongylus spp., Poteriostomum spp., Prostenorchis spp., Protostrongylus spp., Setaria spp., Spicocaulus spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp.), Strongylus spp., Syngamus spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., Trichomosoides spp., Trichonema spp., ruminant nematode (Trichostrongylus colubriformis), Trichostrongylus spp., Trichuris spp., Triodontophorus spp., Uncinaria spp., Wuchereria spp., etc.;.

[0218] Protozoa: Babesis spp., Eimeria acervulina, Eimeria bovis, Eimeria brunette, Eimeria maxima, Eimeria necatrix, Eimeria ovinoidalis, Eimeria spp., Eimeria tenella, Entamoeba histolytica, Giardia spp., Histomanas spp., Plasmodium spp., Theileria spp., Toxoplasma spp., Trichomonadidae spp.), Trypanosomsa cruzi, etc.

[0219] Furthermore, the compounds of the present invention are also effective against pests that have developed resistance to existing insecticides such as organophosphorus compounds, carbamate compounds, and pyrethroid compounds.

[0220] That is, the compound of the present invention can effectively control harmful organisms such as insects belonging to the orders Collembola, Dictyoptera, Orthoptera, Isoptera, Thysanoptera, Hemiptera and Homoptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Siphonaptera, Anoplura, etc., crustaceans such as Lepidoptera, Caligoida, Cyclopoida, mites, gastropods, tapeworms, trematodes, nematodes, protozoa, etc. at low concentrations.

[0221] On the other hand, the compounds of the present invention have almost no adverse effects on mammals, fish, crustaceans and beneficial insects (beneficial insects such as bees and bumblebees, natural enemies of aphid wasps (Aphelinidae), aphid wasps (Aphidiidae), tachinidae, small flower stink bugs, phytoseiidae, etc.), and have extremely useful characteristics.

[0222] When the compound of the present invention is used, it can usually be mixed with an appropriate solid carrier or liquid carrier, and then a surfactant, a penetrant, a developer, a thickener, an antifreeze, a binder, a solidification inhibitor, a disintegrator, a defoamer, a preservative, an anti-decomposition agent, etc. can be added as desired to prepare a preparation in any dosage form such as a liquid preparation (soluble concentrate), an emulsion (emulsifiable concentrate), a wettable powder (wettable powder), a soluble powder (water soluble powder), a water dispersible granule (water dispersible granule), a soluble granule (water soluble granule), a suspension (suspension concentrate), a concentrated emulsion (concentrated emulsion), a suspoemulsion (suspoemulsion), a microemulsion (microemulsion), a dustable powder (dustable powder), a granule (granule), a tablet (tablet), an emulsifiable gel (emulsifiable gel) for practical use. In addition, from the viewpoint of labor saving and safety improvement, the preparation in any of the above dosage forms may be provided sealed in a water-soluble packaging body such as a water-soluble capsule or a bag of a water-soluble film.

[0223] Examples of the solid carrier include natural minerals such as quartz, calcite, sepiolite, dolomite, chalk, kaolinite, pyrophyllite, sericite, halloysite, metahalloysite, organic carbon clay, frog clay, pottery stone, zeeklite, allophane, white sand, mica, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite, and diatomaceous earth; calcined clay, perlite, white sand ball, vermiculite, attapulgite, and diatomaceous earth; calcined products of natural minerals such as clay, calcined diatomaceous earth, etc.; inorganic salts such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium bicarbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, diammonium phosphate, potassium chloride, etc.; sugars such as glucose, fructose, sucrose, lactose, etc.; polysaccharides such as starch, powdered cellulose, dextrin, etc.; organic substances such as urea, urea derivatives, benzoic acid, and salts of benzoic acid; plants such as wood flour, cork flour, corn cobs, walnut shells, and tobacco stems; fly ash, white carbon (such as hydrated synthetic silica, anhydrous synthetic silica, hydrated synthetic silicate, etc.), fertilizers, etc.

[0224] Examples of the liquid carrier include xylene, alkyl (C9 or C 10 Aromatic hydrocarbons such as benzene, phenylxylene ethane, alkyl (C1 or C3, etc.) naphthalene; aliphatic hydrocarbons such as machine oil, normal paraffin, isoparaffin, cycloparaffin; mixtures of aromatic hydrocarbons and aliphatic hydrocarbons such as kerosene; alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol, benzyl alcohol; polyols such as ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol; ethers such as propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol monophenyl ether; ketones such as acetophenone, cyclohexanone, γ-butyrolactone; esters such as fatty acid methyl esters, dialkyl succinates, dialkyl glutamic acid esters, dialkyl adipates, and dialkyl phthalates; N-alkyl (C1, C8 or C 12 Acid amides such as pyrrolidone, etc.; oils such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil, castor oil, etc.; dimethyl sulfoxide, water, etc.

[0225] These solid carriers and liquid carriers may be used alone or in combination of two or more.

[0226] Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl (mono or di) phenyl ethers, polyoxyethylene (mono, di or tri) styryl phenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid (mono or di) esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, castor oil ethylene oxide adducts, acetylene glycol, acetylene alcohol, ethylene oxide adducts of acetylene glycol, ethylene oxide adducts of acetylene alcohol, and alkyl glucosides; alkyl sulfate ester salts, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, Anionic surfactants such as alkylnaphthalenesulfonates, salts of formaldehyde condensates of naphthalenesulfonic acid, salts of formaldehyde condensates of alkylnaphthalenesulfonic acid, polyoxyethylene alkyl ether sulfuric acid or phosphate salts, polyoxyethylene (mono- or di-)alkylphenyl ether sulfuric acid or phosphate salts, polyoxyethylene (mono-, di- or tri-)styrylphenyl ether sulfuric acid or phosphate salts, polycarboxylates (e.g., polyacrylic acid salts, polymaleic acid salts, copolymers of maleic acid and olefins, etc.), polystyrenesulfonates, etc.; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts, amino acid type, betaine type, etc. amphoteric surfactants, silicone surfactants, fluorine surfactants, etc.

[0227] The content of these surfactants is not particularly limited, but is usually preferably in the range of 0.05 to 20 parts by mass relative to 100 parts by mass of the preparation of the present invention. In addition, these surfactants may be used alone or in combination of two or more.

[0228] The application amount of the compound of the present invention varies depending on the application site, application period, application method, cultivated crops, etc., but is usually preferably about 0.005 kg to 50 kg per hectare (ha) as the amount of the active ingredient.

[0229] On the other hand, when the compound of the present invention is used to control internal or external parasites of mammals and birds as livestock and pets, an effective amount of the compound of the present invention can be administered together with an additive for preparation by oral administration; parenteral administration such as injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); percutaneous administration such as immersion, spraying, bathing, washing, pouring (pouring-on) and spraying (spotting-on), dusting (dusting); nasal administration, etc. The compound of the present invention can also be administered by using a molded product such as a fragment, a plate, a belt, a collar (collar), an ear tag (ear mark), a limb band (limbband), a marking device, etc.

[0230] When administered, the compound of the present invention may be prepared into any dosage form suitable for the administration route.

[0231] When the compound of the present invention is used to expel external or internal parasites, the preferred dosage of the compound of the present invention (1) as an active ingredient depends on the type of parasite to be exterminated, the type of animal to be administered, the method of administration, etc., and is usually 0.01 mg / kg to 100 mg / kg, preferably 0.01 mg / kg to 50 mg / kg, relative to the body weight of the animal to be administered. In particular, the dosage for dogs may also vary depending on the type or age of the dog to be administered, or the external parasite to be exterminated, and is usually 1 mg / kg to 5000 mg / kg, preferably 1 mg / kg to 100 mg / kg, relative to 1 kg of the biological body weight of the dog to be administered.

[0232] In the case of expelling external or internal parasites by administering the compounds of the present invention, the interval of administration depends on the type of parasite to be expelled, the type of animal to be administered, the method of administration, etc., and can be set arbitrarily within the range of once a day to once a year. Preferably, once a week to once every 6 months, more preferably, once a day (24 hours), once a month, once a month, once every 2 months, once every 3 months, or once every 6 months.

[0233] In addition, when the compound of the present invention is used to prevent and treat external parasites of dogs, as the timing of applying the compound of the present invention to dogs, for example, can be cited: oral administration to dogs 30 minutes before the start of feeding and 120 minutes after the end of feeding. Here, the behavior of ingesting food provided to dogs for the purpose of nutrient intake 30 minutes before the start of feeding and 120 minutes after the end of feeding is used as a benchmark. For example, when the feeding time of a dog is 20 minutes, the prescribed time is a total of 170 minutes from 30 minutes before the start of feeding to 120 minutes after the end of feeding, taking the eating behavior as a benchmark. It is also included in the case of temporarily interrupting feeding during feeding and continuing feeding after oral administration of the compound of the present invention. It should be noted that in this specification, feeding refers to the behavior of animals eating.

[0234] Generally speaking, the number of times a dog is fed in a day varies depending on the breed, age, and habits of the dog. However, generally, for dogs less than six months old, it is 3 to 4 times a day, for dogs from six months to less than one year old, it is 2 to 3 times a day, for adult dogs from about one to five years old, it is 2 times a day, and for old dogs over six years old, it is about 2 to 3 times a day. In the present invention, feeding refers to the act of eating for the purpose of taking in nutrition, and does not include the act of providing food for the purpose of disciplining or training a dog.

[0235] As any dosage form prepared, there can be mentioned: solid preparations such as powders, granules, wettable powders, granules, tablets, boluses, capsules, and molded products containing active compounds; liquid preparations such as liquid preparations for injection, liquid preparations for oral use, and liquid preparations for use on the skin or in a body cavity; solution preparations such as pour-on agents, spot-on agents, flowable agents, and emulsions; semi-solid preparations such as ointments and gels, etc.

[0236] As dosage forms for oral administration of the compounds of the present invention, there can be mentioned, for example, solid preparations such as tablets, chewables, capsules, pills, boluses, granules, powders, etc.; semi-solid preparations such as pastes and gels; liquid preparations such as drinks, etc.

[0237] In addition, dosage forms for transdermal administration include, for example, solid preparations such as powders; semi-solid preparations such as creams, ointments, pastes, and gels; and liquid preparations such as sprays, aerosols, solutions and emulsions, suspensions, and lotions.

[0238] Furthermore, examples of dosage forms for administration by injection include liquid preparations (Solutions and Emulsions), suspensions and other liquid preparations, and examples of dosage forms for nasal administration include liquid preparations such as aerosols.

[0239] In addition, examples of dosage forms for spraying treatments in animal breeding environments such as livestock sheds include solid preparations such as wettable powders, dusts, and granules; and liquid preparations such as emulsions and suspension concentrates.

[0240] It should be noted that the preparation of the parasite control agent used in the present invention is not limited to these dosage forms.

[0241] Solid preparations can be directly orally administered, or can be used by diluting with water and then administering the preparation percutaneously, or by spraying the preparation on animal breeding environments such as livestock sheds.

[0242] Solid preparations for oral administration can be prepared by mixing the compound (1) of the present invention or a salt thereof with one or more excipients and binders suitable for oral administration and, if necessary, physiologically acceptable additives such as lubricants, disintegrants, dyes, pigments, etc., and molding the mixture into a desired shape.

[0243] Examples of excipients and binders include: sugars or sugar derivatives such as lactose, sucrose, mannitol, and sorbitol; starches such as corn starch, wheat starch, rice starch, and potato starch; cellulose or cellulose derivatives such as methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, and hydroxypropyl methyl cellulose; proteins or protein derivatives such as zein and gelatin; synthetic polymer compounds such as honey, gum arabic paste, polyvinyl alcohol, and polyvinyl pyrrolidone; and the like.

[0244] Examples of lubricants include magnesium stearate, and examples of disintegrators include cellulose, agar, alginic acid, cross-linked polyvinyl pyrrolidone, and carbonates.

[0245] Furthermore, in solid preparations used for oral administration, especially solid preparations such as chewables, additives that impart a taste, texture, or flavor to the animals to which the administration is given may also be used, but the carriers and additives used in the solid preparations of the parasite control composition are not limited to these.

[0246] Liquid preparations can be directly administered percutaneously or by injection, or can be mixed in feed and administered orally, or diluted with water and administered orally or percutaneously, or used by spraying treatment in animal breeding environments such as barns.

[0247] Liquid preparations for injection can be administered intravenously, intramuscularly or subcutaneously. Liquid preparations for injection can be prepared by dissolving the active compound in an appropriate solvent and adding additives such as solubilizers, acids, bases, buffer salts, antioxidants, protective agents, etc. as needed.

[0248] Examples of the suitable solvent include water, ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable plant oils, and synthetic oils suitable for injection.

[0249] Examples of the solubilizing agent include polyvinyl pyrrolidone, polyoxyethylated castor oil, and polyoxyethylated sorbitan esters.

[0250] Examples of the protective agent include benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.

[0251] Liquid preparations for oral administration can be administered directly or after dilution and can be prepared in the same manner as liquid preparations for injection.

[0252] The flowable preparation, emulsion, etc. can be directly applied or diluted and then administered percutaneously or by environmental treatment.

[0253] Liquid preparations for use on the skin can be applied by pouring, spreading, brushing, spraying, or spreading, or by applying by immersion (immersion, bathing, or washing). These liquid preparations can be prepared in the same manner as liquid preparations for injection.

[0254] Pour-on and spot-on preparations can be poured or sprayed onto a limited area on the skin, thereby allowing the active compound to be impregnated into the skin, thereby acting on the whole body.

[0255] Pour-on preparations and spray-on preparations can be prepared by dissolving, suspending, or emulsifying the active ingredient in a suitable skin-compatible solvent or solvent mixture. As required, auxiliary agents such as surfactants, colorants, absorption-promoting substances, antioxidants, light stabilizers, binders, etc. can be added.

[0256] Examples of suitable solvents include water, alkanols, ethylene glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethyl alcohol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, aromatic hydrocarbons and / or aliphatic hydrocarbons, vegetable oils or synthetic oils, DMF (N,N-dimethylformamide), liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone, or 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane.

[0257] Examples of the absorption-promoting substance include DMSO (dimethyl sulfoxide), isopropyl myristate, dipropylene glycol nonanoate, silicone oil, aliphatic esters, triglycerides, and aliphatic alcohols.

[0258] Examples of the antioxidant include sulfites, pyrosulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, and tocopherol.

[0259] Emulsions can be administered orally, percutaneously or by injection. Emulsions can be prepared by dissolving the active ingredient in a hydrophobic phase or a hydrophilic phase, and homogenizing it with a suitable emulsifier and, if necessary, a colorant, an absorption-promoting substance, a protective agent, an antioxidant, a sunscreen, a thickening substance and other auxiliary agents together with the solvent of the other phase.

[0260] Examples of the hydrophobic phase (oil) include paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglycerides, ethyl stearate, di-n-butyl adipate, hexyl laurate, dipropylene glycol nonanoate, esters of branched short-chain fatty acids and saturated fatty acids with a chain length of C16 to C18, isopropyl myristate, isopropyl palmitate, caprylic acid ester / capric acid ester of saturated fatty alcohols with a chain length of C12 to C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and the like.

[0261] Examples of the hydrophilic phase include water, propylene glycol, glycerin, and sorbitol.

[0262] Examples of the emulsifier include: nonionic surfactants such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefin ester, sorbitan monostearate, glyceryl monostearate, polyoxyethylene stearate, and alkylphenol polyethylene glycol ether; amphoteric surfactants such as disodium N-lauryl-β-iminodipropionate and lecithin; anionic surfactants such as sodium lauryl sulfate, fatty alcohol sulfate ether, and monoethanolamine salt of mono / dialkyl polyethylene glycol orthophosphate; cationic surfactants such as hexadecyltrimethylammonium chloride, etc.

[0263] Examples of other auxiliary agents include carboxymethyl cellulose, methyl cellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, methyl vinyl ether, copolymers of maleic anhydride, polyethylene glycol, wax, and colloidal silica.

[0264] Semisolid preparations can be applied to the skin or diffused, or introduced into body cavities for administration. Gels can be prepared by adding a thickener sufficient to produce an ointment-like transparent substance having a viscous consistency to the solution prepared as described above for liquid preparations for injection.

[0265] The following are examples of preparations using the compounds of the present invention. However, the formulation examples of the preparations containing the compounds of the present invention are not limited to these. It should be noted that in the following formulation examples, "parts" refer to parts by mass.

[0266] [Wettable powder]

[0267]

[0268] As other agents, for example, anti-fixing agents, anti-decomposition agents, etc. are mentioned.

[0269] [Emulsion]

[0270]

[0271] Other examples include a developing agent and an anti-decomposition agent.

[0272] [Suspension Concentrate]

[0273]

[0274] Other examples include antifreeze agents and thickeners.

[0275] [Water dispersible granules]

[0276]

[0277] As other ingredients, for example, there are adhesives, anti-decomposition agents, and the like.

[0278] [Liquid preparations]

[0279] 0.01 to 70 parts of the compound of the present invention

[0280] Liquid carrier 20~99.99 parts

[0281] Other 0~10

[0282] Other examples include antifreeze agents and developing agents.

[0283] [Granules]

[0284] 0.01 to 80 parts of the compound of the present invention

[0285] Solid carrier 10~99.99 parts

[0286] Other 0~10

[0287] As other ingredients, for example, there are adhesives, anti-decomposition agents, and the like.

[0288] [powder]

[0289] 0.01 to 30 parts of the compound of the present invention

[0290] Solid carrier 65~99.99 parts

[0291] Other 0~5

[0292] Other examples include drift inhibitors and decomposition inhibitors.

[0293] The following is a more specific example of a formulation using the compound of the present invention as an active ingredient, but the present invention is not limited to these. It should be noted that the compound of the present invention No. 1-001 shown below refers to N-(4-fluorophenyl)-6-[3-(6-fluoropyridin-3-yl)-4-(trifluoromethyl)phenyl]-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide described in Synthesis Example 1 described later.

[0294] [Formulation Example 1] Wettable Powder

[0295]

[0296] The above ingredients are uniformly mixed and crushed to prepare a wettable powder.

[0297] [Formulation Example 2] Emulsion

[0298]

[0299] (Trade name of Toho Chemical Industry Co., Ltd., a mixture of nonionic surfactant and anionic surfactant)

[0300] The above ingredients are uniformly mixed to prepare an emulsion.

[0301] [Formulation Example 3] Suspension

[0302]

[0303] The above ingredients are uniformly mixed and then wet-ground to prepare a suspension.

[0304] [Formulation Example 4] Water-dispersible granules

[0305]

[0306] After the above ingredients are uniformly mixed and pulverized, a small amount of water is added and stirred and mixed, and granulated using an extrusion granulator and dried to prepare a water-dispersible granule.

[0307] [Formulation Example 5] Granules

[0308] Compound No.1-001 of the present invention 5 parts

[0309] 50 parts of bentonite

[0310] 45 parts of talc

[0311] After the above ingredients are uniformly mixed and pulverized, a small amount of water is added and stirred and mixed, and granulated using an extrusion granulator and dried to prepare granules.

[0312] [Formulation Example 6] Powder

[0313]

[0314]

[0315] The above ingredients are uniformly mixed and crushed to form a powder.

[0316] When used, the above preparation is diluted 1 to 10,000 times with water or directly spread without dilution.

[0317] [Formulation Example 7] Wettable powder preparation

[0318]

[0319] [Formulation Example 8] Water-soluble concentrate preparation

[0320]

[0321] [Formulation Example 9] Liquid preparation for spraying

[0322]

[0323] [Formulation Example 10] Liquid preparation for transdermal administration

[0324] 5 copies of compound No.1-001 of the present invention

[0325] Hexanediol 50 parts

[0326] 45 parts of 2-propanol

[0327] [Formulation Example 11] Liquid preparation for transdermal administration

[0328] 5 copies of compound No.1-001 of the present invention

[0329] Propylene glycol monomethyl ether 50 parts

[0330] 45 parts of dipropylene glycol

[0331] [Formulation Example 12] Liquid preparation for transdermal administration (pour-on)

[0332] Compound No.1-001 of the present invention 2 parts

[0333] Light liquid paraffin 98 parts

[0334] [Formulation Example 13] Liquid preparation for transdermal administration (pour-on)

[0335]

[0336] In addition, when the compounds of this invention are used as pesticides or animal medicines, they can be mixed with other types of agents as needed during preparation or application. By mixed application, it can be expected that the cost reduction caused by the reduction of the dosage of the drug, the expansion of the control spectrum caused by the synergistic effect of the mixed agent, and the higher pest control effect can be expected. At this time, it is also possible to combine with a variety of known agents simultaneously.

[0337] For example, as the types of pesticides used in combination with the compounds of the present invention, there can be mentioned, for example, compounds described in The Pesticide Manual, 18th edition, 2018 and The Pesticide Manual, 19th edition, 2021. If antiparasitic drugs and antibiotics used in combination as animal drugs are specifically exemplified by their common names, they are as follows, but are not necessarily limited to these.

[0338] Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acynonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb, allethrin, alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethiphos, azinphos-ethyl, azinphos-methyl, azocyclotin, Bacillus thuringiensis thuringiensis), bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate, benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, bioresmethrin, bistrifluron, broflanilide, bromopropy late), buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chinomethionat, chlorantraniliprole, chlorethxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorobezilate, chloroprallethrin, chlorpyrifos,Chlorpyrifos-methyl, chromafenozide, clofentezine, clothianidin, cyanophos, cyantraniliprole, cyclaniliprole, cycloprothrin, cyenopyrafen, cyetpyrafen, cyflumetofen, cyfluthrin, cyfluthrin (cyhalodiamide), cyhalothrin, cyhexatine, cypermethrin, cyphenothrin, cyproflanilide, cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, dicloromezotiaz, diclofop fol), dienochlor, diflovidazin, diflubenzuron, dimefluthrin, dimethoate, dimethylvinphos, dimpropyridaz, dinotefuran, diofenolan, disulfoton, DNOC, d-tetramethrin, emamectin-benzoate ), empenthrin, endosulfan, EPN, epsilon-metofluthrin, epsilon-momfluorothrin, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etoxazole, etrimfos, Febantel, fenazaquin, fenbutatin oxide,fenitrothion, fenmezoditiaz, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazuron, flubendiamide bendiamide), fluchlorodiniliprole, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox, flufiprole, fluhexafon, flumethrin, flupentiofenox, flupyradifurone, flupyrimin, flupyrimidin, flu pyroxystrobin), fluralaner, fluvalinate, fluxametamide, fonophos, formetanate, formothion, furathiocarb, gamma-cyhalothrin, halfenprox, halofenozide, heptafluthrin, hexaflumuron, hexythiazox thiazox), hydramethylnon, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, indoxacarb-MP, isocycloseram, isofenphos, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin,lambda-cyhalothrin, ledprona, lepimectin, lufenuron, malathion, meperfluthrin, metaflumizone, metolcarb, metaldehyde, methacrifos, methamidophos, methidathion, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromide bromide), metofluthrin, milbemectin, momfluorothrin, monocrotophos, muscalure, nicofluprole, nitenpyram, novaluron, noviflumuron, omethoate, oxazosulfyl, oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl, pentachlorophenol, permethrin, phenothrin , phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos-methyl, Praziquantel, profenofos, profluthrin, propaphos, propargite, prothiofos, protrifenbute, pyflubumide, pymetrozine, pyraclofos, pyrafluprole, pyrethrins, pyridaben,Pyridalyl, pyrifluquinazon, pyrimidifen, pyriprole, pyriproxyfen, resmethrin, rotenone, silafluofen, spidoxamat, spinetoram, spinosad, spirobudifen, spirodiclofen, spiromesifen piromesifen), spiropidion, spirotetramat, spyromesifen, sulfiflumin, sulfotep, sulfoxaflor, sulprofos, tau-fluvalinate, tebufenozide, tebufenpyrad, teflubenzuron, tefluthorin, tebufenoxide, rbufos), tetrachlorantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, tetraniliprole, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon, thiobencarb tiorantraniliprole), tolfenpyrad, tralomethrin, transfluthrin, triazamate, triazuron, trichlorfon, triflumezopyrim, triflumuron, tyclopyrazoflor, vamidothion and zeta-cypermethrin, etc.

[0339] Fungicides: acibenzolar-S-methyl, acypetacs, aldimorph, allyl alcohol, ametoctradin, aminopyrifen, amisulbrom, amobam, ampropylfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide polysulfide), benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamorf, benzovindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, bordeaux mixture, boscalid, bromoconazole, bupirimate, buthiobate, butylamine, calcium sulfur polysulfide), captafol, captan, carbamorph, carbendazim, carboxin, carpropamid, carvone, cheshunt mixture, chinomethionat, chlobenthiazone, chloraniformethane, chloranil, chlorfenazole, chloroneb, chloroinconazide, chloropicrin, chlorothalonil,Chlorquinox, chlozolinate, climbazole, copper acetate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, basic copper sulfate, copper zinc chromate, copper chromate, copper chlor ... chromate), coumoxystrobin, cresol, cufraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole, cyprodinil, cyprofuram, dazomet, debacarb, decafentin, dehydroacetic acid acid), dichlobentiazox, dichlofluanid, dichlone, dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomezine, dicloran, diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinosulfon, dinoterbon,diphenylamine, dipymetitrone, dipyrithione, disulfiram, ditalimfos, dithianon, DNOC, dodemorph, dodine, drazoxolon, edifenphos, enestrobin, enoxastrobin, epoxiconazole, ethaboxam, ethiconazole etaconazole), etem, ethirimol, ethoxyquin, etridiazole, famoxadone, fenamidone, fenaminosulf, fenaminstrobin, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, rice blast fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, florylpicoxamid, fluazinam, flubeneteram, fludioxonil, flufenoxadiazam, fluf enoxystrobin), fluindapyr, flumetylsulforim, flumetover, flumorph, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluotrimazole, fluoxapiprolin, fluoxastrobin, fluoxytioconazole,fluquinconazole, flusilazole, flusulfamide, flutolanil, flutianil, flutriafol, fluxapyroxad, folpet, fosetyl-aluminium, fthalide, fuberidazole, furaxyl, furametpyr, furcarbanil, furconazole furconazole, furconazole-cis, furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexylthiofos, 8-hydroxyquinoline sulfate, hymexazol ol), imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole, ipflufenoquin, iprobenfos, iprodione, iprov alicarb), isofetamid, isoflucypram, isotianil, isoprothiolane, isopyrazam, isovaledione, kasugamycin, kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamid,Maneb, mebenil, mecarbinzid, mefentrifluconazole, mepanipyrim, mepronil, meptyldinocap, metalaxyl, metalaxyl-M, metam, metaylpicoxamid, metazoxolon, metconazole, m ethasulfocarb), methfuroxam, metyltetraprole, metiram, metominostrobin, metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, nabam, naftifine, natamycin, nickel dimethyldithiocarbamate, nitrostyrene, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxine copper), oxpoconazolefumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, 2-phenylphenol, phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxorim, potassium azide,Potassium hydrogencarbonate, probenazole, prochloraz, procymidone, propamocarb hydrochloride hydrochloride), propiconazole, propineb, proquinazid, prothiocarb, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyriminostrobin, pyroquilon, prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrapropoyne, pyrazinamide, raziflumid), pyridachlometyl, pyridinitril, pyriofenone, pyrisoxazole, pyroxychlor, pyroxyfur, quinacetol-sulfate, quinazamid, quinconazole, quinoxyfen, quinofumelin, quintozene, rabenzazole, salicylanilide, seboctylamine, sedaxane, silthiofam, simeconazole, sodium bicarbonate hydrogen carbonate), sodium hypochlorite, spiroxamine, sulfur, tebuconazole, tebufloquin, tecloftalam, tecnazene, tecoram,tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thiochlorfenphim, thiophanate, thiophanate-methyl, thiram, tiadinil, tioxymid, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tributyltin oxide oxide), trichlamide, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, vinclozolin, zarilamid, zinc naphthenate, zinc sulfate, zineb, ziram, zoxamide, shiitake mycelium extract and shiitake fruiting body extract, etc.

[0340] Nematicides: aldoxycarb, benclothiaz, cadusafos, cyclobutrifluram, DBCP, dichlofenthion, DSP, ethoprophos, fenamiphos, fensulfothion, fluazaindolizine, fluensulfone, fosthiazate, fosthietane, imicyafos, isamidofos, isazofos, oxamyl, thionazin, tioxazafen and trifluenfuronate, etc.

[0341] Anti-parasite drugs: esfenvalerate, fenpropathrin, fenvalerate, cypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox, lambda-cyhalothrin, permethrin, tefluthrin, zeta-cypermethrin, acetamiprid acetamiprid), clothianidin, dinotefuran, imidacloprid, nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, pyriproxyfen, triflumuron, chlorpyrifos, chlorpyrifos-methyl, dimethoate diazinon, dichlorvos, fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlorvinphos, ethiprole, fipronil, propoxur, carbaryl, bendiocarb, metoxadiazone, fenobucarb, carbofuran, afoxolaner, fluralaner, fluxametamide, sarolaner, lotilaner, tigolaner, esafoxolaner, modoflaner, umifoxolaner, mivorilaner, avermectin, ivermectin, doramectin, eprinomectin,maduramycin, milbemycin, milbemycin oxime, moxidectin, selamectin, indoxacarb, amitraz, bistrifluron, spinosad, albendazole, atovaquone, bithionol, cambendazole, carnidazole, chloroquine, clazuril, clorsulon, closantel, coumaphos, dichlorophen, diethylcarbamazine, diminazene, dinitolmide, dithiazanine iodide, emodepside, epsiprantel, febantel, fenbendazole, flubendazole, glycalpyramide, imidocarb, levamisole, mebendazole, mebendazole, mefloquine hydrochloride, melarsamine hydrochloride, metronidazole, metyridine, monepantel, morantel tartrate, niclosamide, oxantel pamoate, oxantel tartrate tartrate), oxibendazole, oxyclozanide, piperazine adipate, piperazine citrate, piperazine phosphate, praziquantel, pyrantelpamoate, rafoxanide,Tetramisole hydrochloride, thiabendazole and triclabendazole, etc.

[0342] Antibiotics: amoxicillin, ampicillin, cefapirin, cefazolin sodium sodium), cefquinome, ceftiofur, penicillin, chlortetracycline, oxytetracycline, danofloxacin, difloxacin, oxolinic acid, enrofloxacin, florfenicol, lincomycin, lomefloxacin, marbofloxacin, miloxacin, mirosamycin, norfloxacin, ofloxacin, orbifloxacin, valnemulin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate phosphate), acetyl isovaleryl tylosin, tylosin phosphate, tulathromycin, ketoconazole, miconazole nitrate and clavulanic acid, etc.

[0343] The compounds of the present invention have excellent insecticidal and acaricidal activities against many agricultural pests, spider mites, and internal or external parasites of mammals or birds, and can also exert sufficient control effects on pests that have developed resistance to existing insecticides. Furthermore, there is almost no adverse effect on mammals, fish and beneficial insects, and the load on the environment is also light due to low residual properties. Therefore, the present invention can provide a useful new pest control agent.

[0344] Based on the above, embodiments of the present invention relate to the following [1] to

[83] .

[0345] [1] an aryltetrahydropyridine compound represented by formula (1) or a salt thereof,

[0346]

[0347] [In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q -15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, Q-26, Q-27, Q-28, Q -29, Q-30, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-48, Q-49, Q-50, Q-51, Q-52, Q-53, Q-54, Q-55 or Q-56,

[0348]

[0349]

[0350] Z 1represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo(C1-C6)alkyl group, a halo(C2-C6)alkenyl group, a halo(C2-C6)alkynyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C2-C6 alkoxy(C1-C6)alkoxy group, a C2-C6 alkenyloxy group, a halo(C2-C6)alkenyloxy group, a C2-C6 alkynyloxy group, a halo(C2-C6)alkynyloxy group, a C1-C6 Alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated (C1-C6) alkylthio, halogenated (C1-C6) alkylsulfinyl, halogenated (C1-C6) alkylsulfonyl, C2-C6 alkenylthio, C2-C6 alkenylsulfinyl, C2-C6 alkenylsulfonyl, halogenated (C2-C6) alkenylthio, halogenated (C2-C6) alkenylsulfinyl, halogenated (C2-C6) alkenylsulfonyl, C2-C6 alkynylthio, C2-C6 C2-C6 alkynylsulfinyl, C2-C6 alkynylsulfonyl, halo (C2-C6) alkynylthio, halo (C2-C6) alkynylsulfinyl, halo (C2-C6) alkynylsulfonyl, -NH2, C1-C6 alkylamino, di (C1-C6) alkylamino, halo (C1-C6) alkylamino, dihalo (C1-C6) alkylamino, formyl, carboxyl, C1-C6 alkylcarbonyl, halo (C1-C6) alkylcarbonyl, C1-C6 alkoxy alkylcarbonyl, halogenated (C1-C6) alkoxycarbonyl, C1-C6 alkylaminocarbonyl, halogenated (C1-C6) alkylaminocarbonyl, di(C1-C6) alkylaminocarbonyl, hydroxy, C1-C6 alkylcarbonyloxy, C1-C6 alkoxycarbonyloxy, C1-C6 alkylsulfonyloxy, halogenated (C1-C6) alkylsulfonyloxy, -SO3H, C1-C6 alkylaminosulfonyl, di(C1-C6) alkylaminosulfonyl, -C(=NOR 12 )R 13 , cyano or nitro,

[0351] R 12 represents a hydrogen atom or a C1-C6 alkyl group,

[0352] R 13 represents a hydrogen atom or a C1-C6 alkyl group,

[0353] Z 3 represents a hydrogen atom or a C1-C6 alkyl group,

[0354] J stands for J-1 or J-2,

[0355]

[0356] A 1 represents a nitrogen atom or CH,

[0357] G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G-32, G-33, G-34, G-35, G-36, G-37, G-38, G-39, G-40, G-41, G-42, G-43, G-44, G-45, G-46, G-47, G-48, G-49, G-50, G-51, G-52, G-53, G-54, G-55, G-56, G-57, G-58, G-59, G-60 or G-61,

[0358]

[0359] Z 2represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo(C1-C6)alkyl group, a halo(C2-C6)alkenyl group, a halo(C2-C6)alkynyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkoxy(C1-C6)alkoxy group, a C2-C6 alkenyloxy group, a halo(C2-C6)alkenyloxy group, a C2-C6 alkynyloxy group, a halo(C2-C6)alkynyloxy group, a C1-C6 Alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated (C1-C6) alkylthio, halogenated (C1-C6) alkylsulfinyl, halogenated (C1-C6) alkylsulfonyl, C2-C6 alkenylthio, C2-C6 alkenylsulfinyl, C2-C6 alkenylsulfonyl, halogenated (C2-C6) alkenylthio, halogenated (C2-C6) alkenylsulfinyl, halogenated (C2-C6) alkenylsulfonyl, C2-C6 alkynylthio, C2-C6 C2-C6 alkynylsulfinyl, C2-C6 alkynylsulfonyl, halo (C2-C6) alkynylthio, halo (C2-C6) alkynylsulfinyl, halo (C2-C6) alkynylsulfonyl, -NH2, C1-C6 alkylamino, di (C1-C6) alkylamino, halo (C1-C6) alkylamino, dihalo (C1-C6) alkylamino, formyl, carboxyl, C1-C6 alkylcarbonyl, halo (C1-C6) alkylcarbonyl, C1-C6 alkoxy alkylcarbonyl, halogenated (C1-C6) alkoxycarbonyl, C1-C6 alkylaminocarbonyl, halogenated (C1-C6) alkylaminocarbonyl, di(C1-C6) alkylaminocarbonyl, hydroxy, C1-C6 alkylcarbonyloxy, C1-C6 alkoxycarbonyloxy, C1-C6 alkylsulfonyloxy, halogenated (C1-C6) alkylsulfonyloxy, -SO3H, C1-C6 alkylaminosulfonyl, di(C1-C6) alkylaminosulfonyl, -C(=NOR 14 )R 15 , nitro or cyano,

[0360] R 14 represents a hydrogen atom or a C1-C6 alkyl group,

[0361] R 15 represents a hydrogen atom or a C1-C6 alkyl group,

[0362] Z 4 represents a C1-C6 alkyl group,

[0363] R 1 represents a hydrogen atom, a halogen atom, a halogenated (C1-C6) alkyl group, a C1-C6 alkyl group or a cyano group,

[0364] R 2represents a hydrogen atom, a C1-C6 alkyl group, a halogenated (C1-C6) alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, -C(O)R 4 、-C(O)OR 5 , D-1, D-2 or D-3,

[0365]

[0366] R 4 represents a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylcarbonyl group, a di(C1-C6)alkylamino group, or is replaced by R 6 Substituted (C1-C6) alkyl,

[0367] R 6 represents a halogen atom, a C1-C6 alkoxy group, a cyano group, a nitro group, a phenyl group, or a 8 Substituted phenyl,

[0368] Z 5 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a cyano group or a nitro group,

[0369] R 8 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a cyano group or a nitro group,

[0370] R 5 represents a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, 9 Substituted (C1-C6) alkyl, phenyl or R 10 Substituted phenyl,

[0371] R 9 represents a halogen atom, a C1-C6 alkoxy group, a cyano group, a nitro group, a phenyl group, or a 11 Substituted phenyl,

[0372] R 10 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a cyano group or a nitro group,

[0373] R 11 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a cyano group or a nitro group,

[0374] R 3 represents a hydrogen atom, a C1-C6 alkyl group, a halogenated (C1-C6) alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group or a C1-C6 alkylcarbonyl group,

[0375] X represents an oxygen atom or a sulfur atom,

[0376] Y represents an oxygen atom or a sulfur atom,

[0377] t1 represents an integer of 0 or 1,

[0378] t2 represents an integer of 0, 1 or 2,

[0379] t3 represents an integer of 0, 1, 2 or 3,

[0380] t4 represents an integer of 0, 1, 2, 3 or 4,

[0381] t5 represents an integer of 0, 1, 2, 3, 4 or 5,

[0382] t8 represents an integer of 0, 1, 2, 3 or 4.]

[0383] [2] The aryltetrahydropyridine compound or a salt thereof according to [1] above, wherein A 1 Represents a nitrogen atom.

[0384] [3] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [2] above, wherein

[0385] Z 1 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6)alkylthio group, a halo(C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfonyl group, -NH2, a C1-C6 alkylamino group, a di(C1-C6)alkylamino group, a carboxyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylaminocarbonyl group, a di(C1-C6)alkylaminocarbonyl group, a hydroxyl group, a C1-C6 alkylcarbonyloxy group, a C1-C6 alkylsulfonyloxy group, a cyano group or a nitro group,

[0386] Z 2represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halogenated (C1-C6) alkyl group, a halogenated (C2-C6) alkenyl group, a halogenated (C2-C6) alkynyl group, a C1-C6 alkoxy group, a halogenated (C1-C6) alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halogenated (C1-C6) alkylthio ... ~C6) alkylsulfinyl, halo(C1~C6) alkylsulfonyl, -NH2, C1~C6 alkylamino, di(C1~C6) alkylamino, carboxyl, C1~C6 alkylcarbonyl, C1~C6 alkoxycarbonyl, C1~C6 alkylaminocarbonyl, di(C1~C6) alkylaminocarbonyl, hydroxyl, C1~C6 alkylcarbonyloxy, C1~C6 alkylsulfonyloxy, -C(=NOR 14 )R 15 , nitro or cyano,

[0387] Z 5 represents a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,

[0388] R 1 represents a hydrogen atom, a halogen atom or a halogenated (C1-C6) alkyl group,

[0389] R 2 Represents a hydrogen atom, -C(O)R 4 、-C(O)OR 5 , D-1, D-2 or D-3,

[0390] R 3 represents a hydrogen atom,

[0391] Q means Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-25, Q-26, Q-27, Q-29, Q-30, Q-31, Q-32, Q-33, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-50, Q-51, Q-52 or Q-54,

[0392] G means G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G-32, G-33, G-34, G-35, G-37, G-38, G-40, G-41, G-42, G-43, G-45, G-47, G-48, G-50, G-53, G-54, G-55 or G-57.

[0393] [4] The aryl tetrahydropyridine compound or a salt thereof according to any one of [1] to [3] above, wherein J represents J-1, A 1 Represents a nitrogen atom.

[0394] [5] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [3] above, wherein J represents J-2.

[0395] [6] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [5] above, wherein

[0396] G means G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G -26, G-27, G-28, G-29, G-30, G-31, G-32, G-34, G-35, G-37, G-38, G-40, G-41, G-42, G-43, G-45, G-47, G-48, G-50, G-53, G-55 or G-57.

[0397] [7] The aryltetrahydropyridine compound or a salt thereof according to [1] above, wherein

[0398] Q means Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31, Q-45 or Q-52,

[0399] Z 1represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6)alkylthio group, a carboxyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylaminocarbonyl group, a hydroxyl group, a cyano group or a nitro group,

[0400] G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 or G-40,

[0401] Z 2 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a halogenated (C1-C6) alkyl group, a C1-C6 alkoxy group, a halogenated (C1-C6) alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a di(C1-C6) alkylamino group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a hydroxyl group, -C(=NOR 14 )R 15 , nitro or cyano,

[0402] R 14 represents a C1-C6 alkyl group,

[0403] R 1 represents a hydrogen atom, a halogen atom or a halogenated (C1-C6) alkyl group,

[0404] R 2 Represents a hydrogen atom, -C(O)R 4 、-C(O)OR 5 , D-1, D-2 or D-3,

[0405] R 4 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylcarbonyl group or a 6 Substituted (C1-C6) alkyl,

[0406] R 6 represents a halogen atom or a C1-C6 alkoxy group,

[0407] Z 5 represents a C1-C6 alkyl group,

[0408] R 5 represents a C1-C6 alkyl group or a C2-C6 alkenyl group,

[0409] R3 represents a hydrogen atom,

[0410] X represents an oxygen atom.

[0411] [8] The aryltetrahydropyridine compound or a salt thereof according to [7] above, wherein

[0412] G means G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 or G-40.

[0413] [9] The aryltetrahydropyridine compound or a salt thereof according to [8] above, wherein

[0414] Q means Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29 or Q-45,

[0415] Z 1 represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6)alkylthio group, a C1-C6 alkoxycarbonyl group, a cyano group or a nitro group,

[0416] Z 3 represents a C1-C6 alkyl group,

[0417] Z 2 It represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a hydroxyl group, a nitro group or a cyano group.

[0418]

[10] The aryltetrahydropyridine compound or a salt thereof according to [9] above, wherein

[0419] J stands for J-1,

[0420] A 1 represents nitrogen atom,

[0421] Q means Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-12, Q-13, Q-14 or Q-22,

[0422] G stands for G-1, G-3, G-4 or G-5,

[0423] Z 2 represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group or a nitro group,

[0424] R 2 Represents a hydrogen atom or -C(O)OR 5 ,

[0425] R 5 represents a C1-C6 alkyl group,

[0426] Y represents an oxygen atom.

[0427]

[11] The aryltetrahydropyridine compound or a salt thereof according to

[10] above, wherein

[0428] Q stands for Q-1, Q-2, Q-3, Q-4, Q-6, Q-9 or Q-12,

[0429] Z 1 represents a halogen atom, a C1-C6 alkyl group, a halogenated (C1-C6) alkyl group, a cyano group or a nitro group,

[0430] G means G-1 or G-3,

[0431] Z 2 represents a halogen atom, a C1-C6 alkyl group or a halogenated (C1-C6) alkyl group,

[0432] R 1 represents a halogen atom or a halogenated (C1-C6) alkyl group,

[0433] R 2 Represents a hydrogen atom.

[0434]

[12] The aryltetrahydropyridine compound or a salt thereof according to

[11] above, wherein

[0435] J stands for J-2,

[0436] Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, Q-10, Q-12, Q-20, Q-29 or Q-45,

[0437] Z 1 represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a C1-C6 alkoxycarbonyl group, a cyano group or a nitro group,

[0438] G means G-1, G-3, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 or G-40,

[0439] Z 2 It represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group or a hydroxyl group.

[0440]

[13] The aryltetrahydropyridine compound or a salt thereof according to

[12] above, wherein

[0441] Q stands for Q-1, Q-2, Q-3, Q-4, Q-6, Q-9 or Q-12,

[0442] Z 1 represents a halogen atom, a C1-C6 alkyl group, a halogenated (C1-C6) alkyl group, a cyano group or a nitro group,

[0443] G stands for G-1, G-3 or G-7,

[0444] Z 2 represents a halogen atom, a C1-C6 alkyl group or a halogenated (C1-C6) alkyl group,

[0445] R 2 Represents a hydrogen atom.

[0446]

[14] The aryl tetrahydropyridine compound or a salt thereof according to any one of [1] to [6] above, wherein Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-11, Q-14, Q-15, Q-16, Q-17 or Q-18.

[0447]

[15] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [8] above, wherein Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-11 or Q-14.

[0448]

[16] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[13] above, wherein Q represents Q-1.

[0449]

[17] The aryl tetrahydropyridine compound or a salt thereof according to any one of [1] to [6] above, wherein Q represents Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-14, Q-15, Q-16, Q-17 or Q-18.

[0450]

[18] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [9] above, wherein Q represents Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 or Q-14.

[0451]

[19] The aryl tetrahydropyridine compound or a salt thereof according to any one of [1] to [6] above, wherein Q represents Q-9, Q-10, Q-12, Q-13, Q-19, Q-20, Q-21, Q-22, Q-23, Q-25, Q-26, Q-27, Q-29, Q-30, Q-31, Q-32, Q-33, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-50, Q-51, Q-52 or Q-54.

[0452]

[20] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [8] above, wherein Q represents Q-9, Q-12, Q-13, Q-20, Q-22, Q-31, Q-45 or Q-52.

[0453]

[21] The aryl tetrahydropyridine compound or a salt thereof according to any one of [1] to [6] above, wherein Q represents Q-12, Q-30, Q-31, Q-32, Q-33, Q-40, Q-45, Q-47, Q-49, Q-52, Q-55 or Q-56.

[0454]

[22] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [8] above, wherein Q represents Q-31, Q-45 or Q-52.

[0455]

[23] The aryl tetrahydropyridine compound or a salt thereof according to any one of [1] to [6] above, wherein Q represents Q-9, Q-13, Q-25, Q-26, Q-27, Q-29, Q-39, Q-42, Q-44, Q-46, Q-51 or Q-54.

[0456]

[24] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [8] above, wherein Q represents Q-9 or Q-13.

[0457]

[25] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [6] above, wherein Q represents Q-10, Q-19, Q-20, Q-21, Q-22, Q-23, Q-38, Q-41, Q-43 or Q-50.

[0458]

[26] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [8] above, wherein Q represents Q-10, Q-20 or Q-22.

[0459]

[27] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [8] above, wherein Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, Q-10 or Q-12.

[0460]

[28] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[13] above, wherein Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9 or Q-12.

[0461]

[29] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[13] above, wherein Q represents Q-1, Q-2, Q-3, Q-4 or Q-6.

[0462]

[30] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [8] above, wherein Q represents Q-9, Q-10 or Q-12.

[0463]

[31] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[13] above, wherein Q represents Q-9 or Q-12.

[0464]

[32] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [2] and

[14] to

[31] , wherein Z 1 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo(C1-C6)alkyl group, a halo(C2-C6)alkenyl group, a halo(C2-C6)alkynyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C2-C6 alkoxy(C1-C6)alkoxy group, a C2-C6 alkenyloxy group, a halo(C2-C6)alkenyloxy group, a C2-C6 alkynyloxy group, a halo(C2-C6)alkynyloxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6) Alkylthio, halo(C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfonyl, C2-C6 alkenylthio, C2-C6 alkenylsulfinyl, C2-C6 alkenylsulfonyl, halo(C2-C6)alkenylthio, halo(C2-C6)alkenylsulfinyl, halo(C2-C6)alkenylsulfonyl, C2-C6 alkynylthio, C2-C6 alkynylsulfinyl, C2-C6 alkynylsulfonyl, halo(C2-C6)alkynylthio, halo(C2-C6)alkynylsulfinyl, halo(C2-C6)alkynylsulfonyl, cyano or nitro.

[0465]

[33] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [2] and

[14] to

[31] , wherein Z 1It represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo-substituted (C1-C6) alkyl group, -NH2, a C1-C6 alkylamino group, a di-(C1-C6) alkylamino group, a halo-substituted (C1-C6) alkylamino group, a di-halo-substituted (C1-C6) alkylamino group, a formyl group, a carboxyl group, a C1-C6 alkylcarbonyl group, a halo-substituted (C1-C6) alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a halo-substituted (C1-C6) alkoxycarbonyl group, a C1-C6 alkylaminocarbonyl group, a halo-substituted (C1-C6) alkylaminocarbonyl group, a di-(C1-C6) alkylaminocarbonyl group, a cyano group or a nitro group.

[0466]

[34] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[13] above, wherein Z 1 It represents a halogen atom, a C1-C6 alkyl group, a halogenated (C1-C6) alkyl group, a cyano group or a nitro group.

[0467]

[35] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[13] above, wherein Z 1 It represents a halogen atom, a C1-C6 alkyl group, a halogenated (C1-C6) alkyl group or a cyano group.

[0468]

[36] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[35] above, wherein Z 3 It represents a C1-C6 alkyl group.

[0469]

[37] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[35] above, wherein Z 3 Represents a hydrogen atom.

[0470]

[38] The aryl tetrahydropyridine compound or a salt thereof according to any one of [1] and

[14] to

[37] , wherein G represents G-1, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G-32, G-33, G-34, G-35, G-36, G-37, G-38, G-39, G-40, G-41, G-42, G-43, G-44, G-45, G-46, G-47, G-48, G-49, G-50, G-51, G-52, G-53, G-54, G-55, G-56, G-57, G-58, G-59, G-60 or G-61.

[0471]

[39] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [2] and

[14] to

[37] , wherein G represents G-1, G-3, G-5, G-6, G-7, G-8, G-11, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-32, G-33, G-34, G-35, G-36, G-37, G-38, G-39, G-47, G-48, G-49, G-50, G-51, G-52, G-53, G-54, G-55, G-56, G-57, G-58, G-59, G-60 or G-61.

[0472]

[40] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [6] and

[14] to

[37] , wherein G represents G-1, G-3, G-5, G-7, G-11, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-32, G-34, G-35, G-36, G-37, G-38, G-47, G-48, G-50, G-53, G-55 or G-57.

[0473]

[41] The aryl tetrahydropyridine compound or a salt thereof according to any one of [1] to [5], [7] and

[14] to

[37] above, wherein G represents G-1, G-3, G-5, G-6, G-7, G-8, G-11, G-17 or G-19.

[0474]

[42] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [9] and

[14] to

[37] above, wherein G represents G-1, G-3, G-5, G-7, G-11, G-17 or G-19.

[0475]

[43] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [9],

[12] and

[14] to

[37] above, wherein G represents G-1, G-3, G-7, G-11, G-17 or G-19.

[0476]

[44] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [5] and

[14] to

[37] , wherein G represents G-1, G-2, G-3, G-5, G-7, G-11, G-17, G-18, G-19, G-20, G-21, G-22, G-23 or G-24.

[0477]

[45] The aryl tetrahydropyridine compound or a salt thereof according to any one of [1] to [7] and

[14] to

[37] above, wherein G represents G-1, G-2, G-3, G-5, G-7, G-11, G-17 or G-19.

[0478]

[46] The aryl tetrahydropyridine compound or a salt thereof according to any one of [1] to [9] and

[14] to

[37] above, wherein G represents G-1, G-3, G-5, G-7, G-11, G-17 or G-19.

[0479]

[47] The aryl tetrahydropyridine compound or a salt thereof according to any one of [1] to [9],

[12] and

[14] to

[37] above, wherein G represents G-1, G-3, G-7, G-11, G-17 or G-19.

[0480]

[48] ​​The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to [9],

[12] and

[14] to

[37] above, wherein G represents G-1, G-3 or G-7.

[0481]

[49] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[37] above, wherein G represents G-1 or G-3.

[0482]

[50] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[49] above, wherein

[0483] t1 represents an integer of 0,

[0484] t2 represents an integer of 0,

[0485] t3 represents an integer of 0 or 1,

[0486] t4 represents an integer of 0, 1 or 2,

[0487] t5 represents an integer of 0 or 1.

[0488]

[51] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[50] above, wherein

[0489] Q means Q-2, Q-3, Q-4, Q-6, Q-9, Q-12 or Q-14,

[0490] Z 1 represents a halogen atom or a C1-C6 alkyl group,

[0491] Z 3 represents a C1 alkyl group,

[0492] J stands for J-1 or J-2,

[0493] A 1 represents nitrogen atom,

[0494] G stands for G-1, G-3 or G-7,

[0495] Z 2 represents a halogen atom,

[0496] R 1 represents a halogen atom or a halogenated (C1-C6) alkyl group,

[0497] R 2 represents a hydrogen atom,

[0498] R 3 represents a hydrogen atom,

[0499] X represents an oxygen atom,

[0500] Y represents an oxygen atom,

[0501] t2 represents an integer of 0,

[0502] t4 represents an integer of 0, 1 or 2.

[0503]

[52] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[50] above, wherein

[0504] Q stands for Q-2, Q-3, Q-4, Q-6, Q-9 or Q-12,

[0505] Z 1 represents a halogen atom or a C1-C6 alkyl group,

[0506] Z 3 represents a C1 alkyl group,

[0507] J stands for J-1,

[0508] A 1 represents nitrogen atom,

[0509] G means G-1 or G-3,

[0510] Z 2 represents a halogen atom,

[0511] R 1 represents a halogen atom or a halogenated (C1-C6) alkyl group,

[0512] R 2 represents a hydrogen atom,

[0513] R 3 represents a hydrogen atom,

[0514] X represents an oxygen atom,

[0515] Y represents an oxygen atom,

[0516] t2 represents an integer of 0,

[0517] t4 represents an integer of 0, 1 or 2.

[0518]

[53] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[51] above, wherein

[0519] Q stands for Q-2, Q-3, Q-4, Q-6, Q-9 or Q-12,

[0520] Z 1 represents a halogen atom or a C1-C6 alkyl group,

[0521] Z 3 represents a C1 alkyl group,

[0522] J stands for J-2,

[0523] G means G-1 or G-3,

[0524] Z 2 represents a halogen atom,

[0525] R 1 represents a halogen atom or a halogenated (C1-C6) alkyl group,

[0526] R 2 represents a hydrogen atom,

[0527] R 3 represents a hydrogen atom,

[0528] X represents an oxygen atom,

[0529] Y represents an oxygen atom,

[0530] t2 represents an integer of 0,

[0531] t4 represents an integer of 0, 1 or 2.

[0532]

[54] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[53] above, wherein

[0533] Q means Q-2 or Q-3,

[0534] G means G-1 or G-3,

[0535] t4 represents an integer of 0, 1 or 2.

[0536]

[55] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[54] above, wherein R 1 It represents a halogen atom or a halogenated (C1-C6) alkyl group.

[0537]

[56] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[50] above, wherein

[0538] R 2 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, -C(O)R 4 or-C(O)OR 5 ,

[0539] R 4 represents a C1-C6 alkyl group,

[0540] R 5 It represents a C1-C6 alkyl group.

[0541]

[57] The aryltetrahydropyridine compound or a salt thereof according to

[56] above, wherein R 2 It represents a hydrogen atom or a C1-C6 alkyl group.

[0542]

[58] The aryltetrahydropyridine compound or a salt thereof according to

[57] above, wherein R 2 Represents a hydrogen atom.

[0543]

[59] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[58] above, wherein R 3 Represents a hydrogen atom.

[0544]

[60] The aryltetrahydropyridine compound or a salt thereof according to any one of [1] to

[59] above, wherein

[0545] X represents an oxygen atom,

[0546] Y represents an oxygen atom.

[0547]

[61] An aryltetrahydropyridine compound represented by formula (1) or a salt thereof.

[0548]

[0549] [wherein, Q represents Q-1, Q-2, Q-3 or Q-4,

[0550]

[0551] Z 1 represents a halogen atom, a halogenated (C1-C6) alkyl group or a cyano group,

[0552] G stands for G-1,

[0553]

[0554] Z 2represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group or a cyano group,

[0555] R 1 represents a halogen atom or a halogenated (C1-C6) alkyl group,

[0556] R 2 represents a hydrogen atom,

[0557] R 3 represents a hydrogen atom,

[0558] A 1 represents a nitrogen atom or CH,

[0559] X represents an oxygen atom or a sulfur atom,

[0560] Y represents an oxygen atom or a sulfur atom,

[0561] t3 represents an integer of 0, 1, 2 or 3,

[0562] t4 represents an integer of 0, 1, 2, 3 or 4,

[0563] t5 represents an integer of 0, 1, 2, 3, 4 or 5.]

[0564]

[62] The aryltetrahydropyridine compound or a salt thereof according to

[61] above, wherein

[0565] Q means Q-1,

[0566] Z 1 represents a halogen atom,

[0567] Z 2 represents a halogen atom or a C1-C6 alkoxy group,

[0568] X represents an oxygen atom,

[0569] Y represents an oxygen atom,

[0570] t4 represents an integer of 1,

[0571] t5 represents an integer of 1.

[0572]

[63] An aryltetrahydropyridine compound represented by formula (1) or a salt thereof.

[0573]

[0574] [wherein, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6 or Q-7,

[0575]

[0576] Z 1represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6)alkylthio group or a cyano group,

[0577] G represents G-1, G-2, G-3, G-4, G-5 or G-6,

[0578]

[0579] Z 2 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylcarbonyl group, a nitro group or a cyano group,

[0580] R 1 represents a hydrogen atom, a halogen atom or a halogenated (C1-C6) alkyl group,

[0581] R 2 represents a hydrogen atom, a C1-C6 alkyl group or a C2-C6 alkynyl group,

[0582] R 3 represents a hydrogen atom or a C1-C6 alkyl group,

[0583] A 1 represents a nitrogen atom or CH,

[0584] X represents an oxygen atom or a sulfur atom,

[0585] Y represents an oxygen atom or a sulfur atom,

[0586] t2 represents an integer of 0, 1 or 2,

[0587] t3 represents an integer of 0, 1, 2 or 3,

[0588] t4 represents an integer of 0, 1, 2, 3 or 4,

[0589] t5 represents an integer of 0, 1, 2, 3, 4 or 5.]

[0590]

[64] The aryltetrahydropyridine compound or a salt thereof according to

[63] above, wherein

[0591] Z 1 represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6)alkylthio group or a cyano group,

[0592] Z 2 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylcarbonyl group, a nitro group or a cyano group,

[0593] R 2 represents a hydrogen atom,

[0594] R 3 represents a hydrogen atom,

[0595] X represents an oxygen atom,

[0596] Y represents an oxygen atom.

[0597]

[65] An aryltetrahydropyridine compound represented by formula (1) or a salt thereof.

[0598]

[0599] [wherein, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7 or Q-8,

[0600]

[0601] Z 1 represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6)alkylthio group or a cyano group,

[0602] J stands for J-1 or J-2,

[0603]

[0604] G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8 or G-9,

[0605]

[0606] Z 2 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylcarbonyl group, a nitro group or a cyano group,

[0607] R 1 represents a hydrogen atom, a halogen atom or a halogenated (C1-C6) alkyl group,

[0608] R 2 represents a hydrogen atom, a C1-C6 alkyl group or a C2-C6 alkynyl group,

[0609] R 3 represents a hydrogen atom or a C1-C6 alkyl group,

[0610] A 1 represents a nitrogen atom or CH,

[0611] X represents an oxygen atom or a sulfur atom,

[0612] Y represents an oxygen atom or a sulfur atom,

[0613] t2 represents an integer of 0, 1 or 2,

[0614] t3 represents an integer of 0, 1, 2 or 3,

[0615] t4 represents an integer of 0, 1, 2, 3 or 4,

[0616] t5 represents an integer of 0, 1, 2, 3, 4 or 5.]

[0617]

[66] The aryltetrahydropyridine compound or a salt thereof according to

[65] above, wherein

[0618] Z 1 represents a halogen atom, a C1-C6 alkyl group, a halo-substituted (C1-C6) alkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo-substituted (C1-C6) alkylthio group or a cyano group;

[0619] Z 2 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylcarbonyl group, a nitro group or a cyano group,

[0620] R 2 represents a hydrogen atom,

[0621] R 3 represents a hydrogen atom,

[0622] X represents an oxygen atom,

[0623] Y represents an oxygen atom.

[0624]

[67] An aryltetrahydropyridine compound represented by formula (1) or a salt thereof.

[0625]

[0626] [wherein, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 or Q-9,

[0627]

[0628] Z 1 represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6)alkylthio group, a cyano group or a nitro group,

[0629] J stands for J-1 or J-2,

[0630]

[0631] G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8 or G-9,

[0632]

[0633] Z 2 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylcarbonyl group, a nitro group or a cyano group,

[0634] R 1 represents a hydrogen atom, a halogen atom or a halogenated (C1-C6) alkyl group,

[0635] R 2 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkynyl group or a C1-C6 alkoxycarbonyl group,

[0636] R 3 represents a hydrogen atom or a C1-C6 alkyl group,

[0637] A 1 represents a nitrogen atom or CH,

[0638] X represents an oxygen atom or a sulfur atom,

[0639] Y represents an oxygen atom or a sulfur atom,

[0640] t2 represents an integer of 0, 1 or 2,

[0641] t3 represents an integer of 0, 1, 2 or 3,

[0642] t4 represents an integer of 0, 1, 2, 3 or 4,

[0643] t5 represents an integer of 0, 1, 2, 3, 4 or 5.]

[0644]

[68] The aryltetrahydropyridine compound or a salt thereof according to

[67] above, wherein

[0645] Z 1 represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6)alkylthio group or a cyano group,

[0646] Z 2 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylcarbonyl group, a nitro group or a cyano group,

[0647] R 2 represents a hydrogen atom,

[0648] R 3 represents a hydrogen atom,

[0649] X represents an oxygen atom,

[0650] Y represents an oxygen atom.

[0651]

[69] An aryltetrahydropyridine compound represented by formula (1) or a salt thereof.

[0652]

[0653] [wherein, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12 or Q-13,

[0654]

[0655] Z 1 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halogenated (C1-C6) alkyl group, a C1-C6 alkoxy group, a halogenated (C1-C6) alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halogenated (C1-C6) alkylthio group, a hydroxyl group, a cyano group or a nitro group,

[0656] J stands for J-1 or J-2,

[0657]

[0658] G means G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16 or G-17,

[0659]

[0660] Z 2 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylcarbonyl group, a hydroxyl group, a nitro group or a cyano group,

[0661] R 1 represents a hydrogen atom, a halogen atom or a halogenated (C1-C6) alkyl group,

[0662] R 2 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, -C(O)R 4 , or -C(O)OR 5 ,

[0663] R 4 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylcarbonyl group or a 6 Replaced (C a ~C b )alkyl,

[0664] R 6 represents a halogen atom or a C1-C6 alkoxy group,

[0665] R 5 represents a C1-C6 alkyl group or a C2-C6 alkenyl group,

[0666] R 3 represents a hydrogen atom or a C1-C6 alkyl group,

[0667] A 1 represents a nitrogen atom or CH,

[0668] X represents an oxygen atom or a sulfur atom,

[0669] Y represents an oxygen atom or a sulfur atom,

[0670] t1 represents an integer of 0 or 1,

[0671] t2 represents an integer of 0, 1 or 2,

[0672] t3 represents an integer of 0, 1, 2 or 3,

[0673] t4 represents an integer of 0, 1, 2, 3 or 4,

[0674] t5 represents an integer of 0, 1, 2, 3, 4 or 5.]

[0675]

[70] The aryltetrahydropyridine compound or a salt thereof according to

[69] above, wherein

[0676] Z 2 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a halogenated (C1-C6) alkyl group, a C1-C6 alkoxy group, a halogenated (C1-C6) alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylcarbonyl group, a hydroxyl group, a nitro group or a cyano group,

[0677] R 2 Represents a hydrogen atom, -C(O)R 4 , or -C(O)OR 5 ,

[0678] R 3 represents a hydrogen atom,

[0679] X represents an oxygen atom,

[0680] Y represents an oxygen atom.

[0681]

[71] A production intermediate of an aryltetrahydropyridine compound or a salt thereof represented by formula (1-1) and described in any one of [1] to

[70] above,

[0682]

[0683] [wherein, J represents J-1 or J-2,

[0684]

[0685] A 1 represents nitrogen atom,

[0686] G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 or G-40,

[0687]

[0688] Z 2represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a halogenated (C1-C6) alkyl group, a C1-C6 alkoxy group, a halogenated (C1-C6) alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a di(C1-C6) alkylamino group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a hydroxyl group, -C(=NOR 14 )R 15 , nitro or cyano,

[0689] R 14 represents a C1-C6 alkyl group,

[0690] R 15 represents a hydrogen atom or a C1-C6 alkyl group,

[0691] Z 4 represents a C1-C6 alkyl group,

[0692] R 1 represents a hydrogen atom, a halogen atom or a halogenated (C1-C6) alkyl group,

[0693] R 51 represents a C1-C6 alkyl group,

[0694] t2 represents an integer of 0, 1 or 2,

[0695] t3 represents an integer of 0, 1, 2 or 3,

[0696] t4 represents an integer of 0, 1, 2, 3 or 4,

[0697] t5 represents an integer of 0, 1, 2, 3, 4 or 5.]

[0698]

[72] The intermediate for producing the aryltetrahydropyridine compound or its salt according to

[71] above, wherein

[0699] J stands for J-1,

[0700] G stands for G-1, G-2 or G-3,

[0701] Z 2 represents a halogen atom or a C1-C6 alkyl group,

[0702] R 1 It represents a halogen atom or a halogenated (C1-C6) alkyl group.

[0703]

[73] A production intermediate of an aryltetrahydropyridine compound or a salt thereof according to any one of the above [1] to

[70] and represented by formula (1-2).

[0704]

[0705] [Where R 52 represents a hydrogen atom or a C1-C6 alkyl group,

[0706] R 2 represents a hydrogen atom, -C(O)R 4 or-C(O)OR 5 ,

[0707] R 4 represents a C1-C6 alkyl group,

[0708] R 5 represents a C1-C6 alkyl group,

[0709] Q means Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31, Q-45 or Q-52,

[0710]

[0711] Z 1 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6)alkylthio group, a carboxyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylaminocarbonyl group, a hydroxyl group, a cyano group or a nitro group,

[0712] Z 3 represents a hydrogen atom or a C1-C6 alkyl group,

[0713] t1 represents an integer of 0 or 1,

[0714] t2 represents an integer of 0, 1 or 2,

[0715] t3 represents an integer of 0, 1, 2 or 3,

[0716] t4 represents an integer of 0, 1, 2, 3 or 4,

[0717] t5 represents an integer of 0, 1, 2, 3, 4 or 5.]

[0718]

[74] The intermediate for producing the aryltetrahydropyridine compound or its salt according to

[73] above, wherein

[0719] Q means Q-1, Q-2, Q-3, Q-4, Q-6 or Q-9,

[0720] Z 1represents a halogen atom, a C1-C6 alkyl group or a cyano group,

[0721] R 2 Represents a hydrogen atom or -C(O)OR 5 .

[0722]

[75] A pest control agent comprising, as an active ingredient, one or two or more aryltetrahydropyridine compounds and salts thereof selected from any one of [1] to

[70] above.

[0723]

[76] A pesticide comprising one or more aryltetrahydropyridine compounds and salts thereof selected from any one of [1] to

[70] above as active ingredients.

[0724]

[77] An agent for controlling internal or external parasites of mammals or birds, comprising one or more aryltetrahydropyridine compounds and salts thereof selected from any one of [1] to

[70] as active ingredients.

[0725]

[78] The pest control agent according to the above

[77] , wherein the external parasite is of the order Siphonaptera or the order Acarina.

[0726]

[79] An insecticide or acaricide comprising one or more aryltetrahydropyridine compounds and salts thereof selected from any one of [1] to

[70] above as active ingredients.

[0727]

[80] A seed treatment agent comprising, as an active ingredient, one or two or more selected from the aryltetrahydropyridine compounds and salts thereof described in any one of [1] to

[70] above.

[0728]

[81] The seed treatment agent according to the above

[80] , wherein the seed treatment is performed by immersion treatment.

[0729]

[82] A soil treatment agent comprising one or more aryltetrahydropyridine compounds selected from any one of [1] to

[70] above as active ingredients.

[0730]

[83] The soil treatment agent according to the above

[82] , wherein the soil treatment is performed by soil irrigation treatment.

[0731] Example

[0732] Hereinafter, the present invention will be described in further detail by describing synthesis examples and test examples of the compounds of the present invention as examples, but the present invention is not limited thereto.

[0733] For the medium-pressure fractionation liquid chromatography described in the synthesis examples, a medium-pressure fractionation apparatus YFLC-Wprep (flow rate 18 ml / min, silica gel 40 μm column) manufactured by Yamazen Co., Ltd. was used.

[0734] In addition, the proton nuclear magnetic resonance spectrum (hereinafter referred to as 1 H-NMR. The chemical shift values ​​of ) were measured using Me4Si (tetramethylsilane) as a reference substance in deuterated chloroform solvent at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL) or 400 MHz (model: JNM-ECZ400S, manufactured by JEOL). It should be noted that 1 The symbols in the chemical shift values ​​of H-NMR have the following meanings.

[0735] s: singlet, d: doublet, dd: doublet of doublets, t: triplet, q: quartet, m: multiplet, brs: broad singlet

[0736] Synthesis Example 1: Synthesis of N-(4-fluorophenyl)-6-[3-(6-fluoropyridin-3-yl)-4-(trifluoromethyl)phenyl]-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide (Compound No. 1-001 of the present invention)

[0737] 42 mg of 2-fluoropyridine-5-boric acid, 83 mg of potassium carbonate and 16 mg of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (2-valent) dichloromethane adduct were added to a mixed solution of 94 mg of 6-[3-bromo-4(trifluoromethyl)phenyl]-N-(4-fluorophenyl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide, 1.6 ml of 1,4-dioxane and 0.4 ml of water, and stirred at 90°C for 5 hours under a nitrogen atmosphere. After the reaction was completed, 5 ml of 1 mol / l hydrochloric acid was added, and extraction was performed with ethyl acetate (5 ml × 3 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by medium pressure preparative liquid chromatography [gradient of n-hexane:ethyl acetate=100:0 to 0:100 (volume ratio, the same below)] to obtain 31 mg of the target product as a white solid.

[0738] Melting point: 200℃~202℃

[0739] 1H-NMR (300MHz): δ11.5-12.0(m,1H),8.18(brs,1H),7.85(d,J=8.7Hz,1H),7.65-7.8(m,1H),7.4- 7.65(m,4H),7.33(brs,1H),6.95-7.1(m,3H),5.45-5.7(m,1H),4.8-5.0(m,1H),2.75-3.0(m,2H).

[0740] Synthesis Example 2: Synthesis of 6'-chloro-N-(4-chlorophenyl)-6"-fluoro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3':5',3"-terpyridine]-5-carboxamide (Compound No. 2-035 of the present invention)

[0741] To a mixed solution of 100 mg of 6'-chloro-6"-fluoro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3':5',3"-terpyridine]-5-carboxylic acid ethyl ester and 0.7 ml of 1,4-dioxane was added 32 mg of 4-chloroaniline, and the mixture was stirred at 80°C for 1 hour. After the reaction was completed, the solvent was distilled off under reduced pressure. The obtained residue was washed with a mixed solution of ethyl acetate:n-hexane = 1:2 to obtain 41 mg of the target product as a light brown solid.

[0742] Melting point: 199℃~201℃

[0743] 1 H-NMR(300MHz): δ11.6(brs,1H),8.48(brs,1H),8.29(brs,1H),7.85-8.0(m,1H),7.65-7.8(m,1H),7.4 -7.6(m,2H),7.25-7.35(m,2H),7.05-7.15(m,2H),5.3-5.8(m,1H),4.85-4.95(m,1H),2.7-3.05(m,2H).

[0744] Synthesis Example 3: Synthesis of N-(5-fluoropyridin-2-yl)-6-(3-(2-fluoropyridin-4-yl)-1,2,4-oxadiazol-5-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide (Compound No. 3-036 of the present invention)

[0745] To a mixed solution of 50 mg of 6-(((2-fluoroisonicotinimide)oxy)carbonyl)-N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide and 1.7 ml of toluene was added 17 mg of triethylamine, and the mixture was stirred at 110°C for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. 5 ml of 1 mol / l hydrochloric acid was added to the obtained residue, and extraction was performed with ethyl acetate (5 ml×3 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 1 ml of N,N-dimethylformamide, 3 ml of water and 1 ml of 1 mol / l hydrochloric acid were added to the obtained residue. The precipitated solid was filtered to obtain 39 mg of the target product as a white solid.

[0746] Melting point: 159℃~161℃

[0747] The following is a description of a synthesis example of a production intermediate of the compound of the present invention used in Synthesis Example 2.

[0748] Intermediate Synthesis Example 1: Synthesis of 6'-chloro-6"-fluoro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3':5',3"-terpyridine]-5-carboxylic acid ethyl ester

[0749] Step 1: Synthesis of ethyl 3-(5-bromo-6-chloropyridin-3-yl)-3-(3-ethoxy-3-oxopropionamido)propanoate

[0750] To a mixed solution of 13 g of ethyl 3-amino-3-(5-bromo-6-chloropyridin-3-yl)propanoate, 142 ml of ethyl acetate, 7.2 g of sodium bicarbonate and 142 ml of water was added 6.7 g of ethyl malonyl chloride at 0° C. After the reaction was completed, the obtained organic layer was dehydrated and dried with saturated brine and anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 18 g of the target product as a brown oil.

[0751] 1 H-NMR (300MHz); δ8.3-8.4(m,2H),7.9-7.95(m,1H),5.35-5.5(m,1H),4.24(q,J=7.2Hz,2H),4.13( q,J=7.2Hz,2H),3.36(brs,2H),2.89(d,J=5.7Hz,2H),1.31(t,J=7.2Hz,3H),1.20(t,J=7.2Hz,3H).

[0752] Step 2: Synthesis of ethyl 5'-bromo-6'-chloro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3'-bipyridine]-5-carboxylate

[0753] To a mixed solution of 22 g of ethyl 3-(5-bromo-6-chloropyridin-3-yl)-3-(3-ethoxy-3-oxopropionamido)propanoate and 94 ml of anhydrous ethanol, 2.0 g of sodium hydride [produced by Yoneyama Pharmaceutical Industry Co., Ltd., product name: sodium hydride. Oily (about 63% by mass), purity: 57.5% to 67.5%, product code 03414] was added, and the mixture was stirred at 55°C for 5 hours under a nitrogen atmosphere. After the reaction was completed, the solvent was distilled off under reduced pressure. 150 ml of dipropyl ether was added to the obtained residue, and the mixture was extracted with 150 ml of water. 35% by mass hydrochloric acid was added to the obtained aqueous layer until the pH became 2, and the mixture was extracted with a mixed solution of ethyl acetate:tetrahydrofuran = 9:1 (150 ml × 3 times). The obtained organic layer was dehydrated and dried with saturated saline and anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 16 g of the target product as a brown solid.

[0754] Melting point: 124℃~126℃

[0755] 1 H-NMR(400MHz); δ8.36(d,J=2.0Hz,1H),7.98(d,J=2.4Hz,1H),6.00(brs,1H ),4.7-4.8(m,1H),4.35-4.5(m,2H),2.7-3.05(m,2H),1.40(t,J=7.2Hz,3H).

[0756] Step 3: Production of 6'-chloro-6"-fluoro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3':5',3"-terpyridine]-5-carboxylic acid ethyl ester

[0757] 5'-bromo-6'-chloro-4-hydroxy-6-oxo-1,2,3,6-tetrahydro-[2,3'-bipyridine]-5-carboxylic acid ethyl ester 5.6g, 1,4-dioxane 40ml and water 10ml mixed solution, add 2-fluoropyridine-5-boric acid 1.9g, tripotassium phosphate 9.5g and [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium (2valent) dichloromethane adduct 606mg, under nitrogen atmosphere, stir at 55°C for 2 hours. After the reaction is completed, add diisopropyl ether 200ml, and extract with a mixed solution of potassium carbonate 10g and water 74ml. Add 35% by mass hydrochloric acid to the obtained aqueous layer until the pH becomes 2, and extract with ethyl acetate (150ml×3 times). After the obtained organic layer is dehydrated and dried with saturated brine and anhydrous sodium sulfate, the solvent is distilled off under reduced pressure. The obtained residue was washed with a mixed solution of ethanol:diisopropyl ether=1:2 to obtain 2.0 g of the target product as a light brown solid.

[0758] Melting point: 178℃~180℃

[0759] 1 H-NMR (400MHz); δ8.47(d,J=2.4Hz,1H),8.30(brs,1H),7.9-8.0(m,1H),7.71(d,J=2.0Hz,1H),7.05- 7.1(m,1H),5.70(brs,1H),4.8-4.9(m,2H),4.35-4.5(m,2H),2.7-3.05(m,2H),1.40(t,J=7.2Hz,3H).

[0760] The following is a description of a synthesis example of a production intermediate of the compound of the present invention used in Synthesis Example 3.

[0761] Intermediate Synthesis Example 2: Synthesis of 6-(((2-fluoroisonicotinimide)oxy)carbonyl)-N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide

[0762] Step 1: Synthesis of di-tert-butyl 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-3,6-dihydropyridine-1,2(2H)-dicarboxylate

[0763] To a mixed solution of 18.3 g of di-tert-butyl 4-hydroxy-6-oxo-3,6-dihydropyridine-1,2(2H)-dicarboxylate and 60 ml of acetonitrile, add 4.0 g of imidazole and 6.6 g of 1,1'-carbonyldiimidazole, and stir at 85°C for 30 minutes. After cooling to room temperature, add 6.6 g of 5-fluoropyridin-2-amine, and stir for 18 hours. Add 350 ml of diisopropyl ether, stir at 0°C for 1.5 hours, and filter out the precipitated solid. The obtained solid was washed with a mixed solution of acetonitrile: diisopropyl ether = 1:5 to obtain 26.3 g of the target product as a light red solid.

[0764] Melting point: 152℃~154℃

[0765] Step 2: Synthesis of 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylic acid

[0766] To a mixed solution of 15.4 g of di-tert-butyl 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-3,6-dihydropyridine-1,2(2H)-dicarboxylate and 70 ml of dichloromethane, add 50 ml of trifluoroacetic acid and stir at room temperature for 25 hours. Add 140 ml of toluene and distill off the solvent under reduced pressure. Add 100 ml of toluene and distill off the solvent under reduced pressure. Add 100 ml of toluene and distill off the solvent under reduced pressure. Add 100 ml of chloroform and filter out the solid. The obtained solid was washed with chloroform to obtain 14.6 g of the target product as a white solid.

[0767] Melting point: 223℃~225℃

[0768] Step 3: Synthesis of 6-(((2-fluoroisonicotinimide)oxy)carbonyl)-N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide

[0769] 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 72 mg and 1-hydroxy-7-azabenzotriazole 5 mg were added to a mixed solution of 100 mg of 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylic acid, 55 mg of 2-fluoro-N-hydroxyisonicotinimide and 4 ml of N,N-dimethylformamide, and stirred at room temperature for 1 hour. After the reaction was completed, 12 ml of water and 1 ml of 1 mol / l hydrochloric acid were added, and the precipitated solid was filtered out. The obtained solid was washed with water to obtain 80 mg of the target product as a white solid.

[0770] Melting point: 146℃~148℃

[0771] The compounds of the present invention and the manufacturing intermediates can be synthesized according to the above-mentioned manufacturing methods and synthesis examples. Examples of aryl tetrahydropyridine compounds manufactured in the same manner as in Synthesis Examples 1 to 3 are shown in Tables 7 to 12, but the aryl tetrahydropyridine compounds of the present invention are not limited to these. Examples of manufacturing intermediates manufactured in the same manner as in Intermediate Synthesis Examples 1 to 2 are shown in Tables 13 to 15, but the manufacturing intermediates of the present invention are not limited to these.

[0772] In addition, the records of Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12a, Q-12b, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31a, Q-45a and Q-52a in the table respectively represent the following structures.

[0773]

[0774] In addition, the records of G-1, G-2, G-3, G-4, G-5, G-6a, G-7, G-8a, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 and G-40 in the table respectively represent the following structures.

[0775]

[0776] In addition, the descriptions of D-1, D-2 and D-3 in the table respectively represent the following structures.

[0777]

[0778] It should be noted that the numbers in the above structural formula represent substituents (Z 1 ) t1 ,(Z 1 ) t2 ,(Z 1 ) t3 ,(Z 1 ) t4 ,(Z 1 ) t5 ,(Z 2 ) t2 ,(Z 2 ) t3 ,(Z 2 ) t4 ,(Z 2 ) t5 ,(Z 5 ) t3 ,(Z 5 ) t5 or (Z 5 ) t8 The number of the substitution position, for example, in the table, "Q-1(4-F)" represents "4-fluorophenyl", "G-2" represents "phenyl", and "G-1(2-OCH3,4-OCH3)" represents "2,6-dimethoxypyridin-3-yl".

[0779] In addition, in the table, "i-Bu" represents an isobutyl group, and "c-Pr" represents a cyclopropyl group.

[0780] In addition, "mp" represents the melting point (in °C), and the expression "*1" indicates that the compound is an oily or resinous compound with no melting point. In addition, in the description of the melting point in the table, ">" indicates that the melting point of the compound is higher than the temperature indicated, for example, the expression ">300" means that the compound does not melt at 300°C.

[0781] [Table 7]

[0782]

[0783]

[0784] [Table 8]

[0785]

[0786]

[0787]

[0788]

[0789]

[0790]

[0791]

[0792]

[0793]

[0794]

[0795]

[0796]

[0797] [Table 9]

[0798]

[0799]

[0800]

[0801]

[0802]

[0803]

[0804]

[0805]

[0806]

[0807]

[0808]

[0809] [Table 10]

[0810]

[0811]

[0812] [Table 11]

[0813]

[0814] [Table 12]

[0815]

[0816] [Table 13]

[0817]

[0818]

[0819]

[0820] [Table 14]

[0821]

[0822] [Table 15]

[0823]

[0824]

[0825] The compounds of the present invention for which the melting point is not described 1 H-NMR data are shown in Table 16. In addition, the proton nuclear magnetic resonance spectrum (hereinafter referred to as 1 H-NMR. ) chemical shift values ​​were measured using Me4Si (tetramethylsilane) as a reference substance at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL) or 400 MHz (model: JNM-ECZ400S, manufactured by JEOL). It should be noted that 1 The symbols in the chemical shift values ​​of H-NMR have the following meanings: "*2" means that no signal corresponding to the proton of OH or NH was observed.

[0826] s: singlet, d: doublet, dd: doublet of doublets, t: triplet, q: quartet, m: multiplet, brs: broad singlet

[0827] [Table 16]

[0828]

[0829]

[0830] [Test example]

[0831] Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples, but the present invention is not limited to these.

[0832] Test Example 1: Insecticidal test on brown planthopper

[0833] A 10% by mass emulsion of the compound of the present invention prepared according to the formulation example of the above emulsion is diluted with water added with a developing agent to prepare a 500ppm concentration of the drug solution. The rice leaf sheaths are immersed in the drug solution for about 10 seconds. After the immersion operation is completed, the rice leaf sheaths treated with the drug solution are air-dried and placed in a test tube. The third-instar larvae of the brown planthopper (Nilaparvata lugens) are placed therein in a manner of placing 5 worms in each test tube, and covered with a sponge and stored in a constant temperature chamber at 25°C. After 6 days of storage, the number of dead brown planthoppers in the test tube was investigated, and the mortality rate was calculated by the following calculation formula. It should be noted that the test was carried out twice in a row.

[0834] Death rate (%) = (number of dead insects / number of test insects) × 100

[0835] As a result, the following compounds showed an insect killing rate of 90% or more.

[0836] Compounds of the present invention: 1-001, 1-002, 1-003, 1-013, 1-014, 1-020, 2-001, 2-005, 2-008, 2-009, 2-010, 2-011, 2-012, 2-013, 2-014, 2-016, 2-018, 2-019, 2-020, 2-0 21,2-022,2-023,2-024,2-025,2-027,2-028,2-029,2-030,2-031,2-032,2-033,2-034,2-035,2-036,2-037,2-038,2-039,2-040,2-041,2-042,2- 043,2-044,2-045,2-047,2-048,2-049,2-050,2-051,2-052,2-053,2-054,2-055,2-056,2-057,2-058,2-059,2-060,2-061,2-062,2-063,2-067,2 -069, 2-071, 2-074, 2-076, 2-077, 2-079, 2-080, 2-081, 2-082, 2-083, 2-084, 2-085, 2-086, 2-087, 2-088, 2-089, 2-090, 2-091, 2-092, 2-093, 2-094, 2-095,2-096,2-097,2-098,2-099,2-100,2-101,2-102,2-103,2-104,2-105,2-106,2-107,2-108,2-109,2-110,2-111,2-112,2-113,2-114,2-115 5,2-116,2-117,2-118,2-119,2-120,2-122,2-123,2-124,2-125,2-126,2-127,2-128,2-129,2-130,2-132,2-133,2-134,22-135,2-136,2-137,2- 138,2-139,2-140,2-141,2-142,2-143,2-144,2-145,2-146,2-147,2-150,2-151,2-152,2-153,2-154,2-155,2-156,2-157,2-158,2-159,2-160,2 -161,2-162,2-163,2-164,2-165,2-166,2-167,2-168,2-169,2-170,2-171,2-172,2-173,2-174,2-175,2-176,2-177,2-178,2-179,2-180,2-181,2-182，2-183,2-184，2-186，2-187，2-188，2-189,2-190,2-191,2-192,2-193,2-194,2-195,2-196,2-197，2-198,2-199,2-200，2-201，2-202，2-203，2-204，2-205，2-206，2-207，2-208,2-209,2-211，2-212，2-213，2-214，2-215,2-216，2-217，2-218,2-219，2-222，2-223，2-227,2-228，2-231,2-232,2-233,2-235，2-238，2-240,2-244，2-245,2-246，2-247，2-248，2-249，2-250,2-251，2-252，2-253，2-254，2-255，2-256，2-259，2-260,2-261，2-262,2-263，2-264，2-265,2-267，2-268,2-269,2-271,2-272,2-273,2-276，2-277，2-287，2-288，2-289，2-290,2-297，2-298,2-299,2-300，2-301，2-302，2-303，2-304,2-305，3-001，3-002，3-005，3-006，3-007，3-009，3-010,3-011，3-012,3-013,3-014，3-015，3-016，3-017，3-018,3-020，3-021，3-022，3-023，3-024，3-025,3-026,3-027,3-028,3-029，3-030，3-031，3-032,3-033，3-034，3-035，3-036，3-037，3-038,3-039，3-040，3-041，3-042，3-043,3-044,3-045,3-046，3-047,3-048,3-049,3-050,3-051,3-052,3-053,3-055,3-056,3-057,3-058,3-059,3-060,3-061,3-062,3-063,3-064,3-065,3-066,3-067,3-068,3-069,3-070,3-071,3-072,3-073,3-074,3-075,3-076，3-077，3-078,3-079,3-080,3-081,3-082,3-083,3-084,3-085,3-086,3-087，3-088,3-089,3-090,3-091,3-092，3-093,3-094，3-095,3-096,3-097,3-098，3-100，3-102,3-103,3-104,3-105,3-106,3-107,3-108,3-110,3-111,3-112,3-113,3-114,3-115,3-116,3-119,3-121,3-122，3-123,3-126,3-127，3-129，3-130，3-131，3-132,3-133，3-134,3-135,3-136,3-138,3-139,3-140,3-141，3-144，3-146,3-147，3-152,3-153,3-154,3-155,3-156,3-157，3-158,3-159,3-160,3-161,3-162,3-163,3-164，3-165,3-166，3-168，3-169，3-170，3-171，3-172，3-173,3-174,3-175,3-176,3-177，3-178，3-179,3-180,3-182,3-183,3-184,3-185,3-186,3-187,3-188,3-189,3-190,3-191,3-192,3-193,3-194，3-195,3-196,3-197,3-198,3-199,3-200，3-201,3-202，3-203，3-204，3-205，3-206，3-207,3-208,3-209,3-210，3-213,3-214,3-215,3-216,3-217,3-219,3-220,3-221,3-223,3-224,3-225,3-226,3-227,3-228,3-232,3-233,3-234,3-235,3-236,3-237，3-238,3-239,3-240，3-241,3-242,3-243,3-244,3-245,3-246，3-249，3-250，3-251,3-252,3-253,3-254,3-255,3-256,3-257，3-258，3-259，3-260,3-261,3-262，3-263,3-264，3-265,3-268，3-269，3-270,3-271，3-272，3-273，3-274，3-275，3-276,3-277，3-278，3-279,3-280,3-281, 3-283, 3-284, 3-285, 3-286, 3-287, 3-288, 3-289, 3-290, 3-291, 3-292, 3-293, 3-294, 4-001, 5-001, 5-002, 5-003, 5-004, 5-005, 5-006, 5-007, 5-008, 5-009, 5-010, 5-011, 5-012, 5-013, 5-014, 5-015, 5-016, 6-001, 6-002, 6-003, 6-004, 6-005,

[0837] Test Example 2: Insecticidal test against green peach aphid

[0838] A glass petri dish with an inner diameter of 3 cm was covered with wet absorbent cotton, and a cabbage leaf cut into a circle with a diameter of 3 cm was placed on it, and 4 wingless adults of peach aphids (Myzus persicae) were placed. One day later, a 10% by mass emulsion of the compound of the present invention prepared according to the above emulsion preparation example was diluted with water added with a developing agent to prepare a 500 ppm concentration of the drug solution. The prepared drug solution (2.5 mg / cm 2 ), covered with a lid and stored in a constant temperature chamber at 25° C. After 6 days of storage, the number of dead green peach aphids in the petri dish was counted, and the mortality rate was calculated by the same calculation formula as in Test Example 1. It should be noted that the test was repeated twice.

[0839] As a result, the following compounds showed an insect killing rate of 90% or more.

[0840] Compounds of the present invention: 1-001, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-014, 1-015, 1-016, 1-017, 1-019, 1-020, 1-021, 1-023, 2-003, 2-004, 2-005, 2-006, 2-007, 2-008, 2-009, 2-010, 2-011, 2-012, 2-014, 2-015, 2-016, 2-017, 2-018 05,2-007,2-010,2-023,2-032,2-034,2-035,2-036,2-040,2-041,2-042,2-044,2-045,2-046,2-047,2-048,2-049,2-053,2-054,2-056,2-057,2- 058, 2-062, 2-063, 2-064, 2-067, 2-068, 2-077, 2-083, 2-086, 2-087, 2-091, 2-097, 2-098, 2-099, 2-100, 2-104, 2-112, 2-115, 2-117, 2-120, 2-124, 2-125,2-126,2-137,2-141,2-146,2-151,2-155,2-156,2-157,2-158,2-159,2-160,2-161,2-162,2-163,2-165,2-167,2-169,2-170,2-172,2-173 ,2-179,2-180,2-182,2-183,2-184,2-186,2-189,2-192,2-194,2-196,2-197,2-198,2-199,2-200,2-201,2-202,2-203,2-208,2-213,2-214,2-2 16, 2-217, 2-219, 2-242, 2-244, 2-245, 2-247, 2-250, 2-251, 2-253, 2-254, 2-255, 2-257, 2-264, 2-265, 2-266, 2-267, 2-268, 2-271, 2-273, 2-274, 2- 278, 2-280, 2-281, 2-284, 2-285, 2-292, 2-298, 2-303, 3-002, 3-009, 3-011, 3-013, 3-014, 3-015, 3-017, 3-020, 3-022, 3-024, 3-027, 3-028, 3-033, 3 -039, 3-042, 3-044, 3-049, 3-051, 3-053, 3-054, 3-055, 3-056, 3-058, 3-059, 3-060, 3-064, 3-070, 3-072, 3-074, 3-075, 3-080, 3-095, 3-096, 3-097,3-098,3-099,3-100,3-107,3-109,3-110,3-111,3-112,3-117,3-118,3-119,3-122,3-123,3-125,3-126,3-128,3-129,3-131,3-132,3-133,3-134,3-136,3-137,3-139,3-1 42,3-144,3-148,3-164,3-166,3-167,3-170,3-173,3-174,3-178,3-179,3-181,3-183,3-192,3-194,3-196,3-200,3-202,3-204,3-205,3-206,3-207,3-208,3-210,3-213, 3-215, 3-217, 3-219, 3-222, 3-224, 3-225, 3-226, 3-228, 3-229, 3-230, 3-232, 3-236, 3-241, 3-246, 3-248, 3-249, 3-251, 3-252, 3-253, 3-254, 3-257, 3-265, 3-266, 3-268, 3-2 69, 3-270, 3-271, 3-272, 3-273, 3-274, 3-275, 3-276, 3-277, 3-278, 3-279, 3-280, 3-281, 3-291, 4-001, 5-002, 5-007, 5-009, 5-011, 5-012, 5-013, 5-015, 5-016, 6-001, 6-004,

[0841] Test Example 3: Insecticidal activity against western flower thrips

[0842] A wet filter paper was placed in a styrene cup with an inner diameter of 7 cm, and lentil leaves cut into 3 cm squares were placed on it. 20 larvae of Frankliniella occidentalis were inoculated per leaf. A 10% by mass emulsion of the compound of the present invention prepared according to the above emulsion preparation example was diluted with water added with a developing agent to prepare a 500 ppm concentration of the drug solution. The prepared drug solution (2.5 mg / cm2) was spread using a rotary spreading tower in an amount of 2.5 ml per styrene cup. 2 ). After 2 days, the number of dead western flower thrips in the styrene cup was investigated, and the mortality rate was calculated by the same calculation formula as in Test Example 1. It should be noted that the test was performed twice in succession.

[0843] As a result, the following compounds showed an insect killing rate of 90% or more.

[0844] Compounds of the present invention: 1-001, 1-002, 1-003, 1-005, 1-007, 1-008, 1-009, 1-010, 1-011, 1-013, 1-014, 1-015, 1-016, 1-017, 1-019, 1-020, 1-022, 1-023, 1-024, 2-0 01,2-005,2-008,2-009,2-010,2-011,2-012,2-013,2-014,2-016,2-018,2-019,2-020,2-021,2-022,2-024,2-025,2-027,2-028,2-029,2-030,2- 031,2-032,2-033,2-034,2-035,2-036,2-037,2-038,2-039,2-040,2-041,2-042,2-044,2-045,2-047,2-048,2-049,2-050,2-053,2-054,2-055, 2-056, 2-057, 2-058, 2-059, 2-062, 2-063, 2-067, 2-068, 2-069, 2-071, 2-072, 2-073, 2-074, 2-076, 2-077, 2-078, 2-079, 2-080, 2-081, 2-082, 2-083 ,2-084,2-085,2-086,2-087,2-088,2-089,2-090,2-091,2-092,2-093,2-094,2-095,2-096,2-099,2-100,2-101,2-102,2-103,2-104,2-105,2-1 06,2-107,2-108,2-109,2-110,2-111,2-112,2-113,2-114,2-115,2-116,2-117,2-118,2-119,2-120,2-121,2-122,2-123,2-124,2-125,2-126,2- 127,2-128,2-129,2-130,2-131,2-132,2-133,2-134,2-135,2-136,2-137,2-138,2-139,2-140,2-141,2-142,2-143,2-144,2-145,2-146,2-147,2 -150,2-151,2-152,2-153,2-154,2-155,2-156,2-157,2-158,2-159,2-160,2-161,2-162,2-163,2-164,2-165,2-166,2-167,2-168,2-169,2-170,2-171，2-172,2-173，2-174，2-175，2-176，2-177,2-178,2-179，2-180,2-181,2-182,2-183,2-184,2-186,2-187,2-188,2-189，2-190,2-191,2-192,2-193,2-194,2-195,2-196，2-198，2-199，2-200，2-201,2-202，2-203,2-204,2-206,2-207,2-208,2-209,2-211，2-212，2-213，2-214，2-215，2-216，2-218，2-219，2-220，2-221，2-222，2-223,2-224，2-225，2-226,2-227，2-228，2-229，2-230，2-231，2-232，2-233，2-235，2-238，2-239,2-240，2-244,2-245,2-246,2-247,2-248,2-249,2-250,2-251,2-252,2-253,2-254，2-255,2-256，2-257，2-258，2-259,2-260，2-261,2-262，2-263，2-265，2-269,2-271,2-272,2-273,2-276,2-277，2-279,2-280,2-281,2-282,2-287,2-288,2-296,2-297，2-298,2-299,2-300,2-301,2-302,2-303,2-304，2-305，3-001，3-003,3-005,3-006，3-007，3-009,3-010，3-011,3-012，3-013，3-014，3-015，3-016，3-018，3-020，3-021,3-022,3-023,3-024，3-025，3-026,3-027，3-028，3-029，3-030,3-031，3-032,3-034，3-035,3-036，3-037,3-038，3-039,3-040，3-041,3-042,3-043,3-044，3-045,3-046，3-047，3-048，3-049，3-050，3-051，3-052，3-054,3-055，3-056，3-057，3-058，3-059，3-060，3-061,3-062，3-063，3-064，3-065,3-066,3-067,3-068，3-069,3-070,3-071,3-072，3-073,3-074，3-075,3-076，3-077，3-078，3-079,3-080，3-081，3-082，3-083，3-084，3-085,3-086，3-088，3-089,3-090，3-091，3-092，3-095,3-096,3-097,3-098，3-100，3-102,3-103,3-104,3-105，3-106,3-107,3-108,3-109,3-111，3-113,3-114,3-115,3-116,3-120，3-121,3-122,3-123,3-124,3-126,3-127，3-128,3-129,3-131,3-132,3-133,3-134，3-135,3-138,3-139,3-140,3-141,3-144，3-145，3-146,3-147，3-154,3-155,3-156，3-157,3-159，3-160,3-161,3-163,3-164,3-165,3-169,3-170,3-171,3-172,3-173,3-174,3-175,3-176，3-177,3-179,3-180,3-183，3-184，3-185,3-186，3-187，3-188，3-189,3-190,3-191，3-192,3-195,3-197，3-199,3-200，3-202,3-204，3-205，3-206，3-207，3-208,3-209,3-210，3-213，3-214，3-215，3-216，3-217，3-219，3-220，3-221，3-223，3-224，3-225，3-226，3-227，3-228，3-232,3-233，3-234,3-235，3-236，3-238，3-239,3-240,3-241，3-242,3-243,3-244,3-245,3-246，3-249,3-250,3-252，3-253,3-254,3-255,3-256，3-257，3-258，3-259,3-260，3-261，3-262，3-263，3-264，3-265，3-267，3-268，3-269,3-270,3-271，3-272，3-273，3-274，3-275，3-277，3-278,3-279,3-280, 3-281, 3-282, 3-283, 3-284, 3-285, 3-286, 3-287, 3-288, 3-289, 3-292, 3-294, 4-001, 5-001, 5-002, 5-003, 5-004, 5-005, 5-006, 5-007, 5-008, 5-009, 5-010, 5-011, 5-012, 5-013, 5-014, 5-015, 5-016, 6-001, 6-002, 6-003, 6-004,

[0845] Test Example 4: Insecticidal test on Plutella xylostella

[0846] A 10% by mass emulsion of the compound of the present invention prepared according to the formulation example of the above emulsion is diluted with water added with a developing agent to prepare a 500ppm concentration of the drug solution. The cabbage leaves are immersed in the drug solution for about 10 seconds. After the immersion operation is completed, the cabbage leaves treated with the drug solution are air-dried and placed in a culture dish. The third-instar larvae of the diamondback moth (Plutella xylostella) are placed therein in a manner of placing 5 worms in each culture dish, the lid is closed and stored in a constant temperature chamber at 25°C. After 6 days of storage, the number of dead diamondback moths in the culture dish was investigated, and the mortality rate was calculated by the same calculation formula as in Test Example 1. It should be noted that the test was carried out twice in a row.

[0847] As a result, the following compounds showed an insect killing rate of 90% or more.

[0848] Compounds of the present invention: 1-001, 1-002, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-013, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-020, 1-021, 1-022, 1-023, 1-024, 2-001, 2-005, 2-008, 2-009, 2-010, 2-011, 2-012, 2-013, 2-014, 2-016, 2-017, 2-018, 2-019, 2-020, 2-021, 2-022, 2-023, 2 -025, 2-027, 2-028, 2-029, 2-030, 2-031, 2-032, 2-033, 2-034, 2-035, 2-036, 2-038, 2-039, 2-040, 2-041, 2-042, 2-044, 2-045, 2-048, 2-049, 2-05 0,2-055,2-057,2-058,2-060,2-061,2-062,2-063,2-064,2-066,2-067,2-068,2-069,2-072,2-073,2-076,2-077,2-078,2-079,2-080,2-081,2-0 82, 2-083, 2-084, 2-085, 2-086, 2-087, 2-088, 2-089, 2-090, 2-091, 2-092, 2-093, 2-094, 2-095, 2-096, 2-097, 2-098, 2-099, 2-100, 2-101, 2-102, 2 -103,2-104,2-105,2-106,2-107,2-108,2-109,2-110,2-111,2-112,2-113,2-114,2-115,2-117,2-118,2-119,2-121,2-122,2-123,2-124,2-125 ,2-126,2-127,2-128,2-129,22-130,2-131,2-132,2-133,22-134,2-135,2-136,2-137,2-138,2-139,2-140,2-141,2-142,2-143,2-144,2-145,2 -146, 2-147, 2-148, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-156, 2-157, 2-158, 2-159, 2-160, 2-161, 2-162, 2-163, 2-164, 2-166, 2-167, 2-168,2-169，2-170,2-171,2-172，2-174，2-175,2-176,2-177,2-178,2-179,2-181,2-182,2-183,2-184,2-186,2-187，2-188,2-189,2-190,2-191,2-192,2-193,2-194,2-195,2-196,2-197,2-198,2-199,2-200，2-201，2-202,2-203,2-204，2-205,2-206,2-207,2-208，2-209，2-211，2-212,2-213,2-214，2-215,2-216，2-217，2-218，2-219，2-220，2-221，2-222，2-223,2-224,2-225,2-226,2-227,2-228，2-229，2-231,2-232,2-233，2-234，2-235,2-237，2-240,2-241,2-242,2-243,2-244,2-245,2-246，2-247,2-248，2-249,2-250，2-251，2-252,2-253，2-254，2-255，2-256,2-257，2-259,2-260,2-261，2-262，2-263，2-264，2-265，2-267，2-268,2-269,2-271，2-272，2-273,2-274,2-276,2-277,2-278，2-279，2-280,2-282，，2-283，2-287，2-288,2-295,2-297，2-298，2-299，2-300，2-301，2-302，2-303，2-304，2-305，3-001,3-002，3-003，3-004,3-005，3-006，3-007，3-009,3-010,3-011，3-012，3-013，3-014,3-015,3-016,3-017，3-018,3-019，3-020,3-021，3-022,3-023，3-024,3-025，3-026,3-027，3-028,3-029,3-030，3-031，3-032,3-033,3-034,3-035，3-036，3-037，3-038,3-039,3-040,3-041,3-042,3-043，3-044，3-046，3-048，3-049,3-050，3-051，3-052，3-053,3-054,3-055,3-056，3-057，3-058,3-059，3-060，3-061,3-062，3-063,3-064，3-065,3-066，3-067，3-068,3-069，3-070，3-071,3-072,3-073,3-074，3-075，3-076，3-077,3-078，3-079，3-080,3-081，3-082，3-083，3-084，3-085,3-086，3-088，3-089，3-090,3-092，3-093,3-095,3-096,3-097,3-098,3-099,3-100，3-102，3-103,3-104,3-105,3-106,3-107,3-108,3-109,3-110,3-113,3-114,3-115,3-116,3-119,3-122,3-123,3-124,3-125,3-126，3-127，3-128,3-129,3-131,3-132,3-133,3-134,3-135,3-136，3-138,3-139,3-140.3-141，3-142，3-143，3-144，3-145，3-146,3-147,3-154,3-155,3-156,3-157，3-158,3-159,3-160，3-161,3-162，3-163，3-164，3-165，3-166,3-169,3-170，3-172,3-173,3-174,3-175，3-176,3-177，3-178，3-179,3-180,3-183,3-184,3-185,3-186,3-187，3-188,3-189,3-190,3-191,3-192,3-193,3-194,3-195,3-196,3-197,3-198,3-199,3-200，3-202,3-203，3-204，3-205，3-207，3-208，3-209，3-210，3-212，3-213，3-214，3-215，3-216，3-217，3-219，3-220，3-221,3-222，3-223,33-224，3-225,3-226,3-227,3-228，3-230，3-232，3-233，3-234，3-235，3-236,3-237，3-238,3-239，3-240,3-241，3-243，3-244，3-246,3-248,3-249,3-251,3-252,3-253,3-254,3-255,3-256,3-257,3-258,3-259,3-260,3-262,3-263,3-264,3-265,3-268,3-269,3-270,3-271,3-272,3-273,3-274,3-275,3-276,3-277,3-279,3-280,3-281,3-282,3-283,3-2 84, 3-285, 3-286, 3-292, 4-001, 5-001, 5-002, 5-003, 5-004, 5-005, 5-006, 5-007, 5-008, 5-009, 5-010, 5-011, 5-012, 5-013, 5-014, 5-015, 5-016, 6-001, 6-002, 6-003, 6-004, 6-005,

[0849] Test Example 5: Test on the effect on Rhipicephalus sanguineus

[0850] 1 mg of the compound of the present invention was dissolved in 1 ml of acetone to prepare a 1000 ppm concentration drug solution. 250 μl of the drug solution was applied to the inner wall with a surface area of ​​25 cm 2 After the bottom and side surfaces of the glass container were covered with acetone, the acetone was volatilized to form a thin film of the compound on the inner wall of the glass container. The inner wall of the glass container used was 25 cm 2 , the treatment dose is 10μg / cm 2 .

[0851] Five first nymphs of Rhipicephalus sanguineus (mixed males and females) were placed in the treated glass container, covered and stored in a constant temperature room at 25° C. Two days after the release of the ticks, the number of dead ticks was counted, and the mortality rate was calculated using the same calculation formula as in Test Example 1.

[0852] As a result, the following compounds showed an insect killing rate of 50% or more.

[0853] Compounds of the present invention: 1-006, 1-007, 2-120, 2-127, 2-128, 2-151, 2-153, 3-082, 3-100, 3-101, 3-114, 3-128, 3-129, 3-166, 3-186, 3-200, 3-208

[0854] Test Example 6: Test on the effect on cat fleas

[0855] 1 mg of the compound of the present invention was dissolved in 1 ml of acetone to prepare a 1000 ppm concentration drug solution. 250 μl of the drug solution was applied to the inner wall with a surface area of ​​25 cm 2After the bottom and side surfaces of the glass container were covered with acetone, the acetone was volatilized to form a thin film of the compound on the inner wall of the glass container. The inner wall of the glass container used was 35 cm 2 , the treatment dose is 10μg / cm 2 .

[0856] Five adult fleas of Ctenocephalides felis (male and female mixed) were placed in the treated glass container, covered and stored in a constant temperature room at 25° C. Three days after the release of the fleas, the number of dead fleas was counted, and the mortality rate was calculated using the same calculation formula as in Test Example 1.

[0857] As a result, the following compounds showed an insect killing rate of 50% or more.

[0858] Compounds of the present invention: 1-001, 1-002, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-011, 1-012, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-020, 1-021, 1-022 23,1-024,2-001,2-005,2-008,2-009,2-010,2-011,2-012,2-013,2-014,2-018,2-019,2-020,2-021,2-022,2-024,2-025,2-027,2-028,2-029,2- 030, 2-031, 2-032, 2-033, 2-034, 2-035, 2-036, 2-037, 2-038, 2-039, 2-040, 2-041, 2-042, 2-044, 2-045, 2-047, 2-049, 2-058, 2-062, 2-063, 2-065, 2 -067,2-068,2-069,2-071,2-072,2-073,2-076,2-077,2-078,2-079,2-080,2-081,2-082,2-083,2-084,2-085,2-086,2-087,2-088,2-089,2-090, 2-091, 2-092, 2-093, 2-094, 2-095, 2-096, 2-097, 2-098, 2-099, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112 2,2-113,2-114,2-115,2-116,2-117,2-118,2-119,2-120,2-121,2-122,2-123,2-124,2-125,2-126,2-127,2-128,2-129,2-130,2-131,2-132,2-1 33,2-134,2-135,22-136,2-137,2-138,2-139,2-140,2-141,2-142,2-144,2-145,2-146,2-147,2-148,2-150,2-151,2-152,2-153,2-154,2-155,2 -156,2-157,2-158,2-159,2-160,2-161,2-162,2-163,2-164,2-165,2-166,2-167,2-168,2-169,2-170,2-171,2-172,2-173,2-174,2-175,2-176,2-177,2-178,2-179，2-180，2-181,2-182,2-183,2-184,2-186,2-187,2-188,2-189，2-190，2-191，2-192，2-193，2-194，2-195，2-196,2-197，2198,2-199，2-200，2-201，2-202，2-203，2-204,2-205，2-206,2-207，2-208，2-209，2-211，2-212,2-213,2-214，2-215，2-216，2-217，2-218，2-219，2-220,2-221，2-222，2-223，2-224,2-225,2-226，2-227，2-228,2-229,2-231，2-232,2-233，2-235,2-238,2-240,2-244,2-245,2-246，2-247,2-248,2-249,2-250,2-251,2-252,2-253,2-254,2-255,2-256,2-257,2-259,2-260,2-261,2-263,2-264,2-267，2-269，2-270,2-271,2-272,2-273,2-274,2-275,2-276,2-277，2-278,2-279,2-280,2-282,2-283,2-290,2-297,2-298,2-299,2-300,2-301,2-302,2-303,2-304,2-305,3-001,3-003，3-005,3-006,3-007，3-009，3-010，3-011，3-012,3-013，3-014，3-016，3-018，3-019,3-020,3-021，3-022,3-023，3-024,3-025，3-026,3-027,3-028,3-029,3-030，3-031，3-032，3-033，3-034，3-035,3-036,3-037，3-039，3-040，3-042，3-043，3-044，3-045,3-047，3-048，3-049,3-050,3-053,3-055，3-056,3-057，3-058，3-059,3-060，3-061,3-062，3-063,3-064，3-065,3-066，3-068，3-069，3-071，3-072，3-073，3-074，3-075，3-076，3-077,3-079,3-080，3-081，3-082，3-083，3-084，3-085，3-086,3-088，3-089,3-090，3-091，3-092,3-093,3-094，3-095，3-096，3-097，3-098,3-100，3-101，3-102,3-103,3-105,3-106,3-107,3-108,3-109,3-110,3-113,3-114,3-115,3-121，3-122,3-123,3-127，3-128,3-129,3-131,3-132,3-133,3-135,3-136,3-138,3-139,3-140,3-141,3-144,3-145，3-146,3-154，3-155,3-156,3-157,3-158,3-159,3-160，3-161,3-164,3-166,3-167,3-168,3-169,3-170,3-171,3-172,3-173,3-174，3-175，3-176,3-177,3-178,3-179,3-180,3-181,3-182,3-183,3-184，3-185,3-186,3-187,3-188,3-189,3-190,3-191,3-192,3-193,3-194，3-195,3-196,3-197，3-199,3-200，3-203,3-205,3-207,3-208,3-209,3-210,3-212，3-213，3-214，3-215,3-216，3-217,3-219，3-220,3-221，3-222，3-223，3-224，3-225，3-226，3-227.3-228，3-232，3-233，3-234，3-235,3-236，3-237，3-238,3-239，3-243,3-246，3-248，3-249，3-254,3-257，3-263,3-264，3-265，3-268，3-269,3-270，3-271，3-272,3-273,3-274，3-275，3-277，3-278,3-280，3-281，3-282，3-283，3-284，3-285，3-286，3-287，3-291，3-292,3-294,4-001，5-001，5-002,5-003，5-004，5-005，5-006,5-007，5-008,5-009,5-010,5-011，5-012，5-013,5-014,5-015,5-016,6-001,6-002,6-004,6-005,

[0860] Test Example 7: Test on the effect on Trichostrongylus erxori

[0861] After 60 μl of potato glucose 1% agar medium was injected into each 96-well plate, sterile water containing Trichostrongylus axei eggs and freeze-dried Escherichia coli OP50 strain (5 eggs, 10 μg of Escherichia coli / 10 μl) was added to each well at a volume of 30 μl per well. The test drug solution B of the compound of the present invention was added to each well at a volume of 10 μl per well from above, and the mixture was allowed to stand at 25°C in the dark. The number of unhatched eggs and the number of inactive larvae were measured 4 days after the addition of the drug, and the efficacy (%) relative to the untreated area was calculated by the following formula.

[0862] Efficacy (%) = [(number of unhatched eggs in the treated area + number of inactive larvae) / (number of unhatched eggs in the untreated area + number of inactive larvae + number of active larvae)] × 100

[0863] As a result, among the tested compounds, the following compounds showed efficacy (%) of 50% or more. Compounds of the present invention: 2-003, 2-035, 2-038, 2-056, 2-070, 2-088, 2-103, 2-115, 2-120, 2-126, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-136, 2-138, 2-139, 2-142, 2-144, 2-145, 2-147, 2-153, 2-155, 2-156, 2-158, 2-160, 2-161, 2-164, 2-165, 2-166, 2-167, 2-169, 2-170, 2-171, 2-172, 2-173, 2-177 ,2-179,2-180,2-181,2-184,2-188,2-191,2-192,2-193,2-194,2-197,2-201,2-202,2-203,2-204,2-206,2-208,2-211,2-214,2-218,2-219,2-220,2-221,2-225,2-229,2-232,2-234,2-235,2-238,2-239,2-240,2-244,2-245,2-246,2-247,2-248,2-249,2-250,2-251,2-252,2-254, 2-255, 2-256, 2-262, 2-263, 2-264, 2-266, 2-270, 2-271, 2-272, 2-273, 22-274, 2-275, 2-277, 2-278, 2-279, 2-289, 22-290, 2-291, 2-292, 2-296, 2-297, 2-299, 2-303, 2-304, 3-011, 3-027, 3-031, 3-060, 3-061, 3-064, 3-065, 3-070, 3-071, 3-074, 3-076, 3-078, 3-082, 3-083, 3-085, 3-086 6,3-087,3-089,3-097,3-098,3-100,3-102,3-107,3-110,3-114,3-117,3-121,3-124,3-125,3-126,3-127,3-128,3-129,3-136,3-137,3-138,3-139,3-141,3-143,3-144,3-145,3-146,3-148,3-152,3-154,3-155,3-157,3-158,3-161,3-163,3-164,3-166,3-1693-170,3-171,3-174,3-175, 3-180, 3-183, 3-190, 3-192, 3-195, 3-199, 3-202, 3-209, 3-211, 3-216, 3-222, 3-226, 3-232, 3-233, 3-237, 3-239, 3-249, 3-250, 3-261, 3-263, 3-267, 3-2 68, 3-270, 3-271, 3-274, 3-275, 3-277, 3-279, 3-283, 3-285, 3-293, 5-001, 5-004, 5-005, 5-006, 5-007, 5-009, 5-010, 5-011, 5-012, 5-013, 5-015, 5-016, 6-001,

[0864] Industrial Applicability

[0865] The aryltetrahydropyridine compound or a salt thereof of the present invention has excellent pest control activity and can be used as a pest control agent.

Claims

1. An aryl tetrahydropyridine compound represented by formula (1) or a salt thereof, In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q- 15. Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, Q-26, Q-27, Q-28, Q -29, Q-30, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-48, Q-49, Q-50, Q-51, Q-52, Q-53, Q-54, Q-55 or Q-56, Z 1 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo(C1-C6)alkyl group, a halo(C2-C6)alkenyl group, a halo(C2-C6)alkynyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C2-C6 alkoxy(C1-C6)alkoxy group, a C2-C6 alkenyloxy group, a halo(C2-C6)alkenyloxy group, a C2-C6 alkynyloxy group, a halo(C2-C6)alkynyloxy group, a C1-C6 Alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated (C1-C6) alkylthio, halogenated (C1-C6) alkylsulfinyl, halogenated (C1-C6) alkylsulfonyl, C2-C6 alkenylthio, C2-C6 alkenylsulfinyl, C2-C6 alkenylsulfonyl, halogenated (C2-C6) alkenylthio, halogenated (C2-C6) alkenylsulfinyl, halogenated (C2-C6) alkenylsulfonyl, C2-C6 alkynylthio, C2-C6 C2-C6 alkynylsulfinyl, C2-C6 alkynylsulfonyl, halo (C2-C6) alkynylthio, halo (C2-C6) alkynylsulfinyl, halo (C2-C6) alkynylsulfonyl, -NH2, C1-C6 alkylamino, di (C1-C6) alkylamino, halo (C1-C6) alkylamino, dihalo (C1-C6) alkylamino, formyl, carboxyl, C1-C6 alkylcarbonyl, halo (C1-C6) alkylcarbonyl, C1-C6 alkoxy alkylcarbonyl, halogenated (C1-C6) alkoxycarbonyl, C1-C6 alkylaminocarbonyl, halogenated (C1-C6) alkylaminocarbonyl, di(C1-C6) alkylaminocarbonyl, hydroxy, C1-C6 alkylcarbonyloxy, C1-C6 alkoxycarbonyloxy, C1-C6 alkylsulfonyloxy, halogenated (C1-C6) alkylsulfonyloxy, -SO3H, C1-C6 alkylaminosulfonyl, di(C1-C6) alkylaminosulfonyl, -C(=NOR 12 )R 13 , cyano or nitro, R 12 represents a hydrogen atom or a C1-C6 alkyl group, R 13 represents a hydrogen atom or a C1-C6 alkyl group, Z 3 represents a hydrogen atom or a C1-C6 alkyl group, J stands for J-1 or J-2, A 1 represents a nitrogen atom or CH, G means G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G-32, G-33, G-34, G-35, G-36, G-37, G-38, G-39, G-40, G-41, G-42, G-43, G-44, G-45, G-46, G-47, G-48, G-49, G-50, G-51, G-52, G-53, G-54, G-55, G-56, G-57, G-58, G-59, G-60 or G-61, Z 2 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo(C1-C6)alkyl group, a halo(C2-C6)alkenyl group, a halo(C2-C6)alkynyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkoxy(C1-C6)alkoxy group, a C2-C6 alkenyloxy group, a halo(C2-C6)alkenyloxy group, a C2-C6 alkynyloxy group, a halo(C2-C6)alkynyloxy group, a C1-C6 Alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated (C1-C6) alkylthio, halogenated (C1-C6) alkylsulfinyl, halogenated (C1-C6) alkylsulfonyl, C2-C6 alkenylthio, C2-C6 alkenylsulfinyl, C2-C6 alkenylsulfonyl, halogenated (C2-C6) alkenylthio, halogenated (C2-C6) alkenylsulfinyl, halogenated (C2-C6) alkenylsulfonyl, C2-C6 alkynylthio, C2-C6 C2-C6 alkynylsulfinyl, C2-C6 alkynylsulfonyl, halo (C2-C6) alkynylthio, halo (C2-C6) alkynylsulfinyl, halo (C2-C6) alkynylsulfonyl, -NH2, C1-C6 alkylamino, di (C1-C6) alkylamino, halo (C1-C6) alkylamino, dihalo (C1-C6) alkylamino, formyl, carboxyl, C1-C6 alkylcarbonyl, halo (C1-C6) alkylcarbonyl, C1-C6 alkoxy alkylcarbonyl, halogenated (C1-C6) alkoxycarbonyl, C1-C6 alkylaminocarbonyl, halogenated (C1-C6) alkylaminocarbonyl, di(C1-C6) alkylaminocarbonyl, hydroxy, C1-C6 alkylcarbonyloxy, C1-C6 alkoxycarbonyloxy, C1-C6 alkylsulfonyloxy, halogenated (C1-C6) alkylsulfonyloxy, -SO3H, C1-C6 alkylaminosulfonyl, di(C1-C6) alkylaminosulfonyl, -C(=NOR 14 )R 15 , nitro or cyano, R 14 represents a hydrogen atom or a C1-C6 alkyl group, R 15 represents a hydrogen atom or a C1-C6 alkyl group, Z 4 represents a C1-C6 alkyl group, R 1 represents a hydrogen atom, a halogen atom, a halogenated (C1-C6) alkyl group, a C1-C6 alkyl group or a cyano group, R 2 represents a hydrogen atom, a C1-C6 alkyl group, a halogenated (C1-C6) alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, -C(O)R 4 、-C(O)OR 5 , D-1, D-2 or D-3, R 4 represents a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylcarbonyl group, a di(C1-C6)alkylamino group, or is replaced by R 6 Substituted (C1-C6) alkyl, R 6 represents a halogen atom, a C1-C6 alkoxy group, a cyano group, a nitro group, a phenyl group, or a 8 Substituted phenyl, Z 5 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a cyano group or a nitro group, R 8 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a cyano group or a nitro group, R 5 represents a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, 9 Substituted (C1-C6) alkyl, phenyl or R 10 Substituted phenyl, R 9 represents a halogen atom, a C1-C6 alkoxy group, a cyano group, a nitro group, a phenyl group, or a 11 Substituted phenyl, R 10 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a cyano group or a nitro group, R 11 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a cyano group or a nitro group, R 3 represents a hydrogen atom, a C1-C6 alkyl group, a halogenated (C1-C6) alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group or a C1-C6 alkylcarbonyl group, X represents an oxygen atom or a sulfur atom, Y represents an oxygen atom or a sulfur atom, t1 represents an integer of 0 or 1, t2 represents an integer of 0, 1 or 2, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, t5 represents an integer of 0, 1, 2, 3, 4 or 5, t8 represents an integer of 0, 1, 2, 3 or 4.

2. The aryltetrahydropyridine compound or a salt thereof according to claim 1, wherein A 1 Represents a nitrogen atom.

3. The aryltetrahydropyridine compound or a salt thereof according to claim 1 or 2, wherein Z 1 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6)alkylthio group, a halo(C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfonyl group, -NH2, a C1-C6 alkylamino group, a di(C1-C6)alkylamino group, a carboxyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylaminocarbonyl group, a di(C1-C6)alkylaminocarbonyl group, a hydroxyl group, a C1-C6 alkylcarbonyloxy group, a C1-C6 alkylsulfonyloxy group, a cyano group or a nitro group, Z 2 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halogenated (C1-C6) alkyl group, a halogenated (C2-C6) alkenyl group, a halogenated (C2-C6) alkynyl group, a C1-C6 alkoxy group, a halogenated (C1-C6) alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halogenated (C1-C6) alkylthio ... ~C6) alkylsulfinyl, halo(C1~C6) alkylsulfonyl, -NH2, C1~C6 alkylamino, di(C1~C6) alkylamino, carboxyl, C1~C6 alkylcarbonyl, C1~C6 alkoxycarbonyl, C1~C6 alkylaminocarbonyl, di(C1~C6) alkylaminocarbonyl, hydroxyl, C1~C6 alkylcarbonyloxy, C1~C6 alkylsulfonyloxy, -C(=NOR 14 )R 15 , nitro or cyano, Z 5 represents a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group, R 1 represents a hydrogen atom, a halogen atom or a halogenated (C1-C6) alkyl group, R 2 represents a hydrogen atom, -C(O)R 4 、-C(O)OR 5 , D-1, D-2 or D-3, R 3 represents a hydrogen atom, Q means Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-25, Q-26, Q-27, Q-29, Q-30, Q-31, Q-32, Q-33, Q-38, Q-39, Q-40, Q-41, Q-42, Q-43, Q-44, Q-45, Q-46, Q-47, Q-50, Q-51, Q-52 or Q-54, G means G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G-26, G-27, G-28, G-29, G-30, G-31, G-32, G-33, G-34, G-35, G-37, G-38, G-40, G-41, G-42, G-43, G-45, G-47, G-48, G-50, G-53, G-54, G-55 or G-57.

4. The aryltetrahydropyridine compound or a salt thereof according to any one of claims 1 to 3, wherein J stands for J-1, A 1 Represents a nitrogen atom.

5. The aryltetrahydropyridine compound or a salt thereof according to any one of claims 1 to 3, wherein J stands for J-2.

6. The aryltetrahydropyridine compound or a salt thereof according to any one of claims 1 to 5, wherein G means G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-21, G-22, G-23, G-24, G-25, G -26, G-27, G-28, G-29, G-30, G-31, G-32, G-34, G-35, G-37, G-38, G-40, G-41, G-42, G-43, G-45, G-47, G-48, G-50, G-53, G-55 or G-57.

7. The aryltetrahydropyridine compound or a salt thereof according to claim 1, wherein Q means Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31, Q-45 or Q-52, Z 1 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6)alkylthio group, a carboxyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylaminocarbonyl group, a hydroxyl group, a cyano group or a nitro group, G means G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 or G-40, Z 2 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a halogenated (C1-C6) alkyl group, a C1-C6 alkoxy group, a halogenated (C1-C6) alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a di(C1-C6) alkylamino group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a hydroxyl group, -C(=NOR 14 )R 15 , nitro or cyano, R 14 represents a C1-C6 alkyl group, R 1 represents a hydrogen atom, a halogen atom or a halogenated (C1-C6) alkyl group, R 2 represents a hydrogen atom, -C(O)R 4 、-C(O)OR 5 , D-1, D-2 or D-3, R 4 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylcarbonyl group or a 6 Substituted (C1-C6) alkyl, R 6 represents a halogen atom or a C1-C6 alkoxy group, Z 5 represents a C1-C6 alkyl group, R 5 represents a C1-C6 alkyl group or a C2-C6 alkenyl group, R 3 represents a hydrogen atom, X represents an oxygen atom.

8. The aryltetrahydropyridine compound or a salt thereof according to claim 7, wherein G means G-1, G-3, G-4, G-5, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 or G-40.

9. The aryltetrahydropyridine compound or a salt thereof according to claim 8, wherein Q means Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29 or Q-45, Z 1 represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6)alkylthio group, a C1-C6 alkoxycarbonyl group, a cyano group or a nitro group, Z 3 represents a C1-C6 alkyl group, Z 2 It represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a hydroxyl group, a nitro group or a cyano group.

10. The aryltetrahydropyridine compound or a salt thereof according to claim 9, wherein J stands for J-1, A 1 represents nitrogen atom, Q means Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-12, Q-13, Q-14 or Q-22, G stands for G-1, G-3, G-4 or G-5, Z 2 represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group or a nitro group, R 2 Represents a hydrogen atom or -C(O)OR 5 , R 5 represents a C1-C6 alkyl group, Y represents an oxygen atom.

11. The aryltetrahydropyridine compound or a salt thereof according to claim 10, wherein Q stands for Q-1, Q-2, Q-3, Q-4, Q-6, Q-9 or Q-12, Z 1 represents a halogen atom, a C1-C6 alkyl group, a halogenated (C1-C6) alkyl group, a cyano group or a nitro group, G means G-1 or G-3, Z 2 represents a halogen atom, a C1-C6 alkyl group or a halogenated (C1-C6) alkyl group, R 1 represents a halogen atom or a halogenated (C1-C6) alkyl group, R 2 Represents a hydrogen atom.

12. The aryltetrahydropyridine compound or a salt thereof according to claim 9, wherein J stands for J-2, Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-9, Q-10, Q-12, Q-20, Q-29 or Q-45, Z 1 represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a C1-C6 alkoxycarbonyl group, a cyano group or a nitro group, G means G-1, G-3, G-7, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 or G-40, Z 2 It represents a halogen atom, a C1-C6 alkyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group or a hydroxyl group.

13. The aryltetrahydropyridine compound or a salt thereof according to claim 12, wherein Q stands for Q-1, Q-2, Q-3, Q-4, Q-6, Q-9 or Q-12, Z 1 represents a halogen atom, a C1-C6 alkyl group, a halogenated (C1-C6) alkyl group, a cyano group or a nitro group, G stands for G-1, G-3 or G-7, Z 2 represents a halogen atom, a C1-C6 alkyl group or a halogenated (C1-C6) alkyl group, R 2 Represents a hydrogen atom.

14. An intermediate for producing an aryl tetrahydropyridine compound or a salt thereof according to any one of claims 1 to 13, wherein the intermediate is represented by formula (1-1), In the formula, J represents J-1 or J-2, A 1 represents nitrogen atom, G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7, G-8, G-9, G-10, G-11, G-12, G-13, G-14, G-15, G-16, G-17, G-18, G-19, G-20, G-27, G-28 or G-40, Z 2 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a halogenated (C1-C6) alkyl group, a C1-C6 alkoxy group, a halogenated (C1-C6) alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a di(C1-C6) alkylamino group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a hydroxyl group, -C(=NOR 14 )R 15 , nitro or cyano, R 14 represents a C1-C6 alkyl group, R 15 represents a hydrogen atom or a C1-C6 alkyl group, Z 4 represents a C1-C6 alkyl group, R 1 represents a hydrogen atom, a halogen atom or a halogenated (C1-C6) alkyl group, R 51 represents a C1-C6 alkyl group, t2 represents an integer of 0, 1 or 2, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, t5 represents an integer of 0, 1, 2, 3, 4 or 5.

15. The production intermediate of the aryltetrahydropyridine compound or its salt according to claim 14, wherein J stands for J-1, G stands for G-1, G-2 or G-3, Z 2 represents a halogen atom or a C1-C6 alkyl group, R 1 It represents a halogen atom or a halogenated (C1-C6) alkyl group.

16. An intermediate for producing an aryl tetrahydropyridine compound or a salt thereof according to any one of claims 1 to 13, wherein the intermediate is represented by formula (1-2): In the formula, R 52 represents a hydrogen atom or a C1-C6 alkyl group, R 2 Represents a hydrogen atom, -C(O)R 4 or-C(O)OR 5 , R 4 represents a C1-C6 alkyl group, R 5 represents a C1-C6 alkyl group, Q means Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-20, Q-22, Q-29, Q-31, Q-45 or Q-52, Z 1 represents a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo(C1-C6)alkyl group, a C1-C6 alkoxy group, a halo(C1-C6)alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a halo(C1-C6)alkylthio group, a carboxyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylaminocarbonyl group, a hydroxyl group, a cyano group or a nitro group, Z 3 represents a hydrogen atom or a C1-C6 alkyl group, t1 represents an integer of 0 or 1, t2 represents an integer of 0, 1 or 2, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, t5 represents an integer of 0, 1, 2, 3, 4 or 5.

17. The production intermediate of the aryltetrahydropyridine compound or its salt according to claim 16, wherein Q means Q-1, Q-2, Q-3, Q-4, Q-6 or Q-9, Z 1 represents a halogen atom, a C1-C6 alkyl group or a cyano group, R 2 Represents a hydrogen atom or -C(O)OR 5 .

18. A pest control agent, wherein: The composition contains one or more aryltetrahydropyridine compounds and salts thereof selected from any one of claims 1 to 13 as active ingredients.

19. A pesticide, wherein: The composition contains one or more aryltetrahydropyridine compounds and salts thereof selected from any one of claims 1 to 13 as active ingredients.

20. An agent for controlling internal or external parasites of mammals or birds, wherein: The composition contains one or more aryltetrahydropyridine compounds and salts thereof selected from any one of claims 1 to 13 as active ingredients.

21. The insecticide according to claim 20, wherein External parasites are of the order Siphonaptera or Acarina.

22. An insecticide or acaricide, wherein: The composition contains one or more aryltetrahydropyridine compounds and salts thereof selected from any one of claims 1 to 13 as active ingredients.

23. A seed treatment agent, wherein: The composition contains one or more aryltetrahydropyridine compounds and salts thereof selected from any one of claims 1 to 13 as active ingredients.

24. The seed treatment agent according to claim 23, wherein Seed treatment is carried out by dipping treatment.

25. A soil treating agent, wherein: The composition contains one or more aryltetrahydropyridine compounds selected from any one of claims 1 to 13 as active ingredients.

26. The soil treating agent according to claim 25, wherein Soil treatment was carried out by soil irrigation treatment.

Images