BR112021006860B1 - COMPOUND, PEST CONTROL AGENTS, ECTOPARASITE CONTROL, ENDOPARASITE EXPELLER OR ENDOPARASITE CONTROL, SEED TREATMENT OR TREATMENT OF VEGETATIVE PROPAGATION ORGANS, SOIL TREATMENT AND BAIT, INSECTICIDE OR ACARICIDE, GRANULAR AGROCHEMICAL COMPOSITION, AND PLANT GROWTH PROMOTER - Google Patents

Abstract

COMPOUND, PEST CONTROL AGENTS, ECTOPARASITE CONTROL AGENTS, ENDOPARASITE EXPELLER OR ENDOPARASITE CONTROL AGENTS, SEED TREATMENT AGENTS OR VEGETABLE PROPAGATION ORGANS AGENTS, SOIL TREATMENT AGENTS AND BAIT AGENTS, INSECTICIDE OR ACARICIDE, GRANULAR AGROCHEMICAL COMPOSITION, AND PLANT GROWTH PROMOTER. The present invention deals with the problem of providing a (hetero)arylimidazole compound that has excellent pest control activity, particularly excellent insecticidal activity and/or excellent acaricidal activity, also has excellent safety, and can be advantageously industrially synthesized. The (hetero)arylimidazole compound according to the present invention is a compound represented by formula (I), or an N-oxide compound, a stereoisomer, a tautomer or a hydrate of the compound, or a salt of the compound, the N-oxide compound, the stereoisomer, the tautomer or the hydrate. In formula (I), B1 represents a nitrogen atom or CH; X represents a substituted or unsubstituted C3-8-cycloalkyl group; R1 represents a substituted or unsubstituted C1-6-alkylthio group or a substituted or unsubstituted C1-6-alkylsulfonyl group; R2 represents a substituted or unsubstituted C1-6-alkyl group; and R represents a (...) group.

Description

DESCRIPTION Title of invention

[001] (Hetero)arylimidazole compound and pest control agent.

Technical field

[002] The present invention relates to a (hetero)arylimidazole compound and a pest control agent. More specifically, the present invention relates to a (hetero)arylimidazole compound which has excellent insecticidal activity and/or acaricidal activity, is excellent in safety, and can be advantageously industrially synthesized, and to a pest control agent containing it as an active ingredient.

[003] This application claims priority to Japanese Patent Application No. 2018-202998, filed on October 28, 2018, the contents of which are incorporated herein.

Prior art

[004] Various compounds having insecticidal or acaricidal activity have been proposed. For practical use of such compounds as agrochemicals, it is required not only that they have sufficiently high efficacy but that they are less likely to cause chemical resistance, that they do not cause phytotoxicity to plants or soil pollution, and that they are very low toxic to farm animals, fish, etc.

[005] Patent document 1 describes a compound represented by formula (A), etc.

[006] Patent document 2 describes a compound represented by formula (B), etc.

PRIOR ART DOCUMENTS Patent Documents

[007] Patent document 1: WO2017/104741A.

[008] Patent document 2: WO2016/121997A.

SUMMARY OF THE INVENTION Objectives to be achieved by the invention

[009] An object of the present invention is to provide a (hetero)arylimidazole compound which is excellent in pest control activity, particularly insecticidal activity and/or acaricidal activity, is excellent in safety, and can be advantageously industrially synthesized. Another object of the present invention is to provide a pest control agent, an insecticide or an acaricide, an ectoparasite control agent, or an endoparasite expelling or endoparasite control agent containing the (hetero)arylimidazole compound as an active ingredient. Another object of the present invention is to provide a seed treatment agent, a vegetative propagation organ treatment agent, a granular agrochemical composition for treating paddy rice seedling nursery boxes, a soil treatment agent, a baiting agent, and a plant growth promoter containing the (hetero)arylimidazole compound as an active ingredient.

Means to achieve the objectives

[0010] As a result of diligent studies to achieve the objectives, the present invention including the following forms has been completed.

[0011] [1] A compound represented by formula (I), an N-oxide compound, stereoisomer, tautomer or hydrate thereof or a salt of any of these compounds: in which:B1 represents a nitrogen atom or CH;X represents a substituted or unsubstituted C3-8-cycloalkyl group;R1 represents a substituted or unsubstituted C1-6-alkylthio group or a substituted or unsubstituted C1-6-alkylsulfonyl group;R2 represents a substituted or unsubstituted C1-6-alkyl group; andR represents a substituted or unsubstituted C2-6-alkenyl group.

[0012] [2] The compound according to [1] above, an N-oxide compound, stereoisomer, tautomer or hydrate thereof or a salt of any of these compounds, wherein formula (I) is formula (II): in which:R1, R2, and X have the same meanings as described in formula (I);R3 represents a hydrogen atom or a halogen group;R4 represents a C1-4-haloalkyl group; and the carbon-carbon stereo double bond represents an E form or a Z form, or a mixture thereof.

[0013] [3] A compound represented by any one of formula (III) to formula (X), an N-oxide compound, stereoisomer, tautomer or hydrate thereof or a salt of any of these compounds: where the carbon-carbon double stereo bond represents an E form or a Z form, or a mixture thereof; where the carbon-carbon stereo double bond represents an E form or a Z form, or a mixture thereof;

[0014] [4] A pest control agent comprising at least one compound selected from the group consisting of a compound according to any one of [1] to [3] above, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any one of these compounds.

[0015] [5] An insecticide or an acaricide comprising at least one compound selected from the group consisting of a compound according to any one of [1] to [3] above, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient.

[0016] [6] An ectoparasite control agent comprising at least one compound selected from the group consisting of a compound according to any one of [1] to [3] above, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient.

[0017] [7] An endoparasite-expelling or endoparasite-controlling agent comprising at least one compound selected from the group consisting of a compound according to any one of [1] to [3] above, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient.

[0018] [8] A seed treatment agent or a vegetative propagation organ treatment agent comprising at least one compound selected from the group consisting of a compound according to any one of [1] to [3] above, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient.

[0019] [9] A granular agrochemical composition for treating paddy rice seedling nursery boxes comprising at least one compound selected from the group consisting of a compound according to any one of [1] to [3] above, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any one of these compounds, as an active ingredient.

[0020] [10] A soil treatment agent comprising at least one compound selected from the group consisting of a compound according to any one of [1] to [3] above, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient.

[0021] [11] A baiting agent comprising at least one compound selected from the group consisting of a compound according to any one of [1] to [3] above, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any one of these compounds, as an active ingredient.

[0022] [12] A plant growth promoter comprising at least one compound selected from the group consisting of a compound according to any one of [1] to [3] above, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient.

EFFECT OF THE INVENTION

[0023] The (hetero)arylimidazole compound of the present invention can control pests that are problems associated with agricultural crops or hygiene. Particularly, the (hetero)arylimidazole compound of the present invention can effectively control agricultural insect and mite pests at lower concentration. Furthermore, the (hetero)arylimidazole compound of the present invention can effectively control ectoparasites and endoparasites harmful to humans and animals.

[0024] Also, the (hetero)arylimidazole compound of the present invention can be used as a seed treatment agent, a vegetative propagation organ treatment agent, a granular agrochemical composition for treating paddy rice seedling nursery boxes, a soil treatment agent, a baiting agent, or a plant growth promoter.

METHODS FOR CARRYING OUT THE INVENTION [(hetero)arylimidazole compound]

[0025] The (hetero)arylimidazole compound of the present invention is a compound represented by formula (I) (hereinafter also referred to as compound (I)), an N-oxide compound, stereoisomer, tautomer or hydrate thereof or a salt of any of these compounds. The compound represented by formula (I) includes each stereoisomer that is an enantiomer or a diastereomer.

[0026] In the present invention, the term "unsubstituted" means a group consisting of only one parent nucleus. Only the name of a group consisting of one parent nucleus without the term "substituted" means an "unsubstituted" group unless otherwise specified.

[0027] On the other hand, the term “substituted” means that any hydrogen atom of a group consisting of a parent group is replaced by a group (substituent) having a structure that is the same as that of or different from that of the parent nucleus. Therefore, the “substituent” means another group bonded to the group consisting of a parent nucleus. The number of substituent may be one or more. Two or more substituents are the same or different.

[0028] Terms such as “C1-6” mean that the number of carbon atoms in the group consisting of a parent nucleus is from 1 to 6, etc. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxyl group as a substituent is classified as a C2-alkoxy-C4-alkyl group.

[0029] The “substituent” is not particularly limited as long as the substituent is chemically acceptable and produces the effect of the present invention. Hereinafter, a group capable of serving as the “substituent” is exemplified: a C1-6-alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group, and an n-hexyl group; a C2-6-alkenyl group such as a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, and a 2-methyl-2-propenyl group; a C2-6-alkynyl group such as ethynyl, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, and a 1-methyl-2-propynyl group; a C3-8-cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cubanyl group; a C6-10-aryl group such as a phenyl group and a naphthyl group; an aryl C6-10-C1-6-alkyl group such as a benzyl group and a phenethyl group; a 3- to 6-membered heterocyclyl group; a 3- to 6-membered heterocyclyl C1-6-alkyl group; a hydroxyl group; a C1-6-alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, and a t-butoxy group; a C2-6-alkenyloxy group such as a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group; a C2-6-alkynyloxy group such as an ethynyloxy group and a propargyloxy group; a C6-10-aryloxy group such as a phenoxy group and a naphthoxy group; an aryl C6-10-C1-6-alkoxy group such as a benzyloxy group and a phenethyloxy group; a 5- or 6-membered heteroaryloxy group such as a thiazolyloxy group and a pyridyloxy group; a 5- or 6-membered heteroaryl C1-6-alkyloxy group such as a thiazolylmethyloxy group and a pyridylmethyloxy group; a formyl group; a C1-6-alkylcarbonyl group such as an acetyl group and a propionyl group; a formyloxy group; a C1-6-alkylcarbonyloxy group such as an acetyloxy group and a propionyl group; an aryl C6-10-carbonyl group such as a benzoyl group; a C1-6-alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group; a C 1-6 alkoxycarbonyloxy group such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group, and a t-butoxycarbonyloxy group; a carboxyl group; a halogen group such as a fluoro group, a chloro group, a bromo group, and an iodo group; a C 1-6 haloalkyl group such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group, and a 2,4,6-trichlorohexyl group; a C2-6-haloalkenyl group such as a 2-chloro-1-propenyl group and a group 2-fluoro-1-butenyl; a C2-6 haloalkynyl group such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group; a C1-6 haloalkoxy group such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, and a perfluoropropoxy group; a C2-6 haloalkenyloxy group such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group; a C1-6 haloalkylcarbonyl group such as a chloroacetyl group, a trifluoroacetyl group, and a trichloroacetyl group; an amino group; an amino group substituted with C1-6 alkyl such as a methylamino group, a dimethylamino group, and a diethylamino group; a C1-6 haloalkyl group aryl-C6-10-amino such as an anilino group and a naphthylamino group; an aryl-C6-10-alkyl-C1-6-amino group such as a benzylamino group and a phenethylamino group; a formylamino group; a C1-6-alkylcarbonylamino group such as an acetylamino group, a propanoylamino group, a butyrylamino group, and an i-propylcarbonylamino group; a C1-6-alkoxycarbonylamino group such as a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group, and an i-propoxycarbonylamino group; an unsubstituted or substituted aminocarbonyl group such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group, and an N-phenyl-N-methylaminocarbonyl group; an imino-C1-6-alkyl group such as an iminomethyl group, a (1-imino)ethyl group, and a (1-imino)-n-propyl; an unsubstituted or substituted N-hydroxyimino-C 1-6 alkyl group such as an N-hydroxyiminomethyl group, a (1-(N-hydroxy)-imino)ethyl group, a (1-(N-hydroxy)-imino)propyl group, an N-methoxyiminomethyl group, and a (1-(N-methoxy)-imino)ethyl group; a C 1-6 alkoxyimino group such as a methoxyimino group, an ethoxyimino group, an n-propoxyimino group, an i-propoxyimino group, and an n-butoxyimino group; an aminocarbonyloxy group; an aminocarbonyloxy group substituted with C 1-6 alkyl such as an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy group; a mercapto group; a C 1-6 alkylthio group such as a methylthio group, a ethylthio, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group, and a t-butylthio group; a C 1-6 haloalkylthio group such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group; an aryl C 6-10 thio group such as a phenylthio group and a naphthylthio group; a 5- or 6-membered heteroarylthio group such as a thiazolylthio group and a pyridylthio group; a C 1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group; a C 1-6 haloalkylsulfinyl group such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group; an aryl C 6-10 sulfinyl group such as a phenylsulfinyl; a 5- or 6-membered heteroarylsulfinyl group such as a thiazolylsulfinyl group and a pyridylsulfinyl group; a C 1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group; a C 1-6 haloalkylsulfonyl group such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group; a C 6-10 arylsulfonyl group such as a phenylsulfonyl group; a 5- or 6-membered heteroarylsulfonyl group such as a thiazolylsulfonyl group and a pyridylsulfonyl group; a C 1-6 alkylsulfonyloxy group such as a methylsulfonyloxy group, an ethylsulfonyloxy group, and a t-butylsulfonyloxy group; a C 1-6 alkylsulfonyloxy group such as a methylsulfonyloxy group, an ethylsulfonyloxy group, and a t-butylsulfonyloxy group; haloalkyl-C1-6-sulfonyloxy such as a trifluoromethylsulfonyloxy group and a 2,2,2-trifluoroethylsulfonyloxy group; and an aminothiocarbonyl group; a trialkyl-C1-6-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group, and a t-butyldimethylsilyl group; a triaryl-C6-10-substituted silyl group such as a triphenylsilyl group; a cyano group; and a nitro group.

[0030] For these “substituents”, any hydrogen atom in each substituent may be replaced with a group having a different structure. In this case, as the “substituent”, a C1-6-alkyl group, a C1-6-haloalkyl group, a C1-6-alkoxy group, a C1-6-haloalkoxy group, a halogen group, a cyano group, a nitro group or the like may be exemplified.

[0031] The above-described “3- to 6-membered heterocyclyl group” contains 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as the atoms constituting the ring. The heterocyclyl group may be either monocyclic or polycyclic. The polycyclic heterocyclyl group has at least one heteroring, and the remaining ring(s) may be any of a saturated alicyclic ring, an unsaturated alicyclic ring and an aromatic ring. As the “3- to 6-membered heterocyclyl” group, a 3- to 6-membered saturated heterocyclyl group, a 5- or 6-membered heteroaryl group, a 5- or 6-membered partially unsaturated heterocyclyl group or the like can be exemplified.

[0032] As the 3- to 6-membered heterocyclyl group, an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, a dioxanyl group or the like can be exemplified.

[0033] As the 5-membered heteroaryl group, a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, a tetrazolyl group or the like can be exemplified.

[0034] As the 6-membered heteroaryl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group or the like can be exemplified.

[B1]

[0035] In formula (I), B1 represents a nitrogen atom or CH.

[0036] Specifically, the compound represented by formula (I) is a compound represented by the following formula (I-1) or formula (I-2).

[0037] In formula (I-1) and formula (I-2), X, R1, R2 and R have the same meanings as described in formula (I).

[0038] B1 is preferably a nitrogen atom.

[X]

[0039] In formula (I), X represents a substituted or unsubstituted C3-8-cycloalkyl group.

[0040] As the “C3-8-cycloalkyl” group at X, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cubanyl group or the like can be exemplified.

[0041] As the “substituted C3-8-cycloalkyl group” at X, a 1-methylcyclopropyl group, a 1-cyanocyclopropyl group, a 1-aminocarbonylcyclopropyl group, a 1-aminothiocarbonylcyclopropyl group, a 1-(pyridin-2-yl)cyclopropyl group or the like can be exemplified.

[0042] As the substituent on the “C3-8-cycloalkyl group” at X, a cyano group; an aminocarbonyl group; an aminothiocarbonyl group; a C1-6-alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group, and an n-hexyl group; and a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group can be preferably exemplified.

[0043] X is preferably a substituted or unsubstituted cyclopropyl group, and more preferably an unsubstituted cyclopropyl group. [R1]

[0044] In formula (I), R1 represents a substituted or unsubstituted C1-6 alkylthio group or a substituted or unsubstituted C1-6 alkylsulfonyl group.

[0045] As the “C1-6-alkylthio group” in R1, a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group, a t-butylthio group can be exemplified.

[0046] As the “C1-6-alkylsulfonyl group” in R1, a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group or the like can be exemplified.

[0047] As the substituents on the “C1-6-alkylthio group” and the “C1-6-alkylsulfonyl group” in R1 can be preferably exemplified a halogen group such as a fluoro group, a chloro group, a bromo group, and an iodo group.

[0048] R1 is preferably a C1-6-alkylsulfonyl group, and more preferably an ethylsulfonyl group.

[R2]

[0049] In formula (I), R2 represents a substituted or unsubstituted C1-6-alkyl group.

[0050] The “C1-6-alkyl group” in R2 may be linear or branched. As the “C1-6-alkyl group”, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, an i-hexyl group or the like can be exemplified.

[0051] As the substituent on the “C1-6-alkyl group” in R2, a halogen group such as a fluoro group, a chloro group, a bromo group, and an iodo group can be preferably exemplified.

[0052] R2 is preferably an unsubstituted C1-6-alkyl group, and most preferably a methyl group.

[R]

[0053] In formula (I), R represents a substituted or unsubstituted C2-6-alkenyl group.

[0054] As the “C2-C6-alkenyl group” in R, a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group or the like can be exemplified.

[0055] As the “substituted C2-C6-alkenyl group” in R, a C2-6-haloalkenyl group such as a 2-fluoro-2-bromovinyl group, a 2,2-dichlorovinyl group, a 2-chloro-2-iodovinyl group, a 2-chloro-1-propenyl group, a 2,3,3,3-tetrafluoro-1-propenyl group, a 3,3,3-trifluoro-1-propenyl group, a 2-chloro-3,3,3-trifluoro-1-propenyl group, a 2-bromo-3,3,3-trifluoro-1-propenyl group, a 3,3,3-trifluoro-2-trifluoromethyl-1-propenyl group, a 2-fluoro-1-butenyl group, a 2-fluoro-1-butenyl group, a 2-fluoro-1-butenyl group, a 2-fluoro-1-butenyl group, a 2-chloro ... 3,3,4,4,4-pentafluoro-1-butenyl group, a 2,3,3,4,4,4-hexafluoro-1-butenyl group, a 2-chloro-3,3,4,4,4-pentafluoro-1-butenyl group, a 3,3,4,4,5,5,5-heptafluoro-1-pentenyl group, a 2-chloro-3,3,4,4,5,5,5-heptafluoro-1-pentenyl group, a 2,3,3,4,4,5,5,5-octafluoro-1-pentenyl group, and a 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexenyl group; and a haloalkoxy-C1-6-haloalkyl-C2-6 group such as a 1,2-difluoro-2-trifluoromethoxyvinyl group and a 1,2-difluoro-2-perfluoropropoxyvinyl group.

[0056] As the substituent on the “C2-C6-alkenyl group” in R, a halogen group such as a fluoro group, a chloro group, a bromo group, and an iodo group; and a C1-6-haloalkoxy group such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, and a perfluoropropoxy group can be preferably exemplified.

[0057] R is preferably a C2-6-haloalkenyl group.

[0058] The salt of compound (I) is not particularly limited as long as the salt is agriculturally and horticulturally acceptable. As the salt of compound (I) there can be exemplified, for example, a salt of an inorganic acid such as hydrochloric acid and sulfuric acid; a salt of an organic acid such as acetic acid and lactic acid; a salt of an alkali metal such as lithium, sodium and potassium; a salt of an alkaline earth metal such as calcium and magnesium; a salt of a transition metal such as iron and copper; a salt of an organic base such as ammonia, triethylamine, tributylamine, pyridine, and hydrazine, or the like.

[Compound represented by formula (II)]

[0059] The compound represented by formula (I) is preferably a compound represented by formula (II).

[0060] In formula (II): R1, R2, and X have the same meanings as described in formula (I). R3 represents a hydrogen atom or a halogen group. R4 represents a C1-4-haloalkyl group. In formula (II), the carbon-carbon stereo double bond represents an E form or a Z form, or a mixture thereof. [R3] As the “halogen group” in R3, a fluoro group, a chloro group, a bromo group, an iodo group or the like can be exemplified.

[R4]

[0061] As the “C1-C4-haloalkyl group” in R4, there can be exemplified a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl, a 4-chlorobutyl group or the like.

[0062] R4 is preferably a C1-4-fluoroalkyl group such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, or a perfluorobutyl group.

[0063] The compound represented by formula (I) is preferably any one of the following compounds. where the carbon-carbon double stereo bond represents an E form or a Z form, or a mixture thereof. where the carbon-carbon double stereo bond represents an E form or a Z form, or a mixture thereof.

[Production methods]

[0064] The (hetero)arylimidazole compound of the present invention is not particularly limited by its production method. For example, the (hetero)arylimidazole compound of the present invention can be obtained by known production methods described in the Examples, etc. Alternatively, the N-oxide compound, salt, or the like of compound (I) can be obtained by a known approach from compound (I).

[0065] The (hetero)arylimidazole compound of the present invention can be produced, for example, by the methods set forth below. (Synthesis Method 1) wherein X, R1, and R2 have the same meanings as described above; and Rf represents a C1-4 fluoroalkyl group such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, or a perfluorobutyl group. (Synthesis Method 2) where X, R1, R2 and Rf have the same meanings as described above; and R5 represents a C1-6-alkyl group. (Synthesis Method 3) where X, R1, R2 and Rf have the same meanings as described above. (Synthesis method 4) where X, R1, R2 and Rf have the same meanings as described above. (Synthesis Method 5) where X, R1, R2 and Rf have the same meanings as described above. (Synthesis Method 6) where X, R1, R2 and Rf have the same meanings as described above. (Synthesis Method 7) where X, R1, R2 and Rf have the same meanings as described above. (Synthesis Method 8) where X, R1, R2 and Rf have the same meanings as described above. (Synthesis Method 9) where X, R1, R2 and Rf have the same meanings as described above.

[Plague control effect]

[0066] The (hetero)arylimidazole compound of the present invention is excellent in controlling pests such as various insect pests and agricultural mites that affect plant growth.

[0067] Also, the (hetero)arylimidazole compound of the present invention is a highly safe substance because of low phytotoxicity to agricultural crops and low toxicity to fish and warm-blooded animals. Accordingly, the (hetero)arylimidazole compound of the present invention is useful as an active ingredient for insecticides or acaricides.

[0068] Furthermore, in recent years, many insect pests such as diamondback moth, whiteback planthopper, cicada (leafhopper), and aphid have developed resistance to various existing chemicals, causing problems of insufficient efficacy of these chemicals. Therefore, effective chemicals for insect pests of resistant strains have been desired. The (hetero)arylimidazole compound of the present invention exhibits excellent control effect not only on sensitive strains but also on insect pests of various resistant strains and even on mites of acaricide-resistant strains.

[0069] The (hetero)arylimidazole compound of the present invention is excellent in controlling effect on ectoparasites and endoparasites harmful to humans and animals. Also, the (hetero)arylimidazole compound of the present invention is a highly safe substance because of low toxicity to fish and warm-blooded animals. Accordingly, the (hetero)arylimidazole compound of the present invention is useful as an active ingredient for ectoparasite and endoparasite control agents.

[0070] The (hetero)arylimidazole compound of the present invention exhibits efficacy at any developmental stage of organisms to be controlled, and exhibits an excellent control effect on, for example, eggs, nymphs, larvae, pupae, and adults of mites, insects, and the like.

[Pest control agent]

[0071] The pest control agent of the present invention contains at least one active ingredient selected from the (hetero)arylimidazole compounds of the present invention. The amount of the (hetero)arylimidazole compound contained in the pest control agent of the present invention is not particularly limited as long as the pest control effect is exhibited. The pest control agent is a pest control agent and includes an insecticide or an acaricide, an ectoparasite control agent, or an endoparasite expelling or endoparasite control agent, or the like.

[0072] The pest control agent of the present invention can be used as a mixture or in combination with another active ingredient such as a fungicide, an insecticide or an acaricide, a nematicide, or a pesticide for insect pests; a plant growth regulator, a synergist, a fertilizer, a soil improving agent, animal feed, or the like.

[0073] It may be assumed that the combination of the (hetero)arylimidazole compound of the present invention with another active ingredient has synergistic effects on insecticidal, acaricidal, or nematicidal activity. The synergistic effects may be confirmed by the Colby equation (Colby. S.R.; “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”; Weeds 15, p. 20-22, 1967) according to a standard method.

[0074] Specific examples of the insecticide or acaricide, nematicide, pesticide for soil insect pests, anthelmintic agent, and the like, which can be used as a mixture or in combination with the pest control agent of the present invention will be shown below.

[0075] (1) Acetylcholinesterase inhibitors: (a) carbamate-based: alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxym, butoxycarboxym, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, tiofanox, triazamate, trimetacarb, XMC, xylylcarb, fenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, alixicarb, aminocarb, bufencarb, cloethocarb, metham-sodium, and promecarb; (b) organophosphorus-based: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusaphos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfotone, EPN, ethion, etoprophos, fanfur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imiciaphos, isofenphos, isocarbophos, isoxathione, malathion, mecarbam, methamidophos, methidathione, mevinfos, monocrotophos, naled, omethoate, oxidemeton-methyl, parathion, parathion-methyl, phentoate, phorate, fosalone, phosmet, phosfamidone, phoxim, pirimifos-methyl, profenofos, propetanphos, prothiophos, pyraclophos, pyridafenthion, quinalphos, sulfotep, tebupirinphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorphone, vamidothion; bromophos-ethyl, BRP, carbophenothione, cyanofenphos, CIAP, demeton-S-methyl-sulfone, dialiphos, diclofenthione, dioxabenzophos, ethrymphos, fensulfothione, flupyrazophos, phonofos, formotiona, fosmethylan, isazophos, jodfenfos, metacriphos, pirimiphos-ethyl, phosphocarb, propaphos, protoate, and sulprofos.(2) GABAergic chloride ion channel antagonists: acetoprol, chlordane, endosulfan, etiprol, fipronil, pirafluprole, pyriprole, campefchlor, heptachlor, and dienochlor.(3) Sodium channel modulators: acrinathrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioalethrin, S-cyclopentyl isomers of bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans-isomers], delta-methrin, empenthrin [(EZ)-(1R)-isomers], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfemprox, imiprothrin, cadthrin, permethrin, phenothrin [(1R)-trans-isomers], prallethrin, pyrethrum, resmethrin, silafluofen, tefluthrin, tetramethrin [(1R)-isomers], tralomethrin, transfluthrin; allethrin, pyrethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanolmethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyrithrin, flubrocitrinate, flufenprox, metofluthrin, protrifenbut, pyresmethrin, and teralethrin.(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitempyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradifurone, and flupyrimine.(5) Nicotinic acetylcholine receptor allosteric modulators: spinetoram, and spinosad.(6) Chloride channel activators: abamectin, emamectin benzoate, lepimectin, milbemectin, ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin; milbemycin oxime, and nemadectin.(7) Juvenile hormone-like substances: hydroprene, cynoprene, methoprene, fenoxucarb, pyriproxyfen, diophenol, epofenonan, and triprene.(9) Selective feeding inhibitors for Homoptera: flonicamide, pymetrozine, and pyrifluquinazone.(10) Mite growth inhibitors: clofentezine, diflovidazine, hexythiazox, and etoxazole.(11) Agents derived from microorganisms that disrupt the inner midgut membrane of insects: Bacillus thuringiensis subsp. Isuraerenshi, Bacillus sphaericus, Bacillus thuringiensis subsp. Aizawai, Bacillus thuringiensis subsp. Isuraerenshi, Bacillus thuringiensis subsp. Tenebrionis, and Bt (Bacillus thuringiensis) proteins expressed in agricultural crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, and Cry34Ab1/Cry35Ab1.(12) Inhibitors of mitochondrial ATP biosynthesis enzymes: diafenthiurone, azocyclotin, ciexatin, fenbutatin oxide, propargite, and tetradiphone.(13) Uncoupling agents of oxidative phosphorylation: chlorfenapyr, sulfluramid, DNOC; binapacril, dinobutone, and dinocape.(14) Nicotinic acetylcholine receptor channel blockers: bensultape, cartape hydrochloride; nereistoxin; thiosultape-sodium, and thiocyclam.(15) Chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumurone, lufenuron, novaluron, noviflumurone, teflubenzuron, triflumurone, buprofezin, and fluazuron.(16) Diptera ecdysis-disrupting agents: cyromazine.(17) Ecdysis-inducing hormone receptor agonists: chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.(18) Optopamine receptor agonists: amitraz, demiditraz, and chlordimeform.(19) Mitochondrial electron transport system complex III inhibitors: acequinocyl, fluacrypyrim, and hydramethylnone.(20) Inhibitors of complex I of the mitochondrial electron transport system: fenazaquine, fenpyroximate, pyrimidifen, pyridaben, tebufempyrad, tolfempyrad, and rotenone.(21) Voltage-operated sodium channel blockers: indoxacarb, and metaflumizone.(22) Acetyl-CoA carboxylase inhibitors: spirodiclofen, spiromesifen, and spirotetramate.(23) Inhibitors of complex IV of the mitochondrial electron transport system: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide.(24) Inhibitors of complex II of the mitochondrial electron transport system: cyenopyrafen, cyflumetofen, and piflubumide.(25) Modulators of ryanodine receptor: chlorantraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, and tetraniliprole.(26) Mixed-function oxidase inhibitor compounds: piperonyl butoxide.(27) Latrophyllin receptor agonists: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, and emodepside.(28) Other agents (based on unknown mechanism of action): azadirachtin, benzoximate, bifenazate, bromopropylate, quinomethionate, cryolite, dicofol, pyridalyl, benclothiaz, sulfur, amidoflumeth, 1,3-dichloropropene, DCIP, phenisobromolate, benzomate, metaldehyde, chlorobenzylate, clothiazobene, dicyclanil, fenoxacrim, fentriphanil, flubenzimine, fluphenazine, gossyplure, japonilure, methoxadaiazone, petroleum, potassium oleate, tetrasul, triaratene, afidopyropene, flomethoquin, flufiprol, fluensulfone, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodecanamide, fluralaner, afoxolaner, fluxametamide, 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile (CAS: 943137-49-3), broflanilide, other m-diamides.(29) Anthelmintic agents:(a) benzimidazole based: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, parbendazole, flubendazole, febantel, netobimine, thiophanate; thiabendazole, and cambendazole; (b) salicylanilide-based: closantel, oxyclozanide, rafoxanide, and niclosamide; (c) substituted phenol-based: nitroxynil and nitroscanate; (d) pyrimidine-based: pyrantel and morantel; (e) imidazothiazole-based: levamisole and tetramisole; (f) tetrahydropyrimidine-based: praziquantel and epsiprantel; (g) other anthelmintic agents: cyclodiene, ryania, clorsulone, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorophene, monepantel, tribendimidine, amidantel, thiacetarsamide, melarsomine, and arsenamide.

[0076] Specific examples of the fungicide that can be used as a mixture or in combination with the pest control agent of the present invention will be shown.(1) Nucleic acid biosynthesis inhibitors:(a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, clozylacon, and ofurace;(b) adenosine deaminase inhibitors: bupirimate, dimethirimol, and ethirimol;(c) DNA/RNA synthesis inhibitors: hymexazole and octilinone;(d) DNA topoisomerase II inhibitors: oxolinic acid.(2) Mitotic inhibitors and cell division inhibitors:(a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, and ethaboxam; (b) cell division inhibitors: pencycurone; (c) spectrin-type protein delocalization inhibitors: fluopicolide. (3) Respiration inhibitors: (a) NADH oxidation-reduction enzyme complex I inhibitors: diflumetorim and tolfenpyrad; (b) succinate dehydrogenase complex II inhibitors: benodanil, flutolanil, mepronil, isofetamide, fluopyram; fenfuram, furmecyclox, carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxan, and boscalid; (c) ubiquinol oxidase complex III Qo-site inhibitors: famoxadone; fluoxastrobin, fenamidone, and piribencarb; (d) inhibitors of the Qi site of complex III ubiquinol reductase: cyazofamid and amisulbrom; (e) uncoupling agents of oxidative phosphorylation: binapacryl, meptyldinocap, dinocap, fluazinam, and ferinzone; (f) inhibitors of oxidative phosphorylation (ATP synthase inhibitors): fentin acetate, fentin chloride, and fentin hydroxide; (g) inhibitors of ATP production: silthiofam; (h) inhibitor of the Qx site (unknown) of complex III: cytochrome bc1 (ubiquinone reductase): ametoctradin. (4) Inhibitors of amino acid and protein synthesis: (a) inhibitors of methionine biosynthesis: andoprim, cyprodinil, mepanipyrim, and pyrimethanil;(b) protein synthesis inhibitors: blasticidin-S; kasugamycin, kasugamycin hydrochloride, streptomycin, and oxytetracycline.(5) Signal transduction inhibitors:(a) signal transduction inhibitors: quinoxyfen and proquinazide;(b) MAP/histidine kinase inhibitors in osmotic signal transduction: fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone, and vinclozolin.(6) Lipid and cell membrane synthesis inhibitors:(a) phospholipid biosynthesis inhibitors and methyltransferase inhibitors: edifenfos, iprobenfos, pyrazophos, and isoprothiolane;(b) lipid peroxidizing agents: biphenyl, chloroneb, dichloran, quintozene, tecnazene, tolclofos-methyl, and etridiazole;(c) agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fosetylate, and prothiocarb;(d) microorganisms that disrupt the cell membranes of pathogens: Bacillus subtilis bacteria, Bacillus subtilis strain QST713, Bacillus subtilis strain FZB24, Bacillus subtilis strain MBI600, and Bacillus subtilis strain D747;(e) agents that disrupt cell membranes: Melaleuca alternifolia (tea tree) extracts. [0095](7) Inhibitors of cell membrane sterol biosynthesis: (a) inhibitors of C14 demethylation in sterol biosynthesis: triforin, pirifenox, pyrisoxazole, fenarimol, flurprimidol, nuarimol, imazalil, imazalil sulfate, oxpoconazole, pefurazoate, prochloraz, triflumizole, viniconazole, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fembuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, fluquinconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, and voriconazole; (b) Δ14-reductase and sterol-Δ8^Δ7-isomerase inhibitors in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, and spiroxamine; (c) 3-keto-reductase inhibitors in C4 demethylation in sterol biosynthesis systems: fenexamide and fenpyrazamine; (d) squalene epoxidase inhibitors in sterol biosynthesis systems: pyributicarb, naftifen, and terbinafine. (8) Cell wall synthesis inhibitors: (a) trehalase inhibitors: validamycin; (b) chitin synthase inhibitors: polyoxin and polyoxorim; (c) cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph; benthiavalicarb, iprovalicarb, tolprocarb, valifenalate, and mandipropamide.(9) Melanin biosynthesis inhibitors:(a) reductase inhibitors of melanin biosynthesis: phthalide, pyroquilone, and tricyclazole;(b) anhydrase inhibitors of melanin biosynthesis: carpropamide, diclocimet, and fenoxanil;(10) Host plant resistance-inducing agents:(a) agents acting on the salicylic acid biosynthetic pathway: acibenzolar-S-methyl;(b) others: probenazole, thiadinil, isotianil, laminarin, and giant knotweed (Fallopia sachalinensis) extracts.(11) Agents with unknown mode of action: cymoxanil, fosetyl aluminum, phosphoric acid (phosphate), tecloftalam, triazoxide, flusulfamide, diclomezine, methasulfocarb, cyflufenamide, metrafenone, pyriophenone, dodine, dodine free base, and flutianil.(12) Agents having multiple active sites: copper (copper salts), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, ferbam, mancozeb, maneb, mancobre, metiram, polycarbamate, propineb, thiram, zineb, ziram, captan, captafol, folpet, chlorothalonil, dichlofluanid, tolylfluanid, guazatine, iminoctadine triacetate, iminoctadine trialbesylate, anilazine, dithianone, chinomethionate, and fluoroimide.(13) Other agents: DBEDC, fluorofolpet, guazatine acetate, copper (II) bis(8-quinolinolate), propamidine, chloropicrin, ciprofuram, Agrobacterium, betoxazine, diphenylamine, methyl isothiocyanate (MITC), mildiomycin, capsaicin, curfraneb, cyprosulfamide, dazomet, debacarb, dichlorophen, difenzoquat, difenzoquatmethyl sulfonate, flumetover, fosetyl calcium, fosetyl sodium, irumamycin, natamycin, isopropyl nitrothal, oxamocarb, propanosine sodium, pyrrolnitrin, tebufloquine, tolnifanide, zarilamide, algofase, amicartiazole, oxathiapiprolin, metiram-zinc, benthiazole, triclamide, uniconazole, oxyphenthyine, picarbutrazox.

[0077] Specific examples of the plant regulatory agent that can be used as a mixture or in combination with the pest control agent of the present invention will be shown below.

[0078] Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenurone, thidiazurone, chlorfenurone, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl-aminoethoxyvinylglycine (also called aviglycine), amino-oxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothiol, 1-naphthylacetamide, eticlozate, cloxyfonac, maleic acid hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid, etheion, chlormequat, mepiquat chloride, benzyladenine, and 5-aminolevulinic acid.

[Insecticide or acaricide]

[0079] The insecticide or acaricide of the present invention contains at least one active ingredient selected from the (hetero)arylimidazole compounds of the present invention. The amount of the (hetero)arylimidazole compound contained in the insecticide or acaricide of the present invention is not particularly limited as long as its insecticidal or acaricidal effect is exhibited.

[0080] The insecticide or acaricide of the present invention is preferably used on plants such as cereals; vegetables; root vegetables; tubers and roots; flowers and ornamental plants; fruit trees; ornamental foliage plants and tea trees, coffee trees, cocoa trees, and the like; agricultural crops for food; lawn grasses; and cotton plants.

[0081] In application to plants, the pest control agent or insecticide or acaricide of the present invention may be used on any site such as a leaf, a stem, a stalk, a flower, a flower bud, a fruit, a seed, a shoot, a root, a tuber, a tuberous root, a sprout, or a seedling.

[0082] The insecticide or acaricide of the present invention is not particularly limited by the plant species to which the pest control agent or the insecticide or acaricide is applied. As the plant species, for example, an original species, a variant species, an improved species, a cultivar, a mutant, a hybrid, a genetically modified organism (GMO) or the like can be exemplified.

[0083] The insecticide or acaricide of the present invention may be used in seed treatment, foliar application, soil application, submerged application, or the like for the purpose of controlling various agricultural mites and insect pests.

[0084] Specific examples of various agricultural mites and insect pests controllable with the insecticide or acaricide of the present invention will be shown below. (1) Butterflies or moths of the order Lepidoptera (a) moths of the family Arctiidae, e.g., Hyphantria cunea and Lemyra imparilis; (b) moths of the family Bucculatricidae, e.g., Bucculatrix pyrivorella; (c) moths of the family Carposinidae, e.g., Carposina sasakii; (d) moths of the family Crambidae, e.g., Diaphania indica and Diaphania nitidalis of Diaphania spp.; for example, Ostrinia furnacalis, Ostrinia nubilalis, and Ostrinia scapulalis of Ostrinia spp.; and Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Diatraea grandiosella, Glyphodes pyloalis, Hellula undalis, and Parapediasia teterrella;(and) moths of the family Gelechiidae, e.g., Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, and Sitotroga Cerealella; neustria;(j) moths of the Lymantriidae family, for example, Lymantria dispar and Lymantria monacha from Lymantria spp.; and Euproctis pseudoconspersa and Orgyia thyellina;(k) moths of the family Lyonetiidae, e.g., Lyonetia clerkella and Lyonetia prunifoliella malinella of Lyonetia spp.;(l) moths of the family Noctuidae, e.g., Spodoptera depravata, Spodoptera eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, and Spodoptera litura of Spodoptera spp.; for example, Autographa gamma and Autographa nigrisigna from Autographa spp.; for example, Agrotis ipsilon and Agrotis segetum from Agrotis spp.; for example, Helicoverpa armigera, Helicoverpa assulta, and Helicoverpa zea from Helicoverpa spp.; for example, Heliothis armigera and Heliothis virescens from Heliothis spp.; and Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, Mythimna separata, Naranga aenescens, Panolis japonica, Peridroma saucia, Pseudoplusia includens, and Trichoplusia ni; e.g., Pieris brassicae and Pieris rapae crucivora from Pieris spp.; (o) moths of the family Plutellidae, e.g., Acrolepiopsis sapporensis and Acrolepiopsis suzukiella from Acrolepiopsis spp.; and Plutella xylostella;(p) moths of the family Pyralidae, e.g., Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, and Galleria mellonella;(q) moths of the family Sphingidae, e.g., Manduca quinquemaculata and Manduca sexta of Manduca spp.;(r) moths of the family Stathmopodidae, e.g., Stathmopoda masinissa;(s) moths of the family Tineidae, e.g., Tinea translucens;(t) moths of the family Tortricidae, e.g., Adoxophyes honmai and Adoxophyes orana of Adoxophyes spp.; e.g., Archips breviplicanus and Archips fuscocupreanus of Archips spp.; and Choristoneura fumiferana, Cydia pomonella, Eupoecilia ambiguella, Grapholitha molesta, Homona magnanima, Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana, and Sparganothis pilleriana;(u) moths of the family Yponomeutidae, e.g., Argyresthia conjugella. (2) Insect pests of the order Thysanoptera(a) insect pests of the family Phlaeothripidae, e.g., Ponticulothrips diospyrosi;(b) insect pests of the family Thripidae, e.g., Frankliniella intonsa and Frankliniella occidentalis of Frankliniella spp.; e.g., Thrips palmi and Thrips tabaci of Thrips spp.; and Heliothrips haemorrhoidalis and Scirtothrips dorsalis.(3) Insect pests of the order Hemiptera(A) the suborder Archaeorrhyncha(a) insect pests of the family Delphacidae, e.g., Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, and Sogatella furcifera.(B) the suborder Clypeorrhyncha(a) insect pests of the family Cicadellidae, e.g., Empoasca fabae, Empoasca nipponica, Empoasca onukii, and Empoasca sakaii of Empoasca spp.; and Arboridia apicalis, Balclutha saltuella, Epiacanthus stramineus, Macrosteles striifrons, and Nephotettix cinctinceps.(C) the suborder Heteroptera(a) insect pests of the family Alydidae, e.g., Riptortus clavatus;(b) insect pests of the family Coreidae, e.g., Cletus punctiger and Leptocorisa chinensis;(c) insect pests of the family Lygaeidae, e.g., Blissus leucopterus, Cavelerius saccharivorus, and Togo hemipterus;(d) insect pests of the family Miridae, e.g., Halticus insularis, Lygus lineolaris, Psuedatomoscelis seriatus, Stenodema sibiricum, Stenotus rubrovittatus, and Trigonotylus caelestialium;(e) insect pests of the family Pentatomidae, e.g., Nezara antennata and Nezara viridula from Nezara spp.; for example, Eysarcoris aeneus, Eysarcoris lewisi, and Eysarcoris ventralis of Eysarcoris spp.; and Dolycoris baccarum, Eurydema rugosum, Glaucias subpunctatus, Halyomorpha halys, Piezodorus hybneri, Plautia crossota, and Scotinophora lurida;(f) insect pests of the family Pyrrhocoridae, e.g., Dysdercus cingulatus;(g) insect pests of the family Rhopalidae, e.g., Rhopalus msculatus;(h) insect pests of the family Scutelleridae, e.g., Eurygaster integriceps;(i) insect pests of the family Tingidae, e.g., Stephanitis nashi.(D) the suborder Sternorrhyncha(a) insect pests of the family Adelgidae, e.g., Adelges laricis;(b) insect pests of the family Aleyrodidae, e.g., Bemisia argentifolii and Bemisia tabaci of Bemisia spp.; and Aleurocanthus spiniferus, Dialeurodes citri, and Trialeurodes vaporariorum; (c) insect pests of the family Aphididae, e.g., Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis pomi, Aphis sambuci, and Aphis spiraecola of Aphis spp.; for example, Rhopalosiphum maidis and Rhopalosiphum padi of Rhopalosiphum spp.; for example, Dysaphis plantaginea and Dysaphis radicola from Dysaphis spp.; for example, Macrosiphum avenae and Macrosiphum euphorbiae from Macrosiphum spp.; for example, Myzus cerasi, Myzus persicae, and Myzus varians of Myzus spp.; and Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, Chaetosiphon fragaefolii, Hyalopterus pruni, Hyperomyzus lactucae, Lipaphis erysimi, Megoura viciae, Metopolophium dirhodum, Nasonovia ribis-nigri, Phorodon humuli, Schizaphis graminum, Sitobion avenae, and Toxoptera aurantii;(d) insect pests of the family Coccidae, for example, Ceroplastes ceriferus and Ceroplastes rubens of Ceroplastes spp.;(e) insect pests of the family Diaspididae, Pseudaulacaspis pentagona and Pseudaulacaspis prunicola of Pseudaulacaspis spp.; for example, Unaspis euonymi and Unaspis yanonensis from Unaspis spp.; and Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, and Pseudaonidia paeoniae;(f) insect pests of the family Margarodidae, for example, Drosicha corpulenta and Icerya purchasi;(g) insect pests of the family Phylloxeridae, for example, Viteus vitifolii;(h) insect pests of the family Pseudococcidae, for example, Planococcus citri and Planococcus kuraunhiae from Planococcus spp.; and Phenacoccus solani and Pseudococcus comstocki;(i) insect pests of the family Psyllidae, for example, Psylla mali and Psylla pyrisuga from Psylla spp.; and Diaphorina citri.(4) Insect pests of the suborder Polyphaga(a) insect pests of the family Anobiidae, e.g., Lasioderma serricorne;(b) insect pests of the family Attelabidae, e.g., Byctiscus betulae and Rhynchites heros;(c) insect pests of the family Bostrichidae, e.g., Lyctus brunneus;(d) insect pests of the family Brentidae, e.g., Cylas formicarius;(e) insect pests of the family Buprestidae, e.g., Agrilus sinuatus;(f) insect pests of the family Cerambycidae, e.g., Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, and Xylotrechus pyrrhoderus;(g) insect pests of the family Chrysomelidae, e.g., Bruchus pisorum and Bruchus rufimanus of Bruchus spp.; for example, Diabrotica barberi, Diabrotica undecimpunctata, and Diabrotica virgifera from Diabrotica spp.; for example, Phyllotreta nemorum and Phyllotreta striolata from Phyllotreta spp.; and Aulacophora femoralis, Callosobruchus chinensis, Cassida nebulosa, Chaetocnema concinna, Leptinotarsa decemlineata, Oulema oryzae, and Psylliodes angusticollis;(h) insect pests of the family Coccinellidae, e.g., Epilachna varivestis and Epilachna vigintioctopunctata of Epilachna spp.; of insects of the family Curculionidae, for example, Anthonomus grandis and Anthonomus pomorum of Anthonomus spp.; for example, Sitophilus granarius and Sitophilus zeamais of Sitophilus spp.; (k) insect pests of the family Nitidulidae, e.g., Epuraea domina;(l) insect pests of the family Scarabaeidae, e.g., Anomala cuprea and Anomala rufocuprea of Anomala spp.; and Cetonia aurata, Gametis jucunda, Heptophylla picea, Melolontha melolontha, and Popillia japonica;(m) insect pests of the family Scolytidae, e.g., Ips typographus;(n) insect pests of the family Staphylinidae, e.g., Paederus fuscipes; (o) insect pests of the family Tenebrionidae, e.g., Tenebrio molitor and Tribolium castaneum;(p) insect pests of the family Trogossitidae, e.g., Tenebroides mauritanicus.(5) Insect pests of the order Diptera(A) the suborder Brachycera(a) insect pests of the family Agromyzidae, e.g., Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, and Liriomyza trifolii of Liriomyza spp.; and Chromatomyia horticola and Agromyza oryzae;(b) insect pests of the family Anthomyiidae, e.g., Delia platura and Delia radicum of Delia spp.; and Pegomya cunicularia;(c) insect pests of the family Drosophilidae, e.g., Drosophila melanogaster and Drosophila suzukii of Drosophila spp.;(d) insect pests of the family Ephydridae, e.g., Hydrellia griseola;(e) insect pests of the family Psilidae, e.g., Psila rosae;(f) insect pests of the family Tephritidae, e.g., Bactrocera cucurbitae and Bactrocera dorsalis of Bactrocera spp.; e.g., Rhagoletis cerasi and Rhagoletis pomonella of Rhagoletis spp.; and Ceratitis capitata and Dacus oleae.(B) the suborder Nematocera(a) insect pests of the family Cecidomyiidae, e.g., Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor, and Sitodiplosis mosellana.(b) Insect pests of the order Orthoptera(a) insect pests of the family Acrididae, e.g., Schistocerca americana and Schistocerca gregaria of Schistocerca spp.; and Chortoicetes terminifera, Dociostaurus maroccanus, Locusta migratoria, Locustana pardalina, Nomadacris septemfasciata, and Oxya yezoensis;(b) insect pests of the family Gryllidae, e.g., Acheta domestica and Teleogryllus emma;(c) insect pests of the family Gryllotalpidae, e.g., Gryllotalpa orientalis;(d) insect pests of the family Tettigoniidae, e.g., Tachycines asynamorus.(7) Mites(A) Acaridida of the order Astigmata(a) mites of the family Acaridae, e.g., Rhizoglyphus echinopus and Rhizoglyphus robini of Rhizoglyphus spp.; for example, Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae, and Tyrophagus similis of Tyrophagus spp.; and Acarus siro, Aleuroglyphus ovatus, and Mycetoglyphus fungivorus;(B) Actinedida of the order Prostigmata(a) mites of the family Tetranychidae, e.g., Bryobia praetiosa and Bryobia rubrioculus of Bryobia spp.; for example, Eotetranychus asiaticus, Eotetranychus boreus, Eotetranychus celtis, Eotetranychus geniculatus, Eotetranychus kankitus, Eotetranychus pruni, Eotetranychus shii, Eotetranychus smithi, Eotetranychus suginamensis, and Eotetranychus uncatus of Eotetranychus spp.; for example, Oligonychus hondoensis, Oligonychus ilicis, Oligonychus karamatus, Oligonychus mangiferus, Oligonychus orthius, Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii, and Oligonychus ununguis of Oligonychus spp.; for example, Panonychus citri, Panonychus mori, and Panonychus ulmi of Panonychus spp.; for example, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus ludeni, Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Tetranychus viennensis, and Tetranychus evansi of Tetranychus spp.; for example, Aponychus corpuzae and Aponychus firmianae of Aponychus spp.; for example, Sasanychus akitanus and Sasanychus pusillus of Sasanychus spp.; for example, Schizotetranychus celarius, Schizotetranychus longus, Schizotetranychus miscanthi, Schizotetranychus recki, and Schizotetranychus schizopus of Schizotetranychus spp.; and Tetranychina harti, Tuckerella pavoniformis, and Yezonychus sapporensis; (b) mites of the family Tenuipalpidae, e.g., Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Brevipalpus russulus, and Brevipalpus californicus of Brevipalpus spp.; for example, Tenuipalpus pacificus and Tenuipalpus zhizhilashviliae from Tenuipalpus spp.; and Dolichotetranychus floridanus;(c) mites of the family Eriophyidae, for example, Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, Aceria paradianthi, Aceria tiyingi, Aceria tulipae, and Aceria zoysiea of Aceria spp.; for example, Eriophyes chibaensis and Eriophyes emarginatae of Eriophyes spp.; for example, Aculops lycopersici and Aculops pelekassi from Aculops spp.; for example, Aculus fockeui and Aculus schlechtendali from Aculus spp.; and Acaphylla theavagrans, Calacarus carinatus, Colomerus vitis, Calepitrimerus vitis, Epitrimerus pyri, Paraphytoptus kikus, Paracalacarus podocarpi, and Phyllocotruta citri; and Phytonemus pallidus and Polyphagotarsonemus latus;(e) mites of the family Penthaleidae, e.g. Penthaleus erythrocephalus and Penthaleus major of Penthaleus spp.

[Ectoparasite control agent]

[0085] The ectoparasite control agent of the present invention contains at least one active ingredient selected from the (hetero)arylimidazole compounds of the present invention. The amount of the (hetero)arylimidazole compound contained in the ectoparasite control agent of the present invention is not particularly limited as long as its ectoparasite control effect is exhibited.

[0086] As the host animal to be treated with the ectoparasite control agent of the present invention, there can be exemplified a warm-blooded animal such as a human and a farm animal (e.g., a cow, a horse, a pig, sheep, and a goat), a laboratory animal (e.g., a mouse, a rat, and a sand rat), a pet animal (e.g., a hamster, a guinea pig, a dog, a cat, a horse, a squirrel, and a ferret), wild and zoo animals (e.g., a monkey, a fox, a deer, and a buffalo), a bird (e.g., a turkey, a duck, a chicken, a quail, and a goose), and a pet bird (e.g., a pigeon, a parrot, a mynah bird, a Java sparrow, a parakeet, a Bengalese finch, and a canary bird); and fish such as salmon, trout, and carp. In addition, a bee, a lucanid beetle and a beetle can be exemplified.

[0087] The ectoparasite control agent of the present invention can be applied by a known veterinary approach (local, oral, parenteral or subcutaneous administration). As the method for the same, a method of orally administering to animals tablets, capsules, food or the like containing the ectoparasite control agent can be exemplified; a method of administering to animals the ectoparasite control agent by dipping liquids, suppositories, injection (intramuscular, subcutaneous, intravenous, or intraperitoneal injection, etc.) or the like; a method of locally administering oily or aqueous liquid formulations by spraying, pour-on, spot-on or the like can be exemplified; and a method of kneading the ectoparasite control agent into a resin, shaping the kneaded product into a suitable shape such as a collar or an ear tag, and attaching the same to animals for local administration; or similar.

[0088] Ectoparasites parasitize in or on the body surface of host animals, particularly warm-blooded animals. Specifically, ectoparasites parasitize the backs, armpits, lower abdomens, groins, or the like of host animals and live by obtaining nutrients such as blood or dander from the animals. Examples of ectoparasites include mites, lice, fleas, a mosquito, a stable fly, a flesh fly, or the like. Specific examples of the ectoparasite controllable with the ectoparasite control agent of the present invention will be shown below.(1) MitesMites of the family Dermanyssidae, mites of the family Macronyssidae, mites of the family Laelapidae, mites of the family Varroidae, mites of the family Argasidae, mites of the family Ixodidae, mites of the family Psoroptidae, mites of the family Sarcoptidae, mites of the family Knemidokoptidae, mites of the family Demodixidae, mites of the family Trombiculidae, and insect parasitic mites such as mites of the family Canestriniidae.(2) The order Phthirapteralices of the family Haematopinidae, lice of the family Linognathidae, bird lice of the family Menoponidae, bird lice of the family Philopteridae, and bird lice of the family Trichodectidae.(3) The order SiphonapteraFleas of the family Pulicidae, e.g., Ctenocephalides canis and Ctenocephalides felis of Ctenocephalides spp.; fleas of the family Tungidae, fleas of the family Ceratophyllidae, and fleas of the family Leptopsyllidae.(4) The order Hemiptera(5) Insect pests of the order DipteraMosquitoes of the family Culicidae, black flies of the family Simuliidae, biting midges of the family Ceratopogonidae, horse flies of the family Tabanidae, flies of the family Muscidae, tsetse flies of the family Glossinidae, flesh flies of the family Sarcophagidae, flies of the family Hippoboscidae, flies of the family Calliforidae, and flies of the family Oestridae.

[Endoparasite expelling or endoparasite control agent]

[0089] The endoparasite-expelling or endoparasite-controlling agent of the present invention contains at least one active ingredient selected from the (hetero)arylimidazole compounds of the present invention. The amount of the (hetero)arylimidazole compound contained in the endoparasite-expelling or endoparasite-controlling agent of the present invention is not particularly limited as long as its endoparasite-controlling effect is exhibited.

[0090] The parasite selected by the endoparasite-expelling or endoparasite-control agent of the present invention parasitizes the interior of host animals, warm-blooded animals or fish (endoparasite). As the animal for which the endoparasite-expelling or endoparasite-controlling agent of the present invention is effective, there can be exemplified a warm-blooded animal such as a human and a farm animal (e.g., a cow, a horse, a pig, sheep, and a goat), a laboratory animal (e.g., a mouse, a rat, and a sand rat), a pet animal (e.g., a hamster, a guinea pig, a dog, a cat, a horse, a squirrel, and a ferret), wild and zoo animals (e.g., a monkey, a fox, a deer, and a buffalo), a bird (e.g., a turkey, a duck, a chicken, a quail, and a goose), and a pet bird (e.g., a pigeon, a parrot, a mynah bird, a Java sparrow, a parakeet, a Bengalese finch, and a canary bird); and fish such as salmon, trout, and carp. Parasitic diseases mediated by parasites can be prevented or treated by controlling and expelling the parasites.

[0091] As the parasite to be controlled or expelled, the following can be exemplified.(1) Nematodes of the order Dioctophymatida(a) kidney flukes of the family Dioctophymatidae, for example, Dioctophyma renale from Dioctophyma spp.;(b) kidney flukes of the family Soboliphymatidae, for example, Soboliphyme abei and Soboliphyme baturini from Soboliphyme spp.(2) Nematodes of the order Trichocephalida(a) trichina worms of the family Trichinellidae, for example, Trichinella spiralis from Trichinella spp.;(b) intestinal nematode worms of the family Trichuridae, for example, Capillaria annulata, Capillaria contorta, Capillaria hepatica, Capillaria perforans, Capillaria plica, and Capillaria suis from Capillaria spp.; and Trichuris vulpis, Trichuris discolor, Trichuris ovis, Trichuris skrjabini, and Trichuris suis from Trichuris spp.(3) Nematodes of the order Rhabditidathreadlike nematode worms of the family Strongyloididae, e.g., Strongyloides papillosus, Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, and Strongyloides ratti from Strongyloides spp.(4) Nematodes of the order Strongylidahookworms of the family Ancylostomatidae, e.g., Ancylostoma braziliense, Ancylostoma caninum, Ancylostoma duodenale, and Ancylostoma tubaeforme from Ancylostoma spp.; Uncinaria stenocephala from Uncinaria spp.; and Bunostomum phlebotomum and Bunostomum trigonocephalum from Bunostomum spp.(5) Nematodes of the order Strongylida(a) nematodes of the family Angiostrongylidae, for example, Aelurostrongylus abstrusus from Aelurostrongylus spp.; and Angiostrongylus vasorum and Angiostrongylus cantonesis from Angiostrongylus spp.;(b) nematodes of the family Crenosomatidae, e.g., Crenosoma aerophila and Crenosoma vulpis from Crenosoma spp.;(c) nematodes of the family Filaroididae, e.g., Filaroides hirthi and Filaroides osleri from Filaroides spp.;(d) lungworms of the family Metastrongylidae, e.g., Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus pudendotectus, and Metastrongylus salmi from Metastrongylus spp.;(e) tracheal flukes of the family Syngamidae, e.g., Cyathostoma bronchialis from Cyathostoma spp.; and Syngamus skrjabinomorpha and Syngamus trachea from Syngamus spp.(6) Nematodes of the order Strongylida(a) nematodes of the family Molineidae, e.g., Nematodirus filicollis and Nematodirus spathiger from Nematodirus spp.;(b) nematodes of the family Dictyocaulidae, e.g., Dictyocaulus filaria and Dictyocaulus viviparus from Dictyocaulus spp.;(c) nematodes of the family Haemonchidae, e.g., Haemonchus contortus from Haemonchus spp.; and Mecistocirrus digitatus from Mecistocirrus spp.;(d) nematodes of the family Haemonchidae, e.g., Ostertagia ostertagi from Ostertagia spp.;(e) nematodes of the family Heligmonellidae, e.g., Nippostrongylus braziliensis from Nippostrongylus spp.; (f) nematodes of the family Trichostrongylidae, e.g., Trichostrongylus axei, Trichostrongylus colubriformis, and Trichostrongylus tenuis from Trichostrongylus spp.; Hyostrongylus rubidus from Hyostrongylus spp.; and Obeliscoides cuniculi from Obeliscoides spp.(7) Nematodes of the order Strongylida(a) nematodes of the family Chabertiidae, e.g., Chabertia spp.; and Oesophagostomum brevicaudatum, columbianum, Oesophagostomum dentatum,georgianum, Oesophagostomum maplestonei,quadrispinulatum, Oesophagostomum radiatum,venulosum, and Oesophagostomum watanabei deOesophagostomum spp.;(b) nematodes of the family Stephanuridae, e.g., Stephanurus dentatus of Stephanurus spp.;(c) nematodes of the family Strongylidae, e.g., Strongylus asini, Strongylus edentatus, Strongylus equinus, and Strongylus vulgaris of Strongylus spp.(8) Nematodes of the order Oxiuridanematodes of the family Oxiuridae, e.g., Enterobius anthropopitheci and Enterobius vermicularis of Enterobius spp.; Oxiuris equi from Oxiuris spp.; and Passalurus ambiguous from Passalurus spp.(9) Nematodes of the order Ascaridida(a) nematodes of the family Ascaridiidae, e.g., Ascaridia galli from Ascaridia spp.;(b) nematodes of the family Heterakidae, e.g., Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum, Heterakis pusilla, and Heterakis putaustralis from Heterakis spp.;(c) nematodes of the family Anisakidae, e.g., Anisakis simplex from Anisakis spp.;(d) nematodes of the family Ascarididae, e.g., Ascaris lumbricoides and Ascaris suum from Ascaris spp.; and Parascaris equorum of Parascaris spp.;(e) nematodes of the family Toxocaridae, e.g., Toxocara canis, Toxocara leonina, Toxocara suum, Toxocara vitulorum, and Toxocara cati of Toxocara spp.(10) Nematodes of the order Spirurida(a) nematodes of the family Onchocercidae, e.g., Brugia malayi, Brugia pahangi, and Brugia patei from Brugia spp.; Dipetalonema reconditum from Dipetalonema spp.; Dirofilaria immitis from Dirofilaria spp.; Filaria oculi from Filaria spp.; and Onchocerca cervicalis, Onchocerca gibsoni, and Onchocerca gutturosa from Onchocerca spp.;(b) nematodes of the family Setariidae, e.g., Setaria digitata, Setaria equina, Setaria labiatopapillosa, and Setaria marshalli from Setaria spp.; and Wuchereria bancrofti from Wuchereria spp.;(c) nematodes of the family Filariidae, e.g., Parafilaria multipapillosa from Parafilaria spp.; and Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, and Stephanofilaria stilesi from Stephanofilaria spp.(11) Nematodes of the order Spirurida(a) nematodes of the family Gnathostomatidae, e.g., Gnathostoma doloresi and Gnathostoma spinigerum from Gnathostoma spp.;(b) nematodes of the family Habronematidae, e.g., Habronema majus, Habronema microstoma, and Habronema muscae from Habronema spp.; and Draschia megastoma from Draschia spp.;(c) nematodes of the family Physalopteridae, e.g. Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaloptera ramo, Physaloptera sibirica, and Physaloptera vulpineus of Physaloptera spp.;(d) nematodes of the family Gongylonematidae, e.g., Gongylonema pulchrum of Gongylonema spp.;(e) nematodes of the family Spirocercidae, e.g., Ascarops strongylina of Ascarops spp.;(f) nematodes of the family Thelaziidae, for example, Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Thelazia rhodesi, and Thelazia skrjabini of Thelazia spp.

[Other pest control agent]

[0092] The (hetero)arylimidazole compound of the present invention is additionally excellent in controlling effect on insect pests that have a sting or venom and harm humans and animals, insect pests that mediate pathogens or disease-causing microbes, or insect pests that cause discomfort to humans (toxic pests, hygienic pests, obnoxious pests, etc.).

[0093] Specific examples thereof will be shown below.(1) Insect pests of the order Hymenoptera: bees of the family Argidae, bees of the family Cynipidae, bees of the family Diprionidae, ants of the family Formicidae, bees of the family Mutillidae, and bees of the family Vespidae.(2) Other insect pests: Blattodea, termites, Araneae, centipedes, millipedes, crustaceans, and Cimex lectularius.

[Seed treatment agent or a treatment agent for vegetative propagation organs]

[0094] The seed treatment agent or a vegetative propagation organ treatment agent of the present invention contains at least one active ingredient selected from the (hetero)arylimidazole compounds of the present invention. The amount of the (hetero)arylimidazole compound contained in the seed treatment agent or a vegetative propagation organ treatment agent of the present invention is not particularly limited as long as its control effect is exhibited.

[0095] The vegetative propagation organ means a plant root, a plant stem, a plant leaf, or the like which has the capacity to grow when the site is separated from the body and placed into the soil. As the vegetative propagation organ, for example, there are exemplified a tuberous root, a creeping root, a bulb, a corm or solid bulb, a tuber, a rhizome, a stolon, a rhizophore, a cane seedling, a propagule and a climbing plant. The stolon is also called a climbing plant. The propagule is also called a small or secondary bulb and is classified into a broad shoot and a bulblet. The climbing plant means a shoot (generic name for leaves and stems) of sweet potato, Japanese yam, or the like. The bulb, corm or solid bulb, tuber, rhizome, cane seedling, rhizophore and tuberous root are also collectively called flower bulb. Cultivation of tubers and roots is started by planting the tubers in the soil. The tubers used are generally called seed tubers.

[0096] The seed treatment agent or a vegetative propagation organ treatment agent of the present invention refers to a preparation such as a wettable powder, wettable granules, a flowable concentrate, or a dust formulated by mixing at least one active ingredient selected from the (hetero)arylimidazole compounds of the present invention with a suitable solid carrier or liquid carrier, and, if necessary, adding a surfactant or other formulation adjuvants to the mixture. Also, the composition may contain a binder. As the composition containing a binder, a flowable concentrate (FS) for seed treatment is exemplified.

[0097] An adhesive substance that does not phytotoxically affect plant seeds or vegetative propagating organs is used as the binder. Specifically, at least one substance selected from the group consisting of polyvinyl acetate, polyvinyl alcohol, cellulose including ethyl cellulose, methyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, and carboxymethyl cellulose, polyvinylpyrrolidone, starch, modified starch, dextrin, maltodextrin, polysaccharides including alginate and chitosan, proteins including gelatin and casein, gum arabic, shellac, calcium lignosulfonate, and a methacrylamide monomer may be used.

[0098] Pests can be effectively controlled by treating seed tubers with at least one compound selected from the (hetero)arylimidazole compounds of the present invention. As the method of treating a seed tuber with the (hetero)arylimidazole compound, dipping treatment, dust coating treatment, coating treatment or the like are exemplified. For planting seed tubers using a tractor, the seed tubers can be sprayed with a chemical containing the (hetero)arylimidazole compound onto the seed tubers on the tractor.

[Granular agrochemical composition for treatment of paddy rice seedling nursery boxes]

[0099] The granular agrochemical composition for treating seedling nursery boxes of paddy rice (hereinafter, referred to as the “granular agrochemical composition”) of the present invention contains at least one active ingredient selected from the (hetero)arylimidazole compounds of the present invention. The amount of the (hetero)arylimidazole compound contained in the granular agrochemical composition of the present invention is not particularly limited as long as its control effect is exhibited.

[00100] The granular agrochemical composition can be obtained by various methods, but is obtained, for example, by extrusion granulation or the like of a powder composition combined with one or more active ingredients with a surfactant, a binder and an inorganic carrier, etc., if necessary, by using a wet granulation method. More specifically, the active ingredient adjusted to a predetermined particle size is uniformly mixed with a required surfactant, a binder and an inorganic carrier. Then, an appropriate amount of water is added to the mixture, and the mixture is kneaded, extruded through a screen having open pores, and dried to prepare a granular agrochemical composition. The pore size in this operation is usually preferably 0.5 mm to 1.5 mm.

[00101] The particle size of the granular agrochemical composition thus obtained is not particularly limited, but is preferably from 0.5 mm to 1.5 mm, and particularly preferably from 0.7 mm to 1.5 mm, in terms of average particle size. Granules having such a particle size are obtained by granulation, drying and subsequent sieving.

[00102] In the granular agrochemical composition, if necessary, a surfactant, a binder and an inorganic carrier are combined. Among them, as the surfactant, for example, a nonionic surfactant such as poly(ethylene glycol) ester of higher fatty acid, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene aryl phenyl ether, and sorbitan monoalkylate is exemplified; an anionic surfactant such as alkyl arylsulfonate, dialkylsulfonate, sulfuric acid alkyl ester salt, phosphoric acid alkyl ester salt, sulfuric acid aryl alkyl ester salt, phosphoric acid aryl alkyl ester salt, polyoxyethylene alkyl ether ester salt of sulfuric acid, naphthalenesulfonic acid salt and a condensate thereof, ligninsulfonic acid salt, poly(carboxylic acid) type polymeric surfactant such as a copolymer of acrylic acid and itaconic acid or a copolymer of methacrylic acid and itaconic acid, a copolymer of maleic acid and styrene, a copolymer of maleic acid and diisobutylene and alkali metal salts thereof; polyoxyethylene phenyl aryl ether ester salt of phosphoric acid; polyoxyethylene aryl phenyl ether ester salt of sulfuric acid, or the like. The amount of this surfactant added is usually 0.1 part by weight to 5 parts by weight, although the amount is not particularly limited.

[00103] As the binder to be combined in the granular agrochemical composition, exemplified are, for example, carboxymethyl cellulose metal salt, poly(vinyl alcohol), pregelatinized starch, dextrin, xanthan gum, guar seed gum, sucrose, polyvinylpyrrolidone, poly(acrylic acid) metal salt or the like. The amount of the binder is usually 0.1 part by weight to 5 parts by weight, although the amount is not particularly limited. The inorganic carrier to be combined in the granules is not particularly limited. Exemplified are, for example, clays, calcium carbonate, talc, diatomaceous earth, zeolite, attapulgite, gypsum, porcelain stone or the like.

[Soil treatment agent]

[00104] Soil treatment according to the present invention is, for example, a method of directly controlling pests by applying an active ingredient to the rhizospheres of plants to be protected against damage such as pest devouring, or controlling pests by penetrating and transporting an active ingredient into the bodies of plants from their roots or the like. Specifically, for example, planting hole treatment (planting hole spraying and soil incorporation into planting hole), plant foot treatment (plant foot spraying, soil incorporation into plant foot, plant foot irrigation, and plant foot treatment in the later half of the seedling growth period), planting furrow treatment (planting furrow spraying and soil incorporation into planting furrow), planting row treatment (planting row spraying, soil incorporation into planting row, and planting row spraying in the growth period), planting row treatment at sowing (planting row spraying at sowing and soil incorporation into planting row at sowing), large planting area treatment (large planting area soil spraying and large planting area soil incorporation), strip application, submerged treatment (submerged application in large planting area and submerged application in planting frame), other treatments of soil spraying (foliar spraying of granules in the growing period, spraying under the upper branches and leaves of trees or around the main stems, soil surface spraying, soil surface incorporation, seeding hole spraying, surface spraying over reinforced soil, and inter-plant spraying), other irrigation treatments (soil irrigation, seedling growth period irrigation, chemical injection treatment, irrigation over the base of the plant, chemical drip irrigation, and chemirrigation), seedling nursery box treatment (seedling nursery box spraying, seedling nursery box irrigation, and seedling nursery box flooding with chemicals), seedling nursery tray treatment (seedling nursery tray spraying, seedling nursery tray irrigation, and chemical irrigation), seedling, and spraying of flooded seedling nursery tray), nursery bed treatment (nursery bed spraying, nursery bed irrigation, spraying of flooded nursery bed), seedling dipping, nursery soil incorporation treatment (soil incorporation in seedbed and top dressing soil incorporation), spraying before top dressing at sowing, spraying after top dressing at sowing, stem injection treatment, trunk injection treatment, trunk spray treatment, and other treatments (plowing, topsoil incorporation, soil incorporation in drip lines, planting point treatment, spraying of granules on flower racemes, and mixing of fertilizers in the form of paste).

[Bait Agent]

[00105] The bait agent of the present invention contains at least one active ingredient selected from the (hetero)arylimidazole compounds of the present invention. The amount of the (hetero)arylimidazole compound contained in the bait agent of the present invention is not particularly limited as long as its controlling effect is exhibited.

[00106] The bait agent of the present invention may contain, if necessary, an ingestibility-enhancing component such as a sugar, a carbohydrate, or a milk constituent, a synergist, an aversive agent to prevent accidental ingestion, a preservative, a flavoring, an attractant, or the like. The bait agent of the present invention may typically be prepared by mixing the (hetero)arylimidazole compound with water and, if necessary, other components described above. In preparing the bait agent of the present invention, the (hetero)arylimidazole compound may be the (hetero)arylimidazole compound itself, or may be in the form of a formulation such as a dust, a wettable powder, a microcapsule, or a flowable concentrate.

[00107] As the pest to be effectively controlled with the baiting agent of the present invention, exemplified are a cockroach such as Periplaneta americana, Blattella germanica, and Periplaneta fuliginosa, a click beetle such as Melanotus okinawensis, an ant such as Monomorium intrudens and Formica fusca, a death-watch beetle such as Lasioderma serricorne and Stegobium paniceum, a flour beetle such as Tribolium castaneum and Tribolium confusum, a flat bark beetle such as Oryzaephilus surinamensis and Cryptolestes pusillus, a white ant such as Coptotermes formosanus and Reticulitermes speratus, a fly such as Musca domestica, Fannia canicularis, Foridae, and Phlebotominae, and a mosquito such as Culex pipiens, Aedes albopictus, anopheles (Anopheles), and chironomids.

[00108] The baiting agent of the present invention may be applied as it is, or for example by impregnating a non-woven fabric, a sponge, an absorbent cotton, or the like, for example. This aqueous baiting agent or the non-woven fabric, the sponge, the absorbent cotton or the like impregnated with the baiting agent is positioned within a container such as a cup, a tray, or a bottle, for example, and subjected to expelling insect pests. In this regard, the apparatus for expelling insect pests that is equipped with the container covered on the outside and has some degree of space where insect pests are able to reside for the purpose of ingesting the baiting agent of the present invention generally improves ingestibility and is thus effective.

[Plant growth promoter]

[00109] The plant growth promoter of the present invention contains at least one active ingredient selected from the (hetero)arylimidazole compounds of the present invention. The amount of the (hetero)arylimidazole compound contained in the plant growth promoter of the present invention is not particularly limited as long as its effect of promoting plant growth is exhibited.

[00110] In the plant growth promoter of the present invention, if necessary, other components, a carrier, or the like may be appropriately combined.

[00111] The (hetero)arylimidazole compound of the present invention can be used alone as a plant growth promoter, but can be commonly used as a formulation in a dosage form such as a wettable powder, a liquid formulation, an oily formulation, a dust, a granular formulation, or a suspension (flowable) concentration by mixing the (hetero)arylimidazole compound as an active ingredient with common adjuvants for use in formulation, such as a solid carrier, a liquid carrier, a dispersant, a diluent, an emulsifier, a spreading agent, and a thickener.

[00112] As the solid carrier or the liquid carrier is exemplified, for example, talc, clay, bentonite, kaolin, diatomaceous earth, montmorillonite, mica, vermiculite, gypsum, calcium carbonate, white carbon, wood flour, starch, alumina, silicate, glycopolymer, waxes, water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, ethylenic glycol, benzyl alcohol, etc.), a petroleum fraction (petroleum ether, kerosene, solvent naphtha, etc.), aliphatic or alicyclic hydrocarbons (n-hexane, cyclohexane, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, chlorobenzene, cumene, methylnaphthalene, etc.), halogenated hydrocarbons (chloroform, dichloromethane, etc.), ethers (isopropyl ether, ethylene oxide, tetrahydrofuran, etc.), ketones (acetone, ethyl methyl ketone, cyclohexanone, isobutyl methyl ketone, etc.), esters (ethyl acetate, butyl acetate, ethylene glycol acetate, amyl acetate, etc.), acid amides (dimethylformamide, dimethylacetanilide, etc.), nitriles (acetonitrile, propionitrile, acrylonitrile, etc.), sulfoxides (dimethyl sulfoxide, etc.), alcohol esters (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, etc.) or the like.

[00113] As the adjuvant, for example, a nonionic surfactant (polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene sorbitan alkyl ester, sorbitan alkyl ester, etc.), an anionic surfactant (alkylbenzenesulfonate, alkylsulfosuccinate, polyoxyethylene alkylsulfate, arylsulfonate, etc.), a cationic surfactant (alkylamines, polyoxyethylene alkylamines, quaternary ammonium salts, etc.), an amphoteric surfactant (alkylaminoethylglycine, alkyldimethylbetaine, etc.), poly(vinyl alcohol), hydroxypropyl cellulose, carboxymethyl cellulose, gum arabic, gum tragacanth, xanthan gum, poly(vinyl acetate), gelatin, casein, sodium alginate or the like are exemplified.

[00114] As other components, other active ingredients such as the fungicide, insecticide or acaricide, nematicide, and pesticide for soil insect pests described above; a plant regulating agent, a synergist, a fertilizer, a soil improving agent, animal feed or the like are exemplified.

[00115] The content of the (hetero)arylimidazole compound of the present invention in the plant growth promoter differs variously depending on a preparation form, an application method, and other conditions, but is preferably from 0.5 to 95% by weight, and particularly preferably is in the range of from 2 to 70% by weight.

[00116] The plant to which the plant growth promoter is to be applied is not particularly limited. For example, cereals of the Poaceae family such as rice, barley, wheat, Japanese millet, corn, and foxtail millet; vegetables such as pumpkin, turnip, cabbage, daikon radish, Chinese cabbage, spinach, bell pepper, and tomato; flowers and ornamentals such as chrysanthemum, gerbera, pansy violet, orchid, peony, and tulip; beans such as azuki bean, common bean, soybean, peanut, lima bean, and garden pea; tubers and roots such as potato, sweet potato, eddo yam, Japanese yam, and taro; Allium such as green onion, onion, and rakkyo chive, or the like.

[00117] As an application method, the plant growth promoter of the present invention can be applied to plants (foliage application), applied to plant growth soil (soil application), applied to rice field water (submerged application), applied to seed (seed treatment), or the like.

[00118] The applied amount of the plant growth promoter of the present invention differs depending on the plant to which the plant growth promoter is applied, etc., but is in the range of 1 to 10,000 ppm in terms of active ingredient concentration and preferably 50 to 300 L/10 ares (1,000 m2) of a solution containing 10 to 1,000 ppm of the active ingredient, for foliar application, is preferably 0.1 to 1,000 g/10 ares (1,000 m2) and particularly preferably 10 to 100 g/10 ares (1,000 m2), of the active ingredient for soil application and submerged application. Also, 0.001 to 50 g of the active ingredient is preferably applied per kg of seeds for seed treatment.

[Preparation of formulations]

[00119] Some formulation preparations of the pest control agent, insecticide or acaricide, ectoparasite control agent or endoparasite expelling or endoparasite control agent of the present invention will be shown. However, additives and addition ratios should not be limited by these examples and can be varied within wide ranges. The term "part" in the formulation preparations represents part by weight.

[00120] Hereinafter, formulation preparations for agriculture and horticulture and for paddy rice will be shown.

(Formulation 1: Wettable powder)

[00121] 40 parts of the (hetero)arylimidazole compound of the present invention, 53 parts of diatomaceous earth, 4 parts of sulfuric acid ester of higher alcohol, and 3 parts of alkylnaphthalenesulfonate are uniformly mixed and finely ground to obtain a wettable powder containing 40% of the active ingredient.

(Formulation 2: Emulsion)

[00122] 30 parts of the (hetero)arylimidazole compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene allyl alkyl ether are mixed and dissolved to obtain an emulsion containing 30% of the active ingredient.

(Formulation 3: Granular formulation)

[00123] 5 parts of the (hetero)arylimidazole compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed, finely ground, and then granulated into a 0.5 to 1.0 diameter granular form to obtain a granular formulation containing 5% of the active ingredient.

(Formulation 4: Granular formulation)

[00124] 5 parts of the (hetero)arylimidazole compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctylsulfosuccinate sodium salt, and 1 part of potassium phosphate are well ground and mixed, and after adding water, the mixture is well kneaded, then granulated, and dried to obtain a granular formulation containing 5% of the active ingredient.

(Formulation 5: Suspension)

[00125] 10 parts of the (hetero)arylimidazole compound of the present invention, 4 parts of polyoxyethylene allylic and alkyl ether, 2 parts of poly(carboxylic acid) sodium salt, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet milled until the particle size becomes 3 microns or smaller to obtain a suspension containing 10% of the active ingredient.

[00126] Hereinafter, preparations of the formulation of the ectoparasite control agent or the endoparasite expelling agent or endoparasite control agent will be shown.

(Formulation 6: Granules)

[00127] 5 parts of the (hetero)arylimidazole compound of the present invention are dissolved in an organic solvent to obtain a solution. The solution is sprayed onto 94 parts of kaolin and 1 part of white carbon. Then, the solvent is evaporated under reduced pressure. This kind of granules can be mixed with animal feed.

(Formulation 7: Injectable filler)

[00128] 0.1 to 1 part of the (hetero)arylimidazole compound of the present invention and 99 to 99.9 parts of peanut oil are uniformly mixed, then sterilized by filtration through a sterilizing filter. (Formulation 8: Pore-on formulation)

[00129] 5 parts of the (hetero)arylimidazole compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol are uniformly mixed to obtain a pore-on formulation. [0180]

(Formulation 9: Spot-on formulation)

[00130] 10 to 15 parts of the (hetero)arylimidazole compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol are uniformly mixed to obtain a spot-on formulation.

(Formulation 10: Spray formulation)

[00131] 1 part of the (hetero)arylimidazole compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol are uniformly mixed to obtain a spray formulation.

[00132] In the following, the present invention will be more specifically described with reference to the Examples of compounds. However, the present invention is not limited in any way to the following Examples of compounds. [Example 1] Synthesis of 2-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-5-cydopropyl-3-(ethylsulfonyl)pyridine (Compound No. d-2) (Step 1) Synthesis of 5-bromo-3-(ethylthio)picolinonitrile

[00133] In a reaction vessel, 5-bromo-3-nitropicolinonitrile (1 g) was dissolved in tetrahydrofuran (22 mL), and the space above the solution in the reaction vessel was filled with nitrogen. Then, the solution was cooled to -5 °C and stirred. About 60% sodium hydride (0.2 g) was added to the solution, and the mixture was stirred at 5 °C for 5 minutes. Then, ethyl mercaptan (0.27 g) was added dropwise to the mixture, and the mixture was stirred at 5 °C for 30 minutes. The obtained solution was poured into water, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 0.90 g of the title compound (yield: 84%).

[00134] 1H-NMR of the title compound will be shown below. 1H-NMR (CDCl3) δ: 8.50 (1H, d), 7.83 (1H, d), 3.07 (2H, q), 1.41 (3H, t). (Step 2) Synthesis of 5-bromo-3-(ethylsulfonyl)picolinonitrile

[00135] 5-Bromo-3-(ethylthio)picolinonitrile (149 g) was dissolved in dichloromethane (1800 mL), and the solution was cooled to 0 °C and stirred. 70% m-Chloroperbenzoic acid (333 g) was added to the solution, and the mixture was stirred overnight at room temperature. The obtained solution was poured into a mixed solution of a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution, and extracted with dichloromethane. The obtained organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 167 g of the title compound (yield: 99%).

[00136] 1H-NMR of the title compound will be shown below. 1H-NMR (CDCl3) δ: 9.26 (1H, d), 8.72 (1H, d), 3.60 (2H, q), 1.23 (3H, t). (Step 3) Synthesis of 2-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-1-methyl-1H-imidazole-5-carbaldehyde

[00137] 5-Bromo-3-(ethylsulfonyl)picolinonitrile (20 g) was dissolved in methanol (220 mL). To the solution, a solution of about 5 M sodium methoxide in methanol (1.5 mL) was added dropwise, and the mixture was stirred overnight at room temperature. Ethylamine hydrochloride (4.9 g) was added to the solution, and the mixture was heated and stirred for 2 hours under reflux. Triethylamine (30 mL) was added to the solution to obtain solution A.

[00138] Apart from this, 5-bromomalonaldehyde (16.5 g) and isopropanol (220 mL) were mixed and stirred at 50°C for 1 hour to obtain solution B.

[00139] Solution B was added dropwise to solution A, and the mixture was heated and stirred for 4 hours under reflux. The obtained solution was concentrated under reduced pressure. The obtained residue was added to water, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 12 g of the title compound (yield: 46%).

[00140] 1H-NMR of the title compound will be shown below. 1H-NMR (CDCl3) δ: 9.86 (1H, s), 9.00 (1H, d), 8.62 (1H, d), 7.83 (1H, s), 3.89 (3H, s), 3.79 (2H, q), 1.36 (3H, t). (Step 4) Synthesis of 2-(5-cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-1-methyl-1H-imidazole-5-carbaldehyde

[00141] In a reaction vessel, 2-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-1-methyl-1H-imidazole-5-carbaldehyde (0.35 g) was dissolved in xylene (4.3 mL), and the space above the solution in the reaction vessel was filled with argon. Then, the solution was stirred at room temperature. Potassium cyclopropyltrifluoroborate (0.36 g), palladium(II) acetate (0.043 g), a 20% tricyclohexylphosphine solution in toluene (0.54 g), tripotassium phosphate (0.82 g), and water (0.48 mL) were added to the solution, and the mixture was stirred at 110 °C for 7 h. The obtained solution was poured into water, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 0.27 g of the title compound (yield: 88%).

[00142] 1H NMR of the title compound will be shown below. 1H-NMR (CDCl3) δ: 9.84 (1H, s), 8.70 (1H, d), 8.02 (1H, d), 7.82 (1H, s), 3.84 (3H, s), 3.70 (2H, q), 2.12-2.06 (1H, m), 1.31 (3H, t), 1.28-1.23 (2H, m), 0.95-0.91 (2H, m).(Step 5) Synthesis of 2-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-5-cyclopropyl-3-(ethylsulfonyl)pyridine

[00143] In a reaction vessel, 2-(5-cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-1-methyl-1H-imidazole-5-carbaldehyde (0.3 g) was dissolved in N,N-dimethylformamide (13 mL), and the solution was stirred at room temperature. 1,1,1-Trichloro-2,2,2-trifluoroethane (0.35 g), zinc powder (0.31 g), acetic anhydride (0.14 g), and copper chloride (4.7 mg) were added to the solution, and the void space above the solution in the reaction vessel was filled with argon, followed by stirring overnight at 60 °C. The obtained solution was poured into a 10% Rochelle salt aqueous solution, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 0.23 g of the title compound (E/Z = 17:83, yield: 59%).

[00144] 1H-NMR and 19F-NMR of the title compound will be shown below. 1H-NMR (400 MHz, CDCl3) (a mixture of E/Z isomers) δ: 8.68 (1H, d), 8.04 (1H, s), 8.02 (1H, d), 7.15 (1H, s), 3.74 (2H, q), 3.57 (3H, s), 2.12-2.06 (1H, m), 1.31 (3H, t), 1.28-1.20 (2H, m), 0.94-0.89 (2H, m); 19F-NMR (376 MHz, CDCl3-C6F6): δ -63.5(d) for the (E)-isomer and -68.4(s) for the (Z)-isomer. imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3-yl)cyclopropane-1-carbonitrile (compound no. d-15)(Step 1) Synthesis of 2-(5-(1,3-dioxolan-2-yl)-1-methyl-1H-imidazol-2-yl)-5-bromo-3-(ethylsulfonyl)pyridine

[00145] 2-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-1-methyl-1H-imidazole-5-carbaldehyde (8.0 g) was dissolved in toluene (150 mL), and the solution was stirred at room temperature. Ethylene glycol (17 g) and p-toluenesulfonic acid monohydrate (0.84 g) were added to the solution, and the mixture was heated and stirred overnight under reflux using a Dean-Stark apparatus. The obtained solution was poured into a saturated aqueous sodium bicarbonate solution, and extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 8.5 g of the title compound (yield: 96%).

[00146] 1H-NMR of the title compound will be shown below. 1H-NMR (CDCl3) δ: 8.94 (1H, d), 8.60 (1H, d), 7.19 (1H, s), 6.02 (1H, s), 4.17-4.00 (4H, m), 3.86 (2H, q), 3.64 (3H, s), 1.33 (3H, t).(Step 2) Synthesis of 2-(6-(5-(1,3-dioxolan-2-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3-yl)acetonitrile

[00147] In a reaction vessel, 2-(5-(1,3-dioxolan-2-yl)-1-methyl-1H-imidazol-2-yl)-5-bromo-3-(ethylsulfonyl)pyridine (1.75 g) was dissolved in N,N-dimethylformamide (23 mL), and the void space above the solution in the reaction vessel was filled with argon. Then, the solution was stirred at room temperature. Trimethylsilylacetonitrile (0.98 g), tris(dibenzylideneacetone)dipalladium(0) (0.40 g), XantPhos (0.50 g), and zinc fluoride (0.27 g) were added to the solution, and the mixture was stirred at 100 °C for 3 h. The obtained solution was poured into a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 0.51 g of the title compound (yield: 42%).

[00148] 1H-NMR of the title compound will be shown below. 1H-NMR (CDCl3) δ: 8.98-8.87 (1H, m), 8.46-8.39 (1H, m), 7.21 (1H, s), 6.03 (1H, s), 4.18-4.02 (4H, m), 3.96-3.93 (2H, m), 3.87 (2H, q), 3.65 (3H, s), 1.33 (3H, t).(Step 3) Synthesis of 1-(6-(5-(1,3-dioxolan-2-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3-yl)cyclopropane-1-carbonitrile

[00149] 2-(6-(5-(1,3-Dioxolan-2-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3-yl)acetonitrile (0.50 g) was dissolved in N,N-dimethylformamide (5 mL), and the solution was stirred at 0 °C. Cesium carbonate (0.45 g) was added to the solution. Then, 1,2-dibromoethane (0.52 g) was added dropwise to the solution, and the mixture was stirred at 0 °C for 20 minutes. Cesium carbonate (0.90 g) was added to the mixture, and the mixture was stirred at room temperature for 3 hours. The obtained solution was poured into water, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 0.29 g of the title compound (yield: 54%).

[00150] 1H-NMR of the title compound will be shown below. 1H-NMR (CDCl3) δ: 8.97 (1H, d), 8.17 (1H, d), 7.19 (1H, s), 6.02 (1H, s), 4.18-4.01 (4H, m), 3.85 (2H, q), 3.64 (3H, s), 1.97 (2H, dd), 1.61 (2H, dd), 1.31 (3H, t).(Step 4) Synthesis of 1-(5-(ethylsulfonyl)-6-(5-formyl-1-methyl-1H-imidazol-2-yl)pyridin-3-yl)cyclopropane-1-carbonitrile

[00151] 1-(6-(5-(1,3-Dioxolan-2-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3-yl)cyclopropane-1-carbonitrile (0.24 g) was dissolved in tetrahydrofuran (10 mL), and the solution was stirred at 0 °C. 10% hydrochloric acid (2 mL) was added to the solution, and the mixture was stirred at room temperature for 3 hours. The obtained solution was poured into a saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 0.23 g of the title compound (yield: 54%).

[00152] 1H-NMR of the title compound will be shown below. 1H-NMR (CDCl3) δ: 9.86 (1H, s), 9.00 (1H, d), 8.20 (1H, d), 7.83 (1H, s), 3.88 (3H, s), 3.79 (2H, dd), 2.01 (2H, dd), 1.64 (2H, dd), 1.34 (3H, t).(Step 5) Synthesis of 1-(6-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3-yl)cyclopropane-1-carbonitrile

[00153] In a reaction vessel, 1-(5-(ethylsulfonyl)-6-(5-formyl-1-methyl- 1H-imidazol-2-yl)pyridin-3-yl)cyclopropane-1-carbonitrile (0.23 g) was dissolved in N,N-dimethylformamide (10 mL), and the solution was stirred at room temperature. 1,1,1-Trichloro-2,2,2-trifluoroethane (3.1 g), zinc powder (2.0 g), acetic anhydride (1.0 g), and copper chloride (3.0 mg) were added to the solution, and the void space above the solution in the reaction vessel was filled with argon, followed by stirring overnight at 60 °C. The obtained solution was poured into a saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 0.09 g of the title compound (E/Z = 18:82, yield: 30%).

[00154] 1H-NMR and 19F-NMR of the title compound will be shown below. 1H-NMR (400 MHz, CDCl3) (a mixture of E/Z isomers) δ: 8.99 (1H, d), 8.19 (1H, d), 8.05 (1H, s), 7.16 (1H, s), 3.85 (2H, q), 3.63 (3H, s), 2.00 (2H, dd), 1.63 (2H, dd), 1.34 (3H, t); 19F-NMR (376 MHz, CDCl3-C6F6): δ -63.5 (s) for the (E)-isomer and -68.5 (s) for the (Z)-isomer.

[00155] Some compounds of the present invention produced in the same manner as in the Examples described above are shown in Tables 1 and 2. Table 1 shows the substituents of the compound represented by formula (I). In the tables, physical properties or melting point (m.p.) are also shown as physical properties of each compound.

[00156] In Table 1, Me represents a methyl group, Et represents an ethyl group, cPr represents a cyclopropyl group, and cPen represents a cyclopentyl group.

[00157] The 1H-NMR data of compounds having physical properties of viscous oil or amorphous compound from among the compounds shown in Table 1 are shown below. Compound No. d-6: 1H-NMR (400 MHz, CDCl3): d 8.08 (s, 1H), 7.48 (s, 1H), 7.23 (d, 1H), 7.15 (d, 1H), 6.94 (dd, 1H), 3.47 (s, 3H), 3.42 (s, 3H), 2.79 (q, 2H), 1.98-1.90 (m, 1H), 1.22 (t, 3H), 1.21 (t, 3H), 1.07-1.02 (m, 2H), 0.78-0.84 (m, 2H).Compound no. d-16: 1H-NMR(400 MHz, CDC13): d 8.99 (d, 1H), 8.19 (d, 1H), 7.47 (s, 1H), 7.05-6.98 (m, 1H), 6.22-6.13 (m, 1H), 3.86 (q, 3H), 3.62 (s, 3H), 2.01-1.97 (m, 2H), 1.64-1.60 (m, 2H), 1.34 (t, 3H).

[Biological tests]

[00158] The Test Examples presented below show that the (hetero)arylimidazole compound of the present invention is useful as an active ingredient for pest control agents and ectoparasite control agents. The term “part” is based on weight.

(Test emulsion preparation)

[00159] 5 parts of the (hetero)arylimidazole compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene allylic and alkyl ether were mixed and dissolved to prepare the emulsion (I) containing 5% of the active ingredient.

[00160] For a control, 98.5 parts of dimethylformamide and 1.5 parts of polyoxyethylene allylic and alkyl ether were mixed and dissolved to prepare emulsion (II).

[00161] An insecticidal rate was calculated according to the following expression:Insecticidal rate (%) = (The number of insects killed / The number of insects tested) x 100

(Test Example 1) Test effectiveness on Mythimna separata

[00162] 0.8 g of commercially available artificial food (Insecta LFS, manufactured by Nosan Corp.) and 1 μL of emulsion (I) were well mixed to obtain the test food.

[00163] A plastic test container (capacity: 1.4 mL) was packed with 0.2 g of the test food per treatment batch. Then, two second-instar larvae of Mythimna separata were inoculated into each treatment batch. A plastic lid was placed over the test container to prevent the escape of the second-instar larvae of Mythimna separata. The container was placed in a thermostated chamber at 25°C. On the fifth day, the insecticide rate and food intake were examined. The test was conducted in duplicate.

[00164] The insecticidal rate and food intake of a control batch were examined in the same manner as in Test Example 1 except that emulsion (I) was changed to emulsion (II).

[00165] Compounds of compound Nos. d-1, d-2, d-3, d-4, d-5, d-6, d-7, d-8, d-1, d-12, d-13, d-14, d-15, d-16, d-18, d-19, d-20, d-21, d-22, d-23, d-24, d-27, d-28, d-29, d-30, d-32, d-33, d-34, d-35, d-36, d-37, e-1 and e-4 were tested for their efficacy on Mythimna separata. All compounds had an insecticidal rate of 100% for Mythimna separata or a food intake of 10% or less compared to the control lot. As is evident, the (hetero)arylimidazole compound of the present invention is effective for Mythimna separata.

(Test Example 2) Test effectiveness on Mythimna separata

[00166] The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Corn leaves were dipped in the dilution for 30 s. The resulting corn leaves were placed in a Petri dish, and five second-instar larvae of Mythimna separata were released into the Petri dish. The Petri dish was positioned inside a thermostated chamber having a temperature of 25°C and a humidity of 60%. Life and death were determined after 6 days from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.

[00167] Compounds of compound Nos. d-1, d-2 and d-15 were tested for their efficacy on Mythimna separata. All compounds showed an insecticidal rate of 80% or more on Mythimna separata.

(Test Example 3) Test efficacy on Plutella xylostella

[00168] The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Cabbage leaves were dipped in the dilution for 30 seconds. The resulting cabbage leaves were placed in a Petri dish. Five second instar larvae of Plutella xylostella were released into the Petri dish. The Petri dish was placed in a thermostated chamber having a temperature of 25°C and a humidity of 60%. Life and death were determined after 3 days from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.

[00169] The compounds of compound Nos. d-1, d-2, d-4, d-7, d-9, d-10, d-12, d-13, d-15, d-18, d-20, d-21, d-22, d-23, d-24, d-25, d-26, d-27, d-28, d-29, d-30, d-31, d-33 and d-34 were tested for their efficacy on Plutella xylostella. All compounds showed an insecticidal rate of 80% or greater for Plutella xylostella.

(Test Example 4) Test efficacy on Spodoptera litura

[00170] The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Cabbage leaves were dipped in the dilution for 30 seconds. The resulting cabbage leaves were placed in a Petri dish, and five second-instar larvae of Spodoptera litura were released into the Petri dish. The Petri dish was placed in a thermostated chamber having a temperature of 25°C and a humidity of 60%. Life and death were determined after 6 days from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.

[00171] Compounds of compound No. d-2, d-12 and d-15 were tested for their efficacy on Spodoptera litura. All compounds showed an insecticidal rate of 80% or greater on Spodoptera litura.

(Test Example 5) Test effectiveness on Aphis craccivora

[00172] Black-eyed pea seedlings were grown in 10 cm pots. Aphis craccivora nymphs were inoculated onto the primary leaves. The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. The dilution was sprayed onto the black-eyed peas parasitized by the Aphis craccivora nymphs. The black-eyed peas were placed in a thermostatic chamber having a temperature of 25°C and a humidity of 60%. The life and death of Aphis craccivora were determined after 4 hours from spraying, and the insecticidal rate was calculated. The test was conducted in duplicate.

[00173] The compounds of compound Nos. d-1, d-2, d-3, d-4, d-5, d-6, d-7, d-8, d-11, d-12, d-13, d-15, d-16, d-17, d-18, d-20, d-21, d-22, d-23, d-24, d-25, d-27, d-29, d-30, d-32, d-34, d-35, d-36, d-37 and e-1 were tested for their efficacy on Aphis craccivora. All compounds showed an insecticidal rate of 80% or more for Aphis craccivora.

(Test Example 6) Test efficacy on Phyllotreta striolata

[00174] The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm to prepare a test chemical. The test chemical was sprayed on Qing geng cai seedlings (at the seventh true leaf stage) planted in 10 cm pots. The Qing geng cai seedlings were air-dried and then placed in a plastic cup. Ten adults of Phyllotreta striolata were released into the plastic cup. The plastic cup was stored in a thermostatic chamber having a temperature of 25°C and a humidity of 65%. Life and death were determined after 7 days of insect release, and the insecticidal rate was calculated. The test was conducted in duplicate.

[00175] Compounds of compound Nos. d-1, d-2, d-4, d-9, d-10, d-12, d-13, d-15, d-18, d-20, d-22, d-23, d-25, d-26, d-27, d-29, d-31, d-33, d-34 and e-2 were tested for their efficacy on Phyllotreta striolata adults. All compounds exhibited an insecticidal rate of 80% or greater for Phyllotreta striolata adults.

(Test Example 7) Test effectiveness on Nilaparvata lugens

[00176] The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Young rice seedlings were dipped in the dilution for 30 seconds. The young rice seedlings were air-dried and then placed in a plastic box. Five second instar larvae of Nilaparvata lugens were released into the plastic box. The plastic box was stored in a thermostatic chamber having a temperature of 25°C and a humidity of 65%. Life and death were determined after 7 days from inoculation, and the insecticidal rate was calculated. The test was conducted in duplicate.

[00177] The compounds of compound Nos. d-1, d-2, d-9, d-13, d-15, d-18, d-22, d-23, d-25, d-26, d-30 and d-31 were tested for their efficacy on Nilaparvata lugens. All the compounds showed an insecticidal rate of 80% or more on Nilaparvata lugens.

(Test Example 8) Test effectiveness on Musca domestica

[00178] The compound of the present invention was diluted with acetone and the dilution was added dropwise to 100 ppm of the compounds of the present invention per g of a sugar cube. The sugar cube was placed in a plastic cup. Ten adult females of Musca domestica were released into the plastic cup, and a lid was placed over the plastic cup. The plastic cup was stored at 25°C. Life and death were determined after 24 hours from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.

[00179] A compound of compound No. b-4 was tested for its efficacy on Musca domestica. The compound showed an insecticidal rate of 80% or more on Musca domestica.

(Test Example 9) Test efficacy on Aphis gossypii

[00180] Cucumber seedlings grown in 10 cm pots were taken out of 10 cm pots. The soil attached to the root portions was removed by washing with water, followed by hydroponic culture. Nymphs of Aphis gossypii were inoculated on the cucumber seedlings. The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 31 ppm to obtain a dilution. Tap water was replaced by the dilution, and hydroponic culture was continued with the dilution in a thermostatic chamber having a temperature of 25°C and a humidity of 60%. The life and death of Aphis gossypii were determined after 6 days from the start of hydroponic culture with the dilution, and the insecticidal rate was calculated. The test was conducted in duplicate.

[00181] Compounds of compound Nos. d-1, d-2, d-9, d-15, d-18, d-26, d-27 and d-33 were tested for their efficacy on Aphis gossypii. All compounds showed an insecticidal rate of 80% or more on Aphis gossypii.

(Test Example 10) Test efficacy on Phyllotreta striolata

[00182] The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 31 ppm to prepare a test chemical. The test chemical was sprayed onto Qing geng cai seedlings (at the seventh true leaf stage) planted in 10 cm pots. The Qing geng cai seedlings were air-dried and then placed in a plastic cup. Ten adults of Phyllotreta striolata were released into the plastic cup. The plastic cup was stored in a thermostatic chamber having a temperature of 25°C and a humidity of 65%. Life and death were determined after 7 days from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.

[00183] Compounds of compound Nos. d-1, d-2, d-4, d-9, d-10, d-12, d-13, d-15, d-18, d-20, d-22, d-23, d-25, d-26, d-27, d-29, d-33, d-34 and e-2 were tested for their efficacy on Phyllotreta striolata adults. All compounds exhibited an insecticidal rate of 80% or greater for Phyllotreta striolata adults.

[00184] All the randomly selected compounds from among the (hetero)arylimidazole compounds of the present invention exerted the effect as described above. Therefore, it can be understood that the (hetero)arylimidazole compound of the present invention, including compounds not illustrated, is a compound that has an effect such as a pest control effect, particularly an acaricidal or insecticidal effect. It can also be understood that the (hetero)arylimidazole compound of the present invention is a compound that also has an effect on parasites harmful to humans and animals, such as ectoparasites.

Claims (11)

1. Compound, characterized by the fact that it is represented by formula (II), a compound of N-oxide, stereoisomer, tautomer or hydrate thereof or a salt of any of these compounds: in whichX represents a C3-8-cycloalkyl group which may be substituted by a cyano group or a C1-6-alkyl group;R1 represents a C1-6-alkylthio group or a C1-6-alkylsulfonyl group;R2 represents a C1-6-alkyl group; andR3 represents a hydrogen atom or a halogen group;R4 represents a C1-4-haloalkyl group; and the carbon-carbon stereo double bond represents an E form or a Z form, or a mixture thereof. 2. The compound of claim 1, an N-oxide compound, stereoisomer, tautomer or hydrate thereof or a salt of any of these compounds, characterized in that the compound is the compound represented by any one of formula (III) through formula (X): where the carbon-carbon double stereo bond represents an E form or a Z form, or a mixture thereof; where the carbon-carbon double stereo bond represents an E form or a Z form, or a mixture thereof; 3. Pest control agent, characterized by the fact that it comprises at least one compound selected from the group consisting of a compound as defined in claim 1 or 2, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient. 4. Insecticide or acaricide, characterized by the fact that it comprises at least one compound selected from the group consisting of a compound as defined in claim 1 or 2, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient. 5. Ectoparasite control agent, characterized by the fact that it comprises at least one compound selected from the group consisting of a compound as defined in claim 1 or 2, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient. 6. An endoparasite expelling or endoparasite control agent comprising at least one compound selected from the group consisting of a compound as defined in claim 1 or 2, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient. 7. Seed treatment agent or vegetative propagation organ treatment agent, characterized by the fact that it comprises at least one compound selected from the group consisting of a compound as defined in claim 1 or 2, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient. 8. Granular agrochemical composition for treating seedling nursery boxes of paddy rice, characterized by the fact that it comprises at least one compound selected from the group consisting of a compound as defined in claim 1 or 2, a compound of N-oxide, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient. 9. Soil treatment agent, characterized by the fact that it comprises at least one compound selected from the group consisting of a compound as defined in claim 1 or 2, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient. 10. A baiting agent comprising at least one compound selected from the group consisting of a compound as defined in claim 1 or 2, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient. 11. Plant growth promoter, characterized by the fact that it comprises at least one compound selected from the group consisting of a compound as defined in claim 1 or 2, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient.