RU2813202C2 - (hetero)arylimidazole compound and pest control agent - Google Patents

Abstract

FIELD: pest control products.

SUBSTANCE: invention relates to a (hetero)arylimidazole compound of formula (IV) and its N-oxide, or an agriculturally or horticulturally acceptable salt.

EFFECT: obtaining of a compound that has excellent insecticidal activity and/or acaricidal activity, excellent safety and that can be successfully synthesized in industry, as well as a pest control product containing it as an active ingredient.

7 cl, 2 tbl

Description

Field of technology to which the invention relates

[0001]

The present invention relates to a (hetero)arylimidazole compound and pest control agent. In particular, the present invention relates to a (hetero)arylimidazole compound which has excellent insecticidal and/or acaricidal activity, excellent safety and can be successfully synthesized industrially, as well as a pest control agent containing the same as an active ingredient.

This application claims priority to Japanese Patent Application No. 2018-202998, filed on October 29, 2018, the contents of which are incorporated herein.

State of the art

[0002]

Various compounds having insecticidal or acaricidal activity have been proposed. For the practical use of such compounds as agrochemicals, it is necessary that they not only have a sufficiently high efficiency, but also are less likely to cause chemical resistance, have no phytotoxicity and do not pollute the soil, and be of low toxicity to livestock, fish, etc.

[0003]

Patent Document 1 discloses a compound represented by formula (A), etc.

[0004]

Patent Document 2 discloses the compound represented by formula (B), etc.

Prior Art Documents

Patent documents

[0005]

Patent Document 1: WO2017/104741A

Patent Document 2: WO2016/121997A

The essence of the invention

Problem solved by the invention

[0006]

An object of the present invention is to provide a (hetero)arylimidazole compound which has excellent pest control activity, in particular insecticidal activity and/or acaricidal activity, has excellent safety and can be successfully synthesized industrially. Another object of the present invention is to provide a pest control agent, insecticide or acaricide, ectoparasite control agent or endoparasite control agent or endoparasite control agent containing a (hetero)arylimidazole compound as an active ingredient. Another object of the present invention is to provide a seed treatment, a vegetative propagation treatment, a granular agrochemical composition for treating paddy rice cassettes, a soil treatment, a bait agent and a plant growth stimulant containing a (hetero)arylimidazole compound. as an active ingredient.

Ways to solve the problem

[0007]

As a result of careful research aimed at achieving the objectives, the present invention, including the following form, has been completed.

[0008]

[1] The compound represented by formula (I), its N-oxide, stereoisomer, tautomer or hydrate, or a salt of any of these compounds:

Where

B ¹ represents a nitrogen atom or CH;

X represents a substituted or unsubstituted C3-8 cycloalkyl group;

R ¹ represents a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted C1-6 alkylsulfonyl group;

R ² represents a substituted or unsubstituted C1-6 alkyl group; And

R represents a substituted or unsubstituted C2-6 alkenyl group.

[0009]

[2] A compound as set forth above [1], its N-oxide, stereoisomer, tautomer or hydrate, or a salt of any of these compounds, where formula (I) is formula (II):

Where

R ¹ , R ² and X have the same meanings as described in formula (I);

R ³ represents a hydrogen atom or a halogen group;

R ⁴ represents a C1-4 haloalkyl group; And

A carbon-carbon double bond has an E-form or a Z-form, or a mixture of both.

[0010]

[3] A compound represented by any of formulas (III) to (X), an N-oxide, stereoisomer, tautomer or hydrate thereof, or salts of any of these compounds:

wherein the carbon-carbon double bond is E-form or Z-form, or a mixture thereof;

wherein the carbon-carbon double bond is E-form or Z-form, or a mixture thereof;

And

[0011]

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

[0012]

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

[0013]

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

[0014]

[7] An endoparasite control agent or exfoliant comprising at least one compound selected from the group consisting of a compound according to any one of [1]-[3] above, its N-oxide, stereoisomer, tautomer and hydrate, and salts of any of these compounds, as the active ingredient.

[0015]

[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 of the above [1]-[3], its N-oxide, stereoisomer, tautomer and the hydrate and salt of any of these compounds as the active ingredient.

[0016]

[9] Granular agrochemical composition for treating rice seedling trays, comprising at least one compound selected from the group consisting of a compound according to any of the above [1]-[3], its N-oxide, stereoisomer, tautomer and hydrate , and salts of any of these compounds, as the active ingredient.

[0017]

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

[0018]

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

[0019]

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

Invention effect

[0020]

The (hetero)arylimidazole compound of the present invention can control pests that pose a crop or hygiene problem. In particular, the (hetero)arylimidazole compound of the present invention can effectively control agricultural insect pests and mites at a lower concentration. In addition, the (hetero)arylimidazole compound of the present invention can effectively control ectoparasites and endoparasites harmful to humans and animals.

In addition, 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 rice seedling trays, a soil treatment agent, a bait agent, or a plant growth stimulant.

Method for carrying out the invention

[0021]

[(Hetero)arylimidazole compound]

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

[0022]

In the present invention, the term "unsubstituted" means a group consisting of only the original nucleus. Only the name of the group consisting of the original core without the term "substituted" means the "unsubstituted" group unless otherwise specified.

On the other hand, the term "substituted" means that any hydrogen atom of a group consisting of the original nucleus is replaced by a group (substituent) having a structure that is the same as the structure of the original nucleus, or different. Thus, "substituent" means another group related to the group consisting of the original core. The number of substituents may be one or more. Two or more substituents are the same or different.

Terms such as "C1-6" mean that the number of carbon atoms in the group consisting of the original nucleus is 1-6, 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 ethoxy group as a substituent will be classified as a C2 alkoxy C4 alkyl group.

[0023]

The "substituent" is not particularly limited as long as the substituent is chemically acceptable and produces the effect of the present invention. Further, the group capable of serving as a "substitute" can be represented by the following:

a C1-6 alkyl group such as a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group and n-hexyl group;

C2-6 alkenyl group such as vinyl group, 1-propenyl group, 2-propenyl group (allylic group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group and 2 -methyl-2-propenyl group;

C2-6 alkynyl group such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group and 1-methyl-2-propynyl group;

[0024]

a C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and a cubanyl group;

C6-10 aryl group such as phenyl group and naphthyl group;

a C6-10 aryl C1-6 alkyl group such as a benzyl group and a phenethyl group;

3-6 membered heterocyclyl group;

3-6 membered heterocyclyl C1-6 alkyl group;

[0025]

hydroxy group;

C1-6 alkoxy group such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, isobutoxy group and tert-butoxy group;

C2-6 alkenyloxy group such as vinyloxy group, allyloxy group, propenyloxy group and butenyloxy group;

C2-6 alkynyloxy group such as ethynyloxy group and propargyloxy group;

C6-10 aryloxy group such as phenoxy group and naphthoxy group;

a C6-10 aryl 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;

[0026]

formyl group;

a C1-6 alkylcarbonyl group such as an acetyl group and a propionyl group;

formyloxy group;

C1-6 alkylcarbonyloxy group such as acetyloxy group and propionyloxy group;

a C6-10 arylcarbonyl group such as a benzoyl group;

a C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an isopropoxycarbonyl group, an n-butoxycarbonyl group and a t-butoxycarbonyl group;

C1-6 alkoxycarbonyloxy group such as methoxycarbonyloxy group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group, isopropoxycarbonyloxy group, n-butoxycarbonyloxy group and t-butoxycarbonyloxy group;

carboxy group;

[0027]

a halogen group such as a fluoro group, a chloro group, a bromo group and an iodine group;

C1-6 haloalkyl group such as fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group , perfluoropropyl group, 2,2,2-trifluoro-1-trifluoromethylethyl group, perfluoroisopropyl group, 4-fluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group , chloromethyl group, bromomethyl group, dichloromethyl group, dibromomethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trichloroethyl group, 4-chlorobutyl group, perchlorohexyl group and 2,4,6-trichlorohexyl group;

a C2-6 haloalkenyl group such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group;

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;

C1-6 haloalkoxy group such as trifluoromethoxy group, 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group and perfluoropropoxy group;

C2-6 haloalkenyloxy group such as 2-chloropropenyloxy group and 3-bromobutenyloxy group;

a C1-6 haloalkylcarbonyl group such as a chloroacetyl group, a trifluoroacetyl group and a trichloroacetyl group;

[0028]

amino group;

C1-6 alkyl-substituted amino group such as methylamino group, dimethylamino group and diethylamino group;

C6-10 arylamino group such as anilino group and naphthylamino group;

C6-10 aryl C1-6 alkylamino group such as benzylamino group and phenethylamino group;

formylamino group;

C1-6 alkylcarbonylamino group such as acetylamino group, propanoylamino group, butyrylamino group and isopropylcarbonylamino group;

C1-6 alkoxycarbonylamino group such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group and isopropoxycarbonylamino 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 group;

substituted or unsubstituted N-hydroxyimino C1-6 alkyl group such as N-hydroxy-iminomethyl group, (1-(N-hydroxy)-imino)ethyl group, (1-(N-hydroxy)-imino)propyl group, N -methoxy-iminomethyl group and (1-(N-methoxy)-imino)ethyl group;

C1-6 alkoxyimino group such as methoxyimino group, ethoxyimino group, n-propoxyimino group, isopropoxyimino group and n-butoxyimino group;

aminocarbonyloxy group;

C1-6 alkyl-substituted aminocarbonyloxy group such as ethylaminocarbonyloxy group and dimethylaminocarbonyloxy group;

[0029]

mercapto group;

C1-6 alkylthio group such as methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, sec-butylthio group and t-butylthio group;

C1-6 haloalkylthio group such as trifluoromethylthio group and 2,2,2-trifluoroethylthio group;

C6-10 arylthio group such as phenylthio group and naphthylthio group;

a 5- or 6-membered heteroarylthio group such as a thiazolylthio group and a pyridylthio group;

[0030]

a C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group and a tert-butylsulfinyl group;

a C1-6 haloalkylsulfinyl group such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group;

a C6-10 arylsulfinyl group such as a phenylthionyl group;

a 5- or 6-membered heteroarylsulfinyl group such as a thiazolylsulfinyl group and a pyridylsulfinyl group;

[0031]

a C1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group and a tert-butylsulfonyl group;

a C1-6 haloalkylsulfonyl group such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group;

a C6-10 arylsulfonyl group such as a phenylsulfonyl group;

a 5- or 6-membered heteroarylsulfonyl group such as a thiazolylsulfonyl group and a pyridylsulfonyl group;

C1-6 alkylsulfonyloxy group such as methylsulfonyloxy group, ethylsulfonyloxy group and tert-butylsulfonyloxy group;

C1-6 haloalkylsulfonyloxy group such as trifluoromethylsulfonyloxy group and 2,2,2-trifluoroethylsulfonyloxy group;

and an aminothiocarbonyl group;

[0032]

a tri-C1-6 alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group and a tert-butyldimethylsilyl group;

a tri-C6-10 aryl-substituted silyl group such as a triphenylsilyl group;

cyano group; and a nitro group.

[0033]

In the case of these "substituents", any hydrogen atom in each substituent can be replaced by a group having a specific structure. In this case, as an example of the “substituent”, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halo group, a cyano group, a nitro group and the like can be represented.

[0034]

The "3-6 membered heterocyclyl group" described above contains 1-4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring constituting atoms. The heterocyclyl group may be monocyclic or polycyclic. A polycyclic heterocyclyl group has at least one heteroring, and the other ring(s) may be any saturated alicyclic ring, unsaturated alicyclic ring, and aromatic ring. As an example of the "3-6 membered heterocyclyl group", a 3-6 membered saturated heterocyclyl group, a 5- or 6-membered heteroaryl group, a 5- or 6-membered partially unsaturated heterocyclyl group, and the like can be provided.

[0035]

As an example of the 3-6 membered saturated heterocyclyl group, there can be represented 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 and the like.

[0036]

As an example of the 5-membered heteroaryl group, pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group and tetrazolyl group can be presented. .P.

As an example of the 6-membered heteroaryl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group and the like can be represented.

[0037]

[B1]

In formula (I), B ¹ represents a nitrogen atom or CH.

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

[0038]

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

[0039]

B ¹ preferably represents a nitrogen atom.

[0040]

[X]

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

[0041]

As examples of the "C3-8 cycloalkyl group" in X, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and a cubanyl group and the like can be represented.

[0042]

As examples of the "substituted C3-8 cycloalkyl group" in X, 1-methylcyclopropyl group, 1-cyanocyclopropyl group, 1-aminocarbonylcyclopropyl group, 1-aminothiocarbonylcyclopropyl group, 1-(pyridin-2-yl)cyclopropyl group, etc. can be represented. P.

[0043]

As an example of a substituent on the "C3-8 cycloalkyl group" in X, a cyano group may be represented; aminocarbonyl group; aminothiocarbonyl group; a C1-6 alkyl group such as a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group and n-hexyl group; and as a preferred example, 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 provided.

[0044]

X is preferably a substituted or unsubstituted cyclopropyl group, and more preferably an unsubstituted cyclopropyl group.

[0045]

[R ¹ ]

In formula (I), R ¹ represents a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted C1-6 alkylsulfonyl group.

[0046]

As an example of the "C1-6 alkylthio group" in R ¹ , a methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, sec-butylthio group, tert-butylthio group and the like can be represented.

[0047]

As an example, the "C1-6 alkylsulfonyl group" in R ¹ can be represented by a methylsulfonyl group, an ethylsulfonyl group, a tert-butylsulfonyl group and the like.

[0048]

As an example, the substituents on the "C1-6 alkylthio group" and the "C1-6 alkylsulfonyl group" in R ¹ may preferably be represented by a halogen group such as a fluoro group, a chloro group, a bromo group and an iodo group.

[0049]

R ¹ is preferably a C1-6 alkylsulfonyl group, and more preferably an ethylsulfonyl group.

[0050]

[ ^R2 ]

In formula (I), R ² represents a substituted or unsubstituted C1-6 alkyl group.

[0051]

The "C1-6 alkyl group" in R ² may be straight or branched. As an example of the "C1-6 alkyl group", methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, neopentyl group, 2-methylbutyl group, isohexyl group and the like.

[0052]

As an example of the substituent on the "C1-6alkyl group" in R ² , a halogen group such as a fluoro group, a chloro group, a bromo group and an iodo group may be preferably represented.

[0053]

R ² is preferably an unsubstituted C1-6 alkyl group, and more preferably a methyl group.

[0054]

[R]

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

[0055]

As an example of the "C2-6 alkenyl group" in R, vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group can be represented. group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1 -hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, etc.

[0056]

As an example of the "substituted C2-6 alkenyl group" in R, a C2-6 haloalkenyl group such as 2-fluoro-2-bromovinyl group, 2,2-dichlorovinyl group, 2-chloro-2-iodovinyl group, 2 -chloro-1-propenyl group, 2,3,3,3-tetrafluoro-1-propenyl group, 3,3,3-trifluoro-1=propenyl group, 2-chloro-3,3,3-trifluoro-1- propenyl group, 2-bromo-3,3,3-trifluoro-1-propenyl group, 3,3,3-trifluoro-2-trifluoromethyl-1-propenyl group, 2-fluoro-1-butenyl group, 3,3, 4,4,4-pentafluoro-1-butenyl group, 2,3,3,4,4,4-hexafluoro-1-butenyl group, 2-chloro-3,3,4,4,4-pentafluoro-1- butenyl group, 3,3,4,4,5,5,5-heptafluoro-1-pentenyl group, 2-chloro-3,3,4,4,5,5,5-heptafluoro-1-pentenyl group, 2 ,3,3,4,4,5,5,5-octafluoro-1-pentenyl group and 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexenyl group; and a C1-6 haloalkoxy C2-6 haloalkenyl group such as a 1,2-difluoro-2-trifluoromethoxyvinyl group and a 1,2-difluoro-2-perfluoropropoxyvinyl group.

[0057]

As an example of the substituent on the "C2-6 alkenyl group" in R, a halogen group such as a fluoro group, a chloro group, a bromo group and an iodo group may be preferably represented; 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.

[0058]

R is preferably a C2-6 haloalkenyl group.

[0059]

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

[0060]

[The compound represented by formula (II)]

The compound represented by formula (I) is preferably the compound represented by formula (II).

In formula (II):

R ¹ , R ² and X have the same meanings as described in formula (I).

R ³ represents a hydrogen atom or a halogen group.

R ⁴ represents a C1-4 haloalkyl group.

In formula (II), the carbon-carbon double bond is E-form or Z-form or a mixture thereof.

[0061]

[R ³ ]

As an example of the "halogen group" in R ³ , a fluoro group, a chloro group, a bromo group, an iodo group and the like can be represented.

[0062]

[R ⁴ ]

As an example of the "C1-4 haloalkyl group" in R ⁴ , a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, 2,2, can be represented. 3,3,3-pentafluoropropyl group, perfluoropropyl group, 2,2,2-trifluoro-1-trifluoromethylethyl group, perfluoroisopropyl group, 4-fluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, perfluorobutyl group, chloromethyl group, bromomethyl group, dichloromethyl group, dibromomethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trichloroethyl group, 4-chlorobutyl group and the like.

[0063]

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

[0064]

The compound represented by formula (I) is preferably any of the following compounds.

where the carbon-carbon double bond is E-form or Z-form, or a mixture thereof.

where the carbon-carbon double bond is E-form or Z-form, or a mixture thereof.

[0065]

[Obtainment method]

The (hetero)arylimidazole compound of the present invention is not particularly limited in its production method. For example, the (hetero)arylimidazole compound of the present invention can be produced by known production methods described in Examples, etc. Alternatively, N-oxide salt, etc. compounds (I) can be prepared by a known method from compound (I).

[0066]

The (hetero)arylimidazole compound of the present invention can be produced by methods, for example, by the methods given below.

[0067]

(Synthesis method 1)

where X, R ¹ and R ² have the same meanings as described above; and R ^f represents a C1-4 fluoroalkyl group such as a fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3 ,3-pentafluoropropyl group, perfluoropropyl group, 2,2,2-trifluoro-1-trifluoromethylethyl group, perfluoroisopropyl group, 4-fluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group or perfluorobutyl group.

[0068]

(Synthesis method 2)

where X, R ¹ , R ² and R ^f have the same meanings as described above; and R ⁵ represents a C1-6 alkyl group.

[0069]

(Synthesis method 3)

where X, R ¹ , R ² and R ^f have the same meanings as described above.

[0070]

(Synthesis method 4)

where X, R ¹ , R ² and R ^f have the same meanings as described above.

[0071]

(Synthesis method 5)

where X, R ¹ , R ² and R ^f have the same meanings as described above.

[0072]

(Synthesis method 6)

where X, R ¹ , R ² and R ^f have the same meanings as described above.

[0073]

(Synthesis method 7)

where X, R ¹ , R ² and R ^f have the same meanings as described above.

[0074]

(Synthesis method 8)

where X, R ¹ , R ² and R ^f have the same meanings as described above.

[0075]

(Synthesis method 9)

where X, R ¹ , R ² and R ^f have the same meanings as described above.

[0076]

[Pest Control Effect]

The (hetero)arylimidazole compound of the present invention exhibits excellent control effect on pests such as various agricultural insect pests and mites affecting plant growth.

In addition, the (hetero)arylimidazole compound of the present invention is a safe substance due to lower phytotoxicity to crops and low toxicity to fish and warm-blooded animals. Therefore, the (hetero)arylimidazole compound of the present invention can be used as an active ingredient for insecticides or acaricides.

In addition, in recent years, many insect pests such as cabbage moths, white-backed planthoppers, leafhoppers and aphids have developed resistance to various existing chemicals, raising the issue of the lack of effectiveness of these chemicals. Thus, there is a need for chemicals that are effective against resistant strains of insect pests. The (hetero)aryl-imidazole compound of the present invention shows an excellent control effect not only on susceptible strains, but also on insect pests of various resistant strains, and even mites from acaricide-resistant strains.

[0077]

The (hetero)arylimidazole compound of the present invention exhibits excellent control effect on ectoparasites and endoparasites harmful to humans and animals. In addition, the (hetero)arylimidazole compound of the present invention is a safe substance due to low toxicity to fish and warm-blooded animals. Therefore, the (hetero)arylimidazole compound of the present invention can be used as an active ingredient in agents for controlling ectoparasites and endoparasites.

[0078]

The (hetero)arylimidazole compound of the present invention exhibits effectiveness in every developmental stage of organisms to be controlled, and exhibits excellent control effect on, for example, eggs, nymphs, larvae, pupae and adults of mites, insects and the like.

[0079]

[Pest Control Product]

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 its pest control effect is exhibited. The pest control agent is a pest control agent and includes an insecticide or acaricide, an ectoparasite control agent or an endoparasite control agent or an endoparasite removal agent and the like.

[0080]

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, insecticide or acaricide, nematicide or pesticide, against soil insect pests; plant growth regulating agent, synergist, fertilizer, soil improver, animal feed, etc.

The combination of a (hetero)arylimidazole compound of the present invention with another active ingredient can be expected to have synergistic effects in terms of insecticidal, acaricidal or nematocidal activity. Synergistic effects can 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 the standard method.

[0081]

Specific examples of an insecticide or acaricide, a nematicide, a pesticide against soil pests, an anthelmintic and the like that can be used as a mixture or in combination with the pest control agent of the present invention are shown below.

[0082]

(1) Acetylcholinesterase inhibitors:

(a) carbamates: alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, etiophencarb, phenobucarb, formatenate, furatiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, ti ofanox, triazamate, trimetacarb , XMC, xylylcarb, phenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, allixicarb, aminocarb, bufencarb, cloetocarb, metam sodium and promecarb;

[0083]

(b) organophosphorus compounds: acephate, azamethiophos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprofos, famfour, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imitsiafos, isofenfos, isocarbofos, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxidem eton- methyl, parathion, parathion methyl, phentoate, phorate, phosalon, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiophos, pyraclofos, pyridafention, quinalphos, sulfotep, tebupirimphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, tri chlorfon , vamidothione, bromophos-ethyl, BRP, carbophenothione, cyanofenphos, CYAP, demeton-S-methyl sulfone, dialifos, dichlorofenthione, dioxabenzophos, etrimphos, fensulfothione, flupirazophos, fonofos, formothione, phosmethylane, isazophos, iodfenphos, metacryphos, pirimiphos-ethyl, phosphocarb, propaphos, protoate and sulprophos.

[0084]

(2) GABAergic chloride ion channel antagonists: acetoprole, chlordene, endosulfan, ethiprole, fipronil, pirafluprole, pyriprole, camphechlor, heptachlor and dienochlor.

(3) Sodium channel modulators: acrinatrine, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, 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], deltamethrin, empenthrin [(EZ)-(1R)-isomers], esfenvalerate, etofenprox , fenpropathrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, galfenprox, imiprothrin, cadethrin, permethrin, phenothrin [(1R)-trans-isomers], prallethrin, pyrethrum, resmethrin, silafluofen, tefluthrin, tetramethrin [(1R)-isomers] , tralomethrin, transfluthrin, allethrin, pyrethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyritrin, flubrocitrinate, flufenprox, metofluthrin, protrifenbut, pyresmethrin and terallethrin.

[0085]

(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradifuron and flupirimine.

(5) Allosteric modulators of nicotinic acetylcholine receptors: spinetoram and spinosad.

(6) Chloride channel activators: abamectin, emamectin benzoate, lepimectin and milbemectin, ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime and nemadectin.

(7) Juvenile hormone analog substances: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen, diophenolan, epophenonan and triprene.

(8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, potassium antimonyl tartrate.

(9) Selective inhibitors of homoptera feeding: flonicamid, pymetrozine and pyrifluquinazone.

[0086]

(10) Mite growth inhibitors: clofentesine, difluvidazine, hexythiazox and etoxazole.

(11) Agents that damage the inner lining of the midgut of insects, obtained from microorganisms: Bacillus thuringiensis sp. Isuraerenshi, Bacillus sphaericus, Bacillus thuringiensis sp. Aizawai, Bacillus thuringiensis sp. Kurstaki, Bacillus thuringiensis sp. Tenebrionis and Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Ab1/Cry35Ab1.

(12) Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotine, cyhexatin, phenbutatin oxide, propargite and tetradifon.

(13) Oxidative phosphorylation uncouplers: chlorfenapyr, sulfluramide, DNOC, binapacryl, dinobuton and dinocar.

(14) Nicotinic acetylcholine receptor channel blockers: bensultap, cartap hydrochloride, nereistoxin, sodium thiosultap and thiocyclam.

(15) Chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin and fluazuron.

(16) Compounds that disrupt molting in Diptera: cyromazine.

(17) Molting hormone receptor agonists: chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

(18) Octopamine receptor agonists: amitraz, demidytraz and chlordimeform.

(19) Inhibitors of complex III of the mitochondrial electron transport system: acequinocyl, fluacripyrim and hydramethylnon.

(20) Complex I inhibitors of the mitochondrial electron transport system: phenazachine, fenpyroximate, pyrimidifene, pyridabene, tebufenpyrad, tolfenpyrad and rotenone.

[0087]

(21) Voltage-gated sodium channel blockers: indoxacarb and metaflumizone.

(22) Acetyl-CoA carboxylase inhibitors: spirodiclofen, spiromesifen and spirotetramate.

(23) Complex IV inhibitors of the mitochondrial electron transport system: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide and cyanide.

(24) Inhibitors of complex II of the mitochondrial electron transport system: cyenopyrafen, cyflumetofen and piflubumide.

(25) Ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole and tetraniliprole.

(26) Mixed-function oxidase inhibitor compounds: piperonyl butoxide.

(27) Latrophilin receptor agonists: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, and emodepside.

(28) Other agents (with unknown mechanism of action): azadirachtin, benzoximate, biphenazate, bromopropylate, quinomethionate, cryolite, dicofol, pyridalyl, benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromolate, benzomate, metacetaldehyde, chlorobenzilate, clothiazoben, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine, gossyplur, japonilur, methoxadiazone, petroleum, potassium oleate, tetrasul, triarathene, afidopyropene, flometoquine, flufiprole, fluensulfone, meperfluthrin, tetramethylfluthrin, tralopyril, dimef luthrin, methylneodecanamide, fluralaner, afoxolaner, fluxamethamide , 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 and other m-diamides.

[0088]

(29) Anthelmintics:

(a) benzimidazole-based: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, parbendazole, flubendazole, febantel, netobimine, thiophanate, thiabendazole and cambendazole;

(b) salicylanilide-based: closantel, oxyclozanide, rafoxanide and niclosamide;

(c) based on substituted phenol: nitroxynyl and nitroscanate;

(d) pyrimidine-based: pyrantel and morantel;

(e) based on imidazothiazole: levamisole and tetramizole;

(f) based on tetrahydropyrimidine: praziquantel and epsiprantel;

(g) other anthelmintics: cyclodien, ryania, clorsulon, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorphene, monepantel, tribendimidine, amidantel, thiacetarsamide, melarsomine and arsenamide.

[0089]

Specific examples of a fungicide that can be used as a mixture or in combination with a pest control agent according to the present invention are shown below.

(1) Nucleic acid biosynthesis inhibitors:

(a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixil, closilacone and ofurat;

(b) adenosine deaminase inhibitors: bupirimate, dimethylrimol and ethirimol;

(c) DNA/RNA synthesis inhibitors: hymexazole and octylinone;

(d) DNA topoisomerase II inhibitors: oxolinic acid.

[0090]

(2) Mitosis 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: pencycuron;

(c) spectrin-like protein delocalization inhibitors: fluopicolide.

[0091]

(3) Respiratory inhibitors:

(a) complex I NADH oxidoreductase inhibitors: diflumetorim and tolfenpyrad;

(b) succinate dehydrogenase complex II inhibitors: benodanil, flutolanil, mepronil, isofetamide, fluopyram, fenfuram, furmecyclox, carboxin, oxycarboxin, tifluzamide, benzovindiflupyr, bixafen, fluxapyroxad, furamethpyr, isopyrazam, penflufen, penthiopyrad, sedaxane and boscalid;

(c) ubiquinol oxidase Qo complex III inhibitors: azoxystrobin, cumoxystrobin, cumethoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyramethostrobin, triclopyricarb, kresoxim-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metominostrobin, orysastrobin, famo Xadon, fluoxastrobin, fenamidone and piribencarb ;

(d) ubiquinol reductase Qi complex III inhibitors: cyazofamide and amisulbrome;

(e) oxidative phosphorylation uncouplers: binapacryl, meptyldinocap, dinocap, fluazinam and ferimzone;

(f) oxidative phosphorylation inhibitors (ATP synthase inhibitors): fentine acetate, fentine chloride and fentine hydroxide;

(g) inhibitors of ATP production: silthiophame;

(h) complex III: Qx (unknown) cytochrome bc1 (ubiquinone reductase) inhibitor: ametoctradine.

[0092]

(4) Amino acid and protein synthesis inhibitors

(a) methionine biosynthesis inhibitors: andoprim, cyprodinil, mepanipyrim and pyrimethanil;

(b) protein synthesis inhibitors: blasticidins, kasugamycin, kasugamycin hydrochloride, streptomycin and oxytetracycline.

[0093]

(5) Signal transduction inhibitors:

(a) signal transduction inhibitors: quinoxifene and proquinazide;

(b) MAP/histidine kinase inhibitors for osmotic signal transduction: fenpiclonil, fludioxonil, clozolinate, iprodione, procymidone and vinclozolin.

[0094]

(6) Lipid and cell membrane synthesis inhibitors:

(a) inhibitors of phospholipid biosynthesis, methyltransferase: edifenphos, iprobenfos, pyrazophos and isoprothiolane;

(b) lipid peroxidation agents: biphenyl, chloroneb, diclorane, quintozene, tecnazene, tolclofos-methyl and etridiazole;

(c) agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fosetylate and prothiocarb;

(d) microorganisms that destroy the cell membranes of pathogens: bacteria Bacillus subtilis , Bacillus subtilis strain QST713, Bacillus subtilis strain FZB24, Bacillus subtilis strain MBI600 and Bacillus subtilis strain D747;

(e) cell membrane disruptors: Melaleuca alternifolia (tea tree) extracts.

[0095]

(7) Inhibitors of cell membrane sterol biosynthesis:

(a) Inhibitors of C14-demethylation in sterol biosynthesis: triforin, pyrifenox, pyrizoxazole, fenarimol, flurprimidol, nuarimol, imazalil, imazalil sulfate, oxpoconazole, pefurazoate, prochloraz, triflumizole, viniconazole, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutra zol, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, quinconazole, simeconazole, tebuconazole, tetraconazole zol, triadimefon, triadimenol, triticonazole, prothioconazole and voriconazole;

(b) inhibitors of Δ14-reductase and sterol-Δ8→Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidine, piperaline and spiroxamine;

(c) inhibitors of 3-ketoreductase during C4-demethylation in the sterol biosynthesis system: fenhexamide and phenpyrazamine;

(d) squalene epoxidase inhibitors in the sterol biosynthesis system: pyributicarb, naftifine and terbinafine.

[0096]

(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.

[0097]

(9) Melanin biosynthesis inhibitors

(a) reductase inhibitors in melanin biosynthesis: phthalide, pyroquilone and tricyclazole;

(b) anhydrase inhibitors in melanin biosynthesis: carpropamide, diclocymet and phenoxanil;

[0098]

(10) Inducers of host plant resistance:

(a) agents acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl;

(b) others: probenazole, tiadinil, isothianil, laminarin and Rhinenutria japonica extracts.

[0099]

(11) Drugs with unknown mechanism of action: cymoxanil, fosetyl aluminum, phosphoric acid (phosphate), teklofthalam, triazoxide, flusulfamide, diclomesine, metasulfocarb, cyflufenamide, metrafenone, pyriophenone, dodine, dodine free base and flutianil.

[0100]

(12) Agents having multiple active sites: copper (copper salt), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, ferbam, mancozeb, maneb, mancopper, metiram, polycarbamate, propineb, thiram, zineb, ciram, captan, captafol, folpet, chlorothalonil, dichlofluanid, tolylfluanid, guazatine, iminoctadine triacetate, iminoctadine trialbesylate, anilazine, dithianone, quinomethionate and fluorimide.

[0101]

(13) Other agents: DBEDC, fluorofolpet, guazatine acetate, bis(8-quinolinolato)copper(II), propamidine, chloropicrin, ciprofuram, Agrobacterium, betoxazine, diphenylamine, methyl isothiocyanate (MITC), mildiomycin, capsaicin, kufraneb, cyprosulfamide, dazomet , debacarb, dichlorfen, diphenzoquat, diphenzoquat methylsulfonate, flumetover, fosetyl calcium, fosetyl sodium, irumamycin, natamycin, nitrotal-isopropyl, oxamocarb, propanosine sodium, pyrrolnitrine, tebufloquin, tolnifanide, zarilamide, algofaz, amicartiazole, oxathiapiproline, methiram cin k, benthiazole, trichlamide, uniconazole, oxyphenthiine and picarbutrazox.

[0102]

Specific examples of a plant growth regulator that can be used as a mixture or in combination with a pest control agent according to the present invention are shown below.

Abscisic acid, kyetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydroseatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetylaminoethoxyvinylglycine (also called aviglycine), amino hydroxyacetic acid, nitrate silver, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichloroprop, phenothiol, 1-naphthyl acetamide, ethylosate, cloxiphonac, maleic acid hydrazide, 2,3, 5-tri-iodobenzoic acid, salicylic acid, methyl salicylate, (−)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4 -(2-phenylethyl)aminobutyric acid, ethephon, chlormequat, mepiquat chloride, benzyladenine and 5-aminolevulinic acid.

[0103]

[Insecticide or acaricide]

The insecticide or acaricide according to the present invention contains at least one active ingredient selected from the (hetero)arylimidazole compounds according to the present invention. The amount of the (hetero)arylimidazole compound contained in the insecticide or acaricide according to the present invention is not particularly limited as long as it exhibits an insecticidal or acaricidal effect.

[0104]

The insecticide or acaricide according to the present invention is preferably used on plants such as cereals; vegetable crops; roots; tubers and roots; flowers and ornamental plants; fruit crops; decorative deciduous plants and trees of tea, coffee, cocoa, etc.; feed crops; lawn grasses; and cotton.

When applied to plants, the pest control agent or insecticide or acaricide according to the present invention can be applied to any site such as a leaf, stem, stalk, flower, bud, fruit, seed, seedling, root, tuber, tuberous root, shoot or cutting .

The insecticide or acaricide according to the present invention is not limited to the particular plant species on which the pest control agent or insecticide or acaricide is applied. As an example of plant species, for example, an original species, a variant species, an improved variety, a cultivar, a mutant, a hybrid, a genetically modified organism (GMO), and the like may be presented.

[0105]

The insecticide or acaricide of the present invention can be applied by seed treatment, foliar application, soil application, dipping application, and the like. for the control of various agricultural insect pests and mites.

[0106]

Specific examples of various agricultural insect pests and mites that can be controlled using the insecticide or acaricide according to the present invention are shown below.

[0107]

(1) Butterflies or moths of the genus Lepidoptera ( Lepidoptera )

(a) moths of the Ursa family ( Arctiidae ), such as Hyphantria cunea and Lemyra imparilis ;

(b) a moth of the family Bucculatricidae , for example Bucculatrix pyrivorella ;

(c) moth of the family Carposinidae , for example Carposina sasakii ;

(d) moths of the family Crambidae, for example Diaphania indica and Diaphania nitidalis of Diaphania species; for example, Ostrinia furnacalis , Ostrinia nubilalis and Ostrinia scapulalis species of Ostrinia ; and Chilo suppressalis , Cnaphalocrocis medinalis , Conogethes punctiferalis , Diatraea grandiosella , Glyphodes pyloalis , Hellula undalis and Parapediasia teterrella ;

(e) moths of the family Gelechiidae , such as Helcystogramma triannullella , Pectinophora gossypiella , Phthorimaea operculella and Sitotroga cerealella ;

(f) moth of the moth family ( Geometridae ), for example Ascotis selenaria ;

(g) moths of the moth family Gracillariidae , such as Caloptilia theivora , Phyllocnistis citrella and Phyllonorycter ringoniella ;

(h) butterflies of the family Hesperiidae , for example Parnara guttata ;

(i) moths of the family Lasiocampidae , for example Malacosoma neustria ;

(j) moths of the Lymantriidae family, such as Lymantria dispar and Lymantria monacha of Lymantria species; and Euproctis pseudoconspersa and Orgyia thyellina ;

[0108]

(k) moths of the family Lyonetiidae , for example Lyonetia clerkella and Lyonetia prunifoliella malinella Lyonetia species;

(l) moths of the family Noctuidae , such as Spodoptera depravata , Spodoptera eridania , Spodoptera exigua , Spodoptera frugiperda , Spodoptera littoralis and Spodoptera litura of Spodoptera species; for example, Autographa gamma and Autographa nigrisigna species of Autographa ; for example, Agrotis ipsilon and Agrotis segetum Agrotis species; for example Helicoverpa armigera , Helicoverpa assulta and Helicoverpa zea Helicoverpa species; for example, Heliothis armigera and Heliothis virescens Heliothis species; and Aedia leucomelas , Ctenoplusia agnata , Eudocima tyrannus , Mamestra brassicae , Mythimna separata , Naranga aenescens , Panolis japonica , Peridroma saucia , Pseudoplusia includens and Trichoplusia ni ;

(m) moth of the family Nolidae ( Nolidae ), for example, Earias insulana ;

(n) butterflies of the family Pieridae , for example Pieris brassicae and Pieris rapae crucivora species of Pieris ;

(o) moths of the family Plutellidae , for example Acrolepiopsis sapporensis and Acrolepiopsis suzukiella Acrolepiopsis species; and Plutella xylostella ;

(p) moths of the family Pyralidae , such as Cadra cautella , Elasmopalpus lignosellus , Etiella zinckenella and Galleria mellonella ;

(q) moths of the family Sphingidae , for example, Manduca quinquemaculata and Manduca sexta species of Manduca ;

[0109]

(r) moth of the family Stathmopodidae, for example Stathmopoda masinissa ;

(s) a moth of the family True moths ( Tineidae ), for example Tinea translucens ;

(t) moths of the family Tortricidae , for example Adoxophyes honmai and Adoxophyes orana species of Adoxophyes ; for example, Archips breviplicanus and Archips fuscocupreanus species of Archips ; and Choristoneura fumiferana , Cydia pomonella , Eupoecilia ambiguella , Grapholitha molesta , Homona magnanima , Leguminivora glycinivorella , Lobesia botrana , Matsumuraeses phaseoli , Pandemis heparana and Sparganothis pilleriana ;

(u) moth of the family Ermine moths ( Yponomeutidae ), for example Argyresthia conjugella .

[0110]

(2) Insect pests of the order Thrips ( Thysanoptera )

(a) insect pests of the family Phlaeothripidae, for example Ponticulothrips diospyrosi ;

(b) insect pests of the family Thripidae , for example Frankliniella intonsa and Frankliniella occidentalis Frankliniella species; for example, Thrips palmi and Thrips tabaci Thrips species; and Heliothrips haemorrhoidalis and Scirtothrips dorsalis .

[0111]

(3) Insect pests of the order Hemiptera ( Hemiptera )

(A) suborder Cycads ( Archaeorrhyncha )

(a) insect pests of the family Delphacidae , for example Laodelphax striatella , Nilaparva talugens , Perkinsiella saccharicida and Sogatella furcifera .

[0112]

(B) suborder Clypeorrhyncha

(a) insect pests of the planthopper family ( Cicadellidae ), such as Empoasca fabae , Empoasca nipponica , Empoasca onukii and Empoasca sakaii of the Empoasca species; and Arboridia apicalis , Balclutha saltuella , Epiacanthus stramineus , Macrosteles strifrons and Nephotettix cinctinceps .

[0113]

(C) suborder Bugs ( Heteroptera )

(a) insect pests of the family Alydidae , for example Riptortus clavatus ;

(b) insect pests of the Coreidae family, such as Cletus punctiger and Leptocorisa chinensis ;

(c) insect pests of the family Lygaeidae , such as Blissus leucopterus , Cavelerius saccharivorus and Togo hemipterus ;

(d) insect pests of the horsefly family ( Miridae ), for example, Halticus insularis , Lygus lineolaris , Psuedatomoscelis seriatus , Stenodema sibiricum , Stenotus rubrovittatus and Trigonotylus caelestialium ;

[0114]

(e) insect pests of the family Pentatomidae , for example Nezara antennata and Nezara viridula species of Nezara ; for example, Eysarcoris aeneus , Eysarcoris lewisi and Eysarcoris ventralis species; and Dolycoris baccarum , Eurydema rugosum , Glaucias subpunctatus , Halyomorpha halys , Piezodorus hybneri , Plautia crossota and Scotinophora lurida ;

(f) insect pests of the red bug family ( Pyrrhocoridae ), for example Dysdercus cingulatus ;

(g) insect pests of the clubweed family ( Rhopalidae ), for example Rhopalus maculatus ;

(h) insect pests of the family Scutelleridae , for example Eurygaster integriceps ;

(i) insect pests of the laceweed family ( Tingidae ), such as Stephanitis nashi .

[0115]

(D) suborder Thoracicidae ( Sternorrhyncha )

(a) insect pests of the Hermes family ( Adelgidae ), for example Adelges laricis ;

(b) insect pests of the Whitefly family ( Aleyrodidae ), such as Bemisia argentifolii and Bemisia tabaci Bemisia species; and Aleurocanthus spiniferus , Dialeurodes citri and Trialeurodes vaporariorum ;

(c) insect pests of the family Aphididae , such as Aphis craccivora , Aphis fabae , Aphis forbesi , Aphis gossypii , Aphis pomi , Aphis sambuci and Aphis spiraecola of Aphis species; for example, Rhopalosiphum maidis and Rhopalosiphum padi Rhopalosiphum species; for example, Dysaphis plantaginea and Dysaphis radicola species of Dysaphis ; for example, Macrosiphum avenae and Macrosiphum euphorbiae Macrosiphum species; for example, Myzus cerasi , Myzus persicae and Myzus varians Myzus species; and Acyrthosiphon pisum , Aulacorthum solani , Brachycaudus helichrysi , Brevicoryne brassicae , Chaetosiphon fragaefolii , Hyalopterus pruni , Hyperomyzus lactucae , Lipaphis erysimi , Megoura viciae , Metopolophium dirhodum , Nasonovia ribisnigri , Phorodon humul i , Schizaphis graminum , Sitobion avenae and Toxoptera aurantii ;

[0116]

(d) insect pests of the family Coccidae , for example Ceroplastes ceriferus and Ceroplastes rubens species of Ceroplastes ;

(e) insect pests of the scale family ( Diaspididae ), Pseudaulacaspis pentagona and Pseudaulacaspis prunicola of Pseudaulacaspis species; for example, Unaspis euonymi and Unaspis yanonensis species of Unaspis ; and Aonidiella aurantii , Comstockaspis perniciosa , Fiorinia theae and Pseudaonidia paeoniae ;

(f) insect pests of the Margarodidae family, such as Drosicha corpulenta and Icerya purchasi ;

(g) insect pests of the Phylloxeridae family, for example Viteus vitifolii ;

(h) insect pests of the family Mealybugs ( Pseudococcidae ), such as Planococcus citri and Planococcus kuraunhiae of Planococcus spp.; and Phenacoccus solani and Pseudococcus comstocki ;

(i) insect pests of the Psyllidae family, such as Psylla mali and Psylla pyrisuga Psylla species; and Diaphorina citri .

[0117]

(4) Insect pests of the suborder Polyphaga beetles

(a) insect pests of the Borer family ( Anobiidae ), for example Lasioderma serricorne ;

(b) insect pests of the Attelabidae family, such as Byctiscus betulae and Rhynchites heros ;

(c) insect pests of the family Bostrichidae , for example Lyctus brunneus ;

(d) insect pests of the family Brentidae , for example Cylas formicarius ;

(e) insect pests of the family Buprestidae , such as Agrilus sinuatus ;

(f) insect pests of the longhorned family ( Cerambycidae ), such as Anoplophora malasiaca , Monochamus alternatus , Psacothea hilaris and Xylotrechus pyrrhoderus ;

(g) insect pests of the family Chrysomelidae , for example Bruchus pisorum and Bruchus rufimanus species of Bruchus ; for example, Diabrotica barberi , Diabrotica undecimpunctata and Diabrotica virgifera species of Diabrotica ; for example Phyllotreta nemorum and Phyllotreta striolata Phyllotreta species; and Aulacophora femoralis , Callosobruchus chinensis , Cassida nebulosa , Chaetocnema concinna , Leptinotarsa decemlineata , Oulema oryzae and Psylliodes angusticollis ;

[0118]

(h) insect pests of the ladybird family ( Coccinellidae ), such as Epilachna varivestis and Epilachna vigintioctopunctata Epilachna spp.;

(i) insect pests of the family Weevils ( Curculionidae ), such as Anthonomus grandis and Anthonomus pomorum Anthonomus spp.; for example, Sitophilus granarius and Sitophilus zeamais Sitophilus species; and Echinocnemus squameus , Euscepes postfasciatus , Hylobius abietis , Hypera postica , Lissohoptrus oryzophilus , Otiorhynchus sulcatus , Sitona lineatus and Sphenophorus venatus ;

(j) insect pests of the click beetle family ( Elateridae ), for example Melanotus fortnumi and Melanotus tamsuyensis Melanotus species;

(k) insect pests of the family Nitidulidae , for example Epuraea domina ;

(l) insect pests of the Scarabaeidae family, such as Anomala cuprea and Anomala rufocuprea of Anomala species; and Cetonia aurata , Gametis jucunda , Heptophylla picea , Melolontha melolontha and Popillia japonica ;

(m) insect pests of the family Scolytidae , for example Ips typographus ;

(n) insect pests of the family Staphylinidae , for example Paederus fuscipes ;

(o) insect pests of the Darkling beetle family ( Tenebrionidae ), such as Tenebrio molitor and Tribolium castaneum ;

(p) insect pests of the Darkling family ( Trogossitidae ), such as Tenebroides mauritanicus .

[0119]

(5) Insect pests of the order Diptera ( Diptera )

(A) suborder Brachycera

(a) insect pests of the family Agromyzidae , for example Liriomyza bryoniae , Liriomyza chinensis , Liriomyza sativae and Liriomyza trifolii of Liriomyza species; and Chromatomyia horticola and Agromyza oryzae ;

(b) insect pests of the Flowerwort family ( Anthomyiidae ), such as Delia platura and Delia radicum of Delia species; and Pegomya cunicularia ;

(c) insect pests of the fruit fly family (Drosophilidae), for example Drosophila melanogaster and Drosophila suzukii of the Drosophila species;

(d) insect pests of the Shorefly family ( Ephydridae ), such as Hydrellia griseola ;

(e) insect pests of the family Psilidae , for example Psila rosae ;

(f) insect pests of the family Tephritidae , for example Bactrocera cucurbitae and Bactrocera dorsalis species of Bactrocera ; for example, Rhagoletis cerasi and Rhagoletis pomonella species of Rhagoletis ; and Ceratitis capitata and Dacus oleae .

[0120]

(B) suborder Longwhiskers ( Nematocera )

(a) insect pests of the family Gall midges ( Cecidomyiidae ), such as Asphondylia yushimai , Contarinia sorghicola, Mayetiola destructor and Sitodiplosis mosellana .

[0121]

(6) Insect pests of the order Orthoptera ( Orthoptera )

(a) insect pests of the Acrididae family, such as Schistocerca americana and Schistocerca gregaria of Schistocerca species; and Chortoicetes terminifera , Dociostaurus maroccanus , Locusta migratoria , Locusta napardalina , Nomadacris septemfasciata and Oxya yezoensis ;

(b) insect pests of the family True crickets ( Gryllidae ), such as Acheta domestica and Teleogryllus emma ;

(c) insect pests of the mole cricket family ( Gryllotalpidae ), for example Gryllotalpa orientalis ;

(d) insect pests of the family True grasshoppers ( Tettigoniidae ), for example Tachycines asynamorus .

[0122]

(7) Ticks ( Acari )

(A) Acaridida of the order Astigmata

(a) mites of the family Acaridae , for example Rhizoglyphus echinopus and Rhizoglyphus robini species of Rhizoglyphus ; for example Tyrophagus neiswanderi , Tyrophagus perniciosus , Tyrophagus putrescentiae and Tyrophagus similis Tyrophagus species; and Acarus siro , Aleuroglyphus ovatus and Mycetoglyphus fungivorus ;

[0123]

(B) Actinedida of the order Prostigmata

(a) mites of the family Spider mites ( Tetranychidae ), for example Bryobia praetiosa and Bryobia rubrioculus species of Bryobia ; for example, Eotetranychus asiaticus , Eotetranychus boreus , Eotetranychus celtis , Eotetranychus geniculatus , Eotetranychus kankitus , Eotetranychus pruni , Eotetranychus shii , Eotetranychus smithi , Eotetranychus suginamensis and Eotetranychus uncatus Eotetranychus species; for example, Oligonychus hondoensis , Oligonychus ilicis , Oligonychus karamatus , Oligonychus mangiferus , Oligonychus orthius , Oligonychus perseae , Oligonychus pustulosus , Oligonychus shinkajii and Oligonychus ununguis Oligonychus species; for example Panonychus citri , Panonychus mori and Panonychus ulmi Panonychus species; for example, Tetranychus cinnabarinus , Tetranychus kanzawai , Tetranychus ludeni , Tetranychus quercivorus , Tetranychus phaselus , Tetranychus urticae , Tetranychus viennensis and Tetranychus evansi Tetranychus species; for example, Aponychus corpuzae and Aponychus firmianae Aponychus species; for example, Sasanychusakitanus and Sasanychuspusillus Sasanychus species; for example, Schizotetranychus celarius , Schizotetranychus longus , Schizotetranychus miscanthi , Schizotetranychus recki and Schizotetranychus schizopus Schizotetranychus species; and Tetranychina harti , Tuckerella pavoniformis and Yezonychus sapporensis ;

[0124]

(b) ticks of the family Tenuipalpidae , for example Brevipalpus lewisi , Brevipalpus obovatus , Brevipalpus phoenicis , Brevipalpus russulus and Brevipalpus californicus species of Brevipalpus ; for example, Tenuipalpus pacificus and Tenuipalpus zhizhilashviliae Tenuipalpus species; 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 species; for example, Eriophyes chibaensis and Eriophyes emarginatae species of Eriophyes ; for example, Aculops lycopersici and Aculops pelekassi Aculops species; for example, Aculus fockeui and Aculus schlechtendali Aculus species; and Acaphylla theavagrans , Calacarus carinatus , Colomerus vitis , Calepitrimerus vitis , Epitrimerus pyri , Paraphytoptus kikus , Paracalacarus podocarpi and Phyllocotruta citri ;

(d) ticks of the family Tarsonemidae , for example Tarsonemus bilobatus and Tarsonemus waitei species of Tarsonemus ; and Phytonemus pallidus and Polyphagotarsonemus latus ;

(e) ticks of the family Penthaleidae , for example Penthaleus erythrocephalus and Penthaleus major of Penthaleus species.

[0125]

[Ectoparasite Control Agent]

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.

[0126]

As an example of a host animal to be treated with the ectoparasite control agent of the present invention, there may be a warm-blooded animal such as a human and a farm mammal (for example, a cow, a horse, a pig, a sheep and a goat), a laboratory animal (for example, a mouse , rat and gerbil), pet (eg hamster, guinea pig, dog, cat, horse, squirrel, rabbit and ferret), wild and zoo mammals (eg monkey, fox, deer and buffalo), poultry (eg turkey, duck, chicken, quail and goose) and poultry (such as pigeon, parrot, mynah, parakeet, parakeet, Japanese finch and canary); and fish such as salmon, trout and carp. Additionally, examples may include bee, stag beetle, and beetle.

[0127]

The ectoparasite control agent of the present invention can be administered by a known veterinary method (by topical, oral, parenteral or subcutaneous administration). As a corresponding method, a method of orally administering tablets, capsules, feed, etc. containing an ectoparasite control agent to animals is used; a method of administering an ectoparasite control agent through dipping liquids, suppositories, injection (intramuscular, subcutaneous, intravenous or intraperitoneal injection, etc.), etc. animals; a method of local administration of oily or aqueous liquid formulations by spraying, distribution, spot application, etc.; and a method of mixing an ectoparasite control agent with a resin, molding the mixed product into a suitable shape, such as a collar or ear tag, and attaching it to animals for topical administration; and so on.

[0128]

Ectoparasites parasitize the body or body surface of host animals, especially warm-blooded animals. In particular, ectoparasites parasitize the back, armpits, lower abdomen, inner thighs, etc. animal hosts and live by obtaining nutrients such as blood or exfoliated skin from animals. Examples of ectoparasites include ticks, lice, fleas, mosquitoes, flies, blowflies, etc. Specific examples of an ectoparasite that can be controlled by the ectoparasite control agent of the present invention are shown below.

[0129]

(1) Ticks ( Acari )

ticks of the family Dermanyssidae , ticks of the family Macronyssidae , ticks of the family Laelapidae , ticks of the family Varroidae , ticks of the family Argasidae , ticks of the family Ixodidae , ticks of the family Psoroptidae , ticks of the family Sarcoptidae , ticks of the family Knemidokoptidae , ticks of the family Demodixidae , ticks of the family Trombicul idae and insect-parasitic mites, such like mites of the family Canestriniidae .

(2) Order Lice and lice ( Phthiraptera )

lice of the family Haematopinidae , lice of the family Linognathidae , lice of the family Menoponidae , lice of the family Philopteridae and lice of the family Trichodectidae .

(3) Order Fleas ( Siphonaptera )

fleas of the family Pulicidae , such as Ctenocephalides canis and Ctenocephalides felis Ctenocephalides species;

fleas of the family Tungidae , fleas of the family Ceratophyllidae and fleas of the family Leptopsyllidae .

(4) Order Hemiptera ( Hemiptera )

(5) Insect pests of the order Diptera ( Diptera )

mosquitoes of the family Culicidae , midges of the family Simuliidae , midges of the family Ceratopogonidae , horseflies of the family Tabanidae , flies of the family Muscidae , tsetse flies of the family Glossinidae , gray blowflies of the family Sarcophagidae , bloodsucking flies of the family Hippoboscidae , flies of the family Calliphoridae and botflies of the family Oestridae .

[0130]

[Endoparasite Control Agent or Expellant]

The agent for controlling endoparasites or removing endoparasites (expellant) according to the present invention contains at least one active ingredient selected from the (hetero)arylimidazole compounds according to the present invention. The amount of the (hetero)arylimidazole compound contained in the endoparasite control agent or expellant according to the present invention is not particularly limited as long as its endoparasite control effect is exhibited.

[0131]

The parasite that is the target of the endoparasite control agent or excipient of the present invention is a parasite in the host animal, in particular a warm-blooded animal or fish (endoparasite). As an example of an animal host in which the endoparasite control agent or excipient of the present invention is effective, there may be a warm-blooded animal such as a human and a farm mammal (for example, a cow, a horse, a pig, a sheep and a goat), a laboratory animal ( e.g. mouse, rat and gerbil), pet (e.g. hamster, guinea pig, dog, cat, horse, squirrel, rabbit and ferret), wild and zoo mammals (e.g. monkey, fox, deer and buffalo), poultry (eg turkey, duck, chicken, quail and goose) and poultry (eg pigeon, parrot, mynah, parakeet, parakeet, Japanese finch and canary); and fish such as salmon, trout and carp. Parasitic infestations caused by parasites can be prevented or treated by controlling and expelling the parasites.

[0132]

An example of a parasite that needs to be controlled or expelled includes the following.

(1) Nematodes of the order Dioctophymatida

(a) kidney helminths of the family Dioctophymatidae , for example Dioctophyma renale species of Dioctophyma ;

(b) kidney helminths of the family Soboliphymatidae , for example Soboliphyme abei and Soboliphyme baturini Soboliphyme species.

[0133]

(2) Nematodes of the order Trichocephalida

(a) Trichinella of the family Trichinellidae, for example Trichinella spiralis Trichinella species;

(b) whipworms of the family Trichuridae , such as Capillaria annulata , Capillaria contorta , Capillaria hepatica , Capillaria perforans , Capillaria plica and Capillaria suis Capillaria species; and Trichuris vulpis , Trichuris discolor , Trichuris ovis , Trichuris skrjabini and Trichuris suis Trichuris species.

[0134]

(3) Nematodes of the order Rhabditida

eels of the family Strongyloididae , such as Strongyloides papillosus, Strongyloides planiceps , Strongyloides ransomi , Strongyloides suis , Strongyloides stercoralis , Strongyloides tumefaciens and Strongyloides ratti of the Strongyloides species.

[0135]

(4) Nematodes of the order Strongylida

hookworms of the family Ancylostomatidae , such as Ancylostoma braziliense , Ancylostoma caninum , Ancylostoma duodenale and Ancylostoma tubaeforme Ancylostoma species; Uncinaria stenocephala species of Uncinaria ; and Bunostomum phlebotomum and Bunostomum trigonocephalum Bunostomum species.

[0136]

(5) Nematodes of the order Strongylida

(a) nematodes of the family Angiostrongylidae , for example Aelurostrongylus abstrusus Aelurostrongylus species; and Angiostrongylus vasorum and Angiostrongylus cantonesis Angiostrongylus species;

(b) nematodes of the family Crenosomatidae , for example Crenosoma aerophila and Crenosoma vulpis Crenosoma species;

(c) nematodes of the family Filaroididae , for example Filaroides hirthi and Filaroides osleri Filaroides spp.;

(d) lung nematodes of the family Metastrongylidae , for example Metastrongylus apri , Metastrongylus asymmetricus , Metastrongylus pudendotectus and Metastrongylus salmi Metastrongylus species;

(e) nematodes of the family Syngamidae , for example Cyathostoma bronchialis Cyathostoma spp.; and Syngamus skrjabinomorpha and Syngamus trachea of Syngamus species.

[0137]

(6) Nematodes of the order Strongylida

(a) nematodes of the family Molineidae , for example Nematodirus filicollis and Nematodirus spathiger species of Nematodirus ;

(b) nematodes of the family Dictyocaulidae , for example Dictyocaulus filaria and Dictyocaulus viviparus species of Dictyocaulus ;

(c) nematodes of the family Haemonchidae , for example Haemonchus contortus species of Haemonchus ; and Mecistocirrus digitatus Mecistocirrus species;

(d) nematodes of the family Haemonchidae , for example Ostertagia ostertagi species of Ostertagia ;

(e) nematodes of the family Heligmonellidae , for example Nippostrongylus braziliensis Nippostrongylus species;

(f) nematodes of the family Trichostrongylidae , for example Trichostrongylus axei , Trichostrongylus colubriformis and Trichostrongylus tenuis Trichostrongylus species; Hyostrongylus rubidus Hyostrongylus species; and Obeliscoides cuniculi Obeliscoides species.

[0138]

(7) Nematodes of the order Strongylida

(a) nematodes of the family Chabertiidae , for example Chabertia ovina species of Chabertia ; and Oesophagostomum brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum , Oesophagostomum georgianum , Oesophagostomum maplestonei , Oesophagostomum quadrispinulatum , Oesophagostomum radiatum , Oesophagostomum venulosum and Oesophagostomum watanabei Oesophagostomum species;

(b) nematodes of the family Stephanuridae , for example Stephanurus dentatus Stephanurus spp.;

(c) nematodes of the family Strongylidae , for example, Strongylus asini , Strongylus edentatus , Strongylus equinus and Strongylus vulgaris species of Strongylus .

[0139]

(8) Nematodes of the order Oxyurida

nematodes of the family Oxyuridae , such as Enterobius anthropopitheci and Enterobius vermicularis Enterobius species; Oxyuris equi Oxyuris species; and Passalurus ambiguous species of Passalurus .

[0140]

(9) Nematodes of the order Ascaridida

(a) nematodes of the family Ascaridiidae , for example, Ascaridiagalli species of Ascaridia ;

(b) nematodes of the family Heterakidae , for example Heterakis beramporia , Heterakis brevispiculum , Heterakis gallinarum , Heterakis pusilla and Heterakis putaustralis Heterakis species;

(c) nematodes of the family Anisakidae , for example Anisakis simplex Anisakis species;

(d) nematodes of the family Ascarididae , for example Ascaris lumbricoides and Ascaris suum Ascaris species; and Parascaris equorum Parascaris species;

(e) nematodes of the family Toxocaridae , such as Toxocara canis , Toxocara leonina , Toxocara suum , Toxocara vitulorum and Toxocara cati of Toxocara spp.

[0141]

(10) Nematodes of the order Spirurida

(a) nematodes of the family Onchocercidae , for example Brugia malayi , Brugia pahangi and Brugia patei species of Brugia ; Dipetalonema reconditum Dipetalonema species; Dirofilaria immitis species of Dirofilaria ; Filaria oculi Filaria species; and Onchocerca cervicalis , Onchocerca gibsoni and Onchocerca gutturosa species of Onchocerca ;

(b) nematodes of the family Setariidae , such as Setaria digitata , Setaria equina , Setaria labiatopapillosa and Setaria marshalli of Setaria species; and Wuchereria bancrofti species of Wuchereria ;

(c) nematodes of the family Filariidae , for example Parafilaria multipapillosa species of Parafilaria ; and Stephanofilaria assamensis , Stephanofilaria dedoesi , Stephanofilaria kaeli , Stephanofilaria okinawaensis and Stephanofilaria stilesi of Stephanofilaria species.

[0142]

(11) Nematodes of the order Spirurida

(a) nematodes of the family Gnathostomatidae , for example Gnathostoma doloresi and Gnathostoma spinigerum Gnathostoma species;

(b) nematodes of the family Habronematidae , for example Habronema majus , Habronema microstoma and Habronema muscae Habronema spp.; and Draschia megastoma species of Draschia ;

(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 rara , Physaloptera sibirica and Physaloptera vulpineus Physaloptera species;

(d) nematodes of the family Gongylonematidae , for example Gongylonema pulchrum Gongylonema species;

(e) nematodes of the family Spirocercidae, for example Ascarops strongylina Ascarops species;

(f) nematodes of the family Thelaziidae , for example, Thelazia callipaeda , Thelazia gulosa , Thelazia lacrymalis , Thelazia rhodesi and Thelazia skrjabini of Thelazia species.

[0143]

[Remedy for controlling other pests]

The (hetero)arylimidazole compound of the present invention further provides excellent control of insect pests that have a sting or venom and cause harm to humans and animals, pest insects that spread various pathogens or disease-causing microbes, or pest insects that cause human discomfort. (toxic pests, hygiene pests, nuisance pests, etc.).

[0144]

Specific examples of these are shown below.

(1) Insect pests of the order Hymenoptera ( 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 .

[0145]

(2) Other insect pests

Cockroaches (Blattodea), termites, spiders (Araneae), labiopods, bipedal centipedes, crustaceans and bed bugs (Cimex lectularius).

[0146]

[Seed treatment agent or vegetative propagation organ treatment agent]

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

[0147]

Vegetative propagation organ means a root, stem, leaf of a plant, etc., which has the ability to grow when separated from the plant and placed in soil. As an example of a vegetative propagation organ, there may be, for example, a tuberous root, a creeping root, a bulb, a corm or hard bulb, a tuber, a rhizome, a stolon, a rhizophore, reed cuttings, a sprout and a stem cutting. The stolon is also called the antennae. The sprout is also called an onion and is divided into a mother bud and an aerial bulb. Stem cutting means the shoot (general name for leaves and stems) of sweet potato, Japanese yam, etc. The bulb, corm or hard bulb, tuber, rhizome, reed stalk, rhizophore and tuberous root are also collectively called flower bulb. Growing tubers and roots begins with planting the tubers in the soil. The tubers used are usually called seed tubers.

[0148]

The seed treatment or vegetative propagation treatment of the present invention refers to a preparation, such as a wettable powder, wettable granules, flowable concentrate or dust, prepared by mixing at least one active ingredient selected from the (hetero)arylimidazole compounds of the present invention. the invention, with a suitable solid carrier or liquid carrier and, if necessary, adding a surfactant or other auxiliary substances to the mixture. The composition may also include a binder. An example of a composition containing a binder is a flowable concentrate (FS) for seed treatment.

[0149]

An adhesive substance is used as a binder, which does not have a phytotoxic effect on plant seeds or vegetative propagation organs. In particular, at least one substance selected from the group consisting of polyvinyl acetate, polyvinyl alcohol, cellulose, including ethylcellulose, methylcellulose, hydroxymethylcellulose, hydroxypropylcellulose and carboxymethylcellulose, polyvinylpyrrolidone, starch, modified starch, dextrin, maltodextrin, polysaccharides, including alginate, may be used. and chitosan, proteins including gelatin and casein, gum arabic, shellac, calcium lignosulfonate and methacrylamide monomer.

[0150]

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 an example of a method for treating a seed tuber with a (hetero)arylimidazole compound, dip treatment, aerosol coating, coating and the like can be cited. For planting seed tubers using a tractor, the seed tubers can be treated by applying an aerosol of a chemical containing a (hetero)arylimidazole compound to the seed tubers on a tractor.

[0151]

[Granular agrochemical composition for treating paddy rice cassettes]

The granular agrochemical composition for treating paddy rice cassettes (hereinafter referred to as "granular agrochemical composition") according to the present invention contains at least one active ingredient selected from the (hetero)arylimidazole compounds according to the present invention. The amount of the (hetero)arylimidazole compound contained in the granular agrochemical composition according to the present invention is not particularly limited as long as its control effect is exhibited.

[0152]

The granular agrochemical composition can be produced by various methods, but it is produced, for example, by extrusion granulation and the like. a powder composition containing a combination of one or more active ingredients with a surfactant, a binder and an inorganic carrier, etc., if necessary, using a wet granulation method. More specifically, the active ingredient in the form of particles of a given size was uniformly mixed with the desired surfactant, binder and inorganic carrier. An appropriate amount of water is then added to the mixture, the mixture is mixed, formed by open cell extrusion and dried to obtain a granular agrochemical composition. The pore size used in this operation is generally preferably from 0.5 mm to 1.5 mm.

[0153]

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

[0154]

The granular agrochemical composition optionally combines a surfactant, a binder and an inorganic carrier. Of these, as an example of a surfactant, there can be mentioned, for example, a nonionic surfactant such as polyethylene glycol higher fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene arylphenyl ether and sorbitan monoalkylate; anionic surfactant such as alkylaryl sulfonate, dialkylsulfonate, alkyl sulfuric ester salt, alkyl phosphate ester salt, alkylaryl sulfuric ester salt, alkyl aryl phosphate ester salt, polyoxyethylene alkyl sulfuric ester salt, salt naphthalene sulfonic acid and its condensate, lignin sulfonic acid salt, polycarboxylic acid polymer surfactant such as acrylic acid-iteaconic acid copolymer or methacrylic acid-iteaconic acid copolymer, maleic acid-styrene copolymer, maleic acid-diisobutylene copolymer and salts thereof with alkali metals; polyoxyethylene arylphenyl phosphate ester salt; polyoxyethylene arylphenyl sulfuric ester salt and the like. The added amount of such surfactant is generally from 0.1 part by weight to 5 parts by weight, although the amount is not particularly limited.

[0155]

As an example of the binder combined in the granular agrochemical composition, there may be mentioned, for example, metal salts of carboxymethylcellulose, polyvinyl alcohol, pregelatinized starch, dextrin, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, metal salt of polyacrylic acid, and the like. The amount of binder included is generally from 0.1 part by weight to 5 parts by weight, although the amount is not particularly limited. The inorganic carrier incorporated into the granules is not particularly limited. For example, clays, calcium carbonate, talc, diatomaceous earth, zeolite, attapulgite, gypsum, porcelain stone, etc. are examples.

[0156]

[Tillage agent]

The soil treatment of the present invention is, for example, a method of direct control of pests by applying the active ingredient to the rhizospheres of plants to be protected from harm such as eating by pests, or of controlling pests by penetrating and transporting the active ingredient into the plants from their roots, etc. .P. In particular, for example, treatment of the planting hole (spraying the planting hole and applying to the soil in the planting hole), treating the roots of plants (spraying the root of plants, applying to the soil of the root of plants, irrigating the roots of plants and treating the root of plants in the second half of the period of growing seedlings), treatment of the seed furrow (spraying the seed furrow and applying it to the soil in the seed furrow), processing the planting row (spraying the planting row, applying it to the soil of the planting row and spraying the planting row during the growing season), processing the planting row during sowing (spraying the planting row during sowing and introducing the planting row into the soil during sowing), surface tillage (spraying onto the soil and applying to the soil by area), tillage of the soil strip, submerged treatment (submerged application by area and application to submerged in greenhouses), other types of soil spraying (spraying granules on foliage during the growing season, spraying under tree crowns or around main stems, spraying the soil surface, applying to the soil surface, spraying seed holes, spraying the surface of arable furrows and spraying between rows) , other irrigation methods (soil irrigation, irrigation during seedling growth, chemical injection treatment, irrigation on the root part of the plant, drip irrigation with chemicals and application of chemicals with watering), processing of seedling cassettes (spraying of seedling cassettes, irrigation of seedling cassettes and immersion seedling trays in a chemical solution), treating seedling trays (spraying seedling trays, irrigating seedling trays and immersing seedling trays in a chemical solution), treating seedling areas (spraying seedling areas, irrigating seedling areas, spraying flooded areas with seedlings), immersion of seedlings, treatment by adding to the soil for seedlings (introducing into the soil of a hole with seeds and adding to the soil for digging), spraying before digging in with soil when sowing, spraying after digging in with soil when sowing, treating stems by injection, treating the trunk by injection, trunk spraying and other treatments (ploughing, surface soil application, drip line application, planting point treatment, granule spraying on flower areas and mixing paste fertilizers).

[0157]

[Bait]

The decoy 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 decoy agent of the present invention is not particularly limited as long as its control effect is exhibited.

[0158]

The bait agent of the present invention may optionally contain a palatability enhancing component such as a sugar, a carbohydrate or a milk component, a synergist, an aversive agent to prevent accidental eating, a preservative, a flavoring agent, an attractant and the like. The decoy agent of the present invention can generally be prepared by mixing the (hetero)arylimidazole compound with water and, if necessary, other components described above. In the manufacture of the decoy 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.

[0159]

As an example of a pest that can be effectively controlled using the bait agent of the present invention, 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 , borer beetle such as Lasioderma serricorne and Stegobium paniceum , mealworm such as Tribolium castaneum and Tribolium confusum , flat beetle such as Oryzaephilus surinamensis and Cryptolestes pusillus , termite such as Coptotermes formosanus and Reticulitermes speratus , and fly, such as Musca domestica , Fannia canicularis , Phoridae and Phlebotominae , as well as mosquitoes such as Culex pipiens , Aedes albopictus , malaria mosquitoes and bell mosquitoes.

[0160]

The bait agent of the present invention can be applied directly or by impregnating, for example, non-woven material, sponge, absorbent cotton and the like. This aqueous bait agent or non-woven material, sponge, absorbent cotton, etc., impregnated with the bait agent is placed in a container such as a cup, tray or bottle, and the pests are driven out. In this regard, an insect pest expelling device which is equipped with a container that is closed from the outside and has some space in which the pest insects can be present while eating the bait agent according to the present invention generally improves eating and is thus effective .

[0161]

[Plant growth stimulator]

The plant growth stimulator 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 plant growth promoting effect is exhibited.

[0162]

In the plant growth promoter of the present invention, other components, a carrier and the like may be suitably combined as necessary.

The (hetero)arylimidazole compound of the present invention can be used alone as a plant growth stimulant, but generally can be used as a formulation in dosage form, such as a wettable powder, liquid formulation, oil formulation, dust, granular formulation or suspension concentrate (flowable), by mixing the (hetero)arylimidazole compound as the active ingredient with conventional formulation auxiliaries, such as a solid carrier, a liquid carrier, a dispersant, a diluent, an emulsifier, a spreading agent and a thickener.

[0163]

As an example of the solid carrier or liquid carrier, for example, talc, clay, bentonite, kaolin, diatomite, 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, ethylene glycol, benzyl alcohol, etc.), petroleum fraction (petroleum ether, kerosene, petroleum solvent, etc. .), aliphatic or alicyclic hydrocarbons (n-hexane, cyclohexane, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, chlorobenzene, cumene, methylnaphthalene, etc.), halogenated hydrocarbons (chloroform, dichloromethane and etc.), ethers (isopropyl ether, ethylene oxide, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyl 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 ethers (monomethyl ether ethylene glycol, ethylene glycol monoethyl ether, etc.) etc.

[0164]

As an example of the excipient, for example, nonionic surfactant (polyoxyethylene alkyl ether, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene sorbitan alkyl ether, sorbitan alkyl ether, etc.), anionic surfactant (alkyl benzene sulfonate, alkyl sulfosuccinate, polyoxyethylene arylsulfonate, etc.), cationic surfactant (alkylamines, polyoxyethylene alkylamines, quaternary ammonium salts, etc.), amphoteric surfactant (alkylaminoethylglycine, alkyldimethylbetaine, etc.), polyvinyl alcohol, hydroxypropylcellulose, carboxymethylcellulose , gum arabic, tragacanth, xanthan gum, polyvinyl acetate, gelatin, casein, sodium alginate, etc.

[0165]

As examples of other components, there may be other active ingredients such as a fungicide, an insecticide or acaricide, a nematicide and a pesticide against soil insect pests described above; plant growth regulator, synergist, fertilizer, soil improver, animal feed, etc.

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

[0166]

The plant on which the plant growth stimulator is to be applied is not particularly limited. For example, cereals of the family Poaceae , such as rice, barley, wheat, Japanese millet, corn and mogar, can be specified; vegetables such as pumpkin, turnips, cabbage, daikon radish, bok choy, spinach, bell peppers and tomatoes; flowers and ornamental plants such as chrysanthemum, gerbera, pansy, orchid, peony and tulip; beans such as adzuki, kidney beans, soybeans, peanuts, fava beans and peas; tubers and root vegetables such as potatoes, sweet potatoes, eddo, Japanese yams and taro; onions such as green onions, onions and Chinese onions, etc.

[0167]

As for the application method of the plant growth stimulator according to the present invention, it is possible to apply to plants (foliar application), apply to plant growing soil (soil application), apply to water in a rice field (submerged application), apply to seeds (seed treatment), etc.

[0168]

The applied amount of the plant growth promoter according to the present invention varies depending on the plant on which the plant growth promoter is applied, etc., but ranges from 1 to 10,000 ppm. in terms of the concentration of the active ingredient and preferably from 50 to 300 l/10 refers to a solution containing from 10 to 1000 ppm. of active ingredient for foliar application, preferably from 0.1 to 1000 g/10, and particularly preferably from 10 to 100 g/10 of active ingredient for soil application and submerged application. Furthermore, for seed treatment, it is preferable to apply 0.001 to 50 g of active ingredient per kg of seed.

[0169]

[Production of compositions]

Certain preparations of the pest control agent, insecticide or acaricide, ectoparasite control agent or endoparasite control agent or expellant according to the present invention will be indicated. However, the additives and additive ratios should not be limited to these examples and may vary widely. The term "part" in the composition of drugs means part by weight.

[0170]

Next, preparations for agriculture or horticulture and rice cultivation will be shown.

[0171]

(Composition 1: Wettable powder)

40 parts of the (hetero)arylimidazole compound of the present invention, 53 parts of diatomaceous earth, 4 parts of a higher alcohol sulfuric acid ester and 3 parts of an alkyl naphthalene sulfonate were uniformly mixed and ground finely to obtain a wettable powder containing 40% of the active ingredient.

[0172]

(Composition 2: Emulsion)

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

[0173]

(Composition 3: Granular composition)

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 were mixed uniformly, finely ground, and then granulated to obtain a granular form with a diameter of 0.5-1.0 mm, obtaining a granular composition containing 5% of the active ingredient.

[0174]

(Composition 4: Granular composition)

5 parts of the (hetero)arylimidazole compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of sodium dioctyl sulfosuccinate and 1 part of potassium phosphate were thoroughly ground and mixed, and after adding water, the mixture was thoroughly mixed, then granulated and dried to obtain a granular composition , containing 5% active ingredient.

[0175]

(Composition 5: Suspension)

10 parts of the (hetero)arylimidazole compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of sodium salt of polycarboxylic acid, 10 parts of glycerin, 0.2 parts of xanthan gum and 73.8 parts of water were mixed and wet ground until the particle size became equal to 3 microns or less, resulting in a suspension containing 10% active ingredient.

[0176]

Next, preparations of an ectoparasite control agent or an endoparasite control agent or expellant will be shown.

[0177]

(Ingredient 6: Granules)

5 parts of the (hetero)arylimidazole compound of the present invention were dissolved in an organic solvent to prepare a solution. The solution was sprayed onto 94 parts kaolin and 1 part white soot. The solvent was then evaporated under reduced pressure. This type of kibble can be mixed into animal feed.

[0178]

(Composition 7: Injectable filler)

From 0.1 to 1 part of the (hetero)arylimidazole compound of the present invention and from 99 to 99.9 parts of peanut oil were uniformly mixed and then sterilized by filtration through a sterilizing filter.

[0179]

(Composition 8: Distribution Composition)

5 parts of the (hetero)arylimidazole compound of the present invention, 10 parts of myristic acid ester and 85 parts of isopropanol were mixed homogeneously to obtain a distribution composition.

[0180]

(Formulation 9: Spot-on composition)

10-15 parts of the (hetero)arylimidazole compound of the present invention, 10 parts of palmitic acid ester and 75-80 parts of isopropanol were homogeneously mixed to obtain a spot application composition.

[0181]

(Composition 10: Spray composition)

1 part of the (hetero)arylimidazole compound of the present invention, 10 parts of propylene glycol and 89 parts of isopropanol were mixed uniformly to prepare a spray composition.

[0182]

Hereinafter, the present invention will be more specifically described with reference to Compound Examples. However, the present invention is in no way limited to the following Compound Examples.

[0183]

[Example 1]

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 (compound d-2)

[0184]

(Step 1) Synthesis of 5-bromo-3-(ethylthio)picolinonitrile

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

¹ H-NMR of the resulting title compound is shown below.

¹ H-NMR (CDCl ₃ ) δ: 8.50 (1H, d), 7.83 (1H, d), 3.07 (2H, q), 1.41 (3H, t).

[0185]

(Step 2) Synthesis of 5-bromo-3-(ethylsulfonyl)picolinonitrile

5-Bromo-3-(ethylthio)picolinonitrile (149 g) was dissolved in dichloromethane (1800 ml), 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 resulting solution was poured into a mixed solution of saturated aqueous sodium bicarbonate and saturated aqueous sodium thiosulfate and extracted with dichloromethane. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to obtain 167 g of the title compound (yield: 99%).

¹ H-NMR of the resulting title compound is shown below.

¹ H-NMR (CDCl ₃ ) δ: 9.26 (1H, d), 8.72 (1H, d), 3.60 (2H, q), 1.23 (3H, t).

[0186]

(Step 3) Synthesis of 2-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-1-methyl-1H-imidazole-5-carbaldehyde

5-Bromo-3-(ethylsulfonyl)picolinonitrile (20 g) was dissolved in methanol (220 ml). Approximately 5 M sodium methoxide in methanol (1.5 ml) was added dropwise to the solution and the mixture was stirred overnight at room temperature. Methylamine hydrochloride (4.9 g) was added to the mixture, and the mixture was heated and stirred for 2 hours under reflux. Triethylamine (30 ml) was added to this mixture to obtain solution A.

Separately, 5-bromoaldehyde (16.5 g) and isopropanol (220 ml) were mixed and stirred at 50°C for 1 hour to obtain solution B.

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

¹ H-NMR of the resulting title compound is shown below.

¹ H-NMR (CDCl ₃ ) 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).

[0187]

(Step 4) Synthesis of 2-(5-cyclopropyl-3-(ethylsulfonyl)-pyridin-2-yl)-1-methyl-1H-imidazole-5-carbaldehyde

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 filled reaction vessel with argon. The solution was then stirred at room temperature. Potassium cyclopropyl trifluoroborate (0.36 g), palladium (II) acetate (0.043 g), 20% tricyclohexylphosphine solution in toluene (0.54 g), tripotassium phosphate (0.82 g) and water (0.48 ml) were added to the solution ) and stirred the mixture at 110°C for 7 hours. The resulting solution was poured into water and extracted with ethyl acetate. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to obtain 0.27 g of the title compound (yield: 88%).

¹ H-NMR of the resulting title compound is shown below.

¹ H-NMR (CDCl ₃ ) δ: 9.84 (1H, s), 8.70 (1H, d), 8.02 (1H, d), 7.82 (1H, s), 3.84 ( 3H, s), 3.70 (2H, k), 2.12-2.06 (1H, m), 1.31 (3H, t), 1.28-1.23 (2H, m), 0 .95-0.91 (2H, m).

[0188]

(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

In the 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 stirred the solution 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 filled the reaction vessel with argon, followed by stirring overnight at 60°C. The resulting solution was poured into a 10% aqueous solution of Rochelle salt and extracted with ethyl acetate. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to obtain 0.23 g of the title compound (E/Z=17:83, yield: 59%).

¹ H-NMR and ¹⁹ F-NMR of the resulting title compound are shown below.

^1H -NMR (400 MHz, CDCl ₃ ) (E/Z mixture) 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); ¹⁹ F-NMR (376 MHz, CDCl ₃ -C ₆ F ₆ ): δ -63.5 (d) for (E)-isomer and -68.4 (s) for (Z)-isomer.

[0189]

[Example 2]

Synthesis of 1-(6-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridine -3-yl)cyclopropan-1-carbonitrile (compound d-15)

[0190]

(Step 1) Synthesis of 2-(5-(1,3-dioxolan-2-yl)-1-methyl-1H-imidazol-2-yl)-5-bromo-3-(ethylsulfonyl)pyridine

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 this solution and the mixture was heated and stirred overnight under reflux using a Dean-Stark apparatus. The resulting solution was poured into a saturated aqueous sodium bicarbonate solution and extracted with chlorform. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to obtain 8.5 g of the title compound (yield: 96%).

¹ H-NMR of the resulting title compound is shown below.

¹ H-NMR (CDCl ₃ ) 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).

[0191]

(Step 2) Synthesis of 2-(6-(5-(1,3-dioxolan-2-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3-yl)acetonitrile

In the 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 filled the reaction vessel with argon. The solution was then stirred at room temperature. Trimethylsilylacetonitrile (0.98 g), tris(dibenzylideneacetone)dipalladium (0) (0.40 g), xanthos (0.50 g) and zinc fluoride (0.27 g) were added to the solution and the mixture was stirred at 100°C in within 3 hours. The resulting solution was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to obtain 0.51 g of the title compound (yield: 42%).

¹ H-NMR of the resulting title compound is 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, k), 3.65 (3H, s), 1, 33 (3H, t).

[0192]

(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

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 mixture, 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 resulting solution was poured into water and extracted with ethyl acetate. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to obtain 0.29 g of the title compound (yield: 54%).

¹ H-NMR of the resulting title compound is shown below.

^1H -NMR (CDCl ₃ ) 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).

[0193]

(Step 4) Synthesis of 1-(5-(ethylsulfonyl)-6-(5-formyl-1-methyl-1H-imidazol-2-yl)pyridin-3-yl)cyclopropan-1-carbonitrile

1-(6-(5-(1,3-Dioxolan-2-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3-yl)cyclopropan-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 resulting solution was poured into a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to obtain 0.23 g of the title compound (yield: 54%).

¹ H-NMR of the resulting title compound is shown below.

¹ H-NMR (CDCl ₃ ) 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).

[0194]

(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

In the reaction vessel, 1-(5-(ethylsulfonyl)-6-(5-formyl-1-methyl-1H-imidazol-2-yl)pyridin-3-yl)cyclopropan-1-carbonitrile (0.23 g) was dissolved in N,N-dimethylformamide (10 ml) and stirred the solution at room temperature. To this solution was added 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) and filled the reaction vessel with argon, followed by stirring overnight at 60°C. The resulting solution was poured into a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to obtain 0.09 g of the title compound (E/Z=18:82, yield: 30%).

¹ H-NMR and ¹⁹ F-NMR of the resulting title compound are shown below.

^1H -NMR (400 MHz, CDCl ₃ ) (E/Z mixture) 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, CDCl ₃ -C ₆ F ₆ ): δ -63.5 (s) for (E)-isomer and -68.5 (s) for (Z)-isomer.

[0195]

Some compounds of the present invention, prepared in the same way 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). The tables also show the properties or melting point (Tm) as the physical properties of each compound.

In Table 1, Me is a methyl group, Et is an ethyl group, ^C Pr is a cyclopropyl group, and ^c Pen is a cyclopentyl group.

[0196]

[0197]

Table 1

Conn. X B ¹ R ¹ R ² R Configuration Physical properties d-1 5- ^c Pr N _SO2Et Me CH=CHCF ₂ CF ₃ E Tp:142-143(°C) d-2 5- ^c Pr N _SO2Et Me CH=C(CI)CF ₃ E/Z Tp:180-182(°C) d-3 5- ^c Pr CH _SO2Et Me CH=HCF ₂ CF ₂ CF ₂ E Tp:149-151(°C) d-4 5- ^c Pr N _SO2Et Me CH=CHCF ₂ CF ₂ CF ₂ CF ₃ E Tp:110-112(°C) d-5 5- ^c Pr CH _SO2Et Me CH=CHCF ₂ CF ₃ E Tp:154-156(°C) d-6 5- ^c Pr CH SEt Me CH=C(CI)CF ₃ E/Z viscous oil d-7 5- ^c Pr CH _SO2Et Me CH=C(CI)CF ₃ E/Z Tp:170-172(°C) d-8 5- ^c Pr N _SO2Et Me CH=CCI ₂ - Tp:159-161(°C) d-9 5- ^c Pr N _SO2Et Me CH=C(F)CF ₂ CF ₃ Z Tp:122-124(°C) d-10 5- ^c Pr N _SO2Et Me CH=C(F)CF _Z CF ₃ E Tp;151-153(°C) d-11 5- ^c Pr N _SO2Et Me CH=CBrF E Tp:148-150(°C) d-12 5- ^c Pr N _SO2Et Me CH=C(CI)CF ₂ CF ₃ Z Tp:117-119(°C) d-13 5- ^c Pr N _SO2Et Me CH=C(CI)CF _Z CF ₂ CF ₃ z Tp:103-105(°C) d-14 5- ^c Pr N _SO2Et Me CH=C(I)CI E Tp:121-123(°C) d-15 5-(1-CN- ^c Pr) N SO _z Et Me CH=C(CI) _CFJ E/Z Tp:65-68(°C) d-16 5-(1-CN- ^c Pr) N _SO2Et Me CH=CHCF ₃ E amorphous d-17 5-(1-(CONH _z )- ^c Pr) N _SO2Et Me CH=CCCI)CF ₃ E/Z Tp:205-207(°C) d-18 5-(1-(CSNH ₂ )- ^c Pr) N _SO2Et Me CH=C(CI)CF ₃ E/Z Tp:215-217(°C) d-19 5- ^c Pr N _SO2Et Me CH=C(CF ₃ ) ₂ - Tp:182-186(°C) d-20 5-(1-Me- ^c Pr) N _SO2Et Me CH=C(CI)CF ₃ E/Z Tp:137-139(°C) d-21 5-(1-(pyridin-2-yl)- ^c Pr) N SO _z Et Me CH=C(CI)CF ₃ E/Z Tp:157-159(°C) d-22 54l-CN- ^c Pr) N _SO2Et Me CH=CHCF ₂ CF ₃ E Tp:158-160(°C) d-23 5-(1-CN- ^c Pr) N _SO2Et Me CH=CHCF ₂ CF ₂ CF ₂ E Tp:140-142(°C) d-24 5- ^c Pr N _SO2Et Me CH=C(Br)CF ₃ E/Z Tp:166-168(°C) d-25 5- ^c Pr N SO _z Et Me CH=CHCF ₂ CF ₂ CF ₃ E Tp:143-145(°C) d-26 5-(1-Me- ^c Pr) N _SO2Et Me CH=CHCF ₂ CF ₃ E Tp:94-97(°C) d-27 5- ^c Pr N _SO2Et Me CH=C(F)CF ₂ CF ₂ CF ₃ Z Tp:106-108(°C) d-28 5- ^c Pr N SO ₂ Me Me CH=C(CI)CF ₃ E/Z Tp:196-198(°C) d-29 5-(1-Me- ^c Pr) N _SO2Et Me CH=CHCF ₂ CF ₂ CF ₃ E Tp:153-155(°C) d-30 5- ^c Pr N SO ₂ Me Me CH=C(CI)CF ₂ CF ₃ Z Tp:151-153(°C) d-31 5-(1-Me- ^c Pr) N _SO2Et Me CH=C(F)CF ₂ CF ₃ Z Tp:119-121C°C) d-32 5- ^c Pen N _SO2Et Me CH=C(CI)CF ₃ E/Z Tp:142-144(°C) d-33 5- ^c Pr N _SO2Et Me CH=C(CI)CF ₃ E Tp:159-161(°C) d-34 5- ^c Pr N _SO2Et Me CH=C(CI)CF ₃ Z Tp:169-171(°C) d-35 5- ^c Pr N _SO2Et Me CF=C(F)OCF ₂ CF ₂ CF ₃ Z Tp:113-115(°C) d-36 5- ^c Pr N _SO2Et Me CF=C(F)OCF ₂ CF ₂ CF ₃ E Tp:131-133(°C) d-37 5- ^c Pr N _SO2Et Me CF=C(F)OCF ₃ E/Z Tp:113-116(°C)

[0198]

[0199]

¹ H-NMR data of compounds having the physical properties of a viscous oil or amorphous substance from the compounds shown in Table 1 are shown below.

Compound 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 (k, 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 d-16: ^1H -NMR (400 MHz, _CDCl3 ): 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 (k, 3H), 3.62 (s, 3H), 2.01-1.97 (m, 2H ), 1.64-1.60 (m, 2H), 1.34 (t, 3H).

[0200]

[Biological test]

Test examples below show that the (hetero)arylimidazole compound of the present invention can be used as an active ingredient of pest control agents and ectoparasite control agents. The term "part" is based on weight.

[0201]

(Obtaining the emulsion to be tested)

5 parts of the (hetero)arylimidazole compound of the present invention, 93.6 parts of dimethylformamide and 1.4 parts of polyoxyethylene alkyl aryl ether were mixed and dissolved to obtain an emulsion (I) containing 5% of the active ingredient.

For the control, 98.5 parts of dimethylformamide and 1.5 parts of polyoxyethylene alkyl aryl ether were mixed and dissolved to obtain emulsion (II).

[0202]

The insecticidal activity index was calculated according to the following expression:

Insecticidal Activity Rate (%) = (Number of dead insects/Number of insects tested)×100

[0203]

(Test Case 1) Analysis of effectiveness against armyworm Mythimna separata

0.8 g of a commercially available artificial food (Insecta LFS, manufactured by Nosan Corp.) and 1 μl of emulsion (I) were mixed thoroughly to obtain a test food.

In a plastic test container (capacity: 1.4 ml), 0.2 g of test food was placed on the treatment site. Two second instar Mythimna separata larvae were then placed in each treatment area. A plastic lid was placed on the test container to prevent the emergence of second instar Mythimna separata larvae. The container was placed in a thermostat chamber at 25°C. On the fifth day, insecticidal activity and feed consumption were examined. The analysis was carried out in duplicate.

[0204]

The level of insecticidal activity and feed intake in the control plot were examined in the same way as in Test Example 1, except that emulsion (I) was replaced by emulsion (II).

[0205]

Connections numbered 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 effectiveness against Mythimna separata . All compounds showed a level of insecticidal activity against Mythimna separata of 100% or feed consumption of 10% or less compared to the control plot. As can be seen, the (hetero)arylimidazole compound of the present invention is effective against Mythimna separata .

[0206]

(Test Case 2) Analysis of effectiveness against Mythimna separata

Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Corn leaves were immersed in the dilution for 30 seconds. The prepared corn leaves were placed in a Petri dish and five second instar Mythimna separata larvae were released. The Petri dish was placed in a thermostat chamber with a temperature of 25°C and a humidity of 60%. The number of live and dead individuals was determined 6 days after the release of insects and the level of insecticidal activity was calculated. The analysis was carried out in duplicate.

[0207]

Compounds numbered d-1, d-2 and d-15 were tested for their effectiveness against Mythimna separata . All compounds showed levels of insecticidal activity against Mythimna separata of 80% or greater.

[0208]

(Test Case 3) Analysis of effectiveness against cabbage moth Plutella xylostella

Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Cabbage leaves were immersed in the dilution for 30 seconds. The prepared cabbage leaves were placed in a Petri dish. Five second instar Plutella xylostella larvae were released into a cup. The Petri dish was placed in a thermostat chamber with a temperature of 25°C and a humidity of 60%. The number of live and dead individuals was determined 3 days after the release of insects and the level of insecticidal activity was calculated. The analysis was carried out in duplicate.

[0209]

Connections numbered 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 tested for their effectiveness against Plutella xylostella . All compounds showed levels of insecticidal activity against Plutella xylostella of 80% or greater.

[0210]

(Test Case 4) Analysis of effectiveness against Asian cotton bollworm Spodoptera litura

Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Cabbage leaves were immersed in the dilution for 30 seconds. The prepared cabbage leaves were placed in a Petri dish and five second instar Spodoptera litura larvae were released. The Petri dish was placed in a thermostat chamber with a temperature of 25°C and a humidity of 60%. The number of live and dead individuals was determined 6 days after the release of insects and the level of insecticidal activity was calculated. The analysis was carried out in duplicate.

[0211]

Compounds numbered d-2, d-12 and d-15 were tested for their effectiveness against Spodoptera litura . All compounds showed levels of insecticidal activity against Spodoptera litura of 80% or greater.

[0212]

(Test Case 5) Analysis of effectiveness against Aphis craccivora aphid

Cowpea seedlings were grown in 10 cm pots. Aphis craccivora aphid nymphs were transferred to primary leaves. 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 cowpeas infested with Aphis craccivora nymphs. Cowpeas were placed in a thermostat chamber with a temperature of 25°C and a humidity of 60%. The number of living and dead Aphis craccivora individuals was determined 4 days after spraying and the level of insecticidal activity was calculated. The analysis was carried out in duplicate.

[0213]

Connections numbered 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 effectiveness against Aphis craccivora . All compounds showed levels of insecticidal activity against Aphis craccivora of 80% or greater.

[0214]

(Test Case 6) Analysis of effectiveness against flea beetle Phyllotreta striolata

Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm to prepare the test chemical. The test chemical was sprayed on bok choy seedlings (seventh stage true leaves) planted in 10 cm pots. Bok choy seedlings were air dried and then placed in a plastic cup. Ten adults of Phyllotreta striolata were released into the cup. The plastic cup was stored in a thermostat chamber with a temperature of 25°C and a humidity of 65%. The number of live and dead individuals was determined 7 days after the release of insects and the level of insecticidal activity was calculated. The analysis was carried out in duplicate.

[0215]

Connections numbered 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 effectiveness against Phyllotreta striolata adults. All compounds showed levels of insecticidal activity against Phyllotreta striolata adults of 80% or greater.

[0216]

(Test Case 7) Efficacy Analysis against Brown Rice Planthopper Nilaparvata lugens

Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Young rice seedlings were immersed in dilution for 30 seconds. Young rice seedlings were air dried and then placed in a plastic container. Five second instar Nilaparvata lugens larvae were released into the container. The plastic container was stored in a thermostat chamber with a temperature of 25°C and a humidity of 65%. The number of live and dead individuals was determined 7 days after inoculation and the level of insecticidal activity was calculated. The analysis was carried out in duplicate.

[0217]

Connections numbered 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 tested for their effectiveness against Nilaparvata lugens . All compounds showed levels of insecticidal activity against Nilaparvata lugens of 80% or greater.

[0218]

(Test Case 8) Analysis of effectiveness against housefly Musca domestica

The compound of the present invention was diluted with acetone and diluted at a concentration of 100 ppm. compounds of the present invention were added dropwise per g of lump sugar. Lump sugar was placed in a plastic cup. Ten female Musca domestica adults were released and the plastic cup was covered with a lid. The plastic cup was stored at 25°C. The number of live and dead individuals was determined 24 hours after the release of insects and the level of insecticidal activity was calculated. The analysis was carried out in duplicate.

[0219]

Compound b-4 was tested for its effectiveness against Musca domestica . The compound showed a level of insecticidal activity against Musca domestica of 80% or greater.

[0220]

(Test Case 9) Efficiency analysis against cotton aphid Aphis gossypii

Cucumber seedlings grown in 10 cm pots were removed from 10 cm pots. The soil attached to the root part was washed off with tap water and the root part was immersed in tap water, and then transferred to hydroponic culture. Aphis gossypii nymphs were inoculated onto cucumber seedlings. 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 with dilution and the hydroponic culture with dilution continued to be cultivated in a thermostat chamber at 25°C and 60% humidity. The number of living and dead Aphis gossypii individuals was determined 6 days after the start of the hydroponic dilution culture and the level of insecticidal activity was calculated. The analysis was carried out in duplicate.

[0221]

Compounds numbered d-1, d-2, d-9, d-15, d-18, d-26, d-27 and d-33 were tested for their effectiveness against Aphis gossypii . All compounds showed levels of insecticidal activity against Aphis gossypii of 80% or greater.

[0222]

(Test Case 10) Analysis of effectiveness against flea beetle Phyllotreta striolata

Emulsion (I) was diluted with water such that the concentration of the compound of the present invention was 31 ppm to prepare the test chemical. The test chemical was sprayed on bok choy seedlings (seventh stage true leaves) planted in 10 cm pots. Bok choy seedlings were air dried and then placed in a plastic cup. Ten adults of Phyllotreta striolata were released into a plastic cup. The plastic cup was stored in a thermostat chamber with a temperature of 25°C and a humidity of 65%. The number of live and dead individuals was determined 7 days after the release of insects and the level of insecticidal activity was calculated. The analysis was carried out in duplicate.

[0223]

Connections numbered 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 effectiveness against adults of Phyllotreta striolata . All compounds showed levels of insecticidal activity against Phyllotreta striolata adults of 80% or greater.

[0224]

All compounds randomly selected from the (hetero)arylimidazole compounds of the present invention exhibited the effects as described above. Thus, it can be understood that the (hetero)arylimidazole compound of the present invention, including compounds not shown, is a compound having an effect such as a pest control effect, in particular an acaricidal or insecticidal effect. It can also be understood that the (hetero)arylimidazole compound of the present invention is a compound also having an effect against parasites harmful to humans and animals, such as ectoparasites.

Claims (10)

1. The compound represented by formula (IV), its N-oxide, or an agriculturally or horticulturally acceptable salt of any of these compounds: , Where A carbon-carbon double bond has an E-form or a Z-form, or a mixture of both. 2. An insecticide containing at least one compound, in an amount that exhibits its insecticidal action, selected from the group consisting of a compound according to claim 1, its N-oxide and an agriculturally or horticulturally acceptable salt of any of these compounds, as an active ingredient and excipients. 3. A seed dressing or a treatment agent for vegetative propagation organs, containing at least one compound in an amount that exhibits its control effect, selected from the group consisting of a compound according to claim 1, its N-oxide, and acceptable in agriculture or horticulture salts of any of these compounds, as active ingredients and excipients. 4. A granular agrochemical composition for treating cassettes for growing paddy rice, containing at least one compound in an amount that exhibits its control effect, selected from the group consisting of a compound according to claim 1, its N-oxide, and acceptable in agriculture or horticulture salts of any of these compounds, as active ingredients and excipients. 5. A soil treatment agent containing at least one compound in an amount that exhibits its control effect, selected from the group consisting of a compound according to claim 1, its N-oxide, and an agriculturally or horticulturally acceptable salt of any of these compounds as active ingredient and excipients. 6. A bait agent containing at least one compound in an amount that exhibits its control effect, selected from the group consisting of a compound according to claim 1, its N-oxide and an agriculturally or horticulturally acceptable salt of any of these compounds , as an active ingredient and excipients. 7. A plant growth stimulator containing at least one compound in an amount that exhibits its plant growth stimulating effect, selected from the group consisting of a compound according to claim 1, its N-oxide and an agriculturally or horticulturally acceptable salt of any of these compounds as active ingredient and excipients.