JP2024084158A - Benzimidazole compounds and pest control agents - Google Patents

Abstract

[Problem] To provide a benzimidazole compound useful as a pest control agent. [Solution] A pest control agent, insecticide or acaricide, ectoparasite control agent, or endoparasite control or extermination agent containing a compound represented by formula (I) as an active ingredient. TIFF2024084158000013.tif44150 In the formula, R1 is a substituted or unsubstituted C1-6 alkylsulfonyl group, R2 and R4 are each independently a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, R3 is a hydrogen atom, a halogeno group, or the like, R is a substituted or unsubstituted C1-6 alkyl group, or the like, and R5 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or the like. [Selected Figure] None

Description

The present invention relates to a benzimidazole compound and a pest control agent. More specifically, the present invention relates to a benzimidazole compound that has excellent insecticidal and/or acaricidal activity, is safe, and can be synthesized industrially in an advantageous manner, and to a pest control agent that contains the benzimidazole compound as an active ingredient.

Various compounds with insecticidal and/or acaricidal activity have been proposed. For such compounds to be practically used as pesticides, they must not only be sufficiently effective, but also unlikely to develop drug resistance, not cause plant damage or soil contamination, and have low toxicity to livestock and fish.

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

WO 2017/174449 A1

An object of the present invention is to provide a benzimidazole compound which is excellent in pest control activity, particularly in insecticidal activity and/or acaricidal activity, is safe, and can be synthesized industrially advantageously.
Another object of the present invention is to provide a pest control agent, an insecticide or acaricide, an external parasite control agent, or an internal parasite control or extermination agent which contains the above benzimidazole compound as an active ingredient.

As a result of intensive research to solve the above problems, the present invention has been completed, which includes the following aspects.

式(I)中、
Ｒ¹は、置換若しくは無置換のＣ１～６アルキルスルホニル基であり、
Ｒ²およびＲ⁴は、それぞれ独立して、水素原子、または置換若しくは無置換のＣ１～６アルキル基であり、
Ｒ³は、水素原子、置換若しくは無置換のＣ１～６アルキル基、またはハロゲノ基であり、
Ｒは、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員ヘテロアリール基であり、且つ
Ｒ⁵は、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ１～６アルコキシカルボニル基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～８シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換の５～６員ヘテロアリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換の５～６員ヘテロアリールオキシ基、置換若しくは無置換のアミノ基、置換若しくは無置換のアミノカルボニル基、置換若しくは無置換のヒドラジニル基、ニトロ基、シアノ基、またはハロゲノ基である。 [1] A compound represented by formula (I) or a salt thereof.

In formula (I),
R ¹ is a substituted or unsubstituted C1-6 alkylsulfonyl group,
R ² and R ⁴ each independently represent a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group;
^R3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group;
R is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heteroaryl group, and R ⁵ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5-6 membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5-6 membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group, a cyano group, or a halogeno group .

[2] A pest control agent containing at least one selected from the group consisting of the compound described in [1] and its salt as an active ingredient.

[3] An insecticide or acaricide containing at least one selected from the group consisting of the compounds described in [1] and salts thereof as an active ingredient.

[4] An external parasite control agent containing at least one selected from the group consisting of the compound described in [1] and its salt as an active ingredient.

[5] An agent for controlling or eliminating internal parasites, comprising as an active ingredient at least one selected from the group consisting of the compound described in [1] and its salt.

The benzimidazole compound of the present invention can control harmful organisms that are problematic in terms of agricultural crops and hygiene. In particular, agricultural pests and mites can be effectively controlled at lower concentrations. Furthermore, it can effectively control or eliminate external and internal parasites that harm humans and livestock.

[Benzimidazole Compounds]
The benzimidazole compound of the present invention is a compound represented by formula (I) (hereinafter, may be referred to as compound (I)) or a salt of compound (I).

In the present invention, the term "unsubstituted" means that only the group serving as the mother nucleus is present. When the term "substituted" is not used and only the name of the group serving as the mother nucleus is used, it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that any hydrogen atom of the core group is replaced with a group (substituent) having the same or different structure as the core group. Thus, a "substituent" is another group bonded to the core group. The number of substituents may be one or more. The two or more substituents may be the same or different.
A term such as "C1-6" indicates that the number of carbon atoms in the core group is 1 to 6. This number of carbon atoms does not include the number of carbon atoms in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.

The "substituent" is not particularly limited as long as it is chemically permissible and has the effect of the present invention. Examples of groups that can be the "substituent" are shown below.
C1-6 alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group, or an n-hexyl group;
C2-6 alkenyl groups such as a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, and a 2-methyl-2-propenyl group;
C2-6 alkynyl groups such as an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, or a 1-methyl-2-propynyl group;

C3-8 cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
C6-10 aryl groups such as phenyl groups and naphthyl groups;
C6-10 aryl C1-6 alkyl groups such as a benzyl group and a phenethyl group;
3- to 6-membered heterocyclyl groups;
3-6 membered heterocyclyl C1-6 alkyl group;

Hydroxyl group;
C1-6 alkoxy groups such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, or a t-butoxy group;
C2-6 alkenyloxy groups such as a vinyloxy group, an allyloxy group, a propenyloxy group, or a butenyloxy group;
C2-6 alkynyloxy groups such as ethynyloxy groups, propargyloxy groups, etc.;
C6-10 aryloxy groups such as a phenoxy group and a naphthoxy group;
C6-10 aryl C1-6 alkoxy groups such as a benzyloxy group and a phenethyloxy group;
5- to 6-membered heteroaryloxy groups such as thiazolyloxy groups and pyridyloxy groups;
5-6-membered heteroaryl C1-6 alkyloxy groups such as a thiazolylmethyloxy group and a pyridylmethyloxy group;

Formyl group;
C1-6 alkylcarbonyl groups such as acetyl group and propionyl group;
Formyloxy group;
C1-6 alkylcarbonyloxy groups such as an acetyloxy group or a propionyloxy group;
C6-10 arylcarbonyl groups such as a benzoyl group;
C1-6 alkoxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, or a t-butoxycarbonyl group;
C1-6 alkoxycarbonyloxy groups such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group, or a t-butoxycarbonyloxy group;
Carboxyl group;

halogeno groups such as a fluoro group, a chloro group, a bromo group, or an iodo group;
C1-6 haloalkyl groups such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group, and a 2,4,6-trichlorohexyl group;
C2-6 haloalkenyl groups such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group;
C2-6 haloalkynyl groups such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, or a 5-bromo-2-pentynyl group;
C1-6 haloalkoxy groups such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, or a 2,3-dichlorobutoxy group;
C2-6 haloalkenyloxy groups such as a 2-chloropropenyloxy group, a 3-bromobutenyloxy group, etc.;
C1-6 haloalkylcarbonyl groups such as a chloroacetyl group, a trifluoroacetyl group, or a trichloroacetyl group;

Amino group;
C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group, and diethylamino group;
C6-10 arylamino groups such as anilino group and naphthylamino group;
C6-10 aryl C1-6 alkylamino groups such as a benzylamino group or a phenethylamino group;
Formylamino group;
C1-6 alkylcarbonylamino groups such as an acetylamino group, a propanoylamino group, a butyrylamino group, or an i-propylcarbonylamino group;
C1-6 alkoxycarbonylamino groups such as a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group, or an i-propoxycarbonylamino group;
unsubstituted or substituted aminocarbonyl groups, such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group, or an N-phenyl-N-methylaminocarbonyl group;
imino C1-6 alkyl group such as an iminomethyl group, a (1-imino)ethyl group, or a (1-imino)-n-propyl group;
substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as an N-hydroxy-iminomethyl group, a (1-(N-hydroxy)-imino)ethyl group, a (1-(N-hydroxy)-imino)propyl group, an N-methoxy-iminomethyl group, or a (1-(N-methoxy)-imino)ethyl group;
C1-6 alkoxyimino groups, such as a methoxyimino group, an ethoxyimino group, an n-propoxyimino group, an i-propoxyimino group, or an n-butoxyimino group;
Aminocarbonyloxy group;
C1-6 alkyl-substituted aminocarbonyloxy groups such as an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy group;

Mercapto group;
C1-6 alkylthio groups, such as a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group, or a t-butylthio group;
C1-6 haloalkylthio groups such as a trifluoromethylthio group, a 2,2,2-trifluoroethylthio group, etc.;
C6-10 arylthio groups such as a phenylthio group and a naphthylthio group;
5- to 6-membered heteroarylthio groups such as thiazolylthio groups and pyridylthio groups;

C1-6 alkylsulfinyl groups such as a methylsulfinyl group, an ethylsulfinyl group, or a t-butylsulfinyl group;
C1-6 haloalkylsulfinyl groups such as a trifluoromethylsulfinyl group or a 2,2,2-trifluoroethylsulfinyl group;
C6-10 arylsulfinyl groups such as a phenylsulfinyl group;
5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl groups and pyridylsulfinyl groups;

C1-6 alkylsulfonyl groups such as a methylsulfonyl group, an ethylsulfonyl group, or a t-butylsulfonyl group;
C1-6 haloalkylsulfonyl groups such as a trifluoromethylsulfonyl group or a 2,2,2-trifluoroethylsulfonyl group;
C6-10 arylsulfonyl groups such as a phenylsulfonyl group;
5- to 6-membered heteroarylsulfonyl groups such as thiazolylsulfonyl groups and pyridylsulfonyl groups;
C1-6 alkylsulfonyloxy groups such as a methylsulfonyloxy group, an ethylsulfonyloxy group, or a t-butylsulfonyloxy group;
C1-6 haloalkylsulfonyloxy groups such as a trifluoromethylsulfonyloxy group, a 2,2,2-trifluoroethylsulfonyloxy group, etc.;

triC1-6 alkyl-substituted silyl groups such as a trimethylsilyl group, a triethylsilyl group, or a t-butyldimethylsilyl group;
triC6-10 aryl-substituted silyl groups such as triphenylsilyl groups;
Cyano group;
Nitro group.

In addition, any of the hydrogen atoms in these "substituents" may be replaced with a group of a different structure. In such cases, examples of the "substituents" include C1-6 alkyl groups, C1-6 haloalkyl groups, C1-6 alkoxy groups, C1-6 haloalkoxy groups, halogeno groups, cyano groups, and nitro groups.

The above "3- to 6-membered heterocyclyl group" includes 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring constituent atoms. Examples of the "3- to 6-membered heterocyclyl group" include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered partially unsaturated heterocyclyl groups, and 5- to 6-membered heteroaryl groups.

Examples of the 3- to 6-membered saturated heterocyclyl group include 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, and a dioxanyl group.
Examples of the 5-membered partially unsaturated heterocyclyl group include a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, and an isoxazolinyl group.
Examples of the six-membered partially unsaturated heterocyclyl group include a dihydropyranyl group.
Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group.
Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.

[R ¹ ]
In formula (I), R ¹ is a substituted or unsubstituted C1-6 alkylsulfonyl group.

Examples of the "C1-6 alkylsulfonyl group" in R ¹ include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.

Preferable examples of the substituent on the "C1-6 alkylsulfonyl group" in R ¹ include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group.

[ ^R2 , ^R4 ]
In formula (I), R ² and R ⁴ each independently represent a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.

The "C1-6 alkyl group" in ^R2 and ^R4 may be a straight chain or a branched chain. Examples of the "C1-6 alkyl group" include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, an t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, and an i-hexyl group.

Preferable examples of the substituent on the "C1-6 alkyl group" in ^R2 and ^R4 include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group.

[ ^R3 ]
In formula (I), R ³ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group.

Examples of the "substituted or unsubstituted C1-6 alkyl group" in ^R3 include the same as those exemplified in ^R2 and ^R4 above.
The "halogeno group" in ^R3 includes a fluoro group, a chloro group, a bromo group, an iodo group, and the like.

[R]
In formula (I), R is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heteroaryl group.

Examples of the "substituted or unsubstituted C1-6 alkyl group" in R include the same as those exemplified in ^R2 and ^R4 above.

As the "substituted C1-6 alkyl group" for R, a C1-6 haloalkyl group is preferable.
Examples of a "C1-6 haloalkyl group" include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoromethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group, and a 2,4,6-trichlorohexyl group.

Examples of the "C2-6 alkenyl group" in R include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl 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, and 5-hexenyl group.

As the "substituted C2-6 alkenyl group" for R, a C2-6 haloalkenyl group is preferable.
Examples of the "C2-6 haloalkenyl group" include 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 C2-6 haloalkenyl groups such as 2-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 C1-6 haloalkoxy C2-6 haloalkenyl groups such as 1,2-difluoro-2-trifluoromethoxyvinyl group and 1,2-difluoro-2-perfluoropropoxyvinyl group.

Examples of the "C2-6 alkynyl group" in R include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, and 1,1-dimethyl-2-butynyl group.

As the "substituted C2-6 alkynyl group" for R, a C2-6 haloalkynyl group is preferable.
Examples of the "C2-6 haloalkynyl" include a fluoroethynyl group, a chloroethynyl group, a 3,3-difluoro-1-propynyl group, and a 3,3,3-trifluoro-1-propynyl group.

The "C6-10 aryl group" in R means a monocyclic or polycyclic aromatic hydrocarbon group, and as long as at least one ring of the polycyclic aryl group has a benzene ring structure, the remaining rings may have a benzene ring, a saturated hydrocarbon ring, or an unsaturated hydrocarbon ring structure. Examples include a phenyl group, a naphthyl group, an indenyl group, and an indanyl group.

The "5- to 6-membered heteroaryl group" in R means a 5- to 6-membered aromatic heterocyclic group having 1 to 4 nitrogen, oxygen, or sulfur atoms as heteroatoms. Examples include 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl (specifically, [1.2.3]triazolyl or [1.2.4]triazolyl), oxadiazolyl (specifically, [1.2.4]oxadiazolyl or [1.3.4]oxadiazolyl), thiadiazolyl, and tetrazolyl; and 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl.

As the substituent on the "C6-10 aryl group" or "5- to 6-membered heteroaryl group" in R, preferably, a halogeno group such as a fluoro group, a chloro group, a bromo group, or an iodo group; a C1-6 alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group, or an n-hexyl group; a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4, Examples of C1-6 haloalkyl groups include 4,4-heptafluorobutyl, perfluorobutyl, perfluoropentyl, perfluorohexyl, chloromethyl, bromomethyl, dichloromethyl, dibromomethyl, trichloromethyl, tribromomethyl, 1-chloroethyl, 2,2,2-trichloroethyl, 4-chlorobutyl, perchlorohexyl, and 2,4,6-trichlorohexyl groups; C1-6 alkoxy groups include methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; and C1-6 haloalkoxy groups include 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups.

[ ^R5 ]
In formula (I), R ⁵ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5-6 membered heteroaryl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5-6 membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group, a cyano group, or a halogeno group.

The "substituted or unsubstituted C1-6 alkyl group" and "halogeno group" in ^R5 include the same as those exemplified in ^R2 and ^R3 above.

Examples of the "C1-6 alkylsulfonyl group" in ^R5 include the same as those exemplified for ^R1 above.

Examples of the "C2-6 alkenyl group", "C2-6 alkynyl group", "substituted or unsubstituted C6-10 aryl group" and "substituted or unsubstituted 5- to 6-membered heteroaryl group" in ^R5 include the same as those exemplified for R above.

Examples of the "C1-6 alkoxy group" in ^R5 include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, and a t-butoxy group.

Examples of the "C1-6 alkoxycarbonyl group" in ^R5 include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group.

Examples of the "C1-6 alkylthio group" in ^R5 include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, an i-propylthio group, and an i-butylthio group.

Examples of the "C1-6 alkylsulfinyl group" in ^R5 include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group.

Preferred examples of the substituent on the "C1-6 alkyl group" in ^R5 include halogeno groups such as fluoro, chloro, bromo, and iodo groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; and C1-6 alkoxyimino groups such as methoxyimino, ethoxyimino, n-propoxyimino, i-propoxyimino, and n-butoxyimino groups.

Preferable examples of the substituent on the "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group" and "C1-6 alkylsulfonyl group" in ^R5 include halogeno groups such as fluoro group, chloro group, bromo group and iodo group; and C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group and t-butoxy group.

Examples of the "C3-8 cycloalkyl group" in ^R5 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

Examples of the "C6-10 aryloxy group" in ^R5 include a phenoxy group, a naphthyloxy group, and the like.

Examples of the "5- to 6-membered heteroaryloxy group" in ^R5 include a pyridyloxy group, a pyrimidyloxy group, and the like.

As the substituent on the "C3-8 cycloalkyl group", "C6-10 aryloxy group", and "5- to 6-membered heteroaryloxy group" in ^R5 , preferably, a halogeno group such as a fluoro group, a chloro group, a bromo group, or an iodo group; a C1-6 alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group, or an n-hexyl group; C1-6 haloalkyl groups such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group, and a 2,4,6-trichlorohexyl group; Examples include C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; and C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups.

The "substituted or unsubstituted amino group" for ^R5 is a group represented by "-NR ^a R ^b ", in which R ^a and R ^b are each independently a hydrogen atom, a C1-6 alkyl group, a formyl group, a C1-6 alkylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, or the like.

Examples of the "C1-6 alkyl group" in R ^a and R ^b include the same as those exemplified in R ² and R ³ above.

Examples of the "C1-6 alkylcarbonyl group" in R ^a and R ^b include an acetyl group, a propionyl group, and the like.

Examples of the "substituted or unsubstituted aminocarbonyl group" in R ^a and R ^b include an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a dimethylaminocarbonyl group, and the like.

The "substituted or unsubstituted aminocarbonyl group" in ^R5 includes the same groups as those exemplified above for ^Ra and ^Rb .

The "substituted or unsubstituted hydrazinyl group" for ^R5 is a group represented by the formula (a).

In formula (a), * represents a bonding position, and R ^c , R ^d and R ^e are each independently a hydrogen atom, a C1-6 alkyl group, a substituted or unsubstituted phenylsulfonyl group, or the like.

The "C1-6 alkyl group" in R ^c , R ^d and R ^e includes the same groups as those exemplified for X above.

The "substituted phenylsulfonyl group" for R ^c , R ^d and R ^e can include a paratoluenesulfonyl group.

The salt of compound (I) is not particularly limited as long as it is an agriculturally and horticulturally acceptable salt. Examples of salts of compound (I) include salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium and magnesium; salts of transition metals such as iron and copper; salts of ammonia; and salts of organic bases such as triethylamine, tributylamine, pyridine, and hydrazine.

The method for producing compound (I) or a salt of compound (I) is not particularly limited. For example, compound (I) or a salt of compound (I) of the present invention can be obtained by a known production method described in the Examples, etc. Also, a salt of compound (I) can be obtained from compound (I) by a known method.

The benzimidazole compound of the present invention is highly effective in controlling various agricultural pests and harmful organisms such as mites which affect plant growth.
In addition, the benzimidazole compounds of the present invention are highly safe because they cause little phytotoxicity to crops and have low toxicity to fish and warm-blooded animals, and are therefore useful as active ingredients of insecticides or acaricides.
Furthermore, in recent years, many pests, such as diamondback moths, planthoppers, leafhoppers, and aphids, have developed resistance to various existing pesticides, causing problems in the efficacy of these pesticides, and there is a demand for pesticides that are effective against resistant pests. The benzimidazole compound of the present invention shows excellent control effects not only against susceptible pests, but also against various resistant pests and even against acaricide-resistant mites.

The benzimidazole compound of the present invention is highly effective in controlling or eliminating external and internal parasites that are harmful to humans and animals. In addition, it is a highly safe substance because it has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient in an agent for controlling or eliminating external and internal parasites.

The benzimidazole compounds of the present invention are also effective against all developmental stages of organisms to be controlled, and exhibit excellent control effects against, for example, eggs, nymphs, larvae, pupae and adults of mites and insects.

[Pest control agents]
The pesticide of the present invention contains at least one selected from the benzimidazole compounds of the present invention as an active ingredient. The amount of the benzimidazole compound of the present invention contained in the pesticide of the present invention is not particularly limited as long as it shows a pest control effect. The pesticide is an agent for controlling pests, and includes insecticides or acaricides, external parasite control agents, or internal parasite control or extermination agents.

[Insecticidal or acaricide]
The insecticide or acaricide of the present invention contains at least one selected from the benzimidazole compounds of the present invention as an active ingredient. The amount of the benzimidazole compound of the present invention contained in the insecticide or acaricide of the present invention is not particularly limited as long as it shows an insecticidal or acaricidal effect.

The pest control agent, or insecticide or acaricide of the present invention is preferably used on plants such as grains; vegetables; root vegetables; potatoes; flowers; fruit trees; ornamental plants, trees such as tea, coffee, and cacao; pasture plants; turf; and cotton.
When applied to plants, the pesticide, insecticide or acaricide of the present invention may be applied to any part of the plant, such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, cuttings, etc.
In addition, the pesticide, insecticide or acaricide of the present invention is not particularly limited by the species of the plant to which it is applied. Examples of plant species include original species, varieties, improved varieties, cultivated varieties, mutants, hybrids, genetically modified organisms (GMOs), etc.

The pest control agent of the present invention can be used for seed treatment, foliage application, soil application, water surface application, etc. to control various agricultural pests and mites.

Specific examples of various agricultural pests and mites that can be controlled by the pest control agent of the present invention are shown below.

(1) Butterflies or moths of the order Lepidoptera (a) Arctiidae moths, such as Hyphantria cunea and Lemyra imparilis;
(b) Bucculatricidae moths, for example, Bucculatrix pyrivorella;
(c) moths of the family Carposinidae, for example, the peach fruit moth (Carposina sasakii);
(d) Crambidae moths, for example, Diaphania spp., Diaphania indica, Diaphania nitidalis; for example, Ostrinia spp., Ostrinia furnacalis, Ostrinia nubilalis, Ostrinia scapulalis; others, Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Diatraea grandiosella, Glyphodes pyloalis, Hellula undalis), the grass moth (Parapediasia teterrella);
(e) Gelechiidae moths, for example, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, Sitotroga cerealella;
(f) Geometridae moths, for example, Ascotis selenaria;
(G) Gracilaria family moths, for example, Caloptilia theivora, Phyllocnistis citrella, Phyllonorycter ringoniella;
(h) butterflies of the Hesperiidae family, for example, Parnara guttata;
(i) Lasiocampidae moths, for example, Malacosoma neustria; (j) Lymantriidae moths, for example, Lymantria spp., Lymantria dispar, Lymantria monacha; others, Euproctis pseudoconspersa, Orgyia thyellina;

(K) Lyonetiidae moths, for example, Lyonetia spp., peach leafminer (Lyonetia clerkella), silver leafminer (Lyonetia prunifoliella malinella);
(l) Noctuidae moths, for example, Spodoptera spp., Spodoptera depravata, Spodoptera eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura; for example, Autographa spp., Autographa gamma, Autographa nigrisigna; for example, Agrotis spp., Agrotis ipsilon, Agrotis segetum; Helicoverpa spp., for example, Helicoverpa armigera, Helicoverpa assulta, and Helicoverpa zea; Heliothis spp., for example, Heliothis armigera and Heliothis virescens; and others, for example, Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, Mythimna separata, Naranga aenescens, Panolis japonica, Peridroma saucia), soybean looper (Pseudoplusia includens), nettle grass moth (Trichoplusia ni);
(m) Nolidae moths, for example, Earias insulana;
(n) Butterflies of the family Pieridae, for example, Pieris spp.
) large cabbage white (Pieris brassicae), cabbage white (Pieris rapae crucivora);
(O) Plutellidae moths, for example, Acrolepiopsis spp., Acrolepiopsis sapporensis, Acrolepiopsis suzukiella; others, Plutella xylostella;
(p) moths of the family Pyralidae, for example, Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Galleria mellonella;
(q) Sphingidae moths, for example, Manduca spp., tomato hornworm (Manduca quinquemaculata), tobacco hornworm (Manduca sexta);

(R) Stathmopodidae moths, for example, Stathmopoda masinissa;
(s) moths of the family Tineidae, for example, Tinea translucens;
(t) Tortricidae moths, for example, Adoxophyes spp., Adoxophyes honmai, Adoxophyes orana; Archips spp., Archips breviplicanus, Archips fuscocupreanus; other spruce bud moths, Choristoneura fumiferana, Cydia pomonella, Eupoecilia ambiguella, Grapholitha molesta, Homona magnanima, Leguminivore glycinivorella, Lobesia botrana), Matsumuraeses phaseoli, Pandemis heparana, Sparaganothis pilleriana;
(u) Moths of the family Yponomeutidae, for example, Argyresthia conjugella.

(2) Thysanoptera pests (a) Phlaeothripidae pests, for example, Ponticulothrips diospyrosi;
(b) Thripidae, for example, Frankliniella spp., Frankliniella intonsa, Frankliniella occidentalis; Thrips spp., Thrips palmi, Thrips tabaci; and others, Heliothrips haemorrhoidalis, Scirtothrips dorsalis.

(3) Pests of the Order Hemiptera (A) Archaeorrhyncha
(A) Delphacidae, for example, Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, Sogatella furcifera.

(B) Clypeorrhyncha
(A) Cicadellidae, for example, Empoasca spp., potato leafhopper (Empoasca fabae), persimmon leafhopper (Empoasca nipponica), tea green leafhopper (Empoasca onukii), bean green leafhopper (Empoasca sakaii); other, Arboridia apicalis, Balclutha saltuella, Epiacanthus stramineus, Macrosteles striifrons, Nephotettix cinctinceps.

(C) Heteroptera
(a) Alydidae, for example, Riptortus clavatus;
(b) Coreidae, for example, Cletus punctiger, Leptocorisa chinensis;
(C) Lygaeidae, for example, Blissus leucopterus, Cavelerius saccharivorus, Togo hemipterus;
(D) Miridae, for example, Halticus insularis, Lygus lineolaris, Psuedatomoscelis seriatus, Stenodema sibiricum, Stenotus rubrovittatus, Trigonotylus caelestialium;

(e) Pentatomidae, for example, Nezara spp., Nezara antennata, Nezara viridula; for example, Eysarcoris spp., Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Dolycoris baccarum, Eurydema rugosum, Glaucias subpunctatus, Halyomorpha halys, Piezodorus hybneri), Plautia crossota, Scotinophora lurida;
(F) Pyrrhocoridae, for example, Dysdercus cingulatus;
(G) Rhopalidae, for example, Rhopalus msculatus;
(H) Scutelleridae, for example, Eurygaster integriceps;
(i) Tingidae, for example, Stephanitis nashi.

(D) Sternorrhyncha
(a) Adelgidae, for example, Adelges laricis;
(b) Aleyrodidae, for example, Bemisia spp., Silverleaf whitefly (Bemisia argentifolii), Tobacco whitefly (Bemisia tabaci); Others, Aleurocanthus spiniferus, Dialeurodes citri, Trialeurodes vaporariorum;
(c) Aphididae, for example, Aphis spp., bean aphid (Aphis craccivora), bean black aphid (Aphis fabae), strawberry aphid (Aphis forbesi), cotton aphid (Aphis gossypii), European apple aphid (Aphis pomi), elderberry aphid (Aphis sambuci), snow willow aphid (Aphis spiraecola); for example, Rhopalosiphum spp., corn aphid (Rhopalosiphum maidis), wheat curl aphid (Rhopalosiphum padi); for example, Dysaphis spp., plantago aphid (Dysaphis plantaginea, Dysaphis radicola; Macrosiphum spp., for example Macrosiphum avenae, Macrosiphum euphorbiae; Myzus spp., for example Myzus cerasi, Myzus persicae, Myzus varians; others, Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, Chaetosiphon fragaefolii), Hyalopterus pruni, Hyperomyzus lactucae, Lipaphis erysimi, Megoura viciae, Metopolophium dirhodum, Nasonovia ribis-nigri, Phorodon humuli, Schizaphis graminum, Sitobion avenae, Toxoptera aurantii;

(D) Coccidae, for example, Ceroplastes spp., Ceroplastes ceriferus, Ceroplastes rubens;
(e) Pseudaulacaspis spp. of the family Diaspididae, Pseudaulacaspis pentagona, Pseudaulacaspis prunicola; for example, Unaspis spp. of the family Unaspis, Unaspis euonymi, Unaspis yanonensis; other Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, Pseudaonidia paeoniae;
(F) Margarodidae, for example, Drosicha corpulenta, Icerya purchasi;
(g) Phylloxeridae, for example, Viteus vitifolii;
(h) Pseudococcidae, for example, Planococcus spp., Planococcus citri, Planococcus kuraunhiae; other, Phenacoccus solani, Pseudococcus comstocki;
(i) Psyllidae family, for example, Psylla spp., such as Psylla mali, Psylla pyrisuga; and others, such as Diaphorina citri.

(4) Pests of the suborder Polyphaga (a) of the family Anobiidae, for example, the cigarette beetle (Lasioderma serricorne);
(b) Attelabidae, for example, Byctiscus betulae, Rhynchites heros;
(C) Bostrichidae, for example, Lyctus brunneus;
(d) Brentidae, for example, Cylas formicarius;
(e) Buprestidae, for example, Agrilus sinuatus;
(F) Cerambycidae, for example, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus;
(g) Chrysomelidae, for example, Bruchus spp., pea weevil (Bruchus pisorum), broad bean weevil (Bruchus rufimanus); for example, Diabrotica spp., northern corn rootworm (Diabrotica barberi), southern corn rootworm (Diabrotica undecimpunctata), western corn rootworm (Diabrotica virgifera); for example, Phyllotreta spp., flea beetle (Phyllotreta nemorum), flea beetle (Phyllotreta striolata); other, Aulacophora femoralis, Callosobruchus chinensis, Cassida nebulosa), Chaetocnema concinna, Colorado beetle (Leptinotarsa decemlineata), rice leaf beetle (Oulema oryzae), eggplant long-horned beetle (Psylliodes angusticollis);

(H) Ladybird family (Coccinellidae), for example, Epilachna spp., Epilachna varivestis, Epilachna vigintioctopunctata;
(i) Curculionidae, for example, Anthonomus spp., such as Anthonomus grandis and Anthonomus pomorum; for example, Sitophilus spp., such as Sitophilus granarius and Sitophilus zeamais; other species, such as Echinocnemus squameus, Euscepes postfasciatus, Hylobius abietis, Hypera postica, Lissohoptrus oryzophilus, Otiorhynchus sulcatus, and Otiorhynchus sulcatus. (Sitona lineatus), the grass weevil (Sphenophorus venatus);
(j) Elateridae, for example, Melanotus spp., Melanotus fortnumi, Melanotus tamsuyensis;
(K) Nitidulidae, for example, Epuraea domina;
(l) Scarabaeidae, for example, Anomala spp., Anomala cuprea, Anomala rufocuprea; other, Cetonia aurata, Gametis jucunda, Heptophylla picea, Melolontha melolontha, Popillia japonica;
(m) from the family Scolytidae, for example, Ips typographus;
(n) Staphylinidae, for example, Paederus fuscipes;
(O) Tenebrionidae, for example, Tenebrio molitor, Tribolium castaneum;
(p) Trogossitidae, for example, Tenebroides mauritanicus.

(5) Pests of the order Diptera (A) Suborder Brachycera
(a) Agromyzidae, for example, Liriomyza spp., Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, Liriomyza trifolii; others, Chromatomyia horticola, Agromyza oryzae;
(b) Anthomyiidae, for example, Delia spp., such as Delia platura and Delia radicum; and others, such as Pegomya cunicularia;
(C) Drosophilidae, for example, Drosophila spp., Drosophila melanogaster, Drosophila suzukii;
(D) Ephydridae, for example, Hydrellia griseola;
(e) from the family Psilidae, for example, the carrot fly (Psila rosae);
(F) Tephritidae, for example, Bactrocera spp., Bactrocera cucurbitae, Bactrocera dorsalis; Rhagoletis spp., Rhagoletis cerasi, Rhagoletis pomonella; and others, Ceratitis capitata, Dacus oleae.

(B) Nematocera
(A) Cecidomyiidae, for example, Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor, and Sitodiplosis mosellana.

(6) Orthoptera pests (a) Acrididae, for example, Schistocerca spp., American locust (Schistocerca americana), desert locust (Schistocerca gregaria); other, Australian flying locust (Chortoicetes terminifera), Moroccan locust (Dociostaurus maroccanus), migratory locust (Locusta migratoria), brown locust (Locustana pardalina), red flying locust (Nomadacris septemfasciata), Oxya yezoensis;
(b) from the family Gryllidae, for example, the European house cricket (Acheta domestica), the field cricket (Teleogryllus emma);
(c) Gryllotalpidae, for example, Gryllotalpa orientalis;
(d) From the family Tettigoniidae, for example, Tachycines asynamorus.

(7) Mites (Acari)
(A) Acaridida of the Astigmata order
(a) Acaridae mites, for example, Rhizoglyphus spp., Rhizoglyphus echinopus, Rhizoglyphus robini; for example, Tyrophagus spp., Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; and others, Acarus siro, Aleuroglyphus ovatus, Mycetoglyphus fungivorus;

(B) Prostigmata (Actinedida)
(a) Mites of the Tetranychidae family, for example, Bryobia spp., clover spider mite (Bryobia praetiosa), false clover spider mite (Bryobia rubrioculus); for example, Eotetranychus spp., Eotetranychus asiaticus, Eotetranychus boreus, Eotetranychus celtis, Eotetranychus geniculatus, Eotetranychus kankitus, Eotetranychus pruni, Eotetranychus shii, Eotetranychus smithi, Eotetranychus spp. suginamensis, Eotetranychus uncatus; for example, from Oligonychus spp., Oligonychus hondoensis, Oligonychus ilicis, Oligonychus karamatus, Oligonychus mangiferus, Oligonychus orthius, Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii, Oligonychus ununguis; for example, from Panonychus spp., Panonychus citri, Panonychus Tetranychus spp., for example, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus ludeni, Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Tetranychus viennensis, Tetranychus evansi; Aponychus spp., for example, Aponychus corpuzae, Aponychus firmianae); for example, Sasanychus spp., Sasanychus akitanus, Sasanychus pusillus; for example, Shizotetranychus spp., Shizotetranychus celarius, Shizotetranychus longus, Shizotetranychus miscanthi, Shizotetranychus recki, Shizotetranychus schizopus; and others, Tetranychina harti, Tuckerella pavoniformis, Yezonychus sapporensis;

(b) mites of the Tenuipalpidae family, for example, Brevipalpus spp., grape mites (Brevipalpus lewisi), tea mites (Brevipalpus obovatus), southern mites (Brevipalpus phoenicis), cactus mites (Brevipalpus russulus), onshitsu mites (Brevipalpus californicus); for example, Tenuipalpus spp., orchid mites (Tenuipalpus pacificus),
Tenuipalpus zhizhilashviliae; Others: Dolichotetranychus floridanus;
(c) Eriophyidae mites, for example, Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, Aceria paradianthi, Aceria tiyingi, Aceria tulipae, Aceria zoysiea; for example, Eriophyes spp., Eriophyes chibaensis, Eriophyes emarginatae; for example, Aculops spp., Aculops lycopersici, Aculops zoysiea; pelekassi); for example, Aculus spp., Aculus fockeui, Aculus schlechtendali; others, Acaphylla theavagrans, Calacarus carinatus, Colomerus vitis, Calepitrimerus vitis, Epitrimerus pyri, Paraphytoptus kikus, Paracalacarus podocarpi, Phyllocotruta citri;
(d) mites of the family Transonemidae, for example, Tarsonemus spp., Tarsonemus bilobatus, Tarsonemus waitei; others, Phytonemus pallidus, Polyphagotarsonemus latus;
(e) Mites of the family Penthaleidae, for example, Penthaleus spp., such as Penthaleus erythrocephalus and Penthaleus major.

The pest control agent of the present invention may be mixed or used in combination with other active ingredients such as fungicides, insecticides/acaricides, nematicides, and soil pesticides; plant regulators, synergists, fertilizers, soil conditioners, and animal feed.
The combination of the benzimidazole compound of the present invention with other active ingredients is expected to have a synergistic effect in terms of insecticidal, acaricidal and nematocidal activities. The synergistic effect can be confirmed by the Colby formula (Colby.SR; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, 20-22, 1967) in accordance with a conventional method.

Specific examples of insecticides, acaricides, nematicides, soil pesticides, anthelmintics, etc. that can be mixed or used in combination with the pest control agent of the present invention are shown below.

(1A) Acetylcholinesterase (AChE) inhibitors (carbamate type)
Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb.
Aldoxycarb, alixycarb, aminocarb, bufencarb, cloethocarb, fenothiocarb, promecarb.
(1B) Acetylcholinesterase (AChE) inhibitors (organophosphorus)
Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyphos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Fanflu, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyaphos, Isofenphos, Isopropyl O-(methoxyaminothiophosphoryl) Salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimphos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Trichlorfon, Vamidothion.
Bromophos-ethyl, cyanofenphos, demeton-S-methylsulfone, diaryfos, diclofenthion, dioxabenzophos, etrimphos, fensulfothion, fonofos, formothion, iodofenphos, isazophos, isocarbophos, methacrifos, phosphocarb, pirimiphos-ethyl, propafos, protoate, sulprofos.

(2) GABA-gated chloride ion (chloride ion) channel blockers: chlordane, endosulfan; ethiprole, fipronil.
Acetoprole, camphechlor, dienochlor, heptachlor, pyrafluprole, pyriprole; flufiprole.
(3A) Sodium channel modulators (pyrethroids)
Acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl-isomer, bioresmethrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, en Pentrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadesrin, permethrin, fenothrin [(1R)-trans isomer], prallethrin, pyrethrins, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin.
κ-bifenthrin, biopermethrin, chloroprallethrin, dimefluthrin, fenfluthrin, fenpyrithrin, flufenprox, heptafluthrin, meperfluthrin, ε-metofluthrin, monfluorothrin, ε-monfluorothrin, trans-permethrin, profluthrin, protrifenbut, κ-tefluthrin, terallethrin, tetramethylfluthrin; bioethanomethrin.
(3B) Sodium channel modulators (DDTs)
DDT, methoxychlor.

(4) Nicotinic acetylcholine receptor (nAChR) competitive modulators: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; nicotine; sulfoxaflor; flupyradifurone; triflumezopyrim.
Nithiazine; dichloromezothiaz, flupirimine.
(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators: spinetoram and spinosad.
(6) Glutamate-gated chloride channel (GluCl) allosteric modulators: abamectin, emamectin, emamectin benzoate, lepimectin, and milbemectin.
Doramectin, eprinomectin, ivermectin, moxidectin, selamectin.
(7) Juvenile hormone mimetics: hydroprene, kinoprene, methoprene; fenoxycarb; pyriproxyfen.
Diofenolan, epofenonane, triplen.
(8) Other nonspecific (multi-site) inhibitors: methyl bromide, alkyl halides; chloropicrin; sodium aluminum fluoride, sulfuryl fluoride; borax, boric acid, disodium octaborate, sodium borate, sodium metaborate; tartar emetic; dazomet, metam, metam potassium, metam sodium.
(9) Chordotonal organ TRPV channel modulators Pymetrozine, pyrifluquinazone; afidopiropen.
(10) Mite growth inhibitors Clofentezine, diflobidazine, hexythiazox; etoxazole.

(11) Microorganism-derived insect midgut membrane disrupting agent
Bt subsp. israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, Bt subsp. tenebrionis; proteins in Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1; Bacillus sphaericus.
(12) Mitochondrial ATP synthase inhibitors Diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide; propargite; tetradifon.
(13) Oxidative phosphorylation uncouplers that disrupt the proton gradient: chlorfenapyr, DNOC, and sulfluramide.
Binapacryl, Zinobuton, and Zinocap.
(14) Nicotinic acetylcholine receptor (nAChR) channel blockers Bensultap, cartap hydrochloride, thiocyclam, thiosultap sodium salt.
(15) Chitin biosynthesis inhibitor, type 0
Bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron.
Fluazuron.
(16) Chitin biosynthesis inhibitor, type 1
Buprofezin.
(17) Molting inhibitor: cyromazine.
(18) Ecdysone receptor agonists chromafenozide, halofenozide, methoxyfenozide, tebufenozide.

(19) Octopamine receptor agonist Amitraz.
Chlordimeform.
(20) Mitochondrial electron transport chain complex III inhibitors hydramethylnon; acequinocyl; fluacrypyrim; bifenazate.
(21) Mitochondrial electron transport complex I inhibitor (METI)
Fenazaquin, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad; rotenone.
(22) Voltage-dependent sodium channel blockers Indoxacarb; metaflumizone.
(23) Acetyl-CoA carboxylase inhibitors spirodiclofen, spiromesifen, spirotetramat.
Spiropydione.
(24) Mitochondrial electron transport chain complex IV inhibitors Aluminum phosphide, calcium phosphide, zinc phosphide (Zn-phosphide), phosphine; calcium cyanide, sodium cyanide, potassium cyanide.
(25) mitochondrial electron transport complex II inhibitors cyenopyrafen, cyflumetofen; piflubumid.

(28) Ryanodine receptor modulators Chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide.
Cyhalodiamide, tetrachlorantraniliprole, tetraniliprole.
(29) Chordotonal organ modulator: target site unspecified; flonicamide.
(30) GABA-gated chloride ion (chloride ion) channel allosteric modulators: broflanilide, fluxamethamide.
Isocycloserum; afoxolaner, fluralaner, lotilaner, sarolaner.
(31) Other insecticides and acaricides: Azadirachtin, benzoximate, bromopropylate, quinomethionate, dicofol, lime sulfur mixture, mancozeb, pyridalyl, sulfur.
Acinonapyr, amidoflumet, benzomate, benzpyrimoxane, chlorbenzilate, dicyclanil, fenoxacrim, fentrifanil, flometoquin, flubenzimine, flufendin, fluhexafon, fluopyram, metaflumizone, methoxadiazone, oxazosulfil, tetrasulf, triarane, cyclopyrazoflor.

(32) Anthelmintic agent:
(a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, perbendazole, flubendazole; febantel, netobimin, thiophanate; thiabendazole, cambendazole;
(b) Salicylanilides: closantel, oxyclozanide, rafoxanide, niclosamide;
(c) Substituted phenols: nitroxynil, nitrosucrose;
(d) Pyrimidines: pyrantel, morantel;
(e) Imidazothiazoles: levamisole, tetramisole;
(f) Tetrahydropyrimidines: praziquantel, epsiprantel;
(g) Other anthelmintics: cyclodiene, ryanine, clorsulon, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophene, monepantel, tribendimidine, amidantel; thiacetarsamide, melarsomine, arsenamide.

Specific examples of fungicides that can be mixed or used in combination with the pest control agent of the present invention are shown below.
(1) Nucleic acid biosynthesis inhibitors:
(a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M; oxadixyl; clozylacon, ofrace;
(b) Adenosine deaminase inhibitors: bupirimate, dimethirimol, ethirimol;
(c) DNA/RNA synthesis inhibitors: hymexazole, octhilinone;
(d) DNA topoisomerase II inhibitors: oxolinic acid.

(2) Mitosis inhibitors and cytostatic agents:
(a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate methyl; diethofencarb; zoxamide; ethaboxam;
(b) Cytostatics: pencycuron;
(c) Spectrin-like protein delocalization inhibitor: fluopicolide.

(3) Respiratory inhibitors:
(a) Complex I NADH oxidoreductase inhibitors: diflumetrim; tolfenpyrad;
(b) Complex II succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil; isofetamide; fluopyram; fenfuram, flumecyclox; carboxin, oxycarboxin; thifluzamide; benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid;
(c) Complex III ubiquinol oxidase Qo inhibitors: azoxystrobin, cumoxystrobin, cumethoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin; pyraclostrobin, pyrametostrobin, triclopyricarb; kresoxim-methyl, trifloxystrobin; dimoxystrobin, phenaminestrobin, metominostrobin, orysastrobin; famoxadone; fluoxastrobin; fenamidone; pyribencarb;
(d) Complex III ubiquinol reductase Qi inhibitors: cyazofamid; amisulbrom;
(e) Uncouplers of oxidative phosphorylation: binapacryl, meptyldinocap, dinocap; fluazinam; ferimzone;
(f) Oxidative phosphorylation inhibitors (inhibitors of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide;
(g) ATP production inhibitor: silthiofam;
(h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): ametoctrazine.

(4) Amino acid and protein synthesis inhibitors (a) Methionine biosynthesis inhibitors: andoprim, cyprodinil, mepanipyrim, pyrimethanil;
(b) Protein synthesis inhibitors: blasticidin-S; kasugamycin, kasugamycin hydrochloride; streptomycin; oxytetracycline.

(5) Signal transduction inhibitors:
(a) Signal transduction inhibitors: quinoxyfen, proquinazid;
(b) MAP/histidine kinase inhibitors in osmotic signaling: fenpiclonil, fludioxonil; chlozolimate, iprodione, procymidone, vinclozolin.

(6) Lipid and cell membrane synthesis inhibitors:
(a) Phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos; isoprothiolane;
(b) Lipid peroxidants: biphenyl, chloroneb, dicloran, kindozene, tecnazene, tolclofos-methyl; etridiazole;
(c) Agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fossetylate, prothiocarb;
(d) Microorganisms that disrupt pathogen cell membranes: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain;
(e) Cell membrane disrupting agent: Extract of Tea Tree (Melania campestris).

(7) Sterol biosynthesis inhibitors in cell membranes:
(a) Inhibitors of demethylation at C14 position in sterol biosynthesis: triforine; pyrifenox, pyrisoxazole; fenarimol, flurprimidol, nuarimol; imazalil, imazalil sulfate, oxpoconazole, pefurazoate, prochloraz, triflumizole, viniconazole; Azaconazole, Bitertanol, Bromuconazole, Cyproconazole, Diclobutrazol, Difenoconazole, Diniconazole, Diniconazole-M, Epoxiconazole, Etaconazole, Fenbuconazole, Fluquinconazole, Flusilazole, Flutriafol), Fluconazole, Fluconazole-cis, Hexaconazole, Imibenconazole, Ipconazole, Metconazole, Myclobutanil, Penconazole, Propiconazole, Quinconazole, Simeconazole, Tebuconazole, Tetraconazole, Triadimefon, Triadimenol, Triticonazole; Prothioconazole, Voriconazole;
(b) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidin, piperalin; spiroxamine;
(c) 3-ketoreductase inhibitors in the C4 demethylation of sterol biosynthesis: fenhexamid; fenpyrazamine;
(d) Squalene epoxidase inhibitors of the sterol biosynthesis system: pyributicarb; naftifen, terbinafine.

(8) Cell wall synthesis inhibition (a) trehalase inhibitor: validamycin;
(b) Chitin synthase inhibitors: polyoxins, polyoxolim;
(c) Cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph; benthiavalicarb, iprovalicarb, tolprocarb, valifenalate; mandipropamide.

(9) Melanin biosynthesis inhibitors (a) Reductase inhibitors of melanin biosynthesis: fthalide; pyroquilon; tricyclazole;
(b) Dehydratase inhibitors of melanin biosynthesis: carpropamid; diclocymet; fenoxanil.

(10) Resistance inducer of host plant:
(a) Agents acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl;
(b) Others: probenazole; tiadinil; isotianil; laminarin; Japanese knotweed extract.

(11) Agents of unknown action:
Cymoxanil, fosetyl aluminum, phosphoric acid (phosphate salts), tecloftalam, triazoxide, flusulfamide, diclomedine, metasulfocarb, cyflufenamid, metrafenone, pyriophenone, dodine, dodine free base, flutianil.

(12) Agents having multiple sites of action:
Copper (copper salts), 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, ziram; captan, captafol, folpet; chlorothalonil; dichlofluanid, tolylfluanid; guazatine, iminoctadine triacetate, iminoctadine trialbesilate; anilazine; dithianone; quinomethionate; fluoroimide.

(13) Other agents:
DBEDC, Fluorofolpet, Guazatine acetate, Bis(8-quinolinolato)copper(II), Propamidine, Chloropicrin, Cyprofuram, Agrobacterium, Bethoxazin, Diphenylamine, Methylisothianate (MITC), Mildeomycin, Capsaicin, Kufuraneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophen, Difenzoquat, Difenzoquat methylsulfonate, Flumetober, Fosetyl calcium, Fosetyl sodium, Irmamycin, Na Amiodarone, Nitroisopropyl Nitrosulfate, Oxamocarb, Propamocin Sodium, Pyrrolnitrin, Tebufloquine, Tolnifanide, Zariramide, Algophase, Amicarthiazol, Oxathiapiprolin, Metiram Zinc, Benthiazole, Trichlamide, Uniconazole, Mildeomycin, Oxyfenthiin, Picarbutrazox.

Specific examples of plant regulators that can be mixed or used in combination with the pest control agent of the present invention are shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetylaminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, f Enothiol, 1-naphthylacetamide, ethychlozate, cloxyfonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid; ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid.

[External parasite control agent]
The ectoparasite control agent of the present invention contains at least one selected from the benzimidazole compounds of the present invention as an active ingredient. The amount of the benzimidazole compound of the present invention contained in the ectoparasite control agent of the present invention is not particularly limited as long as it shows an effect of controlling ectoparasites.

Host animals that can be treated with the ectoparasite control agent of the present invention include warm-blooded animals such as humans, domestic mammals (e.g., cattle, horses, pigs, sheep, goats, etc.), laboratory animals (e.g., mice, rats, gerbils, etc.), pet animals (e.g., hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, buffaloes, etc.), poultry (turkeys, ducks, chickens, quails, geese, etc.), and pet birds (pigeons, parrots, mynah birds, Java sparrows, parakeets, Bengalese finches, canaries, etc.); or fish such as salmon, trout, and koi carp. Other examples include honeybees, stag beetles, and rhinoceros beetles.

The ectoparasite control agent of the present invention can be applied by known veterinary methods (topical, oral, parenteral or subcutaneous administration). The methods include orally administering to animals by tablet, capsule, or by mixing with feed; administering to animals by immersion, suppository, or injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); administering to animals locally by spraying, pour-on, or spot-on of an oily or aqueous liquid; kneading the ectoparasite control agent into a resin, forming the kneaded product into an appropriate shape such as a collar or ear tag, and attaching the kneaded product to an animal for local administration;
Some examples include:

Ectoparasites live in and on host animals, particularly warm-blooded animals. More specifically, they live by parasitizing the back, armpits, lower abdomen, inner thighs, etc. of the host animal, obtaining nutrients such as blood and dandruff from the animal. Examples of ectoparasites include mites, lice, fleas, mosquitoes, stable flies, and flesh flies. Specific examples of ectoparasites that can be controlled by the ectoparasite control agent of the present invention are shown below.

(1) Mites (Acari)
Mites that parasitize insects, such as mites from the family Dermanyssidae, mites from the family Macronyssidae, mites from the family Laelapidae, mites from the family Varroidae, mites from the family Argasidae, mites from the family Ixodidae, mites from the family Psoroptidae, mites from the family Sarcoptidae, mites from the family Knemidokoptidae, mites from the family Demodixidae, mites from the family Trombiculidae, and stag beetle mites.

(2) Phthiraptera
Lice from the family Haematopinidae, lice from the family Linognathidae, lice from the family Menoponidae, lice from the family Philopteridae, and lice from the family Trichodectidae.

(3) Siphonaptera
Fleas from the family Pulicidae, for example Ctenocephalides spp., Ctenocephalides canis, Ctenocephalides felis;
Fleas of the Tungidae family, Ceratophyllidae family, and Leptopsyllidae family.

(4) Order Hemiptera.

(5) Pests of the order Diptera: Mosquitoes of the family Culicidae, black flies of the family Simuliidae, midges of the family Ceratopogonidae, horseflies of the family Tabanidae, flies of the family Muscidae, sheathe flies of the family Glossinidae, flesh flies of the family Flesh flies, flies of the family Hippoboscidae, flies of the family Calliphoridae, and flies of the family Oestridae.

[Internal parasite control or extermination agent]
The internal parasite control or extermination agent of the present invention contains at least one selected from the benzimidazole compounds of the present invention as an active ingredient. The amount of the benzimidazole compound of the present invention contained in the internal parasite control or extermination agent of the present invention is not particularly limited as long as it shows an effect of controlling internal parasites.

The parasites targeted by the endoparasite control or extermination agent of the present invention are parasitic within host animals, particularly warm-blooded animals and fish (endoparasites). Examples of host animals for which the endoparasite control or extermination agent of the present invention is effective include warm-blooded animals such as humans, domestic mammals (e.g., cows, horses, pigs, sheep, goats, etc.), laboratory animals (e.g., mice, rats, gerbils, etc.), pet animals (e.g., hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, buffaloes, etc.), poultry (turkeys, ducks, chickens, quails, geese, etc.), and pet birds (pigeons, parrots, mynah birds, Java sparrows, parakeets, Bengalese finches, canaries, etc.); or fish such as salmon, trout, and koi carp. By controlling and eradicating parasites, it is possible to prevent or treat parasitic diseases that are transmitted by the parasites.

Parasites to be controlled or eradicated include the following:
(1) Nematodes of the order Dioctophymatida (a) kidney worms of the family Dioctophymatidae, for example, kidney worms of the genus Dioctophyma (Dioctophyma spp.) (Dioctophyma renale);
(b) kidney worms of the family Soboliphymatidae, for example, Soboliphyme spp., Soboliphyme abei, Soboliphyme baturini.

(2) Nematodes of the order Trichocephalida (a) Trichinella of the family Trichinella, for example, Trichinella spp., Trichinella spiralis;
(b) Trichuridae whipworms, for example, Capillaria spp., Capillaria annulata, Capillaria contorta, Capillaria hepatica, Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris spp., Trichuris vulpis, Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris suis.

(3) Rhabditida Nematodes Strongyloides of the family Strongyloididae, for example, Strongyloides spp., Strongyloides papillosus, Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, Strongyloides ratti.

(4) Strongylida Nematodes Hookworms of the Ancylostomatidae family, for example, Ancylostoma spp., Ancylostoma braziliense, Ancylostoma caninum, Ancylostoma duodenale, Ancylostoma tubaeforme; Uncinaria stenocephala, Uncinaria stenocephala; Bunostomum spp., Bunostomum phlebotomum, Bunostomum trigonocephalum.

(5) Strongylida nematodes (a) Angiostrongylidae nematodes, for example, Aelurostrongylus abstrusus of Aelurostrongylus spp.; Angiostrongylus vasorum of Angiostrongylus spp.; Angiostrongylus cantonesis of Angiostrongylus cantonesis;
(b) nematodes of the family Crenosomatidae, for example, Crenosoma spp., Crenosoma aerophila, Crenosoma vulpis;
(c) nematodes of the family Filaroididae, for example, Filaroides spp., such as Filaroides hirthi and Filaroides osleri;
(D) lungworms of the family Metastrongylidae, for example, Metastrongylus spp., Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus pudendotectus, Metastrongylus salmi;
(e) Syngamidae open-beaked worms, for example, Cyathostoma spp., waterfowl lungworm (Cyathostoma bronchialis); Syngamus spp., Syngamus skrjabinomorpha, chicken open-beaked worm (Syngamus trachea).

(6) Strongylida nematodes (a) Molineidae nematodes, for example, Nematodirus spp., Nematodirus filicollis, Nematodirus spathiger;
(b) nematodes of the family Dictyocaulidae, for example, Dictyocaulus spp., Dictyocaulus filaria, Dictyocaulus viviparus;
(c) nematodes of the family Haemonchidae, for example, Haemonchus spp., Haemonchus contortus; Mecistocirrus spp., Mecistocirrus digitatus;
(D) Haemonchidae nematodes, for example, Ostertagia spp., Ostertagia ostertagi;
(e) Nematodes of the family Heligmonellidae, for example, Nippostrongylus spp., such as Nippostrongylus braziliensis;
(F) nematodes of the Trichostrongylidae family, for example, Trichostrongylus spp., Trichostrongylus axei, Trichostrongylus colubriformis, Trichostrongylus tenuis; Hyostrongylus spp., Hyostrongylus rubidus; Obeliscoides spp., Obeliscoides cuniculi.

(7) Strongylida nematodes (a) Chabertiidae nematodes, for example, Chabertia spp., Chabertia ovina; Oesophagostomum spp., Oesophagostomum brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum, Oesophagostomum georgianum, Oesophagostomum maplestonei, Oesophagostomum quadrispinulatum, Oesophagostomum radiatum, Oesophagostomum goat venulosum), intestinal tubercle worm (wild boar) (Oesophagostomum watanabei);
(b) nematodes of the family Stephanuridae, for example, Stephanurus spp., Stephanurus dentatus;
(c) Nematodes of the family Strongylidae, for example, Strongylus spp., such as Strongylus asini, Strongylus edentatus, Strongylus equinus, and Strongylus vulgaris.

(8) Nematodes of the order Oxyurida Nematodes of the family Oxyuridae, for example, Enterobius spp., chimpanzee pinworm (Enterobius anthropopitheci), pinworm (Enterobius vermicularis);
Oxyuris spp., horse pinworm (Oxyuris equi); Passalurus spp., rabbit pinworm (Passalurus ambiguus).

(9) Nematodes of the order Ascaridida (a) nematodes of the family Ascaridiidae, for example, Ascaridia spp., Ascaridia galli;
(b) nematodes of the Heterakidae family, for example, Heterakis spp., Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum, Heterakis pusilla, Heterakis putaustralis;
(c) Nematodes of the family Anisakidae, for example, Anisakis spp.
Anisakis simplex;
(d) nematodes of the Ascarididae family, for example, Ascaris spp., human roundworm (Ascaris lumbricoides), pig roundworm (Ascaris suum); Parascaris spp., horse roundworm (Parascaris equorum);
(e) Nematodes of the family Toxocaraidae, for example, Toxocara spp., such as Toxocara canis, Toxocara leonina, Toxocarasuum, Toxocara vitulorum, and Toxocara cati.

(10) Nematodes of the order Spirurida (a) Nematodes of the family Onchocercidae, for example, Brugia spp., Brugia malayi, Brugia pahangi, Brugia patei; Dipetalonema spp., Dipetalonema reconditum; Dirofilaria spp., Dirofilaria immitis; Filaria spp., Filaria oculi; Onchocerca spp., Onchocerca cervicalis cervicalis), Onchocerca gibsoni,
Pharyngeal heartworm (Onchocerca gutturosa);
(b) Nematodes of the family Setariidae, for example, Setaria spp., Setaria digitata, Setaria equina, Setaria labiatopapillosa, Setaria marshalli; Wuchereria spp., Wuchereria bancrofti;
(c) nematodes of the family Filariidae, for example, Parafilaria spp., multipapillosa; Stephanofilaria spp., Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.

(11) Nematodes of the order Spirurida (a) Nematodes of the family Gnathostomatidae, for example, Gnathostoma spp., Gnathostoma doloresi, Gnathostoma spinigerum;
(b) nematodes of the family Habronematidae, for example, Habronema spp., Habronema majus, Habronema microstoma, Habronema muscae; Draschia spp., Draschia megastoma;
(c) Physalopteridae nematodes, for example, Physaloptera spp., such as Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaloptera rara, Physaloptera sibirica, Physaloptera vulpinius, Physaloptera vulpineus);
(D) nematodes of the family Gongylonematidae, for example, Gongylonema spp., Gongylonema pulchrum;
(e) nematodes of the family Spirocercidae, for example, Ascarops spp., Ascarops strongylina;
(F) Nematodes of the family Thelaziidae, for example, Thelazia spp., such as Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Thelazia rhodesi, and Thelazia skrjabini.

[Control agents for other pests]
In addition, the benzimidazole compound of the present invention has excellent control effects against pests that have poisonous stingers or poisonous liquids and cause harm to humans and animals, pests that transmit various pathogens and pathogenic bacteria, and pests that cause discomfort to humans (poisonous pests, sanitary pests, nuisance pests, etc.).

Specific examples are given below.
(1) Pests of the Hymenoptera family: bees of the Argidae family, bees of the Cynipidae family, bees of the Diprionidae family, ants of the Formicidae family, bees of the Mutillidae family, and bees of the Vespidae family.

(2) Other pests: Cockroaches (Blattodea), termites (termite), spiders (Araneae), centipedes (cetipede), millipedes (millipede), crustacea, and bedbugs (Cimex lectularius).

[Formulation]
Some formulations of the pesticide, insecticide or acaricide, ectoparasite control agent, or endoparasite control or extermination agent of the present invention are shown below, but the additives and the addition ratios should not be limited to these examples and can be changed in a wide range. Parts in the formulations indicate parts by weight.

The formulations for horticultural and paddy rice use are shown below.

(Formulation 1: Wettable powder)
40 parts of the benzimidazole compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely ground to obtain a wettable powder containing 40% of the active ingredient.

(Formulation 2: Emulsion)
30 parts of the benzimidazole compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsifiable concentrate having an active ingredient content of 30%.

(Formulation 3: Granules)
5 parts of the benzimidazole compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and finely ground, and then granulated into granules having a diameter of 0.5 to 1.0 mm to obtain a granule containing 5% of the active ingredient.

(Formulation 4: Granules)
5 parts of the benzimidazole compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate are thoroughly ground and mixed, water is added, the mixture is thoroughly kneaded, and the mixture is granulated and dried to obtain granules containing 5% of the active ingredient.

(Formulation 5: Suspension)
10 parts of the benzimidazole compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of sodium polycarboxylate, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-pulverized until the particle size becomes 3 microns or less, to obtain a suspension containing 10% of the active ingredient.

The formulations for external parasite control agents, or internal parasite control or extermination agents are shown below.

(Formulation 6: Granules)
5 parts of the benzimidazole compound of the present invention are dissolved in an organic solvent to obtain a solution, which is sprayed onto 94 parts of kaolin and 1 part of white carbon, and then the solvent is evaporated under reduced pressure. This type of granule can be mixed with animal feed.

(Formulation 7: Injection)
0.1 to 1 part of the benzimidazole compound of the present invention and 99 to 99.9 parts of peanut oil are uniformly mixed and then sterilized by filtration through a sterilizing filter.

(Formulation 8: pour-on agent)
A pour-on agent is obtained by uniformly mixing 5 parts of the benzimidazole compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol.

(Formulation 9: Spot-on formulation)
A spot-on agent is obtained by uniformly mixing 10 to 15 parts of the benzimidazole compound of the present invention, 10 parts of a palmitic acid ester, and 75 to 80 parts of isopropanol.

(Formulation 10: Spray)
A spray agent is obtained by uniformly mixing 1 part of the benzimidazole compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol.

Next, the present invention will be described in more detail with reference to examples. However, the present invention is not limited in any way by the following examples.

Example 1
Synthesis of 6-(ethylsulfonyl)-1-methyl-5-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazole (Compound No. A-1)

(Step 1)
Synthesis of 6-(ethylthio)-1-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazole-5-carbaldehyde

5-Bromo-6-(ethylthio)-1-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazole (1.26 g) was dissolved in diethyl ether (20 ml) and the reaction vessel was replaced with nitrogen. It was then cooled to -78°C. 1.55M n-butyllithium n-hexane solution (2.9 ml) was added dropwise to this, and the mixture was stirred at -78°C for 1 hour. N,N-dimethylformamide (0.6 ml) was added to this, and the mixture was stirred at -78°C for 30 minutes. It was then warmed to room temperature and stirred for 1 hour.
The resulting liquid was poured into water and extracted with ethyl acetate. The resulting organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to obtain 0.44 g (yield 41%) of the target product.
^{The 1} H-NMR spectrum of the obtained target product is shown below.
^1H -NMR (400 MHz, _CDCl3 ) δ: 1.39 (3H, t), 3.01 (2H, q), 3.97 (3H, d), 7.44 (1H, s), 8.38 (1H, s), 10.50 (1H, s).

(Step 2)
Synthesis of 6-(ethylthio)-5-(1H-imdazol-2-yl)-1-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazole

6-(ethylthio)-1-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazole-5-carbaldehyde (0.71 g) was dissolved in ethanol (7 ml) and cooled to 0° C. 28% aqueous ammonia solution (3.25 g) and 40% aqueous glyoxal solution (1.94 g) were added dropwise thereto and stirred at 0° C. for 1 hour. The mixture was then warmed to room temperature and stirred overnight.
The resulting liquid was poured into water and extracted with chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to obtain 0.32 g (yield 40%) of the target product.
^{The 1} H-NMR spectrum of the obtained target product is shown below.
^1H -NMR (400 MHz, _CDCl3 ) δ: 1.20 (3H, t), 2.77 (2H, q), 3.95 (3H, s), 7.20 (2H, s), 7.60 (1H, s), 8.62 (1H, d), 11.04 (1H, s).

(Step 3)
Synthesis of 6-(ethylsulfonyl)-5-(1H-imdazol-2-yl)-1-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazole

6-(ethylthio)-5-(1H-imidazol-2-yl)-1-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazole (0.37 g) was dissolved in dichloromethane (11 ml), cooled to 0° C., and stirred. 70% metachloroperbenzoic acid (0.43 g) was added thereto, and stirred at room temperature for 5 hours. The resulting liquid was poured into a mixed solution of saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium thiosulfate, and extracted with dichloromethane. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to obtain 0.29 g of the target product (yield 71%).
^{The 1} H-NMR spectrum of the obtained target product is shown below.
^1H -NMR (400 MHz, _CDCl3 ) δ: 1.13 (3H, t), 3.00 (2H, q), 4.07 (3H, s), 7.23-7.26 (2H, m), 8.31 (1H, s), 8.38 (1H, s), 10.91 (1H, s).

(Step 4)
Synthesis of 6-(ethylsulfonyl)-1-methyl-5-(1-methyl-1H-imdazol-2-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazole

6-(ethylsulfonyl)-5-(1H-imidazol-2-yl)-1-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazole (0.29 g) was dissolved in N,N-dimethylformamide (4 ml) and cooled to 0° C. Potassium carbonate (0.13 g) and iodomethane (0.11 g) were added thereto and stirred at 0° C. for 1 hour. The mixture was then warmed to room temperature and stirred for 2 hours.
The resulting liquid was poured into water and extracted with ethyl acetate. The resulting organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to obtain 0.30 g of the target product (yield 100%).
^{The 1} H-NMR spectrum of the obtained target product is shown below.
^1H -NMR (400 MHz, _CDCl3 ) δ: 1.23 (3H, t), 3.44 (3H, s), 3.51 (2H, q), 4.11 (3H, d), 7.06 (1H, d), 7.14 (1H, d), 7.96 (1H, s), 8.38 (1H, s).

(Step 5)
Synthesis of 5-(5-bromo-1-methyl-1H-imdazol-2-yl)-6-(ethylsulfonyl)-1-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazole

6-(ethylsulfonyl)-1-methyl-5-(1-methyl-1H-imidazol-2-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazole (0.30 g) was dissolved in dichloromethane (4 ml) and cooled to 0° C. N-bromosuccinimide (0.87 g) was added thereto and stirred at 0° C. for 2 hours.
The resulting liquid was poured into water and extracted with dichloromethane. The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to obtain 0.31 g (yield 85%) of the target product.
^{The 1} H-NMR spectrum of the obtained target product is shown below.
^1H -NMR (400 MHz, _CDCl3 ) δ: 1.23 (3H, t), 3.37 (3H, s), 3.47 (2H, q), 4.11 (3H, s), 7.14 (1H, s), 7.95 (1H, s), 8.37 (1H, s).

(Step 6)
Synthesis of 6-(ethylsulfonyl)-1-methyl-5-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazole (Compound No. A-1)

5-(5-bromo-1-methyl-1H-imidazol-2-yl)-6-(ethylsulfonyl)-1-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazole (0.092 g) was dissolved in 1,4-dioxane (1.8 ml). 4-Trifluoromethoxyphenylboronic acid (0.050 g), tetrakis(triphenylphosphine)palladium(0) (0.012 g), cesium carbonate (0.13 g), and water (0.2 ml) were added thereto, and the mixture was stirred overnight under reflux conditions.
The resulting liquid was poured into water and extracted with ethyl acetate. The resulting organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to obtain 0.080 g (yield 74%) of the target product.
The melting point of the obtained target substance was 111-113° C. The ¹ H-NMR data was as follows.
^1H -NMR (400 MHz, _CDCl3 ) δ: 1.25 (3H, t), 3.37 (3H, s), 3.52 (2H, q), 4.12 (3H, s), 7.20 (1H, s), 7.32 (2H, d), 7.52 (2H, t), 8.04 (1H, s), 8.40 (1H, s).

Similarly, compound No. A-2 was synthesized.
The melting point of the obtained compound was 106-108°C.

[Biological Testing]
The usefulness of the benzimidazole compound of the present invention as an active ingredient in pest control agents and ectoparasite control agents will be demonstrated in the following test examples, in which "parts" are by weight.

(Preparation of Test Emulsions)
5 parts of the benzimidazole compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkylaryl ether were mixed and dissolved to prepare an emulsifiable concentrate (I) having an active ingredient content of 5%.

The mortality rate was calculated according to the following formula:

Insect killing rate (%) = (number of dead insects/number of test insects) x 100

(Test Example 1) Efficacy test against Spodoptera litura Emulsion (I) was diluted with water so that the concentration of the benzimidazole compound of the present invention was 125 ppm by mass. Cabbage leaves were immersed in the diluted solution for 30 seconds. The cabbage leaves were air-dried and placed in a petri dish. Five second-instar larvae of Spodoptera litura were released into the cabbage leaves. The petri dish was placed in a thermostatic chamber at a temperature of 25°C and a humidity of 60%. Six days after the release, a live/dead test was performed and the insecticidal rate was calculated. The test was performed in two replicates.
Both of the compounds Nos. A-1 and A-2 showed insecticidal rates of 80% or more.

(Test Example 2) Efficacy test against diamondback moth Emulsion (I) was diluted with water so that the concentration of the benzimidazole compound of the present invention was 125 mass ppm. Cabbage leaves were immersed in the diluted solution for 30 seconds. The cabbage leaves were air-dried and placed in a petri dish. Five second-instar diamondback moth larvae were released into the cabbage leaves. The petri dish was placed in a thermostatic chamber at a temperature of 25°C and a humidity of 60%. Three days after the release, the live/dead status was judged and the insecticidal rate was calculated. The test was performed in two replicates.
Both of the compounds Nos. A-1 and A-2 showed insecticidal rates of 80% or more.

(Test Example 3) Efficacy test against bean aphids Cowpea seedlings were grown in 3-inch pots, and bean aphid nymphs were inoculated onto the primary leaves. Emulsion (I) was diluted with water so that the benzimidazole compound of the present invention became 125 ppm. The diluted solution was sprayed onto cowpeas infested with bean aphid nymphs. The cowpeas were placed in a thermostatic chamber at a temperature of 25°C and a humidity of 60%. Four days after spraying, the bean aphids were judged to be alive or dead, and the insecticidal rate was calculated. The test was performed in duplicate.
Both of the compounds Nos. A-1 and A-2 showed insecticidal rates of 80% or more.

(Test Example 4) Efficacy test against Phyllotreta striolata Emulsion (I) was diluted with water so that the benzimidazole compound of the present invention was 125 ppm. The diluted solution was sprayed on bok choy seedlings (at the seventh true leaf development stage) planted in 3-inch pots. The bok choy seedlings were air-dried and then placed in plastic cups. Ten adult Phyllotreta striolata were released into the cups. The cups were stored in a thermostatic chamber at a temperature of 25°C and a humidity of 65%, and after 7 days from the release, a live/dead count was performed to calculate the insecticidal rate. The test was performed in duplicate.
Both of the compounds Nos. A-1 and A-2 showed insecticidal rates of 80% or more.

Test Example 5: Efficacy test against cat fleas The benzimidazole compound of the present invention was dissolved in isopropanol to prepare a 20 ppm drug solution. 100 μL of this drug solution was applied to the bottom surface of a glass vial (φ330 mm), and the isopropanol was evaporated by air drying to form a thin film of the benzimidazole compound of the present invention on the bottom surface.
Five adult cat fleas (Ctenocephalides felis) (male and female mixed) were released into the vial. The vial was then capped and placed in a thermostatic chamber at 25°C. Four days after release, the cat fleas were counted for survival and the mortality rate was calculated. The test was performed in duplicate.
The compound No. A-1 showed an insecticidal rate of 80% or more.

Since all of the benzimidazole compounds randomly selected from the benzimidazole compounds of the present invention have the above-mentioned effects, it can be understood that the benzimidazole compounds of the present invention, including compounds that have not been exemplified, are compounds that have pest control effects, particularly acaricidal and insecticidal effects, and are also compounds that are effective against external parasites and other parasites that are harmful to humans and livestock.

Claims (5)

A compound represented by formula (I) or a salt thereof:

In formula (I),
R ¹ is a substituted or unsubstituted C1-6 alkylsulfonyl group,
R ² and R ⁴ each independently represent a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group;
^R3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group;
R is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heteroaryl group, and R ⁵ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5-6 membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5-6 membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group, a cyano group, or a halogeno group . A pest control agent containing at least one selected from the group consisting of the compound according to claim 1 and its salt as an active ingredient. An insecticide or acaricide containing at least one selected from the group consisting of the compound and its salts according to claim 1 as an active ingredient. An external parasite control agent containing at least one selected from the group consisting of the compound according to claim 1 and its salt as an active ingredient. An agent for controlling or eliminating internal parasites, comprising as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and its salt.