WO2012060317A1

WO2012060317A1 - Ectoparasite control agent for animals

Info

Publication number: WO2012060317A1
Application number: PCT/JP2011/075049
Authority: WO
Inventors: 岩佐　孝男
Original assignee: 日本曹達株式会社
Priority date: 2010-11-04
Filing date: 2011-10-31
Publication date: 2012-05-10
Also published as: JP2014015397A

Abstract

An ectoparasite control agent having excellent effect at controlling lice, fleas, mosquitoes, gnats, flies, and other ectoparasites contains as an active ingredient at least one compound selected from heterocyclic compounds represented by formula (IV) or another formula, and salts thereof. (In formula (IV), X and X¹ represent halogen atoms or C_1-6 haloalkyl groups or the like; R¹ represents a C_1-6 haloalkyl group or the like; R² represents a hydrogen atom or the like; R³ represents a C_1-6 haloalkyl group or the like; n is an integer from 0 to 5, m is an integer from 0 to 6, E represents a carbon atom or nitrogen atom; and p is an integer of 1 or 2.)

Description

Animal ectoparasite control agent

The present invention relates to an animal ectoparasite control agent, a method for treating an animal suffering from an infection caused by an ectoparasite, and a method for preventing an animal from suffering from an infection caused by an ectoparasite.
This application claims priority in Japan based on Japanese Patent Application No. 2010-247936 filed on November 4, 2010 and Japanese Patent Application No. 2011-153870 filed on July 12, 2011, and its contents Is incorporated herein by reference.

Parasites that are parasitic on the outside of the skin and coat of animals such as livestock, poultry, and pets and that use blood and dandruff as nutrients are known. Representative examples of the parasites include fleas, lice, lice, ticks, acaras, ear scabies (ear mites), scabies (hymenids), claw mites, lung mites, and acne mites (hair follicles). Also known are pests that attach outside the animal's body and use blood, epidermis, dandruff, etc. as nutrients. Representative examples of the pest include diptera pests such as flies, abs and mosquitoes. In the present specification, parasites and pests using nutrients such as animal blood and dandruff as described above are referred to as ectoparasites. When such ectoparasites infest animals, the animals may be affected by infections such as skin diseases. The infection may also infect humans.
As ectoparasite control agents, various compounds containing various compounds as active ingredients have been developed. For example, Patent Document 1, Patent Document 2, and Patent Document 7 have proposed pyrethroid compounds, pyridine compounds, arylpyrazole compounds, isoxazoline compounds, and the like as active ingredients.

Patent Document 3 proposes a nitrogen-containing heterocyclic compound represented by the following formula and the use of the compound as a pest control agent.

In the above formula, R ₀ represents a halogen atom, Z represents an aryl group, A represents a carbon atom or a nitrogen atom, Y represents a nitro group, and D1 represents a 5- to 8-membered hydrocarbon group. Or a heterocyclic group, X1 represents —NR ₁ R ₂ (R ₁ is —C (═W) R ₁₃₀ (W represents an oxygen atom or a sulfur atom, R ₁₃₀ represents an organic group, etc.), etc. R ₂ represents a hydrogen atom, etc.), n1 represents an integer of 0 to 2, and n2 represents an integer of 0 to 3.

Patent Document 6 proposes a nitrogen-containing heterocyclic compound represented by the following formula and the use of the compound as a pest control agent.

In the above formula, the dotted line represents a single bond or a double bond. However, one of the two bonds indicated by the dotted line is a single bond, and the other is a double bond. A ₁ to A ₄ represent a carbon atom or a nitrogen atom, Y 1 represents a halogen atom or the like, n 3 represents an integer of 0 to 4, D 2 represents a methylene group or the like, R 3 represents a haloalkyl group or the like, ₁ and R ₂ represent a group represented by —C (═W) R ₁₃ (W represents an oxygen atom, R ₁₃ represents an alkyl group, a phenyl group, etc.), etc., and Z1 has a substituent. An optionally substituted phenyl group or the like is shown.

Patent Document 4 proposes a nitrogen-containing heterocyclic compound represented by the following formula and the use of the compound as a pest control agent.

In the above formula, X2 represents a carbon atom or an oxygen atom, Z2 represents an unsubstituted or substituted phenyl group or heterocyclic group, Q represents a hydrogen atom, a halogen atom, or the like, and q1 represents an integer of 0 to 7 S represents 0 or 1, A ₁ to A ₄ represent a carbon atom or a nitrogen atom, Y 2 represents a halogen atom or the like, n 4 represents an integer of 0 to 4, and W represents an oxygen atom or a sulfur atom R1 and R2 each independently represent a hydrogen atom or the like.

Patent Document 5 proposes a nitrogen-containing heterocyclic compound represented by the following formula and the use of the compound as a pest control agent.

In the above formula, D3 represents a haloalkyl group, Z3 represents a phenyl group which may have a substituent, X3 represents CH, CH ₂ , NH or the like, Y3 represents a methyl group or the like, n5 Represents an integer of 0 to 4, A ₁ to A ₄ each independently represents a carbon atom or a nitrogen atom, W represents an oxygen atom or a sulfur atom, R 5 and R 6 each independently represents a hydrogen atom, pyridylmethyl Indicates a group or the like.

JP 2002-201133 A JP 2007-529497 A WO2009 / 022746 Pamphlet JP 2008-110971 A JP 2008-133273 A JP 2009-062354 A JP 2010-536733 A

However, some conventional ectoparasite control agents have low ectoparasite control activity, short duration of activity, narrow spectrum of action, high toxicity, and limited use with other compounds There were issues such as. In addition, new problems such as the appearance of ectoparasites that have become resistant to conventional control agents have arisen.
Therefore, there is a demand for the development of a new animal ectoparasite control agent that solves these problems.
It is an object of the present invention to provide an animal ectoparasite control agent having an excellent control effect against ectoparasites and a method for preventing or treating ectoparasite-derived infectious diseases.

The present invention includes the following.
[1] An ectoparasite control agent for animals comprising as an active ingredient at least one compound selected from the heterocyclic compounds represented by formula (I) and salts thereof.

(In the formula (I), X is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2 Represents a -6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
n represents the number of substitutions of X and is an integer of 0 to 5. When n is 2 or more, Xs may be the same as or different from each other.
A ¹ and A ² each independently represent a carbon atom or a nitrogen atom.
B ¹ and B ² each independently represent a carbon atom or a nitrogen atom.
When B ¹ is a carbon atom and B ² is a nitrogen atom, the bond between B ¹ and B ² may be a double bond.
B ³ represents a carbon atom or an oxygen atom.
R ¹ represents a hydrogen atom, a halogen atom, or an unsubstituted or substituted C1-6 alkyl group.
X ⁰ is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group Represents an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
m1 represents the number of substitutions of X ⁰ and is an integer from 0 to 3. When m1 is 2 or more, X ⁰ each other may be the same or different from each other.
R ¹¹ is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted amino group, or an unsubstituted or substituted group A C1-6 alkylaminocarbonyl group having the formula:
R ¹² represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C1-6 alkoxy group, or a halogen atom. Show.
^Further, connected is ^{R 11} and ^{R 12,} together with the carbon atom bonded, 5-8-membered having a hydrocarbon ring or a substituent ^{R 20} 5-8 membered ring having a substituent ^{R 20} A ring heterocycle may be formed.
R ²⁰ represents a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group An unsubstituted or substituted C1-6 alkoxy group, a nitro group, a cyano group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group , An amino group, or a substituent represented by —N (R ² ) COR ³ .
R ² represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-7 acyl group, or an unsubstituted or substituted C1-6 alkoxycarbonyl group Indicates.
R ³ represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C2-6 alkenyloxy group, an unsubstituted or substituted group; And a C2-6 alkynyloxy group having an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heterocyclic group.
E represents a carbon atom or a nitrogen atom. )

[2] An ectoparasite control agent for animals comprising as an active ingredient at least one compound selected from the heterocyclic compounds represented by formula (II) and salts thereof.

(In the formula (II), D represents a 5- to 8-membered hydrocarbon ring or a 5- to 8-membered heterocyclic ring.
R ²¹ is a substituent bonded to D and is an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group, an amino group, or —N ( R ² ) represents a substituent represented by COR ³ .
X ¹ is a substituent bonded to the condensed ring containing D and is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, unsubstituted Or a substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
m represents the number of substitutions of X ¹ and is an integer from 0 to 6. When m is 2 or more, X ¹ may be the same as or different from each other. X ¹ may be substituted on the condensed ring containing D.
X, n, A ¹ , A ² , R ¹ , E, R ² and R ³ have the same meaning as in formula (I). )

[3] An ectoparasite control agent for animals comprising as an active ingredient at least one compound selected from the heterocyclic compounds represented by formula (III) and salts thereof.

(In formula (III), p represents the number of repeating methylene groups in parentheses and is either 1 or 2.
X, n, A ¹ , A ² , R ¹ , X ¹ , m, R ² , R ³ and E have the same meaning as in formula (II). )

[4] An ectoparasite control agent for animals comprising as an active ingredient at least one compound selected from the heterocyclic compounds represented by formula (IV) and salts thereof.

(In formula (IV), X, n, R ¹ , X ¹ , m, E, R ² , R ³ and p have the same meaning as in formula (III).)

[5] Treatment of an animal suffering from an ectoparasite-derived infection comprising administering a veterinary-acceptable amount of the ectoparasite control agent according to any one of [1] to [4] Method.
[6] An animal suffers from an ectoparasite-derived infection comprising administering a veterinary-acceptable amount of the ectoparasite control agent according to any one of [1] to [4]. How to prevent.

The ectoparasite control agent for animals of the present invention can control ectoparasites such as ticks from animals with high effects, has a long duration of effect, has a wide action spectrum, and is low in toxicity. There are few restrictions on mixed use.
By administering the animal ectoparasite control agent of the present invention to an animal, it is possible to prevent the animal from suffering from an ectoparasite-derived infection.
An infectious disease can be treated by administering the animal ectoparasite control agent of the present invention to an animal suffering from an ectoparasite-derived infection.

The present inventor has found that a control agent containing a specific heterocyclic compound as an active ingredient has a particularly excellent ectoparasite control effect. The present invention has been completed based on these findings.

The animal ectoparasite control agent of the present invention is at least one compound selected from heterocyclic compounds represented by the formula (I), formula (II), formula (III) or formula (IV) and salts thereof Is contained as an active ingredient.

(In the formula (I), X is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2 Represents a -6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
n represents the number of substitutions of X and is an integer of 0 to 5. When n is 2 or more, Xs may be the same as or different from each other.
A ¹ and A ² each independently represent a carbon atom or a nitrogen atom.
B ¹ and B ² each independently represent a carbon atom or a nitrogen atom.
When B ¹ is a carbon atom and B ² is a nitrogen atom, the bond between B ¹ and B ² may be a double bond.
B ³ represents a carbon atom or an oxygen atom.
R ¹ represents a hydrogen atom, a halogen atom, or an unsubstituted or substituted C1-6 alkyl group.
X ⁰ is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group Represents an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
m1 represents the number of substitutions of X ⁰ and is an integer from 0 to 3. When m1 is 2 or more, X ⁰ each other may be the same or different from each other.
R ¹¹ is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted amino group, or an unsubstituted or substituted group A C1-6 alkylaminocarbonyl group having the formula:
R ¹² represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C1-6 alkoxy group, or a halogen atom. Show.
^Further, connected is ^{R 11} and ^{R 12,} together with the carbon atoms to which they are attached a 5-8 membered having a hydrocarbon ring or a substituent ^{R 20} 5-8 membered having a substituent ^{R 20} A heterocycle may be formed.
R ²⁰ represents a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group An unsubstituted or substituted C1-6 alkoxy group, a nitro group, a cyano group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group , An amino group, or a substituent represented by —N (R ² ) COR ³ .
R ² represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-7 acyl group, or an unsubstituted or substituted C1-6 alkoxycarbonyl group Indicates.
R ³ represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C2-6 alkenyloxy group, an unsubstituted or substituted group; And a C2-6 alkynyloxy group having an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heterocyclic group.
E represents a carbon atom or a nitrogen atom. )

(In the formula (II), D represents a 5- to 8-membered hydrocarbon ring or a 5- to 8-membered heterocycle.
R ²¹ is a substituent bonded to D and is an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group, an amino group, or —N ( R ² ) represents a substituent represented by COR ³ .
X ¹ is a substituent bonded to the condensed ring containing D and is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, unsubstituted Or a substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
m represents the number of substitutions of X ¹ and is an integer from 0 to 6. When m is 2 or more, X ¹ may be the same as or different from each other.
X, n, A ¹ , A ² , R ¹ , E, R ² and R ³ have the same meaning as in formula (I). )

[Active ingredients]
The animal ectoparasite control agent of the present invention comprises at least one compound selected from the heterocyclic compounds represented by the formula (I) or salts thereof, preferably the heterocyclic compounds represented by the formula (II) or the compounds thereof At least one compound selected from salts, more preferably a heterocyclic compound represented by formula (III) or at least one compound selected from salts thereof, more preferably a heterocyclic compound represented by formula (IV) Or at least 1 type of compound chosen from the salt is included as an active ingredient.

First, the meanings of symbols and terms used in formulas (I) to (IV) will be described.
The term “unsubstituted” means only the group that is the mother nucleus. When there is no description of “having a substituent” and only the name of the group serving as a mother nucleus is used, it means “unsubstituted” unless otherwise specified.
On the other hand, the term “having a substituent” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having the same or different structure from the mother nucleus. Accordingly, the “substituent” is another group bonded to a group serving as a mother nucleus. The number of substituents may be one, or two or more. Two or more substituents may be the same or different.
Terms such as “C1-6” indicate that the group serving as the mother nucleus has 1 to 6 carbon atoms. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.

The “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
Examples of the group that can be a “substituent” include halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl C1-6 alkyl groups such as a group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; C3-8 such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group A cycloalkyl group; a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-hex C2-6 alkenyl groups such as a xenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group; 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group, 4- C3-8 cycloalkenyl groups such as cyclooctenyl group; 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, A C2-6 alkynyl group such as a 1,1-dimethyl-2-butynyl group;

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, t-butoxy group; vinyloxy group, allyloxy group, propenyl C2-6 alkenyloxy groups such as oxy and butenyloxy groups; C2-6 alkynyloxy groups such as ethynyloxy and propargyloxy groups; C6-10 aryl groups such as phenyl and naphthyl groups; phenoxy groups and 1-naphthoxy groups C7-10 aryloxy group such as benzyl group, phenethyl group, etc .; C7-11 aralkyloxy group such as benzyloxy group, phenethyloxy group; formyl group, acetyl group, propionyl group, benzoyl group, Such as cyclohexylcarbonyl group 1-7 acyl groups; C1-7 acyloxy groups such as formyloxy group, acetyloxy group, propionyloxy group, benzoyloxy group, cyclohexylcarbonyloxy group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i- C1-6 alkoxycarbonyl groups such as propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group; carboxyl group;

Hydroxyl group; oxo group; C1-6 haloalkyl such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group Groups; C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group; 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5- C2-6 haloalkynyl groups such as bromo-2-pentynyl group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group and 2,3-dichlorobutoxy group; 2-chloropropenyloxy group, 3-bromo C2-6 haloalkenyloxy groups such as butenyloxy groups; 4-chlorophenyl group, 4-fluorophenyl group, 2,4-dichloro C6-10 haloaryl group such as phenyl group; C6-10 haloaryloxy group such as 4-fluorophenyloxy group, 4-chloro-1-naphthoxy group; chloroacetyl group, trifluoroacetyl group, trichloroacetyl group, 4- Halogen-substituted C1-7 acyl groups such as chlorobenzoyl groups;

Cyano group; Isocyano group; Nitro group; Isocyanato group; Cyanato group; Amino group; C1-6 alkylamino group such as methylamino group, dimethylamino group and diethylamino group; C6-10 arylamino group such as anilino group and naphthylamino group Groups: C7-11 aralkylamino groups such as benzylamino group and phenylethylamino group; C1-7 such as formylamino group, acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group, benzoylamino group Acylamino group; C1-6 alkoxycarbonylamino group such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group; aminocarbonyl group, dimethylaminocarb An unsubstituted or substituted aminocarbonyl group such as a nyl group, a phenylaminocarbonyl group, an N-phenyl-N-methylaminocarbonyl group; an iminomethyl group, a (1-imino) ethyl group, a (1-imino) -n A C1-6 alkyl group substituted by an imino group such as propyl group; hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group, methoxyiminomethyl group, (1-methoxyimino ) A C1-6 alkyl group substituted with a hydroxyimino group such as an ethyl group;

Mercapto group; isothiocyanato group; thiocyanato group; C1-6 alkylthio such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group Groups: C2-6 alkenylthio groups such as vinylthio groups and allylthio groups; C2-6 alkynylthio groups such as ethynylthio groups and propargylthio groups; C6-10 arylthio groups such as phenylthio groups and naphthylthio groups; thiazolylthio groups and pyridylthio groups Heteroarylthio group of C7-11 aralkylthio group such as benzylthio group and phenethylthio group; (methylthio) carbonyl group, (ethylthio) carbonyl group, (n-propylthio) carbonyl group, (i-propylthio) carbonyl , (N- butylthio) carbonyl group, (i-butylthio) carbonyl group, (s-butylthio) carbonyl group, (t-butylthio) (C1 ~ 6 alkylthio), such as a carbonyl group a carbonyl group;

C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C2-6 alkenylsulfinyl groups such as allylsulfinyl group; C2-6 alkynylsulfinyl groups such as propargylsulfinyl group; phenylsulfinyl group, etc. A C6-10 arylsulfinyl group such as: thiazolylsulfinyl group, heteroarylsulfinyl group such as pyridylsulfinyl group; C7-11 aralkylsulfinyl group such as benzylsulfinyl group, phenethylsulfinyl group; methylsulfonyl group, ethylsulfonyl group, t- C1-6 alkylsulfonyl groups such as butylsulfonyl group; C2-6 alkenylsulfonyl groups such as allylsulfonyl group; propargylsulfonyl group C2-6 alkynylsulfonyl groups of C6-10 arylsulfonyl groups such as phenylsulfonyl groups; heteroarylsulfonyl groups such as thiazolylsulfonyl groups and pyridylsulfonyl groups; C7-11 aralkylsulfonyl groups such as benzylsulfonyl groups and phenethylsulfonyl groups Group;

5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; pyridyl, pyrazinyl Groups, 6-membered heteroaryl groups such as pyrimidinyl group, pyridanidyl group, triazinyl group; saturated heterocyclic groups such as aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, piperidyl group, piperazinyl group, morpholinyl group; trimethylsilyl group, triethyl Examples thereof include tri-C1-6 alkyl-substituted silyl groups such as silyl group and t-butyldimethylsilyl group; triphenylsilyl group;

In addition, these “substituents” may be those in which any hydrogen atom in the group is further substituted with another “substituent”.

(X)
X is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group, An unsubstituted or substituted C1-6 alkoxy group, nitro group, or cyano group is shown.
n represents the number of substitutions of X and is an integer of 0 to 5. When n is 2 or more, Xs may be the same as or different from each other.

Examples of the “halogen atom” in X include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

The “C1-6 alkyl group” in X may be a straight chain or a branched chain. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group and t-butyl group. I-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.

Examples of the “C1-6 alkyl group having a substituent” in X include C3-8 cyclohexane such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, 2-cyclooctylethyl group, etc. Alkyl C1-6 alkyl group; fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2- Trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro -1-trifluoromethylethyl group, perfluorohexyl group, perchlor Hexyl group, C1 ~ 6 haloalkyl group such as 2,4,6-trichloro-hexyl group;

Hydroxy C1-6 alkyl groups such as hydroxymethyl group, 2-hydroxyethyl group; methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, n-propoxymethyl group, i-propoxy group C1-6 alkoxy C1-6 alkyl groups such as ethyl group, s-butoxymethyl group, t-butoxyethyl group; methoxymethoxymethyl group, 1-methoxyethoxymethyl group, 2-methoxyethoxymethyl group, 2- (1- C1-6 alkoxy C1-6 alkoxy C1-6 alkyl groups such as methoxyethoxy) ethyl group, 2- (2-methoxyethoxy) ethyl group; dimethoxymethyl group, diethoxymethyl group, 2,2-dimethoxyethyl group, 1 , 2-Dimethoxyethyl group, 3,3-dimethoxyn-propyl Di-C1-6 alkoxy C1-6 alkyl groups such as 2,2-diethoxyethyl group; C1-6 such as formyloxymethyl group, acetoxymethyl group, 2-acetoxyethyl group, propionyloxymethyl group, propionyloxyethyl group, etc. 7 acyloxy C1-6 alkyl group; C1-6 alkyl group substituted by imino group such as iminomethyl group, (1-imino) ethyl group, (1-imino) propyl group; hydroxyiminomethyl group, (1-hydroxyimino C1-6 alkyl groups substituted by hydroxyimino groups such as ethyl, (1-hydroxyimino) -n-propyl, methoxyiminomethyl, (1-methoxyimino) ethyl; unsubstituted or substituted A non-substituted or substituted phenethyl group such as a benzyl group having C7 ~ 11 aralkyl group having conversion of or substituents; and the like.

Examples of the “C2-6 alkenyl group” in X include a 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, 5-hexenyl group and the like.
Examples of the “substituted C2-6 alkenyl group” in X include C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group;

The “C2-6 alkynyl group” in X is an 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 1,1-dimethyl-2-butynyl group and the like.
Examples of the “substituted C2-6 alkynyl group” in X include C2-6 halo such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group, etc. Alkynyl group; and the like.

Examples of the “C1-6 alkoxy group” in X include a methoxy group, an ethoxy group, an i-propoxy group, an n-butoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group, an n-pentyloxy group, i -Pentyloxy group, n-hexyloxy group and the like.
Examples of the “C1-6 alkoxy group having a substituent” in X include a fluoromethoxy group, a chloromethoxy group, a bromomethoxy group, a difluoromethoxy group, a dichloromethoxy group, a dibromomethoxy group, a trifluoromethoxy group, a trichloromethoxy group, Bromomethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, pentafluoroethoxy group, 4-fluorobutoxy group, 3,3,3-trifluoropropoxy group, 2,2 , 2-trifluoro-1-trifluoromethylethoxy group, perfluorohexyloxy group and other C1-6 haloalkoxy groups; methoxymethoxy group, 1-methoxyethoxy group, 2-methoxyethoxy group, ethoxymethoxy group, 1- Ethoxyethoxy group, 2-ethoxyethoxy group, 1-methyl A C1-6 alkoxy C1-6 alkoxy group such as a xy-n-propoxy group, a 2-methoxy-n-propoxy group, a 3-methoxy-n-propoxy group; a cyclopropylmethoxy group, a cyclobutylmethoxy group, a cyclopentylmethoxy group, C3-8 cycloalkyl C1-6 alkoxy groups such as cyclohexylmethoxy group, 2-methylcyclopropylmethoxy group, 2,3-dimethylcyclopropylmethoxy group, 2-cyclopropylethoxy group; benzyloxy group, phenethyloxy group, etc. C7-11 aralkyloxy group; and the like.

Of these, X is preferably a halogen atom or a C1-6 haloalkyl group.

^(A ^{1, A} 2)
A ¹ and A ² each independently represent a carbon atom or a nitrogen atom.
When both A ¹ and A ² are carbon atoms, the aromatic ring containing this represents a benzene ring. When both A ¹ and A ² are nitrogen atoms, the aromatic ring containing it represents a pyrimidine ring. When either A ¹ or A ² is a nitrogen atom and the other is a carbon atom, the aromatic ring containing it represents a pyridine ring. In the present invention, both A ¹ and A ² are preferably carbon atoms.

^{^{^{(B 1, B 2, B}}} 3)
B ¹ and B ² each independently represent a carbon atom or a nitrogen atom. It is preferred that one of B ¹ or B ² is a nitrogen atom.
B ³ represents a carbon atom or an oxygen atom.
When B ¹ is a carbon atom and B 2 is a nitrogen atom, the bond between B ¹ and B ² may be a double bond.
When B ¹ is a nitrogen atom and B ² and B ³ are both carbon atoms, the heterocycle containing the same represents a pyrrolidine ring.
When B ² is a nitrogen atom and both B ¹ and B ³ are carbon atoms, the heterocycle containing the same represents a pyrroline ring (also known as 3,4-dihydro-2H-pyrrole ring).
When B ¹ is a carbon atom, B ² is a nitrogen atom, and B ³ is an oxygen atom, the heterocycle containing this is an isoxazoline ring (also known as a 4,5-dihydroisoxazole ring).

(R ¹ )
R ¹ represents a hydrogen atom, a halogen atom, or an unsubstituted or substituted C1-6 alkyl group.
Examples of the “halogen atom” and “unsubstituted or substituted C1-6 alkyl group” in R ¹ include the same as those exemplified in the above X.
Of these, R ¹ is preferably a C1-6 haloalkyl group.

(X ⁰ )
X ⁰ is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group Represents an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
m1 represents the number of substitutions of X ⁰ and is an integer from 0 to 3. When m1 is 2 or more, X ⁰ each other may be the same or different from each other.
X "halogen atom" in ^0, C2 having "unsubstituted or C1 ~ 6 alkyl group having a substituent", "C2 ~ 6 alkenyl groups having an unsubstituted or substituted group", "unsubstituted or substituted Examples of the “˜6 alkynyl group” and the “unsubstituted or substituted C1-6 alkoxy group” include those exemplified in the above X.

(R ¹¹ , R ¹² )
R ¹¹ is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted amino group, or an unsubstituted or substituted group A C1-6 alkylaminocarbonyl group having the formula:
Examples of the “unsubstituted or substituted C1-6 alkyl group” and the “unsubstituted or substituted C2-6 alkenyl group” in R ¹¹ are the same as those exemplified in the above X. Can do.

As the “C1-6 alkyl group having a substituent” in R ^11, in addition to those exemplified in the above X, a formylaminomethyl group, an acetylaminomethyl group, a 2-acetylaminoethyl group, a propionylaminomethyl group, a propionylamino group A C1-7 acylamino C1-6 alkyl group such as a methyl group;

Examples of the “substituted amino group” in R ¹¹ include a C1-6 alkylamino group such as a methylamino group, an ethylamino group, and a dimethylamino group; a C2-6 alkenylamino group such as a vinylamino group and an allylamino group; And N′-substituted hydrazino groups such as a hydrazino group, an N ′, N′-dimethylhydrazino group, and an N′-methylenehydrazino group.

Examples of the “C1-6 alkylaminocarbonyl group” for R ¹¹ include a methylaminocarbonyl group, ethylaminocarbonyl group, n-propylaminocarbonyl group and the like.
As the “substituted C1-6 alkylaminocarbonyl group” for R ¹¹ , a C1-6 haloalkylaminocarbonyl group such as a trifluoromethylaminocarbonyl group or a 2,2,2-trifluoroethylaminocarbonyl group; C1-6 alkoxy C1-6 alkylaminocarbonyl groups such as aminocarbonyl group and methoxyethylaminocarbonyl group; heteroaryl group substitution C1-6 such as pyridylmethylaminocarbonyl group, pyridylethylaminocarbonyl, pyrimidylmethylaminocarbonyl group Alkylaminocarbonyl group; and the like.

R ¹² represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C1-6 alkoxy group, or a halogen atom. Show.
“Unsubstituted or substituted C1-6 alkyl group”, “Unsubstituted or substituted C2-6 alkenyl group”, “Unsubstituted or substituted C1-6 alkoxy group” in R ¹² , And “halogen atom” may be the same as those exemplified in X above.

^{Also, R 11} and ^{R 12,} they are connected, closed together with the carbon atoms to which they are attached a hydrocarbon ring of 5 to 8-membered ring having a substituent ^{R 20,} or, the substituents ^{R 20} And a 5- to 8-membered heterocycle containing at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom may be formed.
R ²⁰ represents a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group An unsubstituted or substituted C1-6 alkoxy group, a nitro group, a cyano group; an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group , An amino group, or a substituent represented by —N (R ² ) COR ³ .

As the “5- to 8-membered hydrocarbon ring” or “5- to 8-membered heterocycle”, a C5-8 cycloalkene ring such as a cyclopentene ring or a cycloheptane ring; a C6-8 aryl ring such as a benzene ring; And heterocyclic rings such as a dihydrofuran ring, a pyrrole ring, a pyrazole ring, and a 3,4-dihydro-2H-pyran ring;

"Halogen atom" in R ^20, with the "unsubstituted or C1 ~ 6 alkyl group having a substituent", "C2 ~ 6 alkenyl groups having an unsubstituted or substituted group", "unsubstituted or substituted C2 Examples of the “˜6 alkynyl group” and the “unsubstituted or substituted C1-6 alkoxy group” include those exemplified in the above X. Examples of the “unsubstituted or substituted C1-6 alkylaminocarbonyl group” for R ²⁰ include the same groups as those exemplified for R ¹¹ above.

Examples of the “C1-7 acyl group” in R ²⁰ include formyl group, acetyl group, propionyl group, benzoyl group and the like.
Examples of the “substituted C1-7 acyl group” in R ²⁰ include halogen-substituted C1-7 acyl groups such as a chloroacetyl group, a trifluoroacetyl group, a trichloroacetyl group, and a 4-chlorobenzoyl group. .

(R ² )
R ² represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-7 acyl group, or an unsubstituted or substituted C1-6 alkoxycarbonyl group Indicates.

Examples of the “unsubstituted or substituted C1-6 alkyl group” for R ² include the same as those exemplified for X above.
Examples of the “unsubstituted or substituted C1-7 acyl group” in R ² include the same as those exemplified for R ²⁰ above.

Examples of the “C1-6 alkoxycarbonyl group” for R ² include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and the like.
Examples of the “substituted C1-6 alkoxycarbonyl group” for R ² include a cyclopropylmethoxycarbonyl group, a cyclobutylmethoxycarbonyl group, a cyclopentylmethoxycarbonyl group, a cyclohexylmethoxycarbonyl group, a 2-methylcyclopropylmethoxycarbonyl group, 2 , 3-dimethylcyclopropylmethoxycarbonyl group, 2-chlorocyclopropylmethoxycarbonyl group, 2-cyclopropylethoxycarbonyl group and the like C3-8 cycloalkyl C1-6 alkoxycarbonyl group; fluoromethoxycarbonyl group, chloromethoxycarbonyl group, Bromomethoxycarbonyl group, difluoromethoxycarbonyl group, dichloromethoxycarbonyl group, dibromomethoxycarbonyl group, trifluoromethoxycarbonyl group Trichloromethoxycarbonyl group, tribromomethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 2,2,2-trichloroethoxycarbonyl group, pentafluoroethoxycarbonyl group, 4-fluorobutoxycarbonyl group, 3,3 , 3-trifluoropropoxycarbonyl groups, 2,2,2-trifluoro-1-trifluoromethylethoxycarbonyl groups, C1-6 haloalkoxycarbonyl groups such as perfluorohexyloxycarbonyl groups; .

(R ³ )
R ³ represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C2-6 alkenyloxy group, an unsubstituted or substituted group; And a C2-6 alkynyloxy group having an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heterocyclic group.

“Unsubstituted or substituted C1-6 alkyl group”, “Unsubstituted or substituted C2-6 alkenyl group”, “Unsubstituted or substituted C2-6 alkynyl group” in R ³ In addition, examples of the “unsubstituted or substituted C1-6 alkoxy group” include those exemplified for X above.

Examples of the “C3-8 cycloalkyl group” in R ³ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like.
Examples of the “substituted C3-8 cycloalkyl group” for R ³ include a chlorocyclohexyl group, a bromocyclohexyl group, a 2-methylcyclopropyl group, and a 2,3-dimethylcyclopropyl group.

Examples of the “C2-6 alkenyloxy group” in R ³ include a vinyloxy group, a 1-propenyloxy group, a 2-propenyloxy group, a 1-butenyloxy group, a 2-butenyloxy group, a 3-butenyloxy group, and a 1-methyl-2- Propenyloxy group, 2-methyl-2-propenyloxy group, 1-pentenyloxy group, 2-pentenyloxy group, 1-methyl-2-butenyloxy group, 2-methyl-2-butenyloxy group, 1-hexenyloxy group, Examples include 2-hexenyloxy group.
Examples of the “substituted C2-6 alkenyloxy group” in R ³ include C2-6 haloalkenyloxy groups such as 2-chloro-1-propenyloxy group, 2-fluoro-1-butenyloxy group; .

Examples of the “C2-6 alkynyloxy group” in R ³ include ethynyloxy group, 1-propynyloxy group, 2-propynyloxy group, 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1-methyl-2 -Propynyloxy group, 2-methyl-3-butynyloxy group, 1-pentynyloxy group, 2-pentynyloxy group, 1-methyl-2-butynyloxy group, 2-methyl-3-pentynyloxy group, 1- Examples include hexynyloxy group.
Examples of the “substituted C2-6 alkynyloxy group” for R ³ include a 4,4-dichloro-1-butynyloxy group, a 4-fluoro-1-pentynyloxy group, and a 5-bromo-2-pentynyloxy group. C2-6 haloalkynyloxy groups such as and the like;

The “C6-10 aryl group” in R ³ may be monocyclic or polycyclic. In the polycyclic aryl group, as long as at least one ring is an aromatic ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the C6-10 aryl group include a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, and a tetralinyl group.

The “heterocyclic group” in R ³ includes 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom as atoms constituting the ring. The heterocyclic group may be monocyclic or polycyclic.
Examples of the heterocyclic group include a 5-membered heteroaryl group, a 6-membered heteroaryl group, a condensed heteroaryl group, a saturated heterocyclic group, and a partially unsaturated heterocyclic group.

5-membered heteroaryl groups include: pyrrolyl groups such as pyrrol-1-yl, pyrrol-2-yl, and pyrrol-3-yl; furyl groups such as furan-2-yl and furan-3-yl ; Thienyl groups such as thiophen-2-yl group and thiophen-3-yl group; imidazolyl groups such as imidazol-1-yl group, imidazol-2-yl group, imidazol-4-yl group and imidazol-5-yl group A pyrazolyl group such as a pyrazol-1-yl group, a pyrazol-3-yl group, a pyrazol-4-yl group, a pyrazol-5-yl group; an oxazol-2-yl group, an oxazol-4-yl group, an oxazole-5 -Oxazolyl groups such as yl groups; isoxazol-3-yl groups, isoxazol-4-yl groups, isoxazol-5-yl Isoxazolyl groups such as: thiazolyl groups such as thiazol-2-yl group, thiazol-4-yl group, thiazol-5-yl group; isothiazol-3-yl group, isothiazol-4-yl group, isothiazol-5 -An isothiazolyl group such as an yl group; 1,2,3-triazol-1-yl group, 1,2,3-triazol-4-yl group, 1,2,3-triazol-5-yl group, 1,2 , 4-triazol-1-yl group, 1,2,4-triazol-3-yl group, 1,2,4-triazol-5-yl group and the like; 1,2,4-oxadiazole- Oxadiazolyl groups such as 3-yl group, 1,2,4-oxadiazol-5-yl group, 1,3,4-oxadiazol-2-yl group; Groups, thiadiazolyl groups such as 1,2,4-thiadiazol-5-yl group and 1,3,4-thiadiazol-2-yl group; tetrazolyl groups such as tetrazol-1-yl group and tetrazol-2-yl group; Etc.

The 6-membered heteroaryl group includes pyridyl groups such as pyridin-2-yl group, pyridin-3-yl group and pyridin-4-yl group; pyrazinyl groups such as pyrazin-2-yl group and pyrazin-3-yl group A pyrimidinyl group such as a pyrimidin-2-yl group, a pyrimidin-4-yl group and a pyrimidin-5-yl group; a pyridazinyl group such as a pyridazin-3-yl group and a pyridazin-4-yl group; a triazinyl group; It is done.

Other heterocyclic groups include: aziridin-1-yl group, aziridin-2-yl group, epoxy group; pyrrolidin-1-yl group, pyrrolidin-2-yl group, pyrrolidin-3-yl group, tetrahydrofuran-2- Yl group, tetrahydrofuran-3-yl group; piperidin-1-yl group, piperidin-2-yl group, piperidin-3-yl group, piperidin-4-yl group, piperazin-1-yl group, piperazin-2-yl Group, morpholin-2-yl group, morpholin-3-yl group, morpholin-4-yl group; 1,3-benzodioxol-4-yl group, 1,3-benzodioxol-5-yl group 1,4-benzodioxan-5-yl group, 1,4-benzodioxan-6-yl group, 3,4-dihydro-2H-1,5-benzodioxepin-6-yl 3,4-dihydro-2H-1,5-benzodioxepin-7-yl group, 2,3-dihydrobenzofuran-4-yl group, 2,3-dihydrobenzofuran-5-yl group, 2,3 -Dihydrobenzofuran-6-yl group, 2,3-dihydrobenzofuran-7-yl group;

Among these, R ³ is preferably a C1-6 alkyl group, a C1-6 alkoxy C1-6 alkyl group, or a C1-6 alkoxy C1-6 alkoxy C1-6 alkyl group.

(E)
E represents a carbon atom or a nitrogen atom. Of these, E is preferably a carbon atom.

(Heterocyclic compound represented by formula (II))
In the heterocyclic compound represented by the formula (II), in the formula (I), B ¹ is a carbon atom, B ² is a nitrogen atom, B ³ is an oxygen atom, and a bond between B ¹ and B ² is a double bond It is what has become. That is, the heterocyclic compound represented by the formula (II) has an isoxazoline ring (4,5-dihydroisoxazole ring).
Furthermore, the heterocyclic compound represented by the formula (II) has a substituent R ^{21 in} which R ¹¹ and R ¹² in the formula (I) are linked together with the carbon atom to which they are bonded. 5- to 8-membered hydrocarbon ring or 5- to 8-membered heterocycle having substituent R ²¹ and containing at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom It is what forms.
D in the formula (II) represents a 5- to 8-membered hydrocarbon ring or a 5- to 8-membered heterocycle containing at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. .
R ²¹ is a substituent bonded to D and is an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group, an amino group, or —N ( R ² ) represents a substituent represented by COR ³ .

(X ¹ )
X ¹ is a substituent bonded to the condensed ring containing D and is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, unsubstituted Or a substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
m represents the number of substitutions of X ¹ and is an integer from 0 to 6. When m is 2 or more, X ¹ may be the same as or different from each other.
[Halogen atom "in X ^1," C1 ~ 6 alkyl group having an unsubstituted or substituted group "," C2 ~ 6 alkenyl groups having an unsubstituted or substituted group ", C2 having" unsubstituted or substituted Examples of the “˜6 alkynyl group” and the “unsubstituted or substituted C1-6 alkoxy group” include those exemplified in the above X.
X, n, A ¹ , A ² , R ¹ , E, R ² and R ³ in formula (II) have the same meaning as in formula (I).

(Heterocyclic compound represented by formula (III))
In the heterocyclic compound represented by the formula (III), D is a 5- or 6-membered hydrocarbon ring in the formula (II), and R ²¹ is a substituent represented by —N (R ² ) COR ^3. It is what has become. That is, p represents the number of repeating methylene groups in parentheses and is either 1 or 2. p is preferably 1. That is, the heterocyclic compound represented by the formula (III) preferably has an indane ring (also known as a 2,3-dihydroindene ring). X, n, A ¹ , A ² , R ¹ , X ¹ , m, R ² , R ³ and E in formula (III) have the same meaning as in formula (II).

(Heterocyclic compound represented by formula (IV))
The heterocyclic compound represented by the formula (IV) is one in which both A ¹ and A ^{2 in} the formula (III) are carbon atoms. X, n, R ¹ , X ¹ , m, E, R ² , R ³ and p in formula (IV) have the same meaning as in formula (III).

The salt of the heterocyclic compound represented by the formula (I) to the formula (IV) is not particularly limited as long as it is veterinary acceptable, but such as hydrochloride, nitrate, sulfate, phosphate, etc. And salts of inorganic acids; salts of organic acids such as acetate, lactate, propionate and benzoate.

Heterocyclic compounds represented by the formulas (I) to (IV) or salts thereof are produced by referring to the methods described in Patent Document 3, Patent Document 4, Patent Document 5, Patent Document 6, and the like. Or you can get it. For example, the compound represented by the formula (II) can be produced by the method shown below.

In the above formula, X, n, A ¹ , A ² , R ¹ , X ¹ , m, R ²¹ , E, and D have the same meanings as those in formula (II), and J represents a halogen atom.

The compound represented by the formula (2) is obtained by allowing a halogenating agent to act on the compound represented by the formula (1).
The halogenating agent is not particularly limited, and N-halogenosuccinic imides, alkali metal hypohalites, hypohalites, carrier halogens and the like can be used.
The amount of the halogenating agent to be used is generally 1 to 10 equivalents relative to the compound represented by the formula (1).
This reaction is preferably carried out in a solvent. The solvent to be used is not particularly limited as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, aliphatic hydrocarbons such as hexane, alicyclic hydrocarbons such as cyclohexane, chlorobenzene, and the like. Aromatic halogenated hydrocarbons such as dichloromethane, aliphatic halogenated hydrocarbons such as dichloromethane, ethers such as diethyl ether, esters such as ethyl acetate, amides such as N, N-dimethylformamide, alcohols such as methanol , Carboxylic acids such as acetic acid, acetonitrile, water and the like may be used alone or in admixture of two or more.
The reaction temperature is not limited, but is usually in the temperature range from −60 ° C. to the reflux temperature of the reaction mixture.

The compound represented by the formula (2) thus obtained can usually be subjected to the next reaction without isolation. Specifically, after a base is allowed to act on the compound represented by the formula (2), the compound represented by the formula (II) can be obtained by allowing the compound represented by the formula (3) to act. it can.
The base to be used is not particularly limited, and examples thereof include alkali metal hydroxides such as sodium hydroxide, alkali metal carbonates such as sodium carbonate, alkali metal bicarbonates such as sodium bicarbonate, and organic bases such as triethylamine. .
The amount of the base used is usually 1 to 5 equivalents relative to the compound represented by the formula (2).
This reaction is preferably carried out in a solvent. The solvent to be used is not particularly limited as long as it is inert to the reaction. For example, the same solvent as used in the reaction for obtaining the compound represented by the formula (2) can be used.
The reaction temperature is not limited, but is usually in the temperature range from −60 ° C. to the reflux temperature of the reaction mixture.

The salts of the heterocyclic compounds represented by the formulas (I) to (IV) can be obtained, for example, by reacting the heterocyclic compounds represented by the formulas (I) to (IV) with an inorganic acid or an organic acid. Can be manufactured.

In any reaction, after completion of the reaction, it can be purified by a purification means such as distillation, recrystallization or column chromatography, if necessary, after a usual post-treatment operation.
The structure of the target product can be identified and confirmed by analytical means such as elemental analysis, NMR spectrum, IR spectrum, and mass spectrum.

[Other ingredients]
The animal ectoparasite control agent of the present invention may contain components other than the above active ingredients. For example, various vitamins, minerals, hormones, amino acids, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, anticancer agents, antibiotics, endoparasite control agents, antibacterial agents, bactericides, coloring agents, fragrances , Preservatives, vaccines and the like. Further, it may contain a compound having biological activity such as insecticidal, acaricidal, anthelmintic, fungicidal, nematicidal, antiprotozoal, bactericidal and antiviral.

(Dosage form)
The animal ectoparasite control agent of the present invention is not particularly limited by the dosage form. Examples of the dosage form include powders, granules, tablets, powders, capsules, premixes, solutions, emulsions, suspensions, wafers, biscuits, minced meat and the like.
The animal ectoparasite control agent of the present invention contains a carrier such as a liquid carrier, a gaseous carrier, a solid carrier, etc., depending on the dosage form, and if necessary, contains a surfactant and other auxiliary agents for use. You may formulate according to it. Further, the animal ectoparasite control agent of the present invention may be obtained by impregnating a base material such as a porous ceramic plate or a nonwoven fabric with an active ingredient.

Liquid carriers used in formulating liquid preparations include kerosene, xylene; petroleum fractions such as solvent naphtha; cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, NMP, alcohol, acetone, methyl isobutyl ketone, mineral oil , Vegetable oil, water and the like.
Examples of the gaseous carrier used in formulating a propellant include butane gas, LPG, dimethyl ether, carbon dioxide gas and the like.
Solid carriers used when formulating into solid formulations include lactose, sucrose, glucose, starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, soybean powder, wheat flour and other vegetable powders; other commercially available feed ingredients Mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, and clay; organic and inorganic compounds such as calcium carbonate, sodium benzoate, urea, and mirabilite.
Adjuncts used in formulating poison baits include food ingredients such as cereal flour, vegetable oil, sugar and crystalline cellulose, antioxidants such as dibutylhydroxytoluene, preservatives such as dehydroacetic acid, children such as pepper Pest-attracting fragrances such as anti-fouling agents for pets, cheese fragrances, and onion fragrances.

A surfactant can be added so that a uniform and stable form can be obtained in formulation. Non-ionic surfactants such as alkyl ethers added with polyoxyethylene, higher fatty acid esters added with polyoxyethylene, sorbitan higher fatty acid esters added with polyoxyethylene, and tristyryl phenyl ether added with polyoxyethylene Surfactants, sulfates of alkylphenyl ethers with addition of polyoxyethylene, alkylnaphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, isobutylene-maleic anhydride And the like.

Among liquid formulations, pour-on or spot-on formulations are suitably carriers that facilitate rapid dispersion on the skin surface of the host animal or in the fur and are generally considered as spreading agents Containing.
Preferred carriers are, for example, alcohols such as isopropanol, 2-octyldodecanol, oleyl alcohol, benzyl alcohol; glycols such as diethylene glycol, ethyl carbitol; isopropyl myristate, isopropyl palmitate, decyl oleate, hexyl laurate , Long chain fatty acid esters such as oleyl oleate, decyl oleate, capric acid ester of C12-18 alkanol; dicarboxylic acid esters such as dibutyl phthalate, diisopropyl isophthalate, diisopropyl adipate, di-n-butyl adipate And cyclic amides such as pyrrolidone and NMP.
In addition, vegetable oils such as olive oil, peanut oil, sesame oil, pine oil, linseed oil or castor oil; paraffin, silicone oil;

[Method of administration, etc.]
The animal ectoparasite control agent of the present invention can be administered to an animal alone. Also, if necessary, other animal drugs such as antibacterial agents, nutrients, anthelmintics, fungicides, anticoccidial agents, insecticides, acaricides, fungicides, nematicides, antiprotozoal agents, antiviral agents It can be administered together with vaccines, hormonal agents, anticancer agents, antibiotics, antipyretics, sedatives, anti-inflammatory agents, endoparasite control agents, and the like.

Other animal drugs that can be mixed or used in combination with the animal ectoparasite control agent of the present invention are not particularly limited. For example, the following are mentioned.

(1) Organic (thio) phosphates: acephate, azamethiphos, azinephos methyl, azinephos ethyl, bromophos ethyl, bromfenbinphos, BRP, chlorpyrifos, chlorpyrifos methyl, chlorpyrifos ethyl, chlorfenvinphos, kazusafos, Carbophenothione, chloroethoxyphos, chlormefos, coumaphos, cyanophenphos, cyanophos, CYAP, diazinon, dichlorvos, dicrotophos, dimethoate, disulfotone, dimeton-S-methyl, dimethylvinphos, dimeton-S-methylsulfone, diariphos, diazinon , Diclofenthion, dioxabenzophos, disulfoton, ethion, etoprophos, etrimphos, EPN, fenamifos, fenitrothion, fenthion, phensulfothio , Flupyrazophos, phonophos, formothione, phosmethylan, heptenophos, isazophos, iodofenphos, isofenphos, isoxathione, iprobenphos, malathion, mevinphos, methamidophos, methidathion, monocrotophos, mecarbam, methalyphos, nared, ometoate, oxydimethone parathione , Parathion methyl, phentoate, hosalon, phosmet, phosphamidone, folate, phoxime, pyrimifos methyl, pyrimifos ethyl, propenophos, prothiophos, phosthiazate, phosphocarb, propaphos, propetamphos, protoate, pyridafenthion, pyracrophos, quinalphos, sulthiote, sulfophos , Tetrachlorbinphos, ter Host, triazophos, trichlorfon, tebupirimfos, temephos, thiometon, vamidothion;

(2) Carbamate series: alanic carb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, phenoxycarb, phenothiocarb, methiocarb, mesomil, oxamyl, pirimicurve, propoxyl, thiodicarb, triazamate, etiofencarb, MPPC, MPC , MTMC, pyridafenthion, furiothiocarb, XMC, aldoxicarb, arixicarb, aminocarb, bendiocarb, bufencarb, butacarb, butcarboxyme, butoxycarboxyme, cloetocarb, dimethylane, formethanate, isoprocarb, metam sodium, metolcarb, promecarb Fanox, Trimetacarb, Xylylcarb;

(3) Pyrethroids: alletrin, bifenthrin, cyfluthrin, beta cyfluthrin, cyhalothrin, lambda cyhalothrin, ciphenothrin, cypermethrin, alpha cypermethrin, beta cypermethrin, zeta cypermethrin, deltamethrin, esfenvalerate, eth Fenprox, fenpropatoline, fenvalerate, imiprothrin, permethrin, praretrin, pyrethrin, pyrethrin I, pyrethrin II, resmethrin, silafluophene, fulvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, cyclomethrin, promethrin , Halfenprox, flucitrinate, bioareslin, bioethanomethrin, bio Rumetorin, Bioresmethrin, trans permethrin, empenthrin, fenfluthrin Trinh, Fen pyridinium Trinh, full Bro shea tri sulphonate, full Fen flufenprox, flumethrin, metofluthrin, phenothrin, protrifenbute, pyresmethrin, terallethrin;

(4) Growth regulator:
(A) Chitin synthesis inhibitors: chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, nobarulone, teflubenzuron, triflumuron, bistrifluron, nobiflumuron, buprofezin, hexithiaxox, etoxazole, clofente Gin, fluazuron, penfluron;
(B) ecdysone antagonists: halofenozide, methoxyphenozide, tebufenozide, chromafenozide, azadirachtin;
(C) juvenile hormone-like substances: pyriproxyfen, metoprene, geophenolan, epofenanane, hydroprene, quinoprene, triprene;
(D) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat, flonicamid;

(5) Nicotine receptor agonist / antagonist compounds: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, nithiazine, nicotine, bensultap, cartap;
(6) GABA antagonist compound:
(A) acetoprole, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole;
(B) Organic chlorine-based: camfechlor, chlordane, endosulfan, HCH, γ-HCH, heptachlor, methoxychlor;

(7) Macrocyclic lactone insecticides: abamectin, emamectin benzoate, milbemectin, lepimectin, spinosad, ivermectin, selamectin, doramectin, epinomectin, moxidectin;
(8) METI I compounds: phenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, hydramethylnon, fenpyroximate, pyrimidifen, dicophor;
(9) METI II and III compounds: acequinosyl, fluacrylpyrim, rotenone;

(10) Uncoupler compounds: chlorfenapyr, binapacryl, dinobutone, dinocup, DNOC;
(11) Oxidative phosphorylation inhibitor compounds: cyhexatin, diafenthiuron, phenbutatin oxide, propargite, azocyclotin;
(12) molting disrupting compound: cyromazine;
(13) Mixed function oxidase inhibitor compound: piperonyl butoxide;
(14) Sodium channel blocker compounds: indoxacarb, metaflumizone;
(15) Microbial pesticides: BT agent, entomopathogenic virus agent, entomopathogenic fungus agent, nematode pathogenic fungus agent; Bacillus spp. Lilium species;
(16) Latrophilin receptor agonist: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside;

(17) Octopaminergic agent: Amitraz;
(18) Ryanodine derivative agonist: fulbenzamide, chlorantraniliprole, cyantraliniprol;
(19) Inhibitors of magnesium-stimulated ATPase: thiocyclam, thiosultap, nereistoxin;
(20) antifeedant: pymetrozine;
(21) Tick growth inhibitor: clofentezin, etoxazole;
(22) Others: Benclothiaz, Bifenazate, Pyridalyl, Sulfur, Sienopyraphene, Ciflumethofene, Amidoflumet, Tetradiphone, Chlordimeform, 1,3-Dichloropropene, DCIP, Phenisobromolate, Benzomate, Metaaldehyde, Spinetram, Pyrifluquinazone, Benzo Ximate, bromopropyrate, quinomethionate, chlorbenzilate, chloropicrin, clothiazoben, dicyclanyl, phenoxacrime, fentriphanyl, flubenzimine, flufenzine, gossip lure, japonyla, methoxadiazone, petroleum, potassium oleate, sulfluramide, tetrasul, trialacene;

(23) Anthelmintic:
(A) benzimidazole series: fenbendazole, albendazole, triclabendazole, oxybendazole;
(B) Salicylanilide series: closantel, oxyclozanide;
(C) substituted phenol type: nitroxinyl;
(D) pyrimidine series: pyrantel;
(E) imidazothiazole series: levamisole;
(F) tetrahydropyrimidine: praziquantel;
(G) Other anthelmintic drugs: cyclodiene, riania, chlorthrone, metronidazo.

The use ratio of the animal ectoparasite control agent of the present invention to other animal drugs is not particularly limited, but is usually 100: 0 to 1:99 (weight ratio).

Examples of host animals in which the animal ectoparasite control agent of the present invention is effective include dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets; Cattle, horses, pigs, sheep, goats; poultry (eg, ducks, chickens, quails, geese); bees (eg, honey bees, Japanese honey bees);

As ectoparasites that are targets of the animal ectoparasite control agent of the present invention, obtain nutrients such as blood and dandruff from animals that parasitize the back, armpit, lower abdomen, and inner crotch of the host animal. It includes those that inhabit, and those that fly to the back and buttocks of the host animal to obtain nutrients such as blood and dandruff from the animal. Examples of ectoparasites include ticks, lice and fleas.

The following pests are listed as mites (Acari) that are the targets of the control agent.
(1) Mesostigmata mites (mite)
(A) Dermanyssidae mites, for example, Dermanyssus gallinae from the genus Dermanyssus spp .;
(B) mites of the family Mronyssidae, for example, Ornithonyssus spp., Ornithonyssus sylviarum, Ornithonyssus bursa, Ornithonyssus bacoti;
(C) Mites of the family Laelapidae, for example Laelaps echidninus, Laelaps jettmari, Tropilaelaps clarae of the species of the genus Laelaps spp .;
(D) Varroidae mites, for example, Varroa spp., Varroa destructor, Varroa jacobsoni, Varroa underwoodi;

(2) Metastigmata tick (tick)
(A) mites of the family Argasidae, for example Argas spsi., Argas persicus, Argas reflexus; for example Ornithodoros spp. Ornithodoros moubata;
(B) Ixodidae ticks, such as Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis puncta, Haemaphysalis cinnaina, Haemaphysalis cinnaina Haemaphysalis otophila), Haemaphysalis leachi, Haemaphysalis longicornis, ali flis (Haemaphysalis mageshimaensis), physalis tick (Haemaphysalis yeni), tuna swordfish ), Tick tick (Haemaphysalis megaspinosa), Tick tick (Haemaphysalis japonica), Haemaphysalis douglasi; eg, Amblyomma spp. Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma ticken test Tick species (Ixodes spp.), Tick (Ixodes ricinus), Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes rubicundus, Ixodes rubicundus Ixodes scapularis, Ixodes holocyclus, Ixodes ovatus, Ixodes persulcatus, Ixodes nipponensis; Of the subgenus (Boophilus spp.), The tick (Rhipicephalus (Boophilus) microplus), Lipicephalus (Boophilus) decoloratus (Rhipicephalus (Boophilus) decoloratus), Lipicephalus (Boophilus) Annuratus (Rhipicephalus (Boophilus) annulatus) (Bhipophilus) calcerata (Rhipicephalus (Boophilus) calceratus); ), Rhipicephalus evertsi, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus appendiculatus, Rhipicephalus appendiculatus Rhipicephalus turanicus, Rhipicephalus zambeziensis; for example Dermacentor marginatus, Dermacentor marginatus, Dermacentor reticulatica (Dermacentor pictus), Dermacentor albipictus, Dermacentor andersoni, Dermacentor Barrier Squirrel (Dermacentor variabilis);

(3) Astigmata (Acaridida)
(A) Mites of the family Psoroptidae (Psoroptidae), for example Psoroptidae spp., Psoroptes ovis, rabbits Psoroptes cuniculi, Psoroptes equi; Psoroptes equi Chorioptes spp., Chorioptes bovis; Otodectes spp., Otodectes cynotis;
(B) Scaroptidae mites, for example, Sarcoptes spabi., Sarcoptes canis, Sarcoptes bovis, Sarcoptes spis. ovis), Sarcoptes rupicaprae, Sarcoptes equi, Sarcoptes suis; for example, Notoedres spp., Notoedres cati;
(C) a mite of the family Knemidokoptidae, for example, Knemidokoptes mutans of the genus Knemidokoptes spp .;

(4) Prostigmata mites (Actinedida)
(A) Acaridaceae (Demodixidae) mites, for example, Demodex spp., Demodex canis, Demodex bovis, Demodex ovis, Demodex ovis, Demodex caprae, Democratic mites (Demodex equi), Demodex caballi (Demodex caballi), Scarlet mites (Demodex suis), Caterpillar mites (Demodex cati);
(B) Trombiculidae ticks, for example, Troombicula spp., Trombicula alfreddugesi, Trombicula akamushi;

Examples of lice (Phthiraptera) include the following pests.
(1) Louse of Anoplura:
(A) lice of the family Haematopinidae, such as the Haematopinus asini, the Haematopinus eurysternus, the Haematopinus suis of the Haematopinus spp .;
(B) Linognathidae lice, for example, Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus ovillus, Linognathus ovillus Linognathus pedalis, Linognathus stenopsis; for example, Solenopotes spp., Solenopotes capillatus;

(2) Amblycera subs (biting louse):
(A) Mennoponidae larvae, for example, Menacanthus stramineus, Menacanthus cornutus, Menacanthus cornutus, Menacanthus cornutus, Menacanthus corp. Chick gallinae of the genus species (Menopon spp.);

(3) Ischnocera (biting louse):
(A) Philopteridae lice, for example, Columbicola spp., Columbicola columbae; for example, Cuclotogaster spp., Cuclotogaster spp. heterographus); eg, Goniodes spp., Goniodes dissimilis, Goniodes gigas, Goniodes gallinae; eg, Lipeurus spp. caponis);
(B) Trichodectidae, such as Bovicola spp., Bovicola bovis, Bovicola ovis, Bovicola limbata, Bovicola e, Bovicola capra Boccola equi; for example, Trichodectes canis of Trichodectes spp .; for example, Felicola subrostrata of Felicola spp.

The fleas (Siphonaptera) include the following pests.
(A) fleas from the family Tungidae, for example from the genus Tunga spp., Tunga penetrans;
(B) Pulicidae fleas, for example, Ctenocephalides canis, Fleas of Ctenocephalides felis; for example, Hedgehog ); For example, Xenopsylla spp., For example, Xenopsylla cheopis; for example, for Pulex irritans; Flea (Echidnophaga gallinacea);
(C) fleas of the family Ceratophyllidae, for example Ceratophyllus gallinae, Ceratophyllus anisus, for example Ceratophyllus anisus; for example, Nosopsyllus spp. (Nosopsyllus fasciatus),
(D) Fleas of the family Leptopsyllidae, for example, Leptopsylla segnis from the genus Leptopsylla spp.

In addition, examples of ectoparasites that are targets of the animal ectoparasite control agent of the present invention include stink bugs.
The following pests can be cited as insects of the order of the Hemiptera.
(A) insects of the family Cimicidae, for example Cimex lectularius, of the genus Cimex spp .;
(B) Insects of Reduviidae, and also of Triatominae, for example Panstrongylus spp .; for example, Rhodnius spp., Rhodnius prolixus For example, Triatoma infestans from the genus Triatoma spp.

In addition, the ectoparasite-controlling agent of the present invention is also effective against insect pests (Diptera) that are biting insects (chewing flies, adult sucking flies, migratory dipterous larvae, parasitic fly maggots) It is.
The following pests can be mentioned as pests of flies (Diptera).
(1) Nematocera:
(A) Culicidae mosquitoes, such as Culex spp., Culex quinquefasciatus, Culex pipiens pallens, Culex tarsalis, Culex pipiens molestus , Culex pipiens fatigans, Culex tritaeniorhynchus summorosus; eg, Armigeres subalbatus; eg, Anopheles spp. Ele, g. Anopheles maculipennis, Anopheles sinensis, Anopheles lesteri; for example, Aedes aegypti, Aedes aegypti, tus (Aedes taeniorhynchus), Ugouyabuka (Aedes togoi), Kin'iroyabuka (Aedes vexans nipponii);
(B) Simuliidae, such as Simulium spp., Simulium reptans, Simulium ornatum, Simulium venustum, Simulium salopiense For example Prosimulium spp, Prosimulium yezoense;
(C) Ceratopogonidae, such as the Culiodes spp., Culicoides arakawae, Culicoides pictimargo, Culicoides kibunensis, musul, C oxystoma), Nipponukaka (Culicoides nipponensis), Hoshinukaka (Culicoides punctatus), Miyamanukaka (Culicoides maculatus), Matsuzawawanakaka (Culicoides matsuzawai);

(2) Short angle sub-order:
(A) Abs of the Tabidae family, such as Tabanus spm., Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus (Tabanus spp.) Tabanus sudeticus, Cattle ab (Tabanus trigonus), Red cat abu (Tabanus chrysurus), Shirofu ab (Tabanus trigeminus), Kibanjiabu (Tabanus fulvimedioides), Evanus obivi (Tabanus iyoensis); for example, Chrysops spp. caecutiens), Chrysops relictus, Chrysops suavis, Chrysops japonicus;
(B) Muscidae flies, such as Muscina spp., Musca domestica, Musca bezzii, Musca hervei, Musca conducens, Musca conducens Musca stabulans); for example, Stomoxys spp., For Stomoxys calcitrans; , Haematobia stimulans; Fannia spis., Fannia canisularis;
(C) Glossina spp. From the Glossinidae family;
(D) flies of the family Hippoboscidae, for example, Melophagus ovinus of the genus Melofagus spp .;
(E) Calliphoridae flies, eg, Calliphora, Calliphora lata; eg, Lucilia spp., Lucilia (Phaenicia) cuprina, Lucilia (Lucilia) Phaenicia) sericata), Lucilia illustris; for example, Chrysomya hominivorax, Chrysomya chloropyga, Chrysom bezia (Chrysom bez)
(F) Oestridae flies, such as the Cuterebrinae Rabbit genus Cuterebra spp .; for example the Hypodermatinae, and also the Hypoderma spp. (Hypoderma bovis), Hypoderma lineatum; for example, Gasterophilus spp., Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gastrophilus Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum; eg from the Oestrinae family, and also from the genus Oestrus spp. Oestrus ovis).
Among these, fleas and ticks are preferred as the target of the animal ectoparasite control agent of the present invention.

Diseases or other pathological conditions that are transmitted through parasites or injuries caused directly by parasites by administering the animal ectoparasite control agent of the present invention to animals and controlling the above ectoparasites (Hereinafter sometimes referred to as parasitic diseases) can be prevented.
The animal ectoparasite control agent of the present invention is administered to an animal, and the above ectoparasites are suppressed, thereby partially or completely inhibiting the occurrence of parasitic diseases in animals susceptible to parasitic diseases. Can reduce or eliminate disease symptoms and partially or completely cure and treat parasitic diseases.

Diseases transmitted through ectoparasites are, for example, bacterial diseases, viral diseases, and protozoan-borne diseases. Like flies, there are those that cause pathogens to adhere to sticky legs and transport them to other places, and those that develop and multiply in the body of sanitary pests, which become the source of infection.
Specific examples are given below.

(1) Viral diseases (a) Akabane disease infected by Culicoides oxystoma via Akabane virus of Bunyaviridae; Ainovirus infection infected via Aino virus Infectious disease: Ibaraki disease infecting via Reoviridae Ibaraki virus; Chuzan disease infecting via Chuzan virus; Via Bluetongue virus of Orbivirus Bluetongue disease to infect; Arbos that are transmitted through other arboviruses such as Peaton virus, Sathuperi virus, D'Aguilar virus and Shamonda virus Viral disease;
(B) Porcine cholera which Culex quinquefasciatus infects via swine cholera virus of Flaviviridae;
(C) Japanese encephalitis infected by Culex tritaeniorhynchus summorosus and Culex pipiens pallens via Japanese encephalitis virus of Flaviviridae;
(D) Avian Newcastle disease that Fannia canisularis infects via Newcastle disease virus (NDV);
(E) Equine infectious anemia that a blood-sucking insect such as Tabanidae infects via the Equine Infectious Anemia Virus belonging to the genus Retroviridae.

(2) Bacterial diseases (a) Japanese red fever, rickettsia, etc. in dogs infected with Haemaphysalis longicornis via Japanese Rickettsia spp, Rickettsia japonica;
(B) Barbarian disease infected by the tick (Haemaphysalis flava) via the wild moss (Francisella tularensis);
(C) Cat infectious anemia which is transmitted by Candidatus Mycoplasma haemominutum by Ixodes ovatus;
(D) Anaplasmosis in which a tick (Rhipicephalus (Boophilus) microplus) is infected via Anaplasma marginale;
(E) Canine anaplasmosis infected via Anaplasma platys by Rhipicephalus sanguineus; Canine hemobartonellosis infected via Haemobartonella canis.

(3) Protozoan-borne disease (a) Cattle large piroplasmosis infected by Haemaphysalis longicornis through large piroplasma (Babesia ovata); Dogs infected through Gibson dog Babesia (Babesia gibsoni) Piroplasmosis;
(B) Babesiosis, such as bovine Q fever, infected by the tick (Rhipicephalus (Boophilus) microplus) through Futago Babesia (Babesia bigemia), Bovine Babesia (Babesia bovis);
(C) Canine babesiosis infected via Rabicephalus sanguineus via the canine Babesia, Gibson dog Babesia; the canine infecting the canine hepatozoon canis Hepatozonosis;
(D) chicken leucocytozoonosis in which chickens (Culicoides arakawae) are infected via leukocytozoon caulleryi;
(E) Trypanosomiasis such as chronic sleep disease and acute sleep disease, which are infected by a blood-sucking insect such as Tabanidae through Trypanosoma ssp .;
(F) Dogs cats (Ctenocephalides felis) are infected via Diphylidium caninum;
(G) Canine silkworms (Aedes togoi), Aedes albopictus, Culex tritaeniorhynchus summorosus, and Culex pipiens pallens are infected through canine filamentous insects (Dirofilaria immitis).

(4) Bullfly larvae and fountain larvae Some hygienic pests are internally parasitic on the host. For example, cattle fly larvae infested with cows, horsefly larvae in the stomach wall of horses, and sheep fly larvae in the nasal cavity of sheep. In addition, cattle fly larvae parasitize under the back of cattle and make holes in the skin, greatly reducing the value of leather products.
Specific examples are given below.
(A) Cattle fly larvae caused by Hypoderma bovis larvae, Hypoderma lineatum larvae;
(B) the larvae of Gasterophilus intestinalis, the larvae of the Gasterophilus nasalis, the larvae of the fountains caused by the larvae of the Atoll frog (Gasterophilus haemorroidalis);
(C) Flies (myiasis) caused by larvae of Lucilia illustris.

(5) Injuries caused by parasitism or bites When a bite by a mite such as a mite or a claw mite, or an insect such as a mosquito, ab, or a lice, it causes severe itching or pain due to physical injury or injection of a poisonous substance, resulting in large damage to the host. Give stress. Furthermore, secondary infection is caused by the animal scratching the affected area. For this reason, animals suffer from insomnia and loss of appetite, and in livestock, milk production, body weight gain and egg production decline, production efficiency drops, and sometimes death.
Specific examples are given below.
(A) Strong sense of sensation caused by cattle flies (Stomoxys calcitrans) and flies (Haematobia irritans);
(B) Strong sensation caused by pig lice (Haematopinus suis) in pigs;
(C) The sensation caused by dog fleas (Ctenocephalides canis) in dogs and cats;
(D) The sensation caused by chicken hawk (Culicoides arakawae); The strong sensation caused by chicken lice (Menopon gallinae).

(6) Injuries such as blood sucking, anemia, and bleeding Many hygiene pests give blood to the host at the same time as stressing the host by biting. As a result, the host is anemic, causing weakness and poor growth.
Specific examples are given below.
(A) blood sucking on cattle such as Haemaphysalis longicornis, red tick (Rhipicephalus (Boophilus) microplus), Yamato tick (Ixodes ovatus), Tane tick (Ixodes nipponensis), Schulze tick (Ixodes persulcatus);
(B) Blood absorption to dogs such as the tick tick (Haemaphysalis longicornis), the tick mite (Rhipicephalus sanguineus), the tick tick (Haemaphysalis flava), the red tick tick (Ixodes nipponensis), the shruce tick (Ixodes persulcatus);
(C) blood sucking of chickens of Dermanyssus gallinae and avian mite (Ornithonyssus sylviarum), anemia caused by chickens;
(D) Bovine bleeding caused by Simuliidae;
(E) cattle anemia caused by Tabanidae;
(F) Cat long-term anemia caused by cat fleas (Ctenocephalides felis);
(G) Chicken anemia caused by chicken hawk (Culicoides arakawae).

(7) Skin disorders Some sanitary pest parasites and bites cause serious damage to the skin as well as pruritus, redness and swelling. Scarlet mites cause severe hair itch, hair loss, crust formation, wrinkles, and acne mites cause systemic wrinkles due to hair loss and secondary infection. In addition, since blood-sucking pests generally inject a large amount of saliva during blood-sucking, an allergic reaction to it occurs, and redness, swelling, papules, ulcers, etc. occur with strong itching.
Specific examples are given below.
(A) cattle, horses, sheep scabies caused by genus genus genus, genus cuspidaceae; pigs, canine scabies caused by genus genus genus; cat scabies caused by cat genus genus; , Cat ear scabies;
(B) flea allergic dermatitis caused by a cat flea;
(C) folliculosis caused by acarid mites;
(D) Papules, blisters, and edema caused by flyfish.

When the animal ectoparasite control agent of the present invention is used for domestic animals such as cattle and pigs, pets such as dogs and cats, it varies depending on the administration method, administration purpose, disease symptoms, etc. The ratio is 0.01 mg or more and 100 g or less, desirably 0.1 mg or more and 10 g or less, per 1 kg body weight of the host animal.

The animal ectoparasite control agent of the present invention can be applied by a known veterinary technique (topical, oral, parenteral or subcutaneous administration). For example, when the purpose is systemic control, tablets, capsules, soaking solution, feed mixing, suppositories, injection (intramuscular, subcutaneous, intravenous, abdominal cavity) In the case of non-systemic control, the oily or aqueous solution is administered by spraying, pour-on, spot-on, etc., resin And the like, and kneading an ectoparasite control agent, forming the kneaded product into an appropriate shape such as a collar and an ear tag, and attaching it to an animal.

In addition, as described by method, oral administration such as buccal administration and sublingual administration, or parenteral administration such as intravenous administration, intramuscular administration, subcutaneous administration, transdermal administration, nasal administration, and pulmonary administration are performed. be able to.
Specific examples of oral administration include a method of feeding an animal with the control agent of the present invention in the form of tablets, liquids, capsules, wafers, biscuits, minced meat, etc .; mixing the control agent of the present invention into animal feed Let me give it to the animal.
Specific examples of parenteral administration include intramuscular, intradermal, subcutaneous injection or infusion; spot-on, po-on, etc .; spray, shampoo, etc .; The method of attaching it to an animal is mentioned.

The pharmaceutical formulation of the animal drug ectoparasite control agent of the present invention is shown slightly, but the additives and addition ratios are not limited to these descriptions, and can be varied in a wide range. The part in a formulation example shows a weight part (%). The following are prescriptions for prevention and control of animals.

Formulation 1 (granule)
Compound of the present invention 5%
Kaolin 94%
1% white carbon
The compound of the present invention is dissolved in an organic solvent, sprayed onto a carrier, and then the solvent is evaporated under reduced pressure. This type of granule can be mixed with animal food.

Formulation 2 (granule)
Compound of the present invention 10%
Attapulgite 90%

Formulation 3 (Granule)
Compound of the present invention 3%
Polyethylene glycol 3%
Kaolin 94%
Kaolin previously wetted with polyethylene glycol and a finely pulverized product of the compound of the present invention are mixed to obtain a preparation having the granule surface coated with the compound of the present invention.

Formulation 4 (Injection)
Compound of the present invention 0.1-1%
Peanut oil Balance After preparation, filter sterilize with a sterilization filter.

Formulation 5 (Injection)
Compound of the present invention 0.1-1%
Sesame oil balance

Formulation 6 (Pour-on agent)
Compound of the present invention 5%
Myristic acid ester 10%
Isopropanol balance

Formulation 7 (Pour-on agent)
The compound of the present invention 2%
Medium chain triglycerides 15%
Ethanol balance

Formulation 8 (Pour-on agent)
The compound of the present invention 2%
Oleic acid ester 5%
NMP 40%
Isopropanol balance

Formulation 9 (Spot-on agent)
Compound of the present invention 10-15%
Ethyl carbitol balance

Formulation 10 (Spot-on agent)
Compound of the present invention 10-15%
Palmitic acid ester 10%
Isopropanol balance

Formulation 11 (Spot-on agent)
Compound of the present invention 10-15%
Isopropanol 20%
Benzyl alcohol balance

Formulation 12 (spray-on agent)
Compound of the present invention 1%
Isopropanol 40%
Propylene carbonate balance

Formulation 13 (spray-on agent)
Compound of the present invention 1%
Propylene glycol 10%
Isopropanol balance

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to the examples.
The heterocyclic compounds used as active ingredients of the animal ectoparasite control agents according to this example are shown in Table 1.

Test Example 1 Insecticidal test against Haemaphysalis longicornis 0.1175 ml of an acetone solution having an active ingredient concentration of 400 ppm was applied to the inner wall of a 20 mL glass vial. Acetone was volatilized to produce a thin film on the inner wall of the vial. Since the surface area of the inner wall of the used vial is 47 cm ² , the treatment drug amount is 1 μg / cm ² .
Twenty to fifty ticks of the spider mite were released into the vial, and the lid was closed and housed in a thermostatic chamber (25 ° C., dark).
The number of dead insects was counted after 1 day and after 2 days, and the death rate was calculated from the following formula. In addition, the test was conducted in a two-run system.
Further, in a similar manner, the application ^{^{dose, 0.1μg / cm 2, 0.01μg /}} cm 2, 0.001μg / cm 2, and 0.0001 / cm ^2, even test was changed to Been.

The above tests were conducted using the heterocyclic compounds 1-1 and 1-2 shown in Table 1 and the existing compound fipronil as active ingredients. The results are shown in Table 2. (The table shows the average value of each test result performed in duplicate.)

From Table 2, the animal ectoparasite control agent according to the present invention containing Compound 1-1 or Compound 1-2 as an active ingredient is more effective against ectoparasites than the control agent containing the existing compound fipronil. It turns out that it is excellent in immediate effect and low concentration activity.

Test Example 2 Insecticidal test (immersion) against Boophilus microplus
10 mg of the active ingredient was dissolved in 0.5 mL of dimethyl sulfoxide. This solution was diluted with water to obtain an aqueous solution adjusted to a predetermined concentration.
In a perforated plastic beaker, 8 to 10 adult females of the tick were fed, and the beaker was immersed in the aqueous solution for 1 minute. The mites dipped in the aqueous solution were transferred onto the filter paper laid on the plastic tray. After a certain period, tick mortality was calculated.
A mortality rate of 100% means that all ticks have died. A mortality rate of 0% means that all mites have survived.

Compounds 1-1, 1-3 to 1-10, 1-12 to 1-16, 2-1 to 2-3, 3-5, 3-7 and 4-1 to 4-4 shown in Table 1 Was used as an active ingredient, and the above test was conducted. All the compounds showed excellent activity with a mortality rate of 80% or more at an application rate of 100 ppm.

Test Example 3 Insecticidal test for Boophilus microplus (injection)
10 mg of the active ingredient was dissolved in 0.5 mL of dimethyl sulfoxide. This solution was diluted with water to obtain an aqueous solution adjusted to a predetermined concentration.
The above aqueous solution was injected into the abdomen of 15 adult females of mites that were completely fed. Mites were transferred to replication plates and incubated for a period of time in a climate chamber.
After a certain period of time, the egg-laying rate of infertile eggs was measured. 100% means that all eggs are sterilized eggs. 0% means that all eggs are fertilized eggs.

Compounds 1-1, 1-3 to 1-16, 2-1 to 2-3, 3-1 to 3-3, 3-5, 3-7 and 4-1 to 4-4 shown in Table 1 Was used as an active ingredient, and the above test was conducted. All the compounds showed an excellent activity of 80% or more at an application rate of 20 μg / animal.

Test Example 4 Insecticidal test against Rhipicephalus sanguineus (contact)
The active ingredient was dissolved in acetone to prepare an acetone solution having a concentration of 900 ppm.
250 μL of an acetone solution diluted to a specified concentration was poured into a glass vial, the vial was fixed to a lock-type roller, rotated at 10 rpm, and acetone was volatilized over 2 hours. Five adult ticks that were cut off were placed in the vial, and the vial was covered with a perforated cover.
After 2 days, tick mortality was measured. A mortality rate of 100% means that all ticks have died. A mortality rate of 0% means that all mites have survived.
Compounds 1-1, 1-3 to 1-10, 1-12, 1-13, 1-15, 2-2, 2-3, 3-3, 3-5, 3-7 shown in Table 1 The above test was conducted using 4-2 and 4-4 as active ingredients. All the compounds showed excellent activity with a mortality rate of 80% or more at an application rate of 5 μg / cm ² .

Test Example 5 Insecticidal test against cat flea (Ctenocephalides felis)
The active ingredient was dissolved in acetone to prepare an acetone solution having a concentration of 900 ppm.
250 μL of an acetone solution diluted to a specified concentration was poured into a glass vial, the vial was fixed to a lock-type roller, rotated at 10 rpm, and acetone was volatilized over 2 hours. Ten adult cat fleas that were cut off were placed in the vial, and the vial was covered with a perforated cover.
After 2 days, flea mortality was measured. A mortality rate of 100% means that all the fleas have died. A mortality rate of 0% means that all fleas have survived.

Compounds 1-1, 1-3 to 1-10, 1-12 to 1-15, 2-1 to 2-3, 3-1, 3-2 and 4-1 to 4-4 shown in Table 1 Was used as an active ingredient, and the above test was conducted. All the compounds showed excellent activity with a mortality rate of 80% or more at an application rate of 5 μg / cm ² .

Test Example 6 Insecticidal test against cat flea (Ctenocephalides felis) (oral)
10 mg of the active ingredient was dissolved in 0.5 mL of dimethyl sulfoxide. This solution was diluted with livestock blood to prepare a compound solution with a specified concentration.
About 10-15 adult fasted cat fleas were placed in a flea chamber. The bottom of the blood chamber was sealed with parafilm. The compound solution was filled into the blood chamber. Cat fleas can suck blood through paraffin. The blood chamber was kept at 37 ° C. and the flea chamber was kept at room temperature.
After a certain period of time, cat mortality was measured. A mortality rate of 100% means that all cat fleas have died. A mortality rate of 0% means that all cat fleas have survived.

Compounds 1-1, 1-3 to 1-10, 1-12 to 1-16, 2-1 to 2-3, 3-1 to 3-5, 3-7 and 4-1 shown in Table 1 The above test was conducted using ~ 4-4 as active ingredients. All the compounds showed excellent activity with a mortality rate of 80% or more at an application rate of 100 ppm.

Test Example 7 Test on sheep flies (Lucillia cuprina) 10 mg of active ingredient was dissolved in 0.5 mL of dimethyl sulfoxide. This solution was diluted with water to obtain an aqueous solution having a predetermined concentration.
A test tube was charged with 1 cm ³ of ground horse meat and 0.5 mL of the above aqueous solution. About 20-30 sheep larvae were placed on this.
After a certain period of time, fly mortality was measured. A mortality rate of 100% means that all flies have died. A mortality rate of 0% means that all flies have survived.

Compounds 1-1, 1-3 to 1-14, 1-16, 2-1 to 2-3, 3-1 to 3-3, 3-5 to 3-7 and 4-1 shown in Table 1 The above test was conducted using ~ 4-4 as active ingredients. All the compounds showed excellent activity with a mortality rate of 80% or more at an application rate of 100 ppm.

Test Example 8 Test on Housefly (Musca domestica) 10 mg of the active ingredient was dissolved in 0.5 mL of dimethyl sulfoxide. This solution was diluted with water to obtain an aqueous solution having a predetermined concentration.
0.3 ml of the aqueous solution was mixed with 0.2 ml of 40% by weight sugar aqueous solution. This mixed solution was absorbed into a sponge of a predetermined size. A sponge was placed in the test container. Ten adult house flies were released into the test container and the container was covered with a perforated cover.
After a certain period of time, fly mortality was measured. A mortality rate of 100% means that all flies have died. A mortality rate of 0% means that all flies have survived.

Compounds 1-1, 1-3 to 1-10, 1-12, 1-14, 1-16, 2-1 to 2-3, 3-1 to 3-3, 3-5 shown in Table 1 , 3-7, 4-3 and 4-4 were used as active ingredients, respectively, and the above test was conducted. All the compounds showed excellent activity with a mortality rate of 80% or more at an application rate of 100 ppm.

Test Example 9 Test for Cat Fleas in Cats (Ctenocephalides felis) A drug solution prepared to have an active ingredient of 15 mg per kg body weight of cats was dropped onto the skin behind the neck of the cat (between the scapulae). Six such cats were prepared. One day after the chemical treatment, 7 non-fed adult cat fleas per cat were infested around the neck of the cat. The number of surviving cat fleas was counted one day after the day of infestation.
Six days after the chemical treatment, 7 non-feeding adult cat fleas per cat were infested around the neck of the cat. The number of surviving cat fleas was counted one day after the day of infestation.
Similarly, cat flea infestation was performed after 13 days, 20 days, 27 days, 34 days, 41 days, and 48 days after the chemical treatment, and 1 day from the day of infestation. Later, the number of surviving cat fleas was counted.

In this test, 100% mortality means that all cat fleas have died. A mortality rate of 0% means that all cat fleas have survived.
The above test was conducted using compounds 1-1, 1-4, 1-5, 1-8 and 1-9 shown in Table 1 as active ingredients. All compounds showed excellent activity with a mortality rate of 95% or more as measured after 42 days from the day of chemical treatment. Of these, compounds 1-1 and 1-5 showed particularly excellent activity with a mortality rate of 95% or more even when measured after 49 days from the day of chemical treatment.

Test Example 10 Test on tick (Ixodes ricinus) in cats Five non-feeding adult ticks per cat were infested around the neck of the cat. Six such cats were prepared. Two days after the day of infestation, a drug solution prepared so that the active ingredient was 15 mg per kg body weight of the cat was dropped on the skin behind the neck of the cat (between the scapula). The number of surviving ticks was counted two days after the chemical treatment.
Five days after the chemical treatment, 5 non-feeding adult ticks per cat were infested around the neck of the cat. The number of surviving ticks was counted after 2 days from the day of infestation.
Similarly, tick infestation was performed after 12 days, 19 days, 26 days, and 33 days from the day of chemical treatment, and after 2 days from the day of infestation, The number was measured.

In this test, a mortality rate of 100% means that all ticks have died. A mortality rate of 0% means that all ticks have survived.
The above test was conducted using compounds 1-1, 1-4, 1-5, 1-8 and 1-9 shown in Table 1 as active ingredients. All the compounds showed excellent activity with a mortality rate of 90% or more as measured after 14 days from the day of chemical treatment. Compound 1-8 was measured 21 days after the chemical treatment, compound 1-9 was measured 28 days after the chemical treatment, and compounds 1-1 and 1-5 were treated with chemical. Even after 35 days from the date of measurement, the activity was particularly excellent with a mortality rate of 90% or more.

Claims

An animal ectoparasite control agent comprising, as an active ingredient, at least one compound selected from the heterocyclic compounds represented by formula (I) and salts thereof.

(In the formula (I), X is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2 Represents a -6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
n represents the number of substitutions of X and is an integer of 0 to 5. When n is 2 or more, Xs may be the same as or different from each other.
A 1 and A 2 each independently represent a carbon atom or a nitrogen atom.
B 1 and B 2 each independently represent a carbon atom or a nitrogen atom.
When B 1 is a carbon atom and B 2 is a nitrogen atom, the bond between B 1 and B 2 may be a double bond.
B 3 represents a carbon atom or an oxygen atom.
R 1 represents a hydrogen atom, a halogen atom, or an unsubstituted or substituted C1-6 alkyl group.
X 0 is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group Represents an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
m1 represents the number of substitutions of X 0 and is an integer from 0 to 3. When m1 is 2 or more, X 0 each other may be the same or different from each other.
R 11 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted amino group, or an unsubstituted or substituted group A C1-6 alkylaminocarbonyl group having the formula:
R 12 represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C1-6 alkoxy group, or a halogen atom. Show.
Further, connected is R 11 and R 12, together with the carbon atoms to which they are attached a 5-8 membered having a hydrocarbon ring or a substituent R 20 5-8 membered having a substituent R 20 A heterocycle may be formed.
R 20 represents a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group An unsubstituted or substituted C1-6 alkoxy group, a nitro group, a cyano group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group , An amino group, or a substituent represented by —N (R 2 ) COR 3 .
R 2 represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-7 acyl group, or an unsubstituted or substituted C1-6 alkoxycarbonyl group Indicates.
R 3 represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C2-6 alkenyloxy group, an unsubstituted or substituted group; And a C2-6 alkynyloxy group having an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heterocyclic group.
E represents a carbon atom or a nitrogen atom. )
The animal ectoparasite control agent according to claim 1, wherein the formula (I) is the formula (II).

(In the formula (II), D represents a 5- to 8-membered hydrocarbon ring or a 5- to 8-membered heterocycle.
R 21 is a substituent bonded to D and is an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group, an amino group, or —N ( R 2 ) represents a substituent represented by COR 3 .
X 1 is a substituent bonded to the condensed ring containing D and is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, unsubstituted Or a substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
m represents the number of substitutions of X 1 and is an integer from 0 to 6. When m is 2 or more, X 1 may be the same as or different from each other.
X, n, A 1 , A 2 , R 1 , E, R 2 and R 3 have the same meaning as in formula (I). )
The animal ectoparasite control agent according to claim 2, wherein the formula (II) is the formula (III).

(In formula (III), p represents the number of repeating methylene groups in parentheses and is either 1 or 2.
X, n, A 1 , A 2 , R 1 , X 1 , m, R 2 , R 3 and E have the same meaning as in formula (II). )
The animal ectoparasite control agent according to claim 3, wherein the formula (III) is the formula (IV).

(In formula (IV), X, n, R 1 , X 1 , m, E, R 2 , R 3 and p have the same meaning as in formula (III).)
A method of treating an animal suffering from an ectoparasite-derived infection comprising administering an ectoparasite control agent according to any one of claims 1 to 4 in an amount acceptable in veterinary medicine.
A method for preventing an animal from suffering from an ectoparasite-derived infection comprising administering an ectoparasite control agent according to any one of claims 1 to 4 in an amount acceptable in veterinary medicine.