JP2014015397A - External parasite controlling agent for animals - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an external parasite controlling agent for animals having excellent controlling effects on an external parasites such as lice, fleas, mosquitoes, gnats and flies; and a method for preventing or treating infections from external parasites.SOLUTION: An external parasite controlling agent for animals contain at least one kind of compounds selected from a heterocyclic compound represented by the formula (IV) or the like and salts thereof as an active ingredient. A method of preventing or treating infection from an external parasite comprises administering the external parasite controlling agent for animals to an animal.

Description

  The present invention relates to an animal ectoparasite control agent, a method for treating an animal suffering from an ectoparasite-derived infection, and a method for preventing an animal from suffering from an ectoparasite-derived infection.

Parasites that parasitize outside the body of animal skin such as livestock, poultry, and pets, and hair, 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 ticks, and acne mites (hair follicles). Also known are pests that attach outside the body of animals and have 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 that use animal blood, dandruff and the like as nutrients 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 a pyrethroid compound, a pyridine compound, an arylpyrazole compound, an isoxazoline compound, and the like as active ingredients.

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 action spectrum, 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 inventor has eagerly searched to solve the above problems. And this inventor paid attention to the heterocyclic compound or its salt known by patent document 3 etc. as an active ingredient of the chemical | medical agent for assisting growth of agricultural products, and repeated examination. As a result, the present inventors have 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.

That is, 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.

（式（I）中、Ｘは、ハロゲン原子、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ２〜６アルケニル基、無置換のもしくは置換基を有するＣ２〜６アルキニル基、水酸基、無置換のもしくは置換基を有するＣ１〜６アルコキシ基、ニトロ基、またはシアノ基を示す。
ｎは、Ｘの置換数を示し且つ０〜５のいずれかの整数である。ｎが２以上のとき、Ｘ同士は互いに同一でも異なっていてもよい。
Ａ¹およびＡ²はそれぞれ独立に、炭素原子または窒素原子を示す。
Ｂ¹およびＢ²はそれぞれ独立に、炭素原子または窒素原子を示す。
Ｂ¹が炭素原子で且つＢ²が窒素原子である場合、Ｂ¹とＢ²との間の結合は、二重結合となってもよい。
Ｂ³は、炭素原子または酸素原子を示す。
Ｒ¹は、水素原子、ハロゲン原子、または無置換のもしくは置換基を有するＣ１〜６アルキル基を示す。
Ｘ⁰は、ハロゲン原子、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ２〜６アルケニル基、無置換のもしくは置換基を有するＣ２〜６アルキニル基、水酸基、無置換のもしくは置換基を有するＣ１〜６アルコキシ基、ニトロ基、またはシアノ基を示す。
ｍ１は、Ｘ⁰の置換数を示し且つ０〜３のいずれかの整数である。ｍ１が２以上のとき、Ｘ⁰同士は互いに同一でも異なっていてもよい。
Ｒ¹¹は、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ２〜６アルケニル基、無置換のもしくは置換基を有するアミノ基、または無置換のもしくは置換基を有するＣ１〜６アルキルアミノカルボニル基を示す。
Ｒ¹²は、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ２〜６アルケニル基、またはハロゲン原子を示す。
また、Ｒ¹¹とＲ¹²とが繋がって、それらが結合する炭素原子と一緒になって、置換基Ｒ²⁰を有する５〜８員環の炭化水素環または置換基Ｒ²⁰を有する５〜８員環のヘテロ環を形成してもよい。
Ｒ²⁰は、ハロゲン原子、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ２〜６アルケニル基、無置換のもしくは置換基を有するＣ２〜６アルキニル基、水酸基、無置換のもしくは置換基を有するＣ１〜６アルコキシ基、ニトロ基、シアノ基、無置換のもしくは置換基を有するＣ１〜７アシル基、無置換のもしくは置換基を有するＣ１〜６アルキルアミノカルボニル基、アミノ基、または−Ｎ（Ｒ²）ＣＯＲ³で表される置換基を示す。
Ｒ²は、水素原子、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ１〜７アシル基、または無置換のもしくは置換基を有するＣ１〜６アルコキシカルボニル基を示す。
Ｒ³は、水素原子、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ２〜６アルケニル基、無置換のもしくは置換基を有するＣ２〜６アルキニル基、無置換のもしくは置換基を有するＣ３〜８シクロアルキル基、無置換のもしくは置換基を有するＣ１〜６アルコキシ基、無置換のもしくは置換基を有するＣ２〜６アルケニルオキシ基、無置換の若しくは置換基を有するＣ２〜６アルキニルオキシ基、無置換のもしくは置換基を有するＣ６〜１０アリール基、または無置換のもしくは置換基を有するヘテロ環基を示す。
Ｅは、炭素原子または窒素原子を示す。）

(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 -6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
n shows the substitution number of X and is an integer in any one of 0-5. 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 C 1-6 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 , 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 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
R ¹² represents an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, or a halogen atom.
Further, connected is R ¹¹ and R ^12, together with the carbon atoms to which they are attached 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 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, 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 C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted C 2-6 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; 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.

（式（II）中、Ｄは、５〜８員環の炭化水素環または５〜８員環のヘテロ環を示す。
Ｒ²¹は、Ｄに結合する置換基であり且つ無置換のもしくは置換基を有するＣ１〜７アシル基、無置換のもしくは置換基を有するＣ１〜６アルキルアミノカルボニル基、アミノ基、または−Ｎ（Ｒ²）ＣＯＲ³で表される置換基を示す。
Ｘ¹は、Ｄを含む縮合環に結合する置換基であり且つハロゲン原子、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ２〜６アルケニル基、無置換のもしくは置換基を有するＣ２〜６アルキニル基、水酸基、無置換のもしくは置換基を有するＣ１〜６アルコキシ基、ニトロ基、またはシアノ基を示す。
ｍは、Ｘ¹の置換数を示し且つ０〜６のいずれかの整数である。ｍが２以上のとき、Ｘ¹同士は互いに同一でも異なっていてもよい。Ｘ¹は、Ｄを含む縮合環上に置換されてもよい。
Ｘ、ｎ、Ａ¹、Ａ²、Ｒ¹、Ｅ、Ｒ²およびＲ³は、式（I）におけるそれらと同じ意味を示す。）

(In 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 C 1-7 acyl group, an unsubstituted or substituted C 1-6 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 C 1-6 alkyl group, an unsubstituted or substituted C 2-6 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 of 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.

（式（III）中、ｐは括弧内のメチレン基の繰り返し数を示し且つ１または２のいずれかである。
Ｘ、ｎ、Ａ¹、Ａ²、Ｒ¹、Ｘ¹、ｍ、Ｒ²、Ｒ³およびＥは、式（II）におけるそれらと同じ意味を示す。）

(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.

（式（IV）中、Ｘ、ｎ、Ｒ¹、Ｘ¹、ｍ、Ｅ、Ｒ²、Ｒ³およびｐは、式（III）におけるそれらと同じ意味を示す。）

(In the 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 administration of 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 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.

[Active ingredients]
The active ingredient used in the animal ectoparasite control agent of the present invention is at least one compound selected from a heterocyclic compound represented by the formula (I) or a salt thereof, preferably represented by the formula (II). At least one compound selected from heterocyclic compounds or salts thereof, more preferably at least one compound selected from heterocyclic compounds represented by formula (III) or salts thereof, and more preferably in formula (IV) It is at least one compound selected from the heterocyclic compounds represented or salts thereof.

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 number of carbon atoms of the group serving as the mother nucleus is 1-6. 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 groups that can be “substituents” 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 group 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 group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hetenyl group C2-6 alkenyl groups such as 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 group and butenyloxy group; C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group; C6-10 aryl groups such as phenyl group and naphthyl group; phenoxy group and 1-naphthoxy group A C7-10 aralkyl group such as a benzyl group or a phenethyl group; a C7-11 aralkyloxy group such as a benzyloxy group or a phenethyloxy group; a formyl group, an acetyl group, a propionyl group, a benzoyl group, C1- such as a cyclohexylcarbonyl group Acyl group; C1-7 acyloxy group such as formyloxy group, acetyloxy group, propionyloxy group, benzoyloxy group, cyclohexylcarbonyloxy group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group A C1-6 alkoxycarbonyl group such as n-butoxycarbonyl group and 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 Group; C2-6 haloalkenyl group 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 group such as bromo-2-pentynyl group; C1-6 haloalkoxy group such as 2-chloro-n-propoxy group and 2,3-dichlorobutoxy group; 2-chloropropenyloxy group, 3-bromo C2-6 haloalkenyloxy groups such as butenyloxy group; 4-chlorophenyl group, 4-fluorophenyl group, 2,4-dichlorophen C6-10 haloaryl group such as 4-fluorophenyloxy 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 Group: C7-11 aralkylamino group such as benzylamino group, 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, dimethylaminocarbonyl An unsubstituted or substituted aminocarbonyl group such as phenylaminocarbonyl group, N-phenyl-N-methylaminocarbonyl group; iminomethyl group, (1-imino) ethyl group, (1-imino) -n-propyl A C1-6 alkyl group substituted with an imino group such as a group; hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group, methoxyiminomethyl group, (1-methoxyimino) ethyl A C1-6 alkyl group substituted with a hydroxyimino group such as a 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 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 A 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 group, ( - butylthio) carbonyl group, (i-butylthio) carbonyl group, (s-butylthio) carbonyl group, (t-butylthio) (Cl to 6 alkylthio, such as carbonyl groups) 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 and the like A heteroarylsulfinyl group such as thiazolylsulfinyl group and pyridylsulfinyl group; a C7-11 aralkylsulfinyl group such as benzylsulfinyl group and phenethylsulfinyl group; a methylsulfonyl group, an ethylsulfonyl group, t- C1-6 alkylsulfonyl group such as butylsulfonyl group; C2-6 alkenylsulfonyl group such as allylsulfonyl group; C2 such as propargylsulfonyl group A C6-10 arylsulfonyl group such as a phenylsulfonyl group; a heteroarylsulfonyl group such as a thiazolylsulfonyl group or a pyridylsulfonyl group; a C7-11 aralkylsulfonyl group such as a benzylsulfonyl group or a phenethylsulfonyl 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, pyridinyl 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 And a tri-C1-6 alkyl-substituted silyl group such as a silyl group or a t-butyldimethylsilyl group; a triphenylsilyl group;

  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, a nitro group, or a cyano group is shown. n shows the substitution number of X and is an integer in any one of 0-5. When n is 2 or more, Xs may be the same as or different from each other.

  The “C1-6 alkyl group” in X may be a straight chain or a branched chain. As the alkyl group, 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, t-butyl group I-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.

  The “C 1-6 alkyl group having a substituent” in X is a C 3-8 cyclo group 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, perchlorohexene A C1-6 haloalkyl group such as a xyl group or a 2,4,6-trichlorohexyl group;

  Hydroxy C1-6 alkyl groups such as hydroxymethyl group and 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-dimethoxy n-propyl group, Di-C1-6 alkoxy C1-6 alkyl group such as 2-diethoxyethyl group; C1-7 acyloxy such as formyloxymethyl group, acetoxymethyl group, 2-acetoxyethyl group, propionyloxymethyl group, propionyloxyethyl group A C1-6 alkyl group; a C1-6 alkyl group substituted with an imino group such as an iminomethyl group, a (1-imino) ethyl group, or a (1-imino) propyl group; a hydroxyiminomethyl group, (1-hydroxyimino) ethyl A C1-6 alkyl group substituted with a hydroxyimino group such as a group, (1-hydroxyimino) -n-propyl group, methoxyiminomethyl group, (1-methoxyimino) ethyl group; unsubstituted or substituted An unsubstituted or unsubstituted benzyl group, an unsubstituted or substituted phenethyl group, etc. Or a C7-11 aralkyl group having a substituent;

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 “C2-6 alkenyl group having a substituent” in X include C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group;

Examples of the “C2-6 alkynyl group” in X include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2 -Methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group 1,1-dimethyl-2-butynyl group and the like.
Examples of the “C2-6 alkynyl group having a substituent” in X include C2-6 halo such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group and the like. Alkynyl group; and the like.

As the “C 1-6 alkoxy group” in X, 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 -A pentyloxy group, n-hexyloxy group, etc. are mentioned.
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;

  Among 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 them represents a benzene ring. When both A ¹ and A ² are nitrogen atoms, the aromatic ring containing them 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. Any one of B ^{1 and} B ² is preferably 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 represents 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 C 1-6 alkyl group.
Examples of the “C 1-6 alkyl group” for R ¹ include the same as those exemplified for X above.
Of these, R ¹ is preferably a C 1-6 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 , 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 may be the same or different from each other.
Examples of the “C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, and “C1-6 alkoxy group” in X ⁰ are the same as those exemplified in the above X. Can do.

(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
Examples of the “C 1-6 alkyl group” and “C 2-6 alkenyl group” in R ¹¹ include the same groups as those exemplified in the above X.

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

As the “amino group having a substituent” in R ^11, a C1-6 alkylamino group such as a methylamino group, an ethylamino group or a dimethylamino group; a C2-6 alkenylamino group such as a vinylamino group or an allylamino group; And N′-substituted hydrazino groups such as hydrazino group, N ′, N′-dimethylhydrazino group, N′-methylenehydrazino group;

Examples of the “C 1-6 alkylaminocarbonyl group” for R ¹¹ include a methylaminocarbonyl group, an ethylaminocarbonyl group, and an n-propylaminocarbonyl group.
As the “C1-6 alkylaminocarbonyl group having a substituent” 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.
Examples of the “C1-6 alkyl group”, “C2-6 alkenyl group”, and “C1-6 alkoxy group” in R ¹² include the same as those exemplified in the above X.

Also, R ¹¹ and R ^12, they are connected, together with the carbon atoms to which they are attached 5 with a hydrocarbon ring or a substituent R ²⁰ 5-8 membered ring having a substituent R ²⁰ An 8-membered heterocycle may be formed.
R ²⁰ 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, 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;

Examples of the “C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, and “C1-6 alkoxy group” in R ²⁰ include the same as those exemplified in the above X. it can. As the “C 1-6 alkylaminocarbonyl group” for R ^20, the same groups as those exemplified for R ¹¹ can be mentioned.
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 “C1-7 acyl group having a substituent” 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 “C1-6 alkyl group” for R ² include the same as those exemplified for X above.
Examples of the “C1-7 acyl group” for 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 cyclopropylmethoxycarbonyl group, cyclobutylmethoxycarbonyl group, cyclopentylmethoxycarbonyl group, cyclohexylmethoxycarbonyl group, 2-methylcyclopropylmethoxycarbonyl group, 2 , 3-dimethylcyclopropylmethoxycarbonyl group, 2-chlorocyclopropylmethoxycarbonyl group, C3-8 cycloalkyl C1-6 alkoxycarbonyl group such as 2-cyclopropylethoxycarbonyl 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 C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted C 2-6 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; A C2-6 alkynyloxy group having an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heterocyclic group;

Examples of the “C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, and “C1-6 alkoxy group” in R ³ are the same as those exemplified in the above X. Can do.

Examples of the “C3-8 cycloalkyl group” for R ³ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like.
Examples of the “cycloalkyl group having a substituent” 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, 1-propenyloxy group, 2-propenyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 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” for R ³ include C2-6 haloalkenyloxy groups such as 2-chloro-1-propenyloxy group and 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.
The “C2-6 alkynyloxy group having a substituent” for R ³ includes 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, if 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.

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

  Examples of the 6-membered heteroaryl group include 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 group, , 4-Dihydro-2H-1,5-benzodioxepin-7-yl group, 2,3-dihydrobenzofuran-4-yl group, 2,3-dihydrobenzofuran-5-yl group, 2,3-dihydro A benzofuran-6-yl group, a 2,3-dihydrobenzofuran-7-yl group;

Among these, R ³ is preferably a C 1-6 alkyl group, a C 1-6 alkoxy C 1-6 alkyl group, or a C 1-6 alkoxy C 1-6 alkoxy C 1-6 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 B ¹ and B ² are double bonds. 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. those that form a heterocyclic ring of 5- to 8-membered ring having a 5- to 8-membered hydrocarbon ring or a substituent R ²¹ rings.
D in Formula (II) 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 C 1-7 acyl group, an unsubstituted or substituted C 1-6 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 C 1-6 alkyl group, an unsubstituted or substituted C 2-6 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 of 0 to 6. When m is 2 or more, X ¹ may be the same as or different from each other.
"Alkyl group" in X ^1, the "C2~6 alkenyl group", "C2~6 alkynyl group", and "C1~6 alkoxy group" may include the same ones as those exemplified in the 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).

  Examples of the salt of the heterocyclic compound represented by formula (I) to formula (IV) include salts of inorganic acids such as hydrochloride, nitrate, sulfate, and phosphate; acetate, lactate, propionate, benzoate And salts of organic acids such as acid salts.

  Specific examples and production methods of the heterocyclic compounds represented by the formulas (I) to (IV) or salts thereof are described in Patent Document 3, Patent Document 4, Patent Document 5, Patent Document 6, and the like. Therefore, by taking them into consideration, the heterocyclic compounds represented by the formulas (I) to (IV) or salts thereof used in the present invention can be easily produced or obtained.

[Other ingredients]
The animal ectoparasite control agent of the present invention may contain components other than the above-mentioned 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, antigenic, insecticidal or 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, liquids, emulsions, wafers, biscuits, minced meat and the like.
The animal ectoparasite control agent of the present invention may contain a carrier, a surfactant, a solid diluent, a liquid diluent and the like depending on the dosage form. Examples thereof include lactose, sucrose, glucose, starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, calcium carbonate, and other commercially available feed materials.

[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 veterinary 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, carbo Phenothion, chloroethoxyphos, chlormefos, coumaphos, cyanophenphos, cyanophos, CYAP, diazinon, dichlorvos, dicrotophos, dimethoate, disulfotone, dimeton-S-methyl, dimethylvinphos, dimeton-S-methylsulfone, diariphos, diazinon, Diclofenthion, Dioxabenzophos, Disulfoton, Ethion, Etoprofos, Etrimfos, EPN, Phenamifos, Fenitrothion, Fenthion, Fensulfothio , 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, terb Phos, triazophos, trichlorfone, tebupyrimfos, temefos, thiometone, bamidithione;

  2) Carbamate series: Alanicarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, phenoxycarb, phenothiocarb, methiocarb, mesomil, oxamyl, pirimicurve, propoxyl, thiodicarb, triazamate, etiofencarb, MIPC, MPC MTMC, pyridafenthion, furthiocarb, XMC, aldoxicarb, arixicarb, aminocarb, bendiocarb, bufencarb, butacarb, butcarboxyme, butoxycarboxyme, chloetocarb, dimethylane, formethanate, isoprocarb, metam sodium, metolcarb, promecarb, thiofa Knox, Trimetacarb, Xylylcarb;

  3) Pyrethroids: alletrin, bifenthrin, cyfluthrin, beta cyfluthrin, cyhalothrin, lambda cyhalothrin, ciphenothrin, cypermethrin, alpha cypermethrin, beta cypermethrin, zeta cypermethrin, deltamethrin, esfenvalerate, etofen Prox, Fenpropatrin, Fenvalerate, Imiprothrin, Permethrin, Praretrin, Pyretrin, Pyretrin I, Pyretrin II, Resmethrin, Silafluophene, Fluverate, Tefluthrin, Tetramethrin, Tralomethrin, Transfluthrin, Profluthrin, Cymetritoline, Acrinathrin 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 inhibitor: chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novallon, teflubenzuron, triflumuron, bistrifluron, nobiflumuron, buprofezin, hexithiazox B) ecdysone antagonists: halofenozide, methoxyphenozide, tebufenozide, chromafenozide, azadirachtin; c) juvenile hormone-like substances: pyriproxyfen, methoprene, diophenolan, epofenonan, hydroprene, quinoprene, quinoprene, quinoprene, quinoprene, quinoprene 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 compounds: a) acetoprole, ethiprole, fipronil, vanilliprol, pyrafluprole, pyriprole; b) organochlorine: camfechlor, chlordane, endosulfan, HCH, γ-HCH, heptachlor, methoxychlor;

7) Macrocyclic lactone insecticide: abamectin, emamectin benzoate, milbemectin, lepimectin, spinosad, ivermectin, selamectin, doramectin, epinomectin, moxidectin,
8) METI I compounds: phenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, fluphenelim, 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 compounds: 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., White scab fungus, black scab fungus, Pekir Myces sp., Thuringiensins, Verticillium Genus species;
16) Latrophilin receptor agonist: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside;

17) Octopaminergic agents: Amitraz;
18) Ryanodine derivative agonists: fulbenzamide, chlorantraniliprole, cyantraliniprol 19) Inhibitors of magnesium-stimulated ATPase: thiocyclam, thiosultap, nereistoxin;
20) Antifeedant: Pymetrozine;
21) Tick growth inhibitors: clofentezin, etoxazole;
22) Others: Benclothiaz, Bifenazate, Pyridalyl, Sulfur, Sienopyrafen, Ciflumethofene, Amidoflumet, Tetradiphone, Chlordimeform, 1,3-Dichloropropene, DCIP, Phenisobromolate, Benzate, Metaaldehyde, Spinetram, Pyrifluquinazone, Benzoxy Mate, bromopropyrate, quinomethionate, chlorbenzilate, chloropicrin, clothiazoben, dicyclanyl, phenoxacrime, fentriphanyl, flubenzimine, flufenzine, gossip lure, japonyla, metoxadiazone, petroleum, potassium oleate, sulfluramide, tetrasul, trialacene;

  23) Anthelmintic: a) benzimidazole series: fenbendazole, albendazole, triclabendazole, oxybendazole; b) salicylanilide series: closantel, oxyclozanide; c) substituted phenol series: nitroxinyl; d) pyrimidine series: pyrantel E) imidazothiazole series: levamisole; f) tetrahydropyrimidine: praziquantel; g) other anthelmintic drugs: cyclodiene, riania, chlorthrone, metronidazole;

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

  Examples of host animals in which the control agent of the present invention is effective include dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (for example, pigeons, parrots, nine-birds, wild birds, parakeets, juvenile pine, canary); Examples include cattle, horses, pigs, sheep, goats; ducks, chickens, turkeys and ducks.

  The ectoparasites targeted by the animal ectoparasite control agent according to the present invention inhabit the host animal's back, armpit, lower abdomen, inner thigh, etc., and obtain nutrients such as blood and dandruff from the animals. And those that fly to the back, buttocks, etc. of the host animal and inhabit by obtaining nutrients such as blood and dandruff from the animal. Examples of ectoparasites include ticks, lice and fleas.

Examples of mites (Acari) include the following pests.
(1) Mesostigmata mites (mite)
(a) Dermanyssidae mites:
Species of the genus (Dermanyssus spp.) Such as vaccinia (Dermanyssus gallinae);
(b) Mite of the family Macronyssidae:
House dust mite species (Ornithonyssus spp.) Such as avian tick mite (Ornithonyssus sylviarum), netty bird mite (Ornithonyssus bursa), house dust mite (Ornithonyssus bacoti);
(c) Laticidae mites:
Species of the genus genus (Laelaps spp.), Such as the mouse spider mite (Laelaps echidninus), the stag beetle (Laelaps jettmari);

(2) Metastigmata tick (tick)
(a) Mite from Argasidae:
Argas spp., Such as Argas persicus, Argas reflexus; Ornithodoros spp., Such as Ornithodorus moubata;
(b) Ixodidae ticks:
Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, physic physics, Haemaphysalis cinophila, physic physics ), Tick ticks (Haemaphysalis yeni), black ticks (Haemaphysalis campanulata), blue tick ticks (Haemaphysalis pentalagi), tick ticks (Haemaphysalis flava), large ticks (Haemaphysalis megaspinosa), ema physalis tick (Haemaphysalis megaspinosa) Haemaphysalis spp .; Amblyomma americanum, Ambrioma variegatum Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Amblyomma testudinlyly tick (Amblyomma testudinlyly) ), Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes scapularis, Ixodes socularis Tick species (Ixodes spp.) Such as Ixodes ovatus, Ixodes persulcatus, Ixodes nipponensis; Rickicephalus (Boophilus) microplus, Lipisepha Bovine tick subspecies (Rhipicephalus (Boophilus) decoloratus), Ripeicephalus (Boophilus) annulatus (Rhipicephalus (Boophilus) annulatus), Ripeicephalus (Buophilus) Calcertas (Rhipicephalus (Boophilus) calceratus), etc. .); Rhipicephalus evertsi, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus appendiculatus, Rhipicephalus appendiculatus cap Rhipicephalus turanicus, Rhipicephalus zambeziensis and other species of the genus Rhipicephalus spp .; Dermacentor Marginatas (De rmacentor marginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, vari vari D ) And other species (Dermacentor spp.);

(3) Astigmata (Acaridida)
(a) Psoroptidae mites:
Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, and other tick species such as Chorioptes bovis Chorioptes spp.);
(b) Scaroptidae mites:
Sarcoptes scabiei, Sarcoptes canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae, Sarcoptes rupicaprae, Sarcoptes rupicaprae Scaroptes spp., Such as Switzerland (Sarcoptes suis);

(4) Prostigmata mites (Actinedida)
(a) Tick from the Demodixidae family:
Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi ), Demodex swiss (Demodex suis), wilt mite species (Demodex spp.);
(b) Mite from the family Troombiculidae:
Trombiculidae spp., Such as Trombicula alfreddugesi and Trombicula akamushi;

Examples of lice (Phthiraptera) include the following pests.
(1) Louse of Anoplura
(a) Lice from the Haematopinidae family:
Haematopinus asini, bovine lice (Haematopinus eurysternus), porcine louse species (Haematopinus spp.) Such as pig lice (Haematopinus suis);
(b) Linognathidae lice:
Dog lice (Linognathus setosus), Cow horned lice (Linognathus vituli), Linognathus ovillus, Linognathus oviformis, Linognathus oviformis, Linognathus psoris ); Solenopotes spp., Such as Solenopotes capillatus;

(2) Amblycera subs (biting louse)
(a) White-headed lice (Menoponidae):
Menacanthus spp., Such as Chicken Acneus stramineus, Menacanthus cornutus, Menacanthus pallidulus; );Such.

(3) Ischnocera subs (biting louse)
(a) Philopteridae lice:
Columbicola spp. Such as Columbicola columbae; Cuclotogaster spp. Such as Cuclotogaster heterographus; Goniodes dissimilis gas, Goniodes dissimilis Goniodes spp., Such as Goniodes gallinae; Lipiperus spp., Such as Lipeurus caponis;
(b) Trichodectidae lice:
Bovidola spp., Such as Bovicola bovis, Bovicola ovis, Bovicola limbata, Bovicola caprae, Bovicola equip, etc .; Trichodectes spp .; Felicola spp., Such as Felicola subrostrata;

(4) The fleas (Siphonaptera) include the following pests.
(a) Fleas from the Tungidae family:
Species of the genus (Tunga spp.) Such as Sunungomi (Tunga penetrans);
(b) Fleas from the family Flea Family (Pulicidae):
Cunnocephalides (Ctenocephalides canis), Catfish (Ctenocephalides felis) and other species of genus (Ctenocephalides spp.); Hedgehog (Archaeopsylla erinacei); (Xenopsylla spp.); Human flea species (Pulex spp.); Etchidnophaga gallinacea and other species (Echidnophaga spp.);
(c) Ceratophyllidae chisel:
Tortoise (Ceratophyllus gallinae), Yamato mouse (Ceratophyllus anisus) and other species (Ceratophyllus spp.); European mouse (Nosopsyllus fasciatus),
(d) Fleas from the family Leptopsyllidae:
Leptopsylla segnis and other species such as Leptopsylla spp.

Other ectoparasites that are targets of the animal ectoparasite control agent of the present invention include stink bugs.
Examples of the insects of the order of the Hemiptera include the following pests.
(a) Insects of Cimicidae:
Cymex spp., Such as Cimex lectularius;
(b) Reduviidae insects:
(b-1) Insects of the Triatominae family:
Panstrongylus spp .; Rhodnius spp. Such as Rhodnius prolixus; Triatoma spp. Such as Triatoma infestans;

The animal ectoparasite control agent of the present invention is also effective against insect pests (Diptera) that are biting insects (chewing flies, adult sucking flies, migratory dipterous larvae, maggots of parasitic flies) .
The following pests can be mentioned as pests of flies (Diptera).
(1) Nematocera
(a) Culicidae mosquitoes:
Culex quinquefasciatus, Culex pipiens pallens, Culex tarsalis, Culex pipiens molestus, Culex pipiens fatigans, Culex tritamoros spp. .); Almigeres spp., Such as Armigeres subalbatus; Gambia anopheles gambiae, Anopheles maculipennis, Anopheles sinensis, l Genus (Anopheles spp.); Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Aedes togoi, Apones vexans nip, etc. Buka species (Aedes spp.); Such as,
(b) Buyers of Simuliidae:
Promululium species such as Simulium reptans, Simulium ornatum, Simulium venustum, Simulium salopiense; Prosimulium yezoense Prosimulium spp.);

(2) Short angle
(a) Abs from Tabanidae:
Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Tabanus trigonus, Tabanus chrysurus, Tabanus chrysurus Abs species (Tabanus spp.), Such as Tabanus fulvimedioides and Tabanus iyoensis; Chrysops caecutiens, Chrysops relictus, Chrysop (ja), Chrysop (ja) Of the genus Mechrabu (Chrysops spp.);
(b) Muscidae flies:
Muscina spp., Such as Musca domestica, Musca bezzii, Musca hervei, Musca conducens, Musca stabulans, etc .; Stomoxys spp .; Haematobia irritans, Haematobia irritans exigua, Haematobia stimulans, and other species of Haematobia stimulans;
(c) Glossinidae flies:
Such as Glossina spp.
(d) Fly of the Hippoboscidae:
Melophagus spp., Such as lice fly (Melophagus ovinus); etc.
(e) Calliphoridae flies:
Calliphora, such as Calliphora lata; Lucilia spp., Lucilia (Phaenicia) cuprina, Lucilia (Phaenicia) sericata, Lucilia illustris; Chrysomya hominivorax, Chrysomya chloropyga, Chrysomya bezziana and other species of Chrysomya bezziana (Chrysomyia. Spp.);
(f) Oestridae flies:
(f-1) Flying from the Cuterebrinae family:
Rabbit Drosophila species (Cuterebra spp.);
(f-2) Hypodermatinae flies:
Hypoderma bovis, Hypoderma lineatum, and other species of the genus (Hypoderma spp.);
(f-3) Gasterophilinae flies:
Horseflies (Gasterophilus intestinalis), Ataster squirrels (Gasterophilus haemorroidalis), Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis (Gasterophilus nigricornis), Grumophilus pe Gasterophilus spp.);
(f-4) Oestrinae flies:
Oestrus spp., Such as Oestrus ovis;
Among these, fleas and ticks are preferred as the target insects for the animal ectoparasite control agent of the present invention.

When the animal ectoparasite control agent of the present invention is administered to animals, ectoparasites can be controlled. Thereby, it is possible to prevent diseases or other pathological conditions that are transmitted through parasites, or injuries directly caused by parasites (hereinafter sometimes referred to as parasitic diseases).
When the animal ectoparasite control agent of the present invention is administered to animals, ectoparasites can be suppressed. It can partially or completely inhibit the occurrence of parasitic diseases in animals susceptible to parasitic diseases, reduce or eliminate the symptoms of parasitic diseases, or partially or completely cure or treat parasitic diseases be able to.

<1> Diseases Diseases transmitted through ectoparasites are, for example, viral diseases, bacterial diseases, and protozoan-mediated diseases. Like flies, pathogens are attached to sticky legs and transported elsewhere; pathogens develop and multiply in the body of sanitary pests and become the source of infection.
Specific examples are given below.

(1) Viral diseases
(a) Akabane disease in which bovine midge (Culicoides oxystoma) is infected via Akabane virus of Bunyaviridae; Ainovirus infection which is infected via Aino virus; Reoviridae ( Reoviridae) Ibaraki disease infected via Ibaraki virus; Chuzan virus infected via Chuzan virus; Reoviridae Orbivirus bluetongue virus infected via Bluetongue virus; Arbovirus disease transmitted through other arboviruses such as Peaton virus, Sathuperi virus, D'Aguilar virus and Shamonda virus;
(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 the Japanese encephalitis virus of Flaviviridae;
(d) Avian Newcastle disease that Fannia canisularis infects via Newcastle disease virus (NDV);
(e) equine infectious anemia infected by blood-sucking insects, such as Tabanidae, via equine infectious anemia virus of the genus Retroviridae;

(2) Bacterial diseases
(a) Japanese red fever, rickettsiosis, etc. in dogs infected by Haemaphysalis longicornis via Rickettsia japonica
(b) Barbarian disease in which the tick tick (Haemaphysalis flava) is transmitted via the wild moss (Francisella tularensis);
(c) Cat infectious anemia which is transmitted by Candidatus Mycoplasma haemominutum by ticks (Ixodes ovatus);

(3) Protozoan-borne diseases
(a) Cattle large piroplasmosis infected by Babesia ovata by Haemaphysalis longicornis; Canine piroplasmosis infected by Babesia gibsoni;
(b) Babesiosis, such as Q fever in cattle infected by the tick (Rhipicephalus (Boophilus) microplus) via Babesia bigemina, Babesia bovis; Anaplasmosis infected via Anaplasma marginale;
(c) Rabicephalus sanguineus infected by Babesia canis and Babesia gibsoni in dogs with babesiosis; Canine anaplasmosis infected with Anaplasma platys; Hepatozoon canis with infection Hepatozone disease in dogs; Haemobartonella in dogs infected via Haemobartonella canis;
(d) Chicken leucocytozoonosis in which chickens (Culicoides arakawae) are infected via Leukocytozoon caulleryi;
(e) Trypanosomiasis such as chronic sleeping sickness, acute sleeping sickness, etc. infected by blood-sucking insects such as Tabanidae through Trypanosoma ssp .;
(f) Dogs cats (Ctenocephalides felis) are infected via Diphylidium caninum;
(g) Canine filariasis that Aedes togoi, Aedes albopictus, Culex tritaeniorhynchus summorosus, and Culex pipiens pallens infect through the dog filamentous worms;

<2> 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 the back of cattle and make holes in the skin, greatly reducing the value of leather.
Specific examples are given below.
(a) Caterpillar larvae caused by larvae of Hypoderma bovis and larvae of Hypoderma lineatum;
(b) fountain larvae caused by larvae of Gasterophilus intestinalis, larvae of Gasterophilus nasalis, larvae of Gasterophilus haemorroidalis;
(c) Myiasis caused by larvae of Lucilia illustris;

<3> Injuries caused by parasitism or bites When stabbed by ticks such as sword mites and claw mites, insects such as mosquitoes, flies, lice, etc., they cause severe pruritus and pain due to physical injury and injection of poisonous substances, resulting in significant 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) 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 the chicken hawk (Culicoides arakawae); The strong sensation caused by the chicken lice (Menopon gallinae);

<4> Injuries such as blood sucking, anemia, bleeding, etc. Among the pests of hygiene, many of them absorb blood simultaneously with giving stress to 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), yellow tick (Ixodes ovatus), red tick (Ixodes nipponensis), shrze 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 tuna tick (Ixodes nipponensis), and the shruce tick (Ixodes persulcatus);
(c) blood sucking of chickens of Dermanyssus gallinae and Ornithonyssus sylviarum, anemia caused to chickens;
(d) Bovine hemorrhage caused by Simuliidae;
(e) Cattle anemia caused by Tabanidae;
(f) Long-term anemia of cats caused by cat fleas (Ctenocephalides felis);
(g) Chicken anemia caused by chicken hawk (Culicoides arakawae);

<5> Skin disorders Some sanitary pest parasites and bites not only cause pruritus, redness and swelling, but also seriously damage the skin. Scarlet mites cause hair loss, crust formation, wrinkles, etc. with strong pruritus, and acne mites cause systemic wrinkles due to hair loss and secondary infection. In addition, blood-sucking pests generally inject a large amount of saliva at the time of blood-sucking, causing an allergic reaction to it and causing redness, swelling, papules, ulcers, etc. with strong itching.
Specific examples are given below.
(a) Chorioptes bovis, Psoroptidae spp. causes cattle, horses, sheep scabies; Sarcoptes spp. causes swine, dogs scabies; Cat scabies caused by Notoedres cati; dogs, cat ear scabies caused by Otodectes cynotis; chicken scabies caused by Knemidokoptes mutans;
(b) Flea allergic dermatitis caused by cat fleas (Ctenocephalides felis);
(c) folliculosis caused by Demodex canis;
(d) Papules, blisters, edema caused by Simuliidae;

  The dose of the control agent of the present invention varies depending on the administration method, administration purpose, disease symptoms, etc., but is usually 0.01 mg to 100 g, preferably 0.1 mg to 10 g, relative to 1 kg body weight of the host animal. It is.

Administration to the host animal is performed by 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. Can do.
Specific examples of oral administration include a method for 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 with animal feed Let me give it to the animal.

  Specific examples of parenteral administration include intramuscular, intradermal, subcutaneous injection or infusion; spot-on, poon-on, etc .; spray, shampoo, etc .; For example, a method of attaching it to an animal by soaking it.

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

Test Example 1 Insecticidal test for 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 mite tick mites were released in this 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. Note that the test was conducted in a two-track 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 1, 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 compound containing fipronil as an existing compound. It can be seen that the composition is excellent in performance and low concentration activity.

Test Example 2 Insecticidal test (immersion) on 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 male ticks 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, 112 to 1-16, 2-1 to 2-3, 3-5, 3-7 and 4-1 to 4-4 shown in Table 1 The above tests were performed using each as an active ingredient. 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 semen 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 The above tests were performed using each as an active ingredient. 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, 112 to 1-15, 2-1 to 2-3, 3-1, 3-2 and 4-1 to 4-4 shown in Table 1 The above tests were performed using each as an active ingredient. 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 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, 112 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 an active ingredient. 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 filled 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 an active ingredient. 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.
% Sugar was mixed with the 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 The above test was conducted using 3-7, 4-3 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 100 ppm.

Test Example 9 Test for Cat Fleas (Ctenocephalides felis) In cats, a drug solution prepared so as to have an active ingredient of 15 mg per kg body weight of the cat was dropped on the skin behind the neck of the cat (between the scapula). 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 is measured after 21 days from the day of chemical treatment, compound 1-9 is measured after 28 days from the day of chemical treatment, and compounds 1-1 and 1-5 are treated with chemical solution. Even after 35 days from the date of measurement, the activity was particularly excellent with a mortality rate of 90% or more.

Claims (6)

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 -6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
n shows the substitution number of X and is an integer in any one of 0-5. 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 C 1-6 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 , 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 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
R ¹² represents an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, or a halogen atom.
Further, connected is R ¹¹ and R ^12, together with the carbon atoms to which they are attached 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 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, 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 C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted C 2-6 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 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 C 1-7 acyl group, an unsubstituted or substituted C 1-6 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 C 1-6 alkyl group, an unsubstituted or substituted C 2-6 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 of 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 the 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 for treating an animal suffering from an ectoparasite-derived infection, comprising administering a veterinary-acceptable amount of the ectoparasite control agent according to any one of claims 1 to 4.   A method for preventing an animal from suffering from an ectoparasite-derived infection comprising administering a veterinary-acceptable amount of the ectoparasite control agent according to any one of claims 1 to 4.