WO2013047144A1 - Cyclic amine compound and pest control agent - Google Patents

Abstract

A cyclic amine compound represented by formula (I) or a salt thereof. In the formula, Cy¹ represents a phenyl group or the like; each R¹⁰ is a substituent of Cy¹ and independently represents an unsubstituted or substituted C_1-6 alkyl group or the like; m represents the number of the R¹⁰ moieties, said number being an integer of 0-5; Cy² represents a 4-trifluoromethylphenyl group or the like; each R¹¹ is a substituent of Cy² and independently represents an unsubstituted or substituted C_1-6 alkyl group or the like; n represents the number of the R¹¹ moieties, said number being an integer of 0-5; each of R^1a, R^1b, R^2a, R^2b, R^3a, R^3b, R^4a and R^4b independently represents a hydrogen atom or the like; R⁵ represents a hydrogen atom or the like; and p represents the number of the R^4b moieties or the number of the R⁵ moieties, said number being an integer of 0 or 1.

Description

Cyclic amine compounds and pest control agents

The present invention relates to a cyclic amine compound or a salt thereof useful as an active ingredient of a pest control agent that has a certain effect and can be used safely, and in particular, an ectoparasite control agent.
This application claims priority on the basis of Japanese Patent Application No. 2011-213931 filed in Japan on September 28, 2011, the contents of which are incorporated herein by reference.

Ectoparasites are a group of animals that cause various damage to humans and beasts. These damages include direct damage such as anemia and dermatitis caused by ticks and insects directly infesting the host beast and sucking blood and damaging the skin, mediating various pathogens, parasites, etc. There is indirect damage that acts as an intermediate host. In order to prevent these damages, efficient control methods for ectoparasites are required. In general, control by a drug is used, but since the drug is often sprayed not only to the animal body but also to the surrounding environment, safety to the environment and other humans is required. In addition, it has been pointed out that continuous use of a single drug increases the number of drug-resistant ectoparasites. Therefore, there is always a demand for new drugs. In particular, there is a need for a drug that is particularly active and effective, has a long duration, and is highly safe for humans and animals.

As compounds structurally related to the compound of the present invention, Patent Document 1 discloses a trifluoroacetate salt represented by the formula (A), and Patent Document 2 discloses a compound represented by the formula (B).

  　 

WO2007 / 107594 WO2008 / 062182

An object of the present invention is to provide a cyclic amine compound or a salt thereof useful as an active ingredient of a pest control agent, particularly an ectoparasite control agent, which has a certain effect and can be used safely.

Cited Document 1 shows that the trifluoroacetate salt represented by the formula (A) is used as an inhibitor of histone deacetylase (HDAC). Cited Document 2 shows that the compound represented by the formula (B) is used as a production intermediate. It is not known that these compounds have a controlling effect against pests.
In such a situation, the present inventors diligently studied to solve the above-described problems. As a result, a cyclic amine compound having a specific structure or a salt thereof was obtained. The present inventors have found that this cyclic amine compound has a certain effect and can be safely used as an active ingredient of a pest control agent, particularly an ectoparasite control agent. Based on these findings, further studies have been made and the present invention has been completed.

That is, the present invention includes the following.
[1] A cyclic amine compound represented by the formula (I) or a salt thereof.

Here, in formula (I),
Cy ¹ represents a C6-10 aryl group.
R ¹⁰ is a substituent of Cy ¹ and each independently represents an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or A substituted C6-10 aryl group, an unsubstituted or substituted C6-10 aryloxy group, an unsubstituted or substituted C1-6 alkylamino group, an unsubstituted or substituted C1 ~ 6 represents an acylamino group, a cyano group, a nitro group, or a halogen atom.
m represents the number of R ¹⁰ and is an integer of 0 to 5. When m is 2 or more, R ¹⁰ may be the same as or different from each other.

Cy ² represents a C6-10 aryl group or a heterocyclyl group.
R ¹¹ is a substituent of Cy ² and each independently represents an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or A substituted C6-10 aryl group, an unsubstituted or substituted C6-10 aryloxy group, an unsubstituted or substituted C1-6 alkylamino group, an unsubstituted or substituted C1 ~ 6 represents an acylamino group, a cyano group, a nitro group, or a halogen atom.
n represents the number of R ¹¹ and is an integer of 0 to 5. When n is 2 or more, R ¹¹ may be the same as or different from each other.

R ^1a , R ^1b , R ^2a , R ^2b , R ^3a , R ^3b , R ^4a , and R ^4b are each independently a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, or An unsubstituted or substituted C1-6 alkoxy group is shown.
R ^1a and R ^2a or R ^3a and R ^4a are each independently an unsubstituted or substituted C2-6 alkylene group, or an unsubstituted or substituted C2-6 alkenylene group. May be formed.
R ⁵ represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C1-7 acyloxy group Or an unsubstituted or substituted C1-6 alkoxycarbonyloxy group, an unsubstituted or substituted heterocyclyl group, a cyano group, or a halogen atom.
R ^4b and R ⁵ may together form a group represented by —O—.
p represents the number of R ^4b and R ⁵ and is an integer from 0 to 1. When p is 0, a carbon-carbon bond between R ^4b and R ⁵ forms a double bond.

[2] The cyclic amine compound or a salt thereof according to [1], wherein Cy ¹ in formula (I) is a phenyl group.
[3] The cyclic amine compound or a salt thereof according to [1] or [2], wherein in formula (I), Cy ² is a phenyl group, a pyrazolyl group, a thiadiazolyl group, a pyridyl group, a pyrimidinyl group, or a pyridazinyl group.
[4] In Formula (I), Cy ¹ is a phenyl group, Cy ² is a 4-trifluoromethylphenyl group, or a 5-trifluoromethyl-pyridin-2-yl group, and n is any of 0 to 4 The cyclic amine compound or a salt thereof according to [1], which is an integer of

[5] A pest control agent containing, as an active ingredient, at least one selected from the cyclic amine compound or a salt thereof according to any one of [1] to [4].
[6] An ectoparasite control agent comprising, as an active ingredient, at least one selected from the cyclic amine compound or a salt thereof according to any one of [1] to [4].

The cyclic amine compound or a salt thereof according to the present invention has a certain effect and can be used safely as an active ingredient of a pest control agent, particularly an ectoparasite control agent. The pest control agent or ectoparasite control agent according to the present invention can effectively control ectoparasites that cause harm to humans and beasts.

Hereinafter, preferred examples of the present invention will be described, but the present invention is not limited to these examples. Additions, omissions, substitutions, and other modifications can be made without departing from the spirit of the present invention.
[Cyclic amine compound]
The cyclic amine compound according to the present invention is a compound represented by the formula (I) (hereinafter sometimes referred to as a cyclic amine compound (I)). The salt of the cyclic amine compound according to the present invention is a salt of the cyclic amine compound (I).

In this specification, the term “unsubstituted” means that only a group serving as a mother nucleus is present. 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. 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 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-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group C2-6 alkenyl groups such as senyl group and 5-hexenyl group; ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl A C2-6 alkynyl group such as a group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl 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 trifluoromethoxy group, 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group; 2-chloropropenyloxy Groups, C2-6 haloalkenyloxy groups such as 3-bromobutenyloxy group; 4-chlorophenyl group, 4-fluorophenyl C6-10 haloaryl groups such as nyl group and 2,4-dichlorophenyl group; C6-10 haloaryloxy groups such as 4-fluorophenyloxy group and 4-chloro-1-naphthoxy group; chloroacetyl group and trifluoroacetyl group Halogen-substituted C1-7 acyl groups such as trichloroacetyl group and 4-chlorobenzoyl group;

Cyano group; nitro group; amino group; C1-6 alkylamino group such as methylamino group, dimethylamino group, diethylamino group; C6-10 arylamino group such as anilino group, naphthylamino group; benzylamino group, phenylethylamino C7-11 aralkylamino group such as a group; C1-7 acylamino groups such as formylamino group, acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group, benzoylamino group; methoxycarbonylamino group, ethoxy C1-6 alkoxycarbonylamino groups such as carbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group; aminocarbonyl group, dimethylaminocarbonyl group, phenylaminocarbonyl group, N- Aminocarbonyl group having unsubstituted or substituted group such as Eniru -N- methylamino group;

Mercapto group; C1-6 alkylthio group such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group; phenylthio group, naphthylthio C6-10 arylthio group such as a group; C1-6 alkylsulfonyl group such as methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group; C6-10 arylsulfonyl group such as phenylsulfonyl group; pyrrolyl group, furyl group, thienyl Groups, imidazolyl groups, pyrazolyl groups, oxazolyl groups, isoxazolyl groups, thiazolyl groups, isothiazolyl groups, triazolyl groups, oxadiazolyl groups, thiadiazolyl groups, tetrazolyl groups, etc .; pyridyl groups, pyrazinyl groups Pyrimidinyl, pyridazinyl, 6-membered heteroaryl group such as triazinyl group; and the like; aziridinyl group, an epoxy group, a pyrrolidinyl group, tetrahydrofuranyl group, a piperidyl group, a piperazinyl group, a saturated heterocyclyl group such as a morpholinyl group.

In addition, these “substituents” may be those in which any hydrogen atom in the group is further substituted with a group having the same or different structure as the group.

[Cy ¹ , R ¹⁰ ]
Cy ¹ in the formula (I) represents a C6-10 aryl group.
R ¹⁰ in the formula (I) is a substituent of Cy ¹ and is each independently an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy Group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted C6-10 aryloxy group, amino group, unsubstituted or substituted C1-6 acylamino group, cyano group Represents a nitro group or a halogen atom.

m represents the number of R ¹⁰ and is an integer of 0 to 5. When m is 2 or more, R ¹⁰ may be the same as or different from each other.

The “C6-10 aryl group” in Cy ¹ 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 phenyl group, naphthyl group, azulenyl group, indenyl group, indanyl group, tetralinyl group and the like. Of these, the “C6-10 aryl group” in Cy ¹ is preferably a phenyl group.

The “C1-6 alkyl group” for R ¹⁰ may be linear or branched. 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 “substituted C1-6 alkyl group” in R ¹⁰ include C3-8 cycloalkyl C1-6 alkyl groups such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, etc. 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-trifluoromethyl Ethyl group, hexafluoroisopropyl group, pentafluoroisopropyl group, etc. C1 ~ 6 haloalkyl 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 a methyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group; methoxymethoxymethyl group, 1-methoxyethoxymethyl group, 2-methoxyethoxymethyl group , C1-6 alkoxy C1-6 alkoxy C1-6 alkyl groups such as 2- (1-methoxyethoxy) ethyl group, 2- (2-methoxyethoxy) ethyl group; formyloxymethyl group, acetoxymethyl group, 2-acetoxy group Ethyl, propionyloxymethyl, propiyl A C1-7 acyloxy C1-6 alkyl group such as a nyloxyethyl group; an unsubstituted or substituted C7-11 such as an unsubstituted or substituted benzyl group, an unsubstituted or substituted phenethyl group; An aralkyl group; and the like.

As the “C1-6 alkoxy group” in R ¹⁰ , a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group, n -Pentyloxy group, i-pentyloxy group, 2-methylbutoxy group, neopentyl group, n-hexyloxy group and the like.
Examples of the “substituted C1-6 alkoxy group” in R ¹⁰ 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, Tribromomethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, pentafluoroethoxy group, 4-fluorobutoxy group, 3,3,3-trifluoropropoxy group, 2, C1-6 haloalkoxy groups such as 2,2-trifluoro-1-trifluoromethylethoxy group and perfluorohexyloxy group; hydroxy C1-6 alkoxy groups such as 2-hydroxyethoxy group and 2-hydroxypropoxy group; methoxy Methoxy group, 1-methoxyethoxy group, 2-methyl group C1-6 such as xoxyethoxy group, ethoxymethoxy group, 1-ethoxyethoxy group, 2-ethoxyethoxy group, 1-methoxy-n-propoxy group, 2-methoxy-n-propoxy group, 3-methoxy-n-propoxy group, etc. Alkoxy C1-6 alkoxy group; cyclopropylmethoxy group, cyclobutylmethoxy group, cyclopentylmethoxy group, cyclohexylmethoxy group, 2-methylcyclopropylmethoxy group, 2,3-dimethylcyclopropylmethoxy group, 2-cyclopropylethoxy group, etc. C3-8 cycloalkyl C1-6 alkoxy groups; benzyloxy groups, C7-11 aralkyloxy groups such as phenethyloxy groups; C1-7 acyl C1-6 alkoxy groups such as acetylmethoxy groups and 2-acetylethoxy groups; Methoxy group, 2-si Cyano C1-6 alkoxy groups such as noethoxy group; C3-8 cycloalkyl C1 having substituents such as chlorocyclohexylmethoxy group, bromocyclohexylmethoxy group, 2-methylcyclopropylmethoxy group, 2,3-dimethylcyclopropylmethoxy group To 6 alkoxy groups; and the like.

Examples of the “C6-10 aryl group” for R ¹⁰ include the same as those exemplified for Cy ¹ above.

Examples of the “C6-10 aryloxy group” for R ¹⁰ include a phenoxy group and a naphthoxy group.

Examples of the “C1-6 alkylamino group” for R ¹⁰ include a methylamino group, a dimethylamino group, a diethylamino group, and an i-butylamino group.

Examples of the “C1-7 acylamino group” for R ¹⁰ include a formamide group, an acetamide group, an n-propanecarboxamide group, and the like.

Examples of the “halogen atom” in R ¹⁰ include a chlorine atom, a bromine atom, a fluorine atom, and an iodine atom.

[Cy ² , R ¹¹ ]
Cy ² in the formula (I) represents a C6-10 aryl group or a heterocyclyl group.
R ¹¹ in the formula (I) is a substituent of Cy ² and is each independently an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy Group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted C6-10 aryloxy group, amino group, unsubstituted or substituted C1-6 acylamino group, cyano group , A nitro group, or a halogen atom.

n represents the number of R ¹¹ and is an integer of 0 to 5. When n is 2 or more, R ¹¹ may be the same as or different from each other.

Examples of the “C6-10 aryl group” in Cy ² include the same as those exemplified for Cy ¹ above. The “C6-10 aryl group” in Cy ² is preferably a phenyl group.
The “heterocyclyl group” in Cy ² contains 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom as ring constituent elements. The heterocyclyl group may be monocyclic or polycyclic.
Examples of the heterocyclyl group include a 5-membered heteroaryl group and a 6-membered heteroaryl group.

Examples of 5-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. .

Examples of the 6-membered heteroaryl group include pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group and the like.

Among these, as the “heterocyclyl group” in Cy ² , a 5-membered heteroaryl group or a 6-membered heteroaryl group is preferable, and a pyrazolyl group, a thiadiazolyl group, a pyridyl group, a pyrimidinyl group, or a pyridazinyl group is preferable.

“Unsubstituted or substituted C1-6 alkyl group”, “Unsubstituted or substituted C1-6 alkoxy group”, “Unsubstituted or substituted C6-10 aryl group” in R ¹¹ , “Unsubstituted or substituted C6-10 aryloxy group”, “unsubstituted or substituted C1-7 alkylamino group”, “unsubstituted or substituted C1-7 acylamino group” As the “halogen atom”, the same as those exemplified in the above R ¹⁰ can be mentioned.

In the cyclic amine compound according to the present invention, Cy ¹ is preferably a phenyl group, and Cy ² is preferably a phenyl group, a pyrazolyl group, a thiadiazolyl group, a pyridyl group, a pyrimidinyl group, or a pyridazinyl group, and Cy ¹ is a phenyl group More preferably, Cy ² is a 4-trifluoromethylphenyl group or a 5-trifluoromethyl-pyridin-2-yl group, and n is an integer of 0 to 4.

[R ^1a , R ^1b , R ^2a , R ^2b , R ^3a , R ^3b , R ^4a , and R ^4b ]
In formula (I), R ^1a , R ^1b , R ^2a , R ^2b , R ^3a , R ^3b , R ^4a , and R ^4b (hereinafter these may be referred to as R ^1a etc.) are each independent. Represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, or an unsubstituted or substituted C1-6 alkoxy group.
R ^1a and R ^2a or R ^3a and R ^4a are each independently a C2-6 alkylene group having an unsubstituted or substituted group, or a C2-6 alkenylene group having an unsubstituted or substituted group. It may be formed. A group formed by R ^1a and R ^2a or R ^3a and R ^4a together may be referred to as a “bridged portion”.

Examples of the “unsubstituted or substituted C1-6 alkyl group” and the “unsubstituted or substituted C1-6 alkoxy group” in R ^{1a and the} like are the same as those exemplified for R ¹⁰ above. be able to.

The “C2-6 alkylene group” formed by R ^1a and R ^2a or R ^3a and R ^4a together includes an ethylene group (also known as ethane-1,2-diyl group) and a trimethylene group (also known as propane). -1,3-diyl group), tetramethylene group (alias: butane-1,4-diyl group), propylene group (alias: propane-1,2-diyl group), ethaneethylene group (alias: butane-1, 2-diyl group). Of these, C2-4 alkylene groups are preferred.
The “C2-6 alkenylene group” includes a vinylene group (also known as ethene-1,2-diyl group), a propenylene group (also known as prop-1-ene-1,3-diyl group), and a 2-butenylene group. (Alternative name: But-2-ene-1,4-diyl group), 1-methyl-1-butenylene group (Alternative name: penta-3-ene-1,4-diyl group) and the like. Of these, C3-4 alkenylene groups are preferred.
In the C2-6 alkylene group having a substituent or the C2-6 alkenylene group having a substituent, preferred groups which can be a substituent include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a methyl group, an ethyl A C1-6 alkyl group such as a group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; C3-6 cycloalkyl groups such as propyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group A C1-6 alkoxy group such as t-butoxy group; a hydroxyl group; a chloromethyl group, a chloroethyl group, a trifluoromethyl group, etc. And the like; C1 ~ 6 haloalkyl group.

[R ^5]
R ⁵ in formula (I) represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted group. Or a C1-7 acyloxy group having an unsubstituted or substituted C1-6 alkoxycarbonyloxy group, a heterocyclyl group having an unsubstituted or substituted group, a cyano group, or a halogen atom.
R ^4b and R ⁵ may together form a group represented by —O—.
p represents the number of R ^4b and R ⁵ and is an integer from 0 to 1. When p is 0, a carbon-carbon bond between R ^4b and R ⁵ forms a double bond.

In R ^5, the "C1 ~ 6 alkyl group having an unsubstituted or substituted group", "C1 ~ 6 alkoxy group having unsubstituted or substituted group" include the same ones as those exemplified in the R ¹⁰ be able to.
Examples of the “unsubstituted or substituted heterocyclyl group” in R ⁵ include the same ones as exemplified in Cy ^{2 and the} like.

Examples of the “C1-7 acyloxy group” in R ⁵ include formyloxy group, acetyloxy group, propionyloxy group, benzoyloxy group, cyclohexylcarbonyloxy group and the like.
Examples of the “C1-6 alkoxycarbonyloxy group” for R ⁵ include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an i-propoxycarbonyloxy group and the like.
Examples of the “halogen atom” in R ⁵ include a chlorine atom, a bromine atom, a fluorine atom, and an iodine atom.

In the cyclic amine compound according to the present invention, the compound represented by the formula (I) may be a compound represented by the formula (II) (hereinafter sometimes referred to as a cyclic amine compound (II)). preferable.

Here, n1 represents the number of R ¹¹ and is an integer from 0 to 4. When n1 is 2 or more, R ¹¹ may be the same as or different from each other.
E represents a carbon atom or a nitrogen atom. Other symbols have the same meaning as described in formula (I).

[Salt of cyclic amine compound]
The salt of the cyclic amine compound according to the present invention is not particularly limited as long as it is a chemically acceptable salt. For example, salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium, magnesium and barium; iron, Examples thereof include salts of transition metals such as copper and silver; salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine and hydrazine. The salt of the cyclic amine compound according to the present invention can be obtained from the cyclic amine compound according to the present invention by a known method.

〔Production method〕
The method for producing the cyclic amine compound according to the present invention is not particularly limited. Here, in order to contribute to an understanding of the method for producing the cyclic amine compound according to the present invention, some typical examples are given.

     

  　 

Compounds represented by formula (1) (wherein R ¹⁰ and n have the same meaning as described above. Met represents an alkali metal, an alkaline earth metal, etc.) are usually used in the field of organic synthesis. The nucleophilic metal species used.

Compound represented by formula (2) (wherein R ¹¹ , m and Cy ¹ have the same meaning as described above. R ^c represents an unsubstituted or substituted C1-6 alkyl group. p represents the number of R ^c and is an integer of any one of 0 to 4.) can be synthesized by, for example, the method described in WO2007 / 62175 and the like.

The compound represented by the formula (2) is represented by, for example, a compound represented by the formula (4) (wherein R ^c and p have the same meanings as described above) and a formula (5). (Wherein R ¹¹ , m, and Cy ¹ have the same meanings as described above. Lv represents a leaving group) In the formula, R ¹¹ , m, Cy ¹ , R ^c , and p have the same meaning as described above.), Or the compound after the functional group conversion of the compound represented by the formula (6) is subjected to hydrolysis. It can be synthesized after that. A series of conversion methods from coupling to hydrolysis are described in, for example, JOC. 2000, 65, 1158-1174, US2003 / 144263, WO2008 / 42925, and the like.

Thus, a compound represented by formula (3) (wherein R ¹⁰ , n, R ¹¹ , m, etc.) is obtained by coupling between the compound represented by formula (1) and the compound represented by formula (2). Cy ¹ , R ^c , and p have the same meanings as described above). A specific method is described in, for example, JMC. 1986, 29, 2028-2033, WO2008 / 12623, and the like.

Next, the compound represented by formula (7) (wherein R ¹⁰ , n, R ¹¹ , m, Cy ¹ , R ^c , and p have the same meaning as described above) is represented by formula (3). It can synthesize | combine by dehydration reaction of the compound represented by these. A specific method is described in, for example, JMC. 1995, 38, 1998-2008, EP 2005/1140830, and the like.

A compound represented by formula (8) (wherein R ¹⁰ , n, R ¹¹ , m, Cy ¹ , R ^c , and p have the same meanings as described above) is represented by formula (7). Can be synthesized from the compound by known catalytic hydrogen reduction.
Further, the compound represented by the formula (8) can be synthesized from the compound represented by the formula (3) by direct or indirect reduction reaction. Specific methods are described in, for example, JMC. 1998, 41, 1997-2009, a method using Et ₃ SiH / CF ₃ CO ₂ H is described in WO 2008/113360, and a method using Bu ₃ SnH reduction is described in WO 2004/87156.

The compound represented by formula (10) (wherein R ¹⁰ , n, R ^c , and p have the same meanings as described above. PG represents a protecting group such as a benzyl group) is represented by the formula (10 3) A compound represented by formula (1) and a compound represented by formula (9) in the same manner as the method for synthesizing the compound represented by 3) (wherein R ^c , p and PG are the same as above) Can be synthesized. Among the compounds represented by the formula (9), a commercially available product can be used as it is for the compound in which PG is a benzyl group or a Boc group.

The compound represented by the formula (11) (wherein R ¹⁰ , n, R ^c , p, and PG have the same meanings as described above) is a synthesis of the compound represented by the formula (8). It can be synthesized by a method similar to the method.

The compound represented by the formula (12) (wherein R ¹⁰ , n, R ^c , and p have the same meanings as described above) can be synthesized by known catalytic hydrogen reduction or acid treatment.
A compound represented by the formula (8) can be synthesized by coupling the compound represented by the formula (12) and the compound represented by the formula (5). A specific method is, for example, JOC. 2000, 65, 1158-1174, WO2005 / 095380, and the like.

     

  　 

The compound represented by the formula (3) is subjected to a normal alkylation reaction, whereby the compound represented by the formula (13) (wherein R ¹⁰ , n, R ¹¹ , m, Cy ¹ , R ^c , and p has the same meaning as described above, and R ^d represents an unsubstituted or substituted C1-6 alkyl group.

[Pesticides]
The pest control agent of the present invention contains at least one selected from the cyclic amine compound or a salt thereof (sometimes referred to as the present compound) according to the present invention as an active ingredient.

Examples of ectoparasites that are targets of the pesticidal agent of the present invention, particularly ectoparasite control agents, are parasitized on the back, armpit, lower abdomen, inner crotch, etc. of the host animal, such as blood and dandruff. It includes those that inhabit by obtaining nutrients, and those that fly to the back, buttocks, etc. of host animals and obtain nutrients such as blood and dandruff from animals. Examples of ectoparasites include ticks, lice and fleas.
Examples of host animals in which the 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, quail, geese); bees (eg, honey bees, Japanese honey bees);

The following pests can be cited as mites (Acari) that are targeted for the control agent.
(1) Mesostigmata mites (mite)
(A) Dermanyssidae mites, for example, Dermanyssus gallinae from the genus Dermanyssus spp .;
(B) Mite of the family Monicidae (Macronyssidae), for example, the mite genus species (Ornithonyssus spp.), The tick mite (Ornithonyssus sylviarum), the mite mite (Ornithonyssus bursa), the mite (Ornithonyssus bacoti);
(C) Mites of the family Laelapidae, for example, Laelaps echidninus, Laelaps jettmari; for example, Tropilaelaps spp., Honeybee mites of the genus Tropilaelaps spp. (Tropilaelaps clareae), Tropilaelaps koenigerum;
(D) Varroidae ticks, for example, Varroa destructor, Varroa jacobsoni, Varroa underwoodi from Varroa spp .;

(2) Metastigmata tick (tick)
(A) mites from the family Argasidae, for example, Argas spsi., Argas persicus, Argas reflexus; for example, Ornithodoros spp. Ornithodoros moubata;
(B) Ixodidae ticks, eg Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinna, Haemaphysalis cinna, Haemaphysalis cinna (Haemaphysalis otophila), Haemaphysalis leachi, Haemaphysalis longicornis, ali seri (Haemaphysalis mageshimaensis), physalis tick (Haemaphysalis yeni), tick physics flava), Haemaphysalis megaspinosa, Haemaphysalis japonica, Haemaphysalis douglasi; for example, Amblyomma spp. Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Aennlymacaj, tick For example, ticks (Ixodes spp.), Ticks (Ixodes ricinus), Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus , Ixodes scapularis, Ixodes holocyclus, Ixodes ovatus, Ixodes persulcatus, Ixodes nipponensis; From the genus Boophilus spp., The tick (Rhipicephalus (Boophilus) microplus), Lipipesphalus (Boophilus) decoloratus, Lipisephalus (Buophilus) Annuratus (Rhipicephalus (Boophilus) annutus (Boophilus) anntus (Bhipophilus) / Carceratas (Rhipicephalus (Boophilus) calceratus); for example, Rhipicephalus spp. ), Rhipicephalus evertsi, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus appendiculatus, Rhipicephalus appendiculatus Rhipicephalus turanicus, Rhipicephalus zambeziensis; for example, Dermacentor marginatus, Dermacentor reticulatus (Dermacentor reticulatica) Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, Dermacentor Bali Birisu (Dermacentor variabilis);

(3) Astigmata (Acaridida)
(A) Psoroptidae mites, for example, Psoroptes ovis, Psoroptes cuniculi, Psoroptida equi, (Psoroptes equi) For example, Chorioptes spp., Chorioptes bovis; Otodectes spp., Otodectes cynotis;
(B) Mites of the family Sarcoptidae, for example, Sarcoptes scabiei, Sarcoptes canis, Sarcoptes bovis, Scaroptes bovis, Scaroptida spp. Sarcoptes ovis), Sarcoptes rupicaprae, Sarcoptes equi, Sarcoptes suis; for example, Notoedres spp., Notoedres cati;
(C) mites of the family Knemidokoptidae, for example, Knemidokoptes mutans of the genus Knemidokoptes spp .;

(4) Prostigmata mites (Actinedida)
(A) Acarids of the family Demodexidae, for example, Demodex spp., Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae , Demodex equis, Demodex caballi, Demodex suis, Demodex cati;
(B) Trombiculidae ticks, for example, Troombicula alfreddugesi, Troombicula akamushi from the species of the genus Trombicula spp .;

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

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

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

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

In addition, examples of ectoparasites that are targets of the 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 the Cimicidae family, for example, Cimex hemipterus, Cimex lectularius, of the genus Cimex spp .;
(B) Insects of Reduviidae, and also of Triatominae, for example Panstrongylus spp .; for example, Rhodnius spp., Rhodnius spp. 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, for example, Culex spp., Culex quinquefasciatus, Culex pipiens pallens, Culex tarsalis, Culex pipiens molestus ), Culex pipiens fatigans, Culex tritaeniorhynchus summorosus; for example, Armigeres subalbatus; for example, Anopheles spoph. gambiae), Anopheles maculipennis, Anopheles sinensis, Anopheles lesteri; for example, Aedes spp., Aedes aegypti, tus Aedes・ Aedes taeniorhys nchus), Aedes togoi, 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, for example, Culiodes spp., Culicoides arakawae, Culicoides pictimargo, Culicoides kibunensis, musul Culicoides oxystoma), Culicoides nipponensis, Culicoides punctatus, Culicoides maculatus, Matsuzawai matsuzawai;

(2) Short-horned subfamily (a) Abs of the Tabidae family, such as Tabanus spm., Tabanus bromius, Tabanus spodopterus, Tabranus atratus ( Tabanus atratus, Tabanus sudeticus, Bob ab (Tabanus trigonus), Red-headed abalone (Tabanus chrysurus), Shirofu ab (Tabanus trigeminus), Kisjiabu (Tabanus fulvimedioides), Acer genus (Tabanus iyoens) .) Of Chrysops caecutiens, Chrysops relictus, Chrysops suavis, Chrysops japonicus;
(B) Muscidae flies, for example, Muscina spp., Musca domestica, Musca bezzii, Musca hervei, Musca conducens, Euphorae (Musca stabulans); e.g., Stomoxys spp., Stomoxys calcitrans; e.g., Haematobia spp. exigua), Haematobia stimulans; for example, Fannia canisularis from the genus Fannia spp .;
(C) Glossina spp. From the Glossinidae family;
(Hippoboscidae flies, for example, Melophagus ovinus, from the genus Melofagus spp .;
(D) Calliphoridae flies, for example, Calliphora, Calliphora lata; for example, Lucilia spp., Lucilia (Phaenicia) cuprina, Lucilia (Phaenicia) sericata), for example Lucilia illustris; for example, Chrysomya hominivorax, Chrysomya chloropyga, Chrysomia zz;
(E) Flies of the Oestridae family, for example, the Cuterebrinae Rabbit genus (Cuterebra spp.); , Hypoderma bovis, Hypoderma lineatum; for example, Gasterophilus spp., Gasterophilus intestinalis, Gasterophilus haemorroids, Gasterophilus haemorroids, Gasterophilus haemorroids, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum; for example, Oestrinae, and also Oestrus sp. Of the Oestrus ovis;

By administering the ectoparasite control agent of the present invention to an animal and controlling the above ectoparasites, diseases or other pathological conditions that are transmitted through the parasites, or injuries caused directly by the parasites (hereinafter referred to as “parasites”) (Sometimes called parasitic diseases).
By administering the ectoparasite control agent of the present invention to animals and suppressing the above ectoparasites, the occurrence of parasitic diseases in animals susceptible to parasitic diseases is partially or completely inhibited. Symptoms can be reduced and eliminated, and parasitic diseases can be partially or completely cured and treated.

Diseases transmitted through ectoparasites are, for example, bacterial diseases, viral diseases, and protozoan-borne diseases. Like flies, there are those that cause pathogenic bacteria 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) Newcastle disease of birds 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 of the genus Retroviridae;

(2) Bacterial diseases (a) Japanese red fever and rickettsiosis in dogs infected with Haemaphysalis longicornis via Rickettsia japonica, a Japanese spotted fever rickettsia (Richettsia 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; Rabicephalus 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 silkworms (Dirofilaria immitis);

(4) Bullfly larvae and fountain larvae Some hygienic pests are internally parasitic on the host. For example, bullfly larvae infest the bovine skin, horsefly larvae in the stomach wall of the horse, and sheep fly larvae in the nasal cavity of the 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) foal larvae caused by larvae of Gasterophilus intestinalis, larvae of Gasterophilus nasalis, larvae of Gasterophilus haemorroidalis;
(C) 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 to 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 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) Catfish, horses, sheep scabies caused by genus genus genus, genus Culex genus genus, swine scabies caused by genus genus genus, swine 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, edema caused by flyfish;

In addition, the pest control agent of the present invention is effective against endoparasites such as dogs and cats. By controlling and controlling these endoparasites, it is possible to control, prevent and treat protozoan-borne diseases derived from endoparasites.

Endoparasites can be broadly divided into protozoa and helminths. Examples of the protozoa include the following protozoa.
(1) Kinotoplast (Cinetoplastida) flagellates (a) Trypanosomatidae flagellates, eg Leishmania spp., Leishmania donovani, infant Leishmania ( Leishmania intantum), large Leishmania major, Leishmania tropica, Leishmania braziliensis; Trypanosoma spp., Trypanosoma brucei, cruise Trypanosoma cruzi, Trypanosoma equiperdum, Trypanosoma evansi;
(B) Hexamitidae flagellates, eg, Giardia spp., Giardia canis, Giardia duodenalis, Giardia intestinalis, Giardia intestinalis Giardia muris; Hexamita spp., Hexamita meleagridis, Hexamita parva;

(2) Trichomonadidae flagellates (a) Monocercomonadidae flagellates, for example, Histomonas spp., Histomonas meleagridis;
(B) Trichomonadidae flagellates, for example, Trichomonas tenax, Trichomonas gallinae, Trichomonas gallinarum, Trichomonas gallinarum; Trichomonas gallinarum; (Pentatrichomonas spp.), Pentatrichomonas hominis;

(3) Eucoccidiorida spores (a) Eimeriidae spores, for example Eimeria acervulina, Eimeria acervulina, Eimeria adenides (Eimeria spp.) adenoeides, Eimeria ahsata, Eimeria anseris, Eimeria arloingi, Eimeria auburnensis, Eimeria bateri (Eimeria bateri) ), Eimeria brunetti, Eimeria christenseni, Eimeria danailova, Eimeria debliecki, Eimeria dispersa, Eimeria dispersa, Eimeria dispersa Eime ria ellipsoidalis, Eimeria gallopavonis, Eimeria irresidua, Eimeria kotlani, Eimeria magna, Eimeria matsubayim, Eimaria matsubayashi ), Eimeria media, Eimeria meleagrimitis, Eimeria nagpurensis, Eimeria necatrix, Eimeria neoleporis, Eimeria neoleporis, Eimeria neoleporis Eimeria ninakohlyakimovae, Eimeria nocens, Eimeria ovinoidalis, Eimeria perforans, Eimeria piriformi s), Eimeria polita, Eimeria saitamae, Eimeria scabra, Eimeria spinosa, rabbit liver coccidium (Eimeria stiedae), chicken cecal coccidium (Eimeria tenella) , Eimeria tsunodai, Eimeria truncata, Eimeria uzura, Eimeria wyomingensis, Eimeria zuernii; Isospora sp. Of Isospora alamataensis, porcine isospora (Isospora suis);

(B) Cryptosporidiidae spores, for example, Cryptosporidium spis., Canine Cryptosporidium canis, cat Cryptosporidium felis, human Cryptosporidium hominis Turkey cryptosporidium meleagridis, cryptosporidium muris, small cryptosporidium parvum, Cryptosporidium baileyi;
(C) Hepatozoidae spores, for example, hepatozoon canis of the genus Hepatozoons spp .;
(D) Sarcocystidae spores, for example, Sarcocystis spp., Sarcocystis canis, Sarcocystis felis, human meat Sarcocystis hominis, Sarcocystis neurona, Sarcocystis ovicanis, Sarcocystis cruzi, Sarcocystis cuniculi, Sarcocystis micheriana ), Sarcocystis porcifelis, Sarcocystis suihominis, Sarcocystis tenella;
(E) Toxoplasmaida sp., For example, Toxoplasma gondii of Toxoplasma spp .;

(4) Haemosporida sporozoa (a) Leucocytozoidae, for example, Leucocytozoon spp., Leucocytozoon spp., Leucocytozoon caulleryi ), Leucocytozoon andrewsi, Leucocytozoon galli, Leucocytozoon sabrazesi, Leucocytozoon soutedeni, Leucocytozoon schoutedeni, Leucocytozoon schoutedeni, Leucocytozoon schoutedeni simondi), Leucocytozoon smithi;
(B) Plasmodiidae spores such as Plasmodium spp., Plasmodium falciparum, Plasmodium malariae, Plasmodium ovale ), Plasmodium vivax, Plasmodium circumflexum, Plasmodium elongatum, Plasmodium gallinaceum, Plasmodium juxta Nucleae (Plasmodium juxtanucleare), Plasmodium lophurae, Plasmodium relictum;

(5) Piroplasmida sporozoa (a) Babesiidae spores such as Babesia spp., Babesia bigemia, Babesia bovis, large Babesia caballi, Babesia canis, Babysia felis, Gibson dog Babesia, Babesia ovata, Babesia divergens, Babesia diakis ), Babesia major, Babesia occultans;
(B) Theileriidae sporozoites, eg, Theileria spp., East Coastal Thermal Theileria parva, Tropical Piroplasmosis Theileria annulata, Pseudo-coastal Thermal Theileria (Theileria mutans) ), Small Piroplasma (Theileria orientalis), Theileria sergenti;

Examples of helminths include the following tapeworms, flukes, baldnesses and nematodes.
(1) Cytophyllidea (Cestoda)
(A) The tapeworm of Anoplocephalidae, for example, the genus Anoplocephala spp., Anoplocephala magna, Anoplocephala perfoliata; Avitellina, Avitellina centripunctata; Moniezia spp., Beneden, Moniezia expansa; Paranoplocephala spp. Parasites (Paranoplocephala mamillana), Stilesia spp., Stilesia globipunctata, Stilesia hepatica; Thysanosoma spp., Sasanosoma spp. -Thysanisia actinioides; Thysaniezia giardi of Thysaniezia spp .;
(B) Davaineidae tapeworms, for example, Raillietina spp., Rotate crustacea (Raillietina cesticillus), Rarelietina echinobothrida, Raillietina kashiwarensis ), Raillietina tetragona;
(C) Dilepididae tapeworms, for example, Amoebotaenia sphenoides of Amoebotaenia spp .; Choanotaenia infundibulum of Choanotaenia spp .; Metroliaces spp., Quail tapeworm (Metroliasthes coturnix);
(D) Dipylidiidae tapeworms, for example, Dipylidium caninum, of the genus Dipylidium spp .;
(E) Hymenolepididae tapeworms, for example Hymenolepis diminuta, Hymenolepis spp. Species;
(F) Mesocestoididae, for example, Mesocestoidesi spp., Mesocestoides corti, Mesocestoides litteratus, raccoone Mesocestoides paucitesticulus);
(G) Taeniidae tapeworms, for example, Echinococcus multilocularis of Echinococcus spp., Echinococcus granulosus; Taenia spp. Taenia saginata, Taenia solium, Tenia asiatica, Taenia balaniceps, Taenia brachysoma, Tenia cerbi (Taenia) cervi), Tenia crassiceps, Taenia gaigeri, Taenia hydatigena, Taenia multiceps, Taenia ovis, Taenia pisiformis ), Tenia punica, Taenia serialis, Catentic tapeworm (Taenia taeniaeformis); Coenurus cerebralis, cattle that are larvae of the Tenia spp. Cysti (Cysti cercus bovis), cystic worms (Cysticercus cellulosae), cysticercus tenuicollis;

(2) Crustacea of Pseudophyllidea (a) Tapeworms of the family Diphyllobothriidae, for example, broad-banded crustaceans (Diphyllobothrium spp.) Diphyllobothrium latum), Diphyllobothrium caninum; Spirometra spp., Spirometra erinacei;

(3) Strigeidida flukes (Trematoda)
(A) Schistosomatidae flukes, for example, Schistosoma spp., Schistosoma japonicum; Fasciola spp., Gigantica (Fasciola gigantica), Fasciola hepatica;

(4) Echinostomida flukes (a) Echinostomatidae spp. Spp., For example, Echinostoma spp. Echinostoma cinetorchis), Echinostoma hortense;

(5) Plamoorchiidae flukes (a) Dicrocoeliidae flukes, for example, Dicrocoelium spp., Dicrocoelium chinensis, 槍Dicrocoelium dendriticu, African crab worm (Dicrocoelium hospes); Eurytrema coelomaticum, Eurytrema pancreaticum of Eurytrema spp .;
(B) Paragonimidae flukes, for example, Paragonimus spp., Paragonimus miyazakii, Paragonimus ohirai, Westerman pulmonate (Paragonimus westermani);

(6) Opisthorchiida flukes (a) Opisthorchiidae flukes, such as Amphimerus guayaquilensis, for example, Amphimerus spp. Amphimerus noverca; Clonorchis spp., Clonorchis sinensis; Metrochis spp., Metrochis albidus, Metrokis conjunctus (Metorchis conjunctus), oriental fluke (Metorchis orientalis); of the genus Opistorchis spp., Opistorchis felineu, Opistorchis tonkae, Opistorchis tonkae; Seed (Paropisthorchis spp.), Dog liver fluke (Paropisthorchis caninus); pseudoamphist -Pseudamphistomum truncatum, Pseudamphistomum spp .;
(B) Heterophyidae flukes, for example, Pygidiopsis summa of Pygidiopsis spp .;

(7) Oligacanthorhynchida (Archiacanthocephala)
(A) Oligacanthorhynchidae bald worms, for example, Macroracanthorhynchus hirudinaceus, from the genus Macroracanthorhynchus spp .;
(8) Monifrimidae (Moniliformida) larvae of the order (a) Moniliforidae (Moniliformidae), for example, Moniliformis spp., Moniliformis moniliformis;
(9) Enoplida nematodes (a) nematodes of the Dioctophymatidae family, for example, Dioctophyma spp. Nematode (Dioctophyma spp.);
(B) nematodes of the family Soboliphymatidae, for example, Soboliphyme abei, Soboliphyme abei, from the species of Soboliphyme spp .;

(10) Enoplida nematodes (a) Trichinellidae trichinella, for example, Trichinella spp. Trichinella spiralis;
(B) Trichuridae trichinella, for example Capillaria spp., Capillaria annulata, Capillaria contorta, hepatic trichomes (Capillaria spp.) Capillaria hepatica, Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris vulpis, Trichuris vulpis, cattle Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris suis;

(11) Rhabditida nematodes (a) Strongyloididae faecal nematodes, eg, Strongyloides spp., Strongyloides papillosus ), Cat feminine nematode (Strongyloides planiceps), pig fecal nematode (Strongyloides ransomi), pig fecal nematode (Strongyloides suis), fecal nematode (Strongyloides stercoralis), American cat fecal nematode (Strongyloides tumefaciens), rat fecal nematode ( Strongyloides ratti);

(12) Strongylida nematodes (a) Helminths of Ancylostomatidae, for example, Ancylostoma braziliense, Ancylostoma caninum of Ancylostoma spp. , Ancylostoma duodenale, Ancylostoma tubaeforme; Uncinaria stenocephala, Uncinaria stenocephala; Bunostomum spp., Bunostomum phle Sheepworm (Bunostomum trigonocephalum);

(13) Strongylida nematodes (a) Nematodes of the family Angiostrongylidae, for example, Aelurostrongylus abstrusus, of the species Aelurostrongylus spp. From the genus Angiostrongylus spp., Angiostrongylus vasorum, Angiostrongylus cantonesis;
(B) Crenosomatidae nematodes, for example, Crenosoma aerophila, Crenosoma vulpis of the genus Crenosoma spp .;
(C) Filaroididae nematodes, for example, Filaroides hirthi, Filaroides osleri of Filaroides spp .;
(D) Pneumoniae from the family Metastrongylidae, eg, Metastrongylus aprius, Metastrongylus asymmetricus, Metastrongylus asymmetricus, Metastrongylus spendectus (Metastrongylus spp.) Metastrongylus pudendotectus), Metastrongylus salmi;
(E) C. elegans of Syngamidae, for example, Cyathostoma bronchialis of Cyathostoma spp .; Scrijabin larva of Syngamus spp. Syngamus skrjabinomorpha), chicken worm (Syngamus trachea);

(14) Strongylida nematodes (a) Nematodes of the Molineidae family, for example, Nematodirus spp., Nematodirus filicollis, Nematodirus spa Tigger (Nematodirus spathiger);
(B) Nematodes of the Dictyocaulidae family, for example, Dictyocaulus spp., Dictyocaulus filaria, Dictyocaulus viviparus;
(C) Nematodes of the Haemonchidae family, for example, Haemonchus contortus of Haemonchus spp .; Bovine tortoises of Mecistocirrus spp. (Mecistocirrus digitatus);
(D) Haemonchidae nematodes, for example, Ostertagia ostertagi from the genus Ostertagia spp .;
(E) Nematodes of the family Heligmonellidae, for example, Nippostrongylus braziliensis of the genus Nippostrongylus spp .;
(F) Trichostrongylidae nematodes, for example, Trichostrongylus axei, Trichostrongylus colubriformis, Trichostrongylus spp., Trichostrongylus axei ), Trichostrongylus tenuis; Hyostrongylus spp., Hyostrongylus rubidus; Obeliscoides spp., Obeliscoides cuniculi );

(15) Strongylida nematodes (a) Nematodes of the Chabertiidae family, for example, Chabertia spp., Chabertia ovina; Intestinal nodules From the genus Oesophagostomum spp., Oesophagostomum brevicaudatum, Oesophagostomum dentatum, Oesophagostomum dentatum, Oesophagostomum dentatum, Oesophagostomum spp. Oesophagostomum maplestonei, Oesophagostomum quadrispinulatum, Oesophagostomum radiatum, Oesophagostomum venulosum, Oesophanastomum (Oeswat)
(B) Nematodes of Stephanuridae, for example, Stephanurus dentatus of Stephanurus spp .;
(C) Strongylidae nematodes, for example, the species of Strongylus spp., Strongylus asini, edentulous (Strongylus edentatus), Strongylus equinus , Common roundworm (Strongylus vulgaris);

(16) Oxyurida nematodes (a) Oxyuridae nematodes, for example, Enterobius anthropopitheci, Enterobius vermicularis, Enterobius vermicularis; Oxylus Oxyuris spp., Oxyuris equi; Passalurus spp., Rabbit worm (Passalurus ambiguus);

(17) Ascaridida nematodes (a) Acaridiidae nematodes, for example, Ascaridia galli from the genus Ascaridia spp .;
(B) Heterakidae nematodes, for example, Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum of Heterakis spp. , Heterakis pusilla, Heterakis putaustralis;
(C) Anisakis nematodes, for example, Anisakis simplex from the genus Anisakis spp .;
(D) Ascarididae nematodes, for example, Ascaris spp., Ascaris lumbricoides, Ascaris suum; Parascaris spp., Horse roundworm (Parascaris equorum);
(E) Toxocaridae nematodes, for example, Toxocara spp., Toxocara canis, Toxocara leonina, Toxocara suum, Toxocara vitulorum), Toxocara cati;

(18) Spirurida nematodes (a) Nematodes of Onchocercidae, for example, Brugia spp., Brugia malayi, Brugia pahangi (Brugia pahangi), Brugia patei; Dipetalonema reconditum of Dipetalonema spp .; Dirofilaria spp., Dirofilaria spp. immitis); Filaria spp., Filaria oculi; Onchocerca spp., Onchocerca cervicalis, Gibson fungus (Onchocerca gibsoni), Pharyngeal Insect (Onchocerca gutturosa);
(B) Nematodes of Setariidae, for example, Setaria spp., Setaria digitata, Horseworm, Setaria equina, Setaria labiatopapillosa , Setaria marshalli; from Wuchereria spp., Wuchereria bancrofti;
(C) Filariidae nematodes, for example, Parafilaria spp., Parafilaria multipapillosa; Stephanofilaria spp., Stephanofilaria spum. Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi;

(19) Nematodes of Spirurida (a) Nematodes of Gnathostomatidae, for example, Gnathostoma doloresi of Gnathostoma spp. , Gnathostoma spinigerum;
(B) Nematodes of the family Habronematidae (Habronema spp.), For example, Habronema majus, Habronema microstoma, Habronema muscae; Draschia megastoma of the genus species (Draschia spp.);
(C) Physalopteridae nematodes, for example, Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaoptera pseudopraerutialis rara), Physaloptera sibirica, Physaloptera vulpineus;
(D) Gongylonematidae nematodes, for example, Gongylonema pulchrum of the genus Gongylonema spp .;
(E) Spirocercidae nematodes, for example, Ascarops strongylina from Ascarops spp .;
(F) Nematodes of Thelaziidae, for example, Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Rhodesian eyes of the genus Thelazia spp. Insects (Thelazia rhodesi), Scriabin eyeworms (Thelazia skrjabini);

In addition, the pest control agent of the present invention can be used to control pests such as mites attached to agricultural crops. In particular, it has excellent control effects on crops, fruit trees, flower buds and mites attached to trees.

Examples of mites (Acari) to be controlled are shown below.
(1) Astigmata (Acaridida)
(A) Acaridae mites, for example, Rhizoglyphus echinopus, Rhizoglyphus echinipus, Rhizoglyphus robini; Tyrophagus spp., Tyrophagus spp. , Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus simus, Others, Acarus siro, Fungus mite

(2) Prostigmata mites (Actinedida)
(A) Mites of Tetranychidae, for example, Bryobia spp., Clover spider mite (Bryobia praetiosa), Fowl spider mite (Bryobia rubrioculus); eg, Eotetranychus spp. , Eotetranychus boreus, Eotetranychus geniculatus, Chestnut mite (Eotetranychus uncatus), Mite spider mite (Eotetranychus shii), Tick spider mite (Eotetranychus shii) Eotetranychus smithi), Eotetranychus asiaticus, Eotetranychus kankitus; for example, Oligonychus mangiferus, Oligonychus mantis, Oligonychus pere , Larix spider mite (Oligonychus karamatus), Sugino spider mite (Oligonychus hondoensis), Citrus spider mite (Oligonychus ununguis), Rice spider mite (Oligonychus shinkajii), Sugar spider mite (Oligonychus shinkajii); , Citrus spider mite (Panonychus citri), swan spider mite (Panonychus mori), apple spider mite (Panonychus ulmi); ), Spider mite (Tetranychus phaselus), spider mite (Tetranychus cinnabarinus), Kanzawa spider mite (Tetranychus kanzawai), spider mite (Tetranychus urticae); for example, Aponychus spp. s firmianae); eg, Sasanychus spp., Sasanychus akitanus, Sasanychus pusillus; eg, Shizotetranychus spp., Shizotetranychus spp. Mizothani spider mite (Shizotetranychus miscanthi), Shirazo spider mite (Shizotetranychus schizopus), Himesa spider mite (Shizotetranychus schizopus), Tickerella mite (Tuckerella pavoniformis

(B) Tenuipalpidae ticks, for example, Brevipalpus spp., Brevipalpus rusisi, Cactus spider mite (Brevipalpus russulus), Crested spider mite (Brevipalpus obovatus), phoenicis); for example, Tenuipalpus pacificus of Tenuipalpus spp., Tenuipalpus zhizhilashviliae; other, Dolichotetranychus floridanus;
(C) Eriophyidae mites such as Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, carnation Rust mites (Aceria paradianthi), Black spider mites (Aceria tiyingi), Tulip spider mites (Aceria tulipae), Shibahamakifushi mite (Aceria zoysiea); for example, Eriophyes spp. emarginatae); e.g., Aculops spp., Aculops lycopersici, Aculops pelekassi; e.g., Aculus spp., Aculus fockeui, Aculus schlechtendali); other grape ticks (Colomerus vitis), grapevine Spider mite (Calepitrimerus vitis), Ryukyu mandarin mite (Phyllocotruta citri), Maxi spider mite (Paracalacarus podocarpi), Chinese spider mite (Calacarus carinatus), Chinese spider mite (Acaphylla theavagrans), Antarctic spider mite (Paraphytoptus krim) (Paraphytoptus krim)
(D) Mites of the family Transonemidae (eg, Tarsonemus spp.), Tarsonemus bilobatus, Tarsonemus waitei; Others, Phytonemus pallidus, lamus );
(E) Penthaleidae mites, for example, Penthaleus spp., Penthaleus erythrocephalus, Penthaleus major;

Furthermore, the pest control agent of the present invention can be used to control pests such as pests other than mites, hygiene pests, storage shell pests, clothing pests and house pests attached to agricultural crops.
Examples of pests to be controlled are shown below.
(1) Lepidoptera pests such as Spodoptera litura, Mamestra brassicae, Agrotis ypsilon, Autographa nigrisigna, Plutella xylostella, Adeno hon, mai, hon Homona magnanima), peach sigai (Carposina sasakii), pear tiger squirrel (Grapholitha molesta), mandarin moth (Phyllocnistis citrella), chanohosoga (Caloptilia theivora), kinmonhosoga (Phyllonorycter ringoniella), maiparigai (Lymanttis quaga) suppressalis, Cnaphalocrocis medinalis, European corn borer (Ostrinia nubilalis), Hyphantria cunea, Cadra cautella, Heliothis spp., Heliobelpa (. Agrotis spp) (Helioverpa), Agurotisu species, clothes moth (Tinea translucens), codling moth (Cydia pomonella), pink bollworm (Pectinophora gossypiella);

(2) Hemiptera pests, for example, Myzus persicae, cotton aphids (Aphis gossypii), black-headed aphids (Lipaphis erysimi), Rhopalosiphum padi, Riptortus clava Crocodile bug (Acrosternum hilare), billworm (Unaspis yanonensis), stag beetle (Pseudococcus comstocki), whitefly (Trialeurodes vaporariorum), tobacco whitefly (Bemisia tabaci), genti olila Stephanitis nashi, brown planthopper (Nilaparvata lugens), brown planthopper (Laodelphax stratella), white-tailed planthopper (Sogatella furcifera), leafhopper (Nephotettix cincticeps);

(3) Coleoptera pests, for example, Phyllotreta striolata, Aulacophora indica, Colorado potato beetle (Leptinotarsa decemlineata), rice weevil (Lissorhoptrus oryzophilus), Sweeophilus osooryza (Sitophilus osooryza) japonica, Anomala rufocuprea, Diabrotica spp., Tobacco beetle (Lasioderma serricorne), Lyctus brunneus, Monochamus alternatca (Monochamus alternatca), Monochamus alternatca Agriotes spp.), Epilachna vigintioctomaculata, Tenebroides mauritanicus, Cotton weevil (Anthonomus grandis);

(4) Diptera pests, for example, Bactrocera cucurbitae, Bactrocera dorsalis, Delia platura, Hydrellia griseola, Drosophila melanogaster;
(5) Thripidae pests, for example, Thrips palmi, Scirtothrips dorsalis;
(6) Hymenoptera pests, for example, Monomorium pharaonis, Vespa simillima, Athalia rosae;
(7) Diptera pests, for example, Locusta migratoria;

(8) Cockroaches (Blattodea) pests, for example, Blattella germanica, Periplaneta fuligginosa, Periplaneta japonica, Periplaneta americana, Periplaneta australasiae;
(9) Termite pests, for example, termites (Coptotermes formosanus), termites (Reticulitermes speratus);
(10) Plant-parasitic nematodes such as, for example, Meloidogyne incognita, Negusale nematodes, soybean cyst nematodes (Heterodera glycines), rice pest nematodes (Aphelenchoides besseyi), pine wood nematodes (Bursaphelenchus xylophilus;

The pest control agent of the present invention can contain the compound of the present invention as an active ingredient alone or in combination of two or more.
The pest control agent of the present invention may be mixed or used in combination with other active ingredients (insecticide / acaricide, anthelmintic agent) and the like.
Examples of active ingredients that can be used together and used include the following insecticides, acaricides, and anthelmintic agents.

(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, furthiocarb, XMC, aldoxicarb, alixicarb, aminocarb, butencarb, butacarb, butcarboxyme, butoxycarboxyme, cloetocarb, dimethylane, formethanate, isoprocarb, metam sodium, metorcarb, promecarb, thiophanox, 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, flupiradiflon;
(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 insecticide: abamectin, emamectin benzoate, milbemectin, lepimectin, spinosad, ivermectin, selamectin, doramectin, epinomectin, moxidectin, milbemycin, milbemycin oxime;
(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;
(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, demiditraz;

The pest control agent of the present invention may contain only the cyclic amine compound represented by the formula (I) or a salt thereof, or a carrier such as a liquid carrier, a gaseous carrier or a solid carrier, and if necessary. It may contain a surfactant and other adjuvants, and may be formulated according to the application. Moreover, the pest control agent of the present invention may be obtained by impregnating a substrate such as a porous ceramic plate or a nonwoven fabric with a cyclic amine compound represented by the formula (I) or a salt thereof.

The pest 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.

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.

Of the 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;

Furthermore, various components other than the above components may be included. For example, various vitamins, minerals, hormones, amino acids, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, anticancer agents, antibiotics, antibacterial agents, bactericides, coloring agents, fragrances, preservatives, vaccines, etc. Is mentioned.

When the pest control agent of the present invention, particularly the ectoparasite control agent, is used for domestic animals such as cattle and pigs, and pets such as dogs and cats, The cyclic amine compound can be used in an amount of 0.01 to 1000 mg. The ectoparasite control agent of the present invention can be applied by a known veterinary technique (topical, oral, parenteral or subcutaneous administration). For example, for the purpose of systemic control, the animal is treated by tablets, capsules, immersion liquid, feed mixing, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.). In the case of non-systemic control, the oil or aqueous solution is administered by spraying, pour-on, spot-on, etc., ectoparasite control agent on resin And the like, and the kneaded product is formed into an appropriate shape such as a collar and an ear tag, and is attached to an animal.

Next, the present invention will be described in more detail with reference to examples.

Example 1
Production of 4- [2-ethoxy-4- (trifluoromethyl) phenyl] -1- [5- (trifluoromethyl) -2-pyridyl] piperidine (Compound No. a-63) (Step 1)
Preparation of 4- [2-ethoxy-4- (trifluoromethyl) phenyl] -1- [5- (trifluoromethyl) -2-pyridyl] piperidin-4-ol (Compound No. a-24)

     

  　 

Compound (1) can be synthesized by reacting 2-bromo-5- (trifluoromethyl) phenol with ethyl iodide. To a solution of compound (1) (1.55 g) in tetrahydrofuran (15 ml) was added 1.6 M n-BuLi (3.6 ml) at −70 ° C. in a nitrogen atmosphere, and the mixture was stirred for 30 minutes. To this mixture was added a solution of compound (2) (1.41 g) in tetrahydrofuran (15 ml), the temperature was slowly raised to room temperature, and the mixture was further stirred for 1 hour. After completion of the reaction, the mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Thereafter, the organic layer was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (hexane-ethyl acetate 7/3) to obtain a viscous oily compound (3) (1.42 g).

¹ H-NMR (CDCl ₃ , δppm) 8.40 (d, 1H), 7.62 (dd, 1H), 7.40 (d, 1H), 7.22 (d, 1H), 7.12 (s, 1H), 6.71 (d, 1H ), 4.34-4.29 (m, 2H), 4.15 (q, 2H), 3.87 (s, 1H), 3.57-3.48 (m, 2H), 2.20-2.03 (m, 4H), 1.42 (t, 3H)

(Process 2)
4- [2-Ethoxy-4- (trifluoromethyl) phenyl] -1- [5- (trifluoromethyl) -2-pyridyl] -1,2,3,6-tetrahydro-pyridine (Compound No. c-26) )Manufacturing of

     

  　 

A solution of compound (3) (0.70 g) in acetic acid (7.7 ml) was cooled to 0 to 5 ° C. Thereafter, concentrated sulfuric acid (1.9 ml) was added, the temperature was raised to 70 ° C., and the mixture was stirred for 1.5 hours. After completion of the reaction, the mixture was cooled, poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Thereafter, the organic layer was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (hexane-ethyl acetate 5/1) to obtain Compound (4) (0.51 g). m.p. 99-103 ° C.

¹ H-NMR (CDCl ₃ , δppm) 8.43 (d, 1H), 7.65 (dd, 1H), 7.27 (d, 1H), 7.19 (d, 1H), 7.07 (s, 1H), 6.64 (d, 1H ), 5.96-5.94 (m, 1H), 4.22-4.12 (m, 2H), 4.08 (q, 2H), 3.92 (t, 2H), 2.68-2.64 (m, 2H), 1.44 (t, 3H)

(Process 3)
Preparation of 4- [2-ethoxy-4- (trifluoromethyl) phenyl] -1- [5- (trifluoromethyl) -2-pyridyl] piperidine (Compound No. a-63)

     

  　 

To a solution of compound (4) (0.36 g) in ethanol (10 ml), 5% palladium-carbon (0.07 g) was added to form a suspension, and the suspension was stirred overnight in a hydrogen atmosphere. Thereafter, the suspension was further heated to 60 ° C. and stirred for 4 hours. After completion of the reaction, the suspension was cooled, filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (hexane-ethyl acetate 5/1) to obtain the title compound (0.29 g). Mp 69-73 ° C

¹ H-NMR (CDCl ₃ , δppm) 8.40 (d, 1H), 7.61 (dd, 1H), 7.22 (d, 1H), 7.16 (d, 1H), 7.04 (s, 1H), 6.68 (d, 1H ), 4.56 (brd, 2H), 4.09 (q, 2H), 3.34-3.23 (m, 1H), 3.09-3.00 (m, 2H), 1.95-1.91 (m, 2H), 1.78-1.64 (m, 2H ), 1.44 (t, 3H)

(Example 2)
1- [2-Fluoro-4- (trifluoromethyl) phenyl] -4- [4- (trifluoromethyl) phenyl] piperidine (Compound No. b-54)

     

  　 

To a solution of compound (5) (0.45 g) and compound (6) (0.40 g) in toluene (3.3 ml) was added t-butoxy sodium (0.22 g), Pd ₂ (dba) ₃ (7.6 mg). And 2- (dicyclohexylphosphino) -2 ′-(N, N-dimethylamino) biphenyl (10 mg) were added and the mixture was heated to reflux for 8 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was cooled, poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. Thereafter, the organic layer was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (hexane-ethyl acetate 10/1) to obtain the title compound (0.1 g). mp 112-113 ℃

¹ H-NMR (CDCl ₃ , δppm) 7.59 (d, 2H), 7.39-7.21 (m, 4H), 7.03 (t, 1H), 3.67 (d, 2H), 2.96-2.70 (m, 3H), 2.05 -1.89 (m, 4H)

The compounds of the present invention that can be obtained by a method similar to the above production method are shown in Tables 1 to 3. Table 1 shows compounds represented by formula (Ia), Table 2 shows compounds represented by formula (Ib), and Table 3 shows substituents in compounds represented by formula (Ic). Moreover, the numerical value attached | subjected before the substituent has shown the substitution position. Et is ethyl group, ⁱ Pr is isopropyl group, ⁿ Pr is n-propyl group, ⁿ Bu is n-butyl group, ^t Bu is t-butyl group, ⁿ Hex is n-hexyl group, Ac is acetyl group, Py is Pyridyl group and Ph each represent a phenyl group. Tables 1 to 3 show the melting point (° C.) or properties (viscous oily (vis) or amorphous (amo)) as physical property values.

     

     
  　 

     
　　

“220 up” in Table 3 means that it did not melt at 220 ° C., which is the detection limit of the measuring device.

Although some formulation examples of the pest control agent of the present invention are shown, the additives and addition ratios should not be limited to these examples, and can be varied in a wide range. The part in a formulation example shows a weight part (%). In addition, “balance” in formulation examples represents the amount of the remaining components.
Examples of formulation for prevention of disease and animals are shown below.

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

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

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

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

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

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

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

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

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

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

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

Examples of agricultural and horticultural preparations are shown below.

Formulation Example 14 (Wetting Agent)
The compound of the present invention 40%
Diatomaceous earth 53%
Higher alcohol sulfate 4%
Alkyl naphthalene sulfonate 3%
The above was uniformly mixed and finely pulverized to obtain a wettable powder with an active ingredient of 40%.

Formulation Example 15 (Emulsion)
Compound of the present invention 30%
Xylene 33%
Dimethylformamide 30%
Polyoxyethylene alkyl allyl ether 7%
The above was mixed and dissolved to obtain an emulsion containing 30% active ingredient.

The following test examples show that the compound of the present invention is useful as an active ingredient of a pest control agent.

(Test Example 1) Insecticidal test against Haemaphysalis longicornis To a 20 mL glass vial, 0.118 ml of an acetone solution having a concentration of the present compound of 400 ppm was added. While rotating the glass vial, the inside was blown with a dryer to volatilize acetone to produce a thin film containing the compound of the present invention on the inner wall of the vial. Since the surface area of the inner wall of the glass vial used is 47 cm ² , the amount of treatment drug is 1 μg / cm ² .
Into this vial, 15 to 40 larvae of spider mite were released, and the glass vial was placed in a constant temperature room at 25 ° C. in the dark.
The number of dead insects was examined after 1 day and after 2 days, and the death rate was calculated from the following formula.
Mortality (%) = (number of dead ticks) / (number of ticks to be tested) x 100

Insecticidal tests were carried out for the compound Nos. A-1, a-5, a-10, a-18, a-17, a-24, a-54, and a-63 against the spider mite. All compounds had a death rate of 100% after 2 days at 1 μg / cm ² .

(Test Example 2) Insecticidal test against white spider mite (Tetranychus urticae) Seventeen male spider mites that are resistant to organophosphates are inoculated on the first true leaf 7 to 10 days after the germination of green beans seeded in a 3-inch pot. did. Next, an emulsion obtained according to the formulation shown in Formulation Example 15 was diluted with water so that the compound concentration was 125 ppm, 31 ppm, or 8 ppm, and the diluted solution was sprayed on the kidney beans. The green beans were placed in a constant temperature and humidity chamber having a temperature of 25 ° C. and a humidity of 65%. Adults were examined for viability after 4 days from spraying. The test was performed in duplicate.
Compound Nos. A-1, a-7, a-11, a-20, a-35, a-36, a-39,
a-42, a-45, a-54, a-55, a-60, a-62, a-64,
a-79, b-10, b-30, b-53, c-25, c-26, c-27,
The c-31, c-34, and c-36 compounds were tested for insecticides against the spider mite at a compound concentration of 125 ppm. All the compounds showed an excellent insecticidal rate of 90% or more.
Compound Nos. A-10, a-21, a-25, a-26, a-27, a-28,
a-33, a-37, a-40, a-41, a-44, a-65, a-67,
a-69, a-72, a-77, b-11, b-16, b-17, b-21,
b-25, b-26, b-27, b-28, b-29, b-34, b-35,
For the compounds b-41, c-30, and c-32, insecticidal tests were conducted at a compound concentration of 31 ppm. All the compounds showed an excellent insecticidal rate of 90% or more.
Insecticidal tests were conducted on compound Nos. A-24, a-63, a-66, a-68, a-71, a-73, and a-74 at a compound concentration of 8 ppm. All the compounds showed an excellent insecticidal rate of 90% or more.

(Test Example 3) Insecticidal test against citrus spider mite (Panonychus citri) Eight female citrus spider mites were inoculated on citrus leaves placed in a petri dish. Next, an emulsion having the formulation shown in Formulation Example 2 was prepared. The emulsion was diluted with water to a compound concentration of 125 ppm, 31 ppm, or 8 ppm, and the diluted solution was sprayed on the citrus leaves using a rotary spray tower. The mandarin orange leaf was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. The life and death of adults were investigated 3 days after spraying.
Compound Nos. A-10, a-42, a-60, b-11, b-17, b-25,
For the compounds b-26, b-27, b-28, b-29, b-34, b-35, and b-41, an insecticidal test against citrus red mite was performed at a compound concentration of 125 ppm. All the compounds showed an excellent insecticidal rate of 90% or more.
Insecticidal tests were carried out on the compounds Nos. A-21, a-24, a-54, a-55, a-62, a-77, and b-16 at a compound concentration of 31 ppm. All the compounds showed an excellent insecticidal rate of 90% or more.
For the compounds of Compound Nos. A-63, a-66, a-68, a-69, and a-71, insecticidal tests were conducted at a compound concentration of 8 ppm. All the compounds showed an excellent insecticidal rate of 90% or more.

The present invention can provide a cyclic amine compound or a salt thereof useful as an active ingredient of a pest control agent, particularly an ectoparasite control agent, which has a certain effect and can be used safely.

Claims (6)

1. A cyclic amine compound represented by the formula (I) or a salt thereof.
   

   

   
   
   
   [In Formula (I),
   Cy ¹ represents a C6-10 aryl group.
   R ¹⁰ is a substituent of Cy ¹ and each independently represents an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or A substituted C6-10 aryl group, an unsubstituted or substituted C6-10 aryloxy group, an unsubstituted or substituted C1-6 alkylamino group, an unsubstituted or substituted C1 ~ 6 represents an acylamino group, a cyano group, a nitro group, or a halogen atom.
   m represents the number of R ¹⁰ and is an integer of 0 to 5. When m is 2 or more, R ¹⁰ may be the same as or different from each other.
   Cy ² represents a C6-10 aryl group or a heterocyclyl group.
   R ¹¹ is a substituent of Cy ² and each independently represents an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or A substituted C6-10 aryl group, an unsubstituted or substituted C6-10 aryloxy group, an unsubstituted or substituted C1-6 alkylamino group, an unsubstituted or substituted C1 ~ 6 represents an acylamino group, a cyano group, a nitro group, or a halogen atom.
   n represents the number of R ¹¹ and is an integer of 0 to 5. When n is 2 or more, R ¹¹ may be the same as or different from each other.
   R ^1a , R ^1b , R ^2a , R ^2b , R ^3a , R ^3b , R ^4a , and R ^4b are each independently a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, or An unsubstituted or substituted C1-6 alkoxy group is shown.
   R ^1a and R ^2a or R ^3a and R ^4a are each independently an unsubstituted or substituted C2-6 alkylene group, or an unsubstituted or substituted C2-6 alkenylene group. May be formed.
   R ⁵ represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C1-7 acyloxy group Or an unsubstituted or substituted C1-6 alkoxycarbonyloxy group, an unsubstituted or substituted heterocyclyl group, a cyano group, or a halogen atom.
   R ^4b and R ⁵ may together form a group represented by —O—.
   p represents the number of R ^4b and R ⁵ and is an integer from 0 to 1. When p is 0, a carbon-carbon bond between R ^4b and R ⁵ forms a double bond. ]
2. The cyclic amine compound or a salt thereof according to claim ¹ , wherein Cy ¹ in formula (I) is a phenyl group.
3. The cyclic amine compound or a salt thereof according to claim 1 or 2, wherein Cy ² in formula (I) is a phenyl group, a pyrazolyl group, a thiadiazolyl group, a pyridyl group, a pyrimidinyl group, or a pyridazinyl group.
4. In the formula (I), Cy ¹ is a phenyl group, Cy ² is a 4-trifluoromethylphenyl group or a 5-trifluoromethyl-pyridin-2-yl group, and n is an integer from 0 to 4. The cyclic amine compound or salt thereof according to claim 1.
5. A pesticidal agent containing as an active ingredient at least one selected from the cyclic amine compounds or salts thereof according to any one of claims 1 to 4.
6. An ectoparasite control agent comprising, as an active ingredient, at least one selected from the cyclic amine compound according to any one of claims 1 to 4 or a salt thereof.