JP2019112398A - Fused heterocyclic compound and pest control agent - Google Patents

Abstract

To provide a pest control agent, an insecticide or acaricide, an ectoparasite control agent, or an endoparasite control or extermination agent.SOLUTION: The invention provides a compound represented by formula (I) or a salt thereof, where Q is a group represented by formula (Q-1).SELECTED DRAWING: None

Description

  The present invention relates to fused heterocyclic compounds and pest control agents. More specifically, the present invention provides a fused heterocyclic compound having excellent insecticidal and / or acaricidal activity, which is excellent in safety, and which can be industrially advantageously synthesized, and a pest containing the same as an active ingredient. It relates to a control agent.

  Various compounds having insecticidal and acaricidal activity have been proposed. In order to put such a compound into practical use as a pesticide, it is not only highly effective, it is difficult to cause drug resistance, does not cause phytotoxicity to plants and causes soil contamination, and has low toxicity to livestock and fish. Etc. are required.

By the way, the compound etc. which are represented by Formula (A) are disclosed by patent document 1. FIG.

Patent Document 2 discloses a compound represented by Formula (B), and the like.

WO2016 / 091731A WO 2017 / 026384A

  An object of the present invention is to provide a fused heterocyclic compound which is excellent in pest control activity, particularly, insecticidal activity and / or acaricidal activity, is excellent in safety, and can be advantageously synthesized industrially. Another object of the present invention is to provide a pest control agent containing a fused heterocyclic compound as an active ingredient, in particular, an insecticidal or acaricidal agent, an ectoparasitic agent, or an endoparasitic agent or control agent. is there.

  As a result of earnest studies to solve the above problems, the present invention including the following embodiments has been completed.

（式（I）中、
Ａ¹は、Ｎ、またはＣＨであり、
Ａ²は、Ｎ、またはＣＲ²であり、
Ｒ¹は、Ｃ１〜６アルキル基であり、
Ｒ²およびＲ³は、それぞれ独立して、水素原子、置換若しくは無置換のＣ１〜６アルキル基、置換若しくは無置換のＣ２〜６アルケニル基、置換若しくは無置換のＣ２〜６アルキニル基、水酸基、置換若しくは無置換のＣ１〜６アルコキシ基、置換若しくは無置換のＣ１〜６アルコキシカルボニル基、ホルミル基、置換若しくは無置換のＣ１〜６アルキルチオ基、置換若しくは無置換のＣ１〜６アルキルスルフィニル基、置換若しくは無置換のＣ１〜６アルキルスルホニル基、置換若しくは無置換のＣ３〜８シクロアルキル基、置換若しくは無置換のＣ６〜１０アリール基、置換若しくは無置換の３〜６員ヘテロシクリル基、置換若しくは無置換のＣ６〜１０アリールオキシ基、置換若しくは無置換の５〜６員ヘテロアリールオキシ基、置換若しくは無置換のアミノ基、置換若しくは無置換のアミノカルボニル基、置換若しくは無置換のヒドラジニル基、ニトロ基、シアノ基またはハロゲノ基であり、且つ
Ｑは、式（Q-1）で表される基である。

（式（Q-1）中、＊は結合位置を示し、
Ｒ⁵は、Ｃ１〜６アルキル基であり、且つ
Ｒ⁶は、置換若しくは無置換のＣ１〜６アルキル基、置換若しくは無置換のＣ１〜６アルコキシ基、置換若しくは無置換のＣ１〜６アルキルチオ基、置換若しくは無置換のＣ１〜６アルキルスルフィニル基、置換若しくは無置換のＣ１〜６アルキルスルホニル基、置換若しくは無置換のＣ６〜１０アリール基、置換若しくは無置換の５〜６員ヘテロアリール基、ニトロ基、シアノ基、ハロゲノ基、トリフルオロメチルスルホニルオキシ基またはペンタフルオロスルファニル基である。）） [1] A compound represented by the formula (I) or a salt thereof.

(In the formula (I),
A ¹ is N or CH,
A ² is N or CR ² ,
R ¹ is a C1-6 alkyl group,
R ² and R ³ each independently represent a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, Substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C1-6 alkoxycarbonyl group, formyl group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted Or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-8 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted 3 to 6 membered heterocyclyl group, substituted or unsubstituted C 6-10 aryloxy group, substituted or unsubstituted 5-6 membered heteroaryloxy group, substituted Or unsubstituted amino group, substituted or unsubstituted aminocarbonyl group, substituted or unsubstituted hydrazinyl group, nitro group, cyano group or halogeno group, and Q is a group represented by formula (Q-1) It is.

(In the formula (Q-1), * represents a bonding position,
R ⁵ is C1~6 alkyl group and R ⁶ is a substituted or unsubstituted C1~6 alkyl group, a substituted or unsubstituted C1~6 alkoxy group, a substituted or unsubstituted C1~6 alkylthio group, Substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted 5-6 membered heteroaryl group, nitro group A cyano group, a halogeno group, a trifluoromethylsulfonyloxy group or a pentafluorosulfanyl group. )))

[2] A pest control agent containing, as an active ingredient, at least one selected from the group consisting of the compound according to the above [1] and a salt thereof.

[3] An insecticidal or acaricidal agent comprising, as an active ingredient, at least one selected from the group consisting of the compounds described in the above [1] and salts thereof.

[4] An ectoparasite control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to the above [1] and a salt thereof.

[5] An endoparasite control or control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to the above-mentioned [1] and a salt thereof.

  The fused heterocyclic compound of the present invention can control pests that cause problems in agricultural products and hygiene. In particular, agricultural pests and mites can be effectively controlled at lower concentrations. Furthermore, it can effectively control ectoparasites and endoparasites that harm humans and animals.

[Fused heterocyclic compound]
The fused heterocyclic compound of the present invention is a compound represented by Formula (I) (hereinafter sometimes referred to as Compound (I)) or a salt of Compound (I).

In the present invention, the term "unsubstituted" means that it is only a mother core group. When there is no description of "substituted" and only the name of the mother core group is described, it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that any hydrogen atom of a group to be a mother nucleus is substituted with a group (substituent) having the same or a different structure as that of the mother nucleus. Thus, the “substituent” is another group bonded to the mother core. The number of substituents may be one or two or more. The two or more substituents may be the same or different.
Terms such as "C1 to 6" indicate that the number of carbon atoms of a group to be a mother nucleus is 1 to 6, and the like. The 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 into a C2 alkoxy C4 alkyl group.

The “substituent” is chemically acceptable and is not particularly limited as long as the effects of the present invention are obtained. The groups that can be "substituents" are exemplified below.
C1-6 such as methyl group, ethyl 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 An alkyl group;
Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, etc. A C2-6 alkenyl group of
A C 2-6 alkynyl group such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group;

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

Hydroxyl group;
C1-6 alkoxy group such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and the like;
C 2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group;
A C 2-6 alkynyloxy group such as ethynyloxy group, propargyloxy group;
A C6-10 aryloxy group such as phenoxy group and naphthoxy group;
C6-10 aryl C1-6 alkoxy groups such as benzyloxy group, phenethyloxy group and the like;
5- to 6-membered heteroaryloxy group such as thiazolyloxy group, pyridyloxy group and the like;
5- to 6-membered heteroaryl C1-6 alkyloxy group such as thiazolylmethyloxy group, pyridylmethyloxy group;

Formyl group;
C1-6 alkylcarbonyl group such as acetyl group, propionyl group;
Formyloxy group;
C1-6 alkyl carbonyloxy group such as acetyloxy group, propionyloxy group, etc.
C6-10 arylcarbonyl groups such as benzoyl group;
C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group and the like;
C1-6 alkoxy carbonyloxy groups such as methoxy carbonyloxy group, ethoxy carbonyloxy group, n-propoxycarbonyloxy group, i-propoxycarbonyloxy group, n-butoxycarbonyloxy group, t-butoxycarbonyloxy group and the like;
Carboxyl group;

Halogeno groups such as fluoro, chloro, bromo and iodo;
C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group and the like;
C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group, 2-fluoro-1-butenyl group;
C 2-6 haloalkynyl groups such as 4, 4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group;
C1-6 haloalkoxy groups such as trifluoromethoxy, 2-chloro-n-propoxy, 2,3-dichlorobutoxy and the like;
C 2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group, 3-bromobutenyloxy group;
C1-6 haloalkyl carbonyl group such as chloroacetyl group, trifluoroacetyl group, trichloroacetyl group;

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

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

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

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

Tri C 1-6 alkyl substituted silyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
Tri C 6-10 aryl substituted silyl groups such as triphenylsilyl groups;
Cyano group; nitro group;

  Moreover, as for these "substituents", any hydrogen atom in the said substituent may be substituted by the group of a different structure. In that case, examples of the "substituent" include C1-6 alkyl group, C1-6 haloalkyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, halogeno group, cyano group, nitro group and the like.

  Moreover, said "3-6 membered heterocyclyl group" is a thing containing 1-4 hetero atoms chosen from the group which consists of a nitrogen atom, an oxygen atom, and a sulfur atom as a ring constituting atom. The heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, when at least one ring is a hetero ring, the remaining rings may be any of saturated alicyclic, unsaturated alicyclic or aromatic rings. Examples of the “3 to 6-membered heterocyclyl group” include a 3 to 6-membered saturated heterocyclyl group, a 5 to 6-membered heteroaryl group, and a 5 to 6-membered partially unsaturated heterocyclyl group.

  Examples of the 3- to 6-membered saturated heterocyclyl group include aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group and the like.

Examples of 5-membered heteroaryl groups include pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc. Can.
Examples of the 6-membered heteroaryl group include pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and triazinyl group.

[R ¹ ]
In formula (I), R ¹ is a C1-6 alkyl group.

The “C1-6 alkyl group” in R ¹ may be linear, or may be branched as long as it has 3 or more carbon atoms. As an alkyl group, a methyl group, an ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group And i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.

[A ¹ ]
In formula (I), A ¹ is N or CH.

[A ² ]
In formula (I), A ² is N or CR ² .

[R ² , R ³ ]
In formula (I), R ² and R ³ each independently represent a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C1-6 alkoxycarbonyl group, formyl group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1 group 6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-8 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted 3 to 6-membered heterocyclyl Group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted 5 to 6 membered heteroarylo. Shi group, a substituted or unsubstituted amino group, a substituted or unsubstituted amino group, a substituted or unsubstituted hydrazinyl group, a nitro group, a cyano group or a halogeno group.

Examples of the "C1-6 alkyl group" for R ² and R ³ include the same as those exemplified for R ¹ above.

Examples of the “substituted C1-6 alkyl group” for R ² and R ³ include fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, 3,3, 3-trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, perfluoropropyl group, 2,2,2-trifluoro-1-trifluoromethylethyl group, perfluoroisopropyl group, 4 -Fluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, chloromethyl group, bromomethyl group, dichloromethyl group, Dibromomethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trichloroethyl group Group, C1-6 haloalkyl group such as 4-chlorobutyl group, perchlorohexyl group and 2,4,6-trichlorohexyl group; cyano group substituted C1-6 alkyl such as cyanomethyl group and 2-cyanopropan-2-yl group And 1-cyano-2-ethoxy- 2- oxonethyl group; and the like.

Preferred examples of the substituent on the "C1-6 alkyl group" for R ² and R ³ include halogeno groups such as fluoro, chloro, bromo and iodo; methoxycarbonyl, ethoxycarbonyl and n-propoxycarbonyl groups And C1-6 alkoxycarbonyl groups such as i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group and the like; cyano groups;

As the "C2-6 alkenyl group" for R ² and R ³ , a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2- Propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group etc. can be mentioned.

Examples of the “C2-6 alkynyl group” as R ² and R ³ include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-yl group Propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, Examples thereof include 1-hexynyl group and 1,1-dimethyl-2-butynyl group.

As the "C1-6 alkoxy group" in R ² and R ³ , a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, an t-butoxy group Groups can be mentioned.

Examples of the “C1-6 alkoxycarbonyl group” in R ² and R ³ include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group and the like It can be mentioned.

The “C1-6 alkylthio group” in R ² and R ³ is a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, an i-propylthio group, an i-butylthio group And the like.

Examples of the “C1-6 alkylsulfinyl group” in R ² and R ³ include a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group and the like.

Examples of the “C1-6 alkylsulfonyl group” in R ² and R ³ include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group and the like.

"C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C1-6 alkoxycarbonyl group", "C1-6 alkylthio group", "C1-6 alkyl group" in R ² and R ³ The substituent on the 6 alkylsulfinyl group "and" C1-6 alkylsulfonyl group "is preferably a halogeno group such as a fluoro group, a chloro group, a bromo group or an iodo group; a methoxy group, an ethoxy group, an n-propoxy group, i -C1-6 alkoxy groups such as propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and the like;

Examples of the “C3-8 cycloalkyl group” in R ² and R ³ include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cuvanyl group.

Examples of the “substituted C3-8 cycloalkyl group” for R ² and R ³ include cyano-substituted C 3-8 cycloalkyl groups such as 1-cyanocyclopropyl group; 6 such as 1- (pyridin-2-yl) cyclopropyl group Member heteroaryl group substituted C3-8 cycloalkyl group etc. can be mentioned.

As "C6~10 aryl group" in R ² and R ^3, it may be mentioned phenyl group, a naphthyl group.

The “3 to 6-membered heterocyclyl group” in R ² and R ³ includes, as a constituent atom of the ring, 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms. The heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, when at least one ring is a hetero ring, the remaining rings may be any of saturated alicyclic, unsaturated alicyclic or aromatic rings. Examples of the “3 to 6-membered heterocyclyl group” include a 3 to 6-membered saturated heterocyclyl group, a 5 to 6-membered heteroaryl group, and a 5 to 6-membered partially unsaturated heterocyclyl group.
Examples of the 3- to 6-membered saturated heterocyclyl group include aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group and the like.
Examples of the 5- to 6-membered partially unsaturated heterocyclyl group include 2-oxopyridine-1 (2H) -yl group and the like.
Examples of 5-membered heteroaryl groups include pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc. Can.
Examples of the 6-membered heteroaryl group include pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and triazinyl group.

The "C6~10 aryl group" in R ² and R ^3, include phenoxy group, naphthyloxy group.

Examples of the “5- to 6-membered heteroaryloxy group” as R ² and R ³ include pyridyloxy group, pyrimidyloxy group and the like.

"C3-8 cycloalkyl group", "C6-10 aryl group", "3-6 membered heterocyclyl group", "C6-10 aryloxy group", "5-6 membered heteroaryloxy group" in R ² and R ³ As a substituent on the above, preferably, halogeno groups such as fluoro, chloro, bromo and iodo; methyl, ethyl, n-propyl, i-propyl, n-butyl and s-butyl C1-C6 alkyl group such as i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoro Ethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, perfluoropropyl group, 2,2,2-triyl Fluoro-1-trifluoromethylethyl group, perfluoroisopropyl group, 4-fluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, perfluorobutyl group, perfluoropentyl group, Perfluorohexyl group, chloromethyl group, bromomethyl group, dichloromethyl group, dibromomethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trichloroethyl group, 4-chlorobutyl group, per C1-6 haloalkyl groups such as chlorohexyl group, 2,4,6-trichlorohexyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group Group, C1-6 alkoxy group such as t-butoxy group; 2-chloro-n-propoxy group, 2,3- And C6-C6 haloalkoxy groups such as dichlorobutoxy group and trifluoromethoxy group; 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and triazinyl group; cyano group;

The "substituted or unsubstituted amino group" in R ² and R ³ is a group represented by the formula: "-NR ^a R ^b ". In the formula, R ^a and R ^b are not particularly limited. For example, R ^a and R ^b are each independently a hydrogen atom, a C1-6 alkyl group, a formyl group, a C1-6 alkylcarbonyl group, a C3-8 cycloalkylcarbonyl group, a substituted or unsubstituted aminocarbonyl group Etc.

Examples of the "C1-6 alkyl group" for R ^a and R ^b include the same as those exemplified for R ¹ above.

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

Examples of the "C3-8 cycloalkylcarbonyl group" for R ^a and R ^b include a cycloalkylcarbonyl group and the like.

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

Examples of the “substituted or unsubstituted aminocarbonyl group” in R ² and R ³ include the same as those exemplified for the aforementioned R ^a and R ^b .

式(a)中、＊は結合位置であり、Ｒ^c、Ｒ^dおよびＲ^eは、それぞれ独立して、水素原子、Ｃ１〜６アルキル基、または置換若しくは無置換のフェニルスルホニル基などである。 The “substituted or unsubstituted hydrazinyl group” in R ² and R ³ is, for example, a group represented by formula (a).

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

Examples of the "C1-6 alkyl group" for R ^c , R ^d and R ^e include the same as those exemplified for the aforementioned X.

^Examples of the “substituted phenylsulfonyl group” in R ^c , R ^d and R ^e include a p-toluenesulfonyl group and the like.

Examples of the "halogeno group" in R ² and R ³ include fluoro, chloro, bromo and iodo groups.

[Q]
In formula (I), Q is a group represented by formula (Q-1). In formula (Q-1), * indicates a bonding position.

[R ⁵ ]
In formula (Q-1), R ⁵ is a C1-6 alkyl group.

Examples of the “C1-6 alkyl group” in R ⁵ include the same as those specifically exemplified in R ¹ .

[R ⁶ ]
In formula (Q-1), R ⁶ represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted group C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted 5-6 membered heteroaryl group, nitro group, cyano group, halogeno A trifluoromethylsulfonyloxy group or a pentafluorosulfanyl group.

Examples of the “C1-6 alkyl group” in R ⁶ include the same as those specifically exemplified in R ¹ .

“Substituted C1-6 alkyl group”, “substituted or unsubstituted C1-6 alkoxy group”, “substituted or unsubstituted C1-6 alkylthio group”, and “substituted or unsubstituted C1-6 alkylsulfinyl group” in R ⁶ As the “substituted or unsubstituted C1-6 alkylsulfonyl group”, “substituted or unsubstituted C6-10 aryl group” and “substituted or unsubstituted 5-6 membered heteroaryl group”, R ² and R may be ^The same as those specifically exemplified in ³ can be mentioned.

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

  The salt of compound (I) or compound (I) is not particularly limited depending on the method for producing it. For example, Compound (I) or a salt of Compound (I) of the present invention can be obtained by a known production method described in the Examples and the like. In addition, the salt of compound (I) can be obtained from compound (I) by a known method.

The fused heterocyclic compound of the present invention is excellent in the control effect of various agricultural pests and pests such as mites which affect the growth of plants.
In addition, the fused heterocyclic compound of the present invention is a substance with high safety because it is less harmful to crops and less toxic to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of an insecticide or acaricide.
Furthermore, in recent years, resistance to various existing drugs has developed in many pests such as monaga, planthoppers, leafhoppers and aphids, causing problems of lack of efficacy of these drugs, and drugs effective against pests of resistant strains are desired ing. The fused heterocyclic compound of the present invention exhibits an excellent control effect not only on susceptible lines, but also on pests of various resistant lines, and further on mites of acaricide-resistant lines.

  The fused heterocyclic compound of the present invention is excellent in the control effect of ectoparasites and endoparasites which harm animals. In addition, the substance is highly safe because it has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of a control agent of ectoparasite and endoparasite.

  In addition, the fused heterocyclic compound of the present invention is effective at all developmental stages of the organism to be controlled, and has excellent control effects on, for example, ticks, eggs such as insects, nymphs, larvae, moths and adults. Indicates

[Pest control agent]
The pest control agent of the present invention contains at least one selected from the fused heterocyclic compounds of the present invention as an active ingredient. The amount of the fused heterocyclic compound contained in the pest control agent of the present invention is not particularly limited as long as the pest control effect is exhibited. Pest control agents are control agents for controlling pests, and include insecticides or acaricides, ectoparasiticides, endoparasitides or pesticides, and the like.

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

The insecticides or acaricides of the present invention are grains, vegetables, root vegetables, potatoes, florets, fruits, house plants, teas, coffee, trees such as cacao, grasses, grasses, grasses, cottons, etc. It is preferred to use on plants.
For application to plants, the insecticidal or acaricidal agent of the present invention may be used at any site such as leaves, stems, handles, flowers, buds, fruits, seeds, sprouts, roots, tubers, tubers, shoots, cuttings, etc. .
Also, the insecticidal or acaricidal agent of the present invention is not particularly limited by the species of the plant to be applied. Plant species include, for example, original species, varieties, improved varieties, cultivars, mutants, hybrids, genetically modified organisms (GMO) and the like.

  The insecticidal or acaricidal agent of the present invention can be used for seed treatment, foliage application, soil application, water surface application and the like in order to control various agricultural pests and mites.

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

(1) Butterflies or moths of Lepidoptera (a) moths of the family Arctiidae, for example, Hyphantria cunea, Scutellariae (Lemyra imparilis);
(B) moths of the family Bucculatricidae, eg, Bacculatrix pyrivorella;
(C) Carposinidae, eg, Carposina sasakii;
(D) Mosquitoes of the family Rubiaceae (Crambidae), for example, of the species of the genus Diaphania (Diaphania spp.), The cotton helicoid moth (Diaphania indica), the leafhopper moth (Diaphania nitidalis); No. 1 (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), azukinomeiga (Ostrinia scapulalis); others, Chiropodella moth (Cnaphalocrocis medinalis); Diatraea grandiosella), Glyphodes pyloalis, Hyalunella (Hellula undalis), Shibatoga (Parapediasia teterrella);
(E) moths of the family Gelechiidae, such as, for example, Helicystogramma triannulella, Red-headed Peach (Pectinophora gossypiella), Potato yellow-billed moth (Phthorimaea operculella),
(F) A moth of the family Geometriidae (Geometridae), for example, anemone beetle (Ascotis selenaria);
(G) moths of the family Oscaridae (Gracillariidae), such as, for example, Chanophosoga (Caloptilia theivora), mandarin oranges (Phyllocnistis citrella), kinmonhosoga (Phyllonorycter ringoniella);
(H) A butterfly of the family Hesperiidae (Hesperiidae), eg, Parnaria guttata;
(I) moths of the family Lasiocampidae, such as Malacosoma neustria; (j) moths of the family Lycantidae (Lymantriidae), such as the giant leaf moth, Lymantria dispar, of the species Lymantria spp. (Lymantria monacha); Other, Eurasian moth (Euproctis pseudoconspersa), Eurasian moth (Orgyia thyellina);

(K) moths of the family Molyrigidae (Lyonetidae), such as, for example, Lyonetia clerkella of the species Lyonetia sp. (Lyonetia spp.);
(L) A moth of Noctidae (eg, Spodoptera spp.), Spodoptera depravata, Southern armyworm (Spodoptera eridania), Spodoptera exigua, Spodoptera frugipergiperda , Spodoptera littoralis, Spodoptera litura; eg, of the Autographa spp., Autographa gamma, Tamakihaginwaba (Autographa nigrisigna); eg, Agrotis sp. (Agrotis spp.) For example, Agrotis ipsilon, Agrotis segetum; eg Helicoverpa spp., Helicoverpa armigera, Helicoverpa assulta, cotton ball worm (Helicoverpa zea); eg Heliochis spp. Cottontail (Heliothis spp.) (Heliothis armigera), False American tobacco moth (Heliothis virescens); and others, Aedia leucomames, Citenoplusia agnata, Eudocima tyrannus, ト ウ M (Mamestra brassicae), (Naranga aenescens), Matsuri rig (Panolis japonica), Niceata moth (Peridroma saucia), Soy bean looper (Pseudoplusia includens), Nettle moth (Trichoplusia ni);
(M) Moths of the family Nolidae (Nolidae), eg, Missia olega (Earias insulana);
(N) A butterfly of the family Piridae (Pieridae), for example, a butterfly (Pieris brassicae) of the genus Piralis sp. (Pieris spp.), A butterfly (Pieris rapae crucivora);
(O) moths of the family Palcellidae (Plutellidae), such as Acrolepiopsis spp., Acrolepiopsis sapporensis, Phyllaceae (Acrolepiopsis suzukiella); and others, Psylola xylostella;
(P) moths of the family Myridae (Pyralidae), such as, for example, red-tailed moth (Cadra cautella), scorpionfish moth (Elasmopalpus lignosellus), silkworm moth (Etiella zinckenella), honeybee moth (Galleria mellonella);
(Q) moths of the family Sphingidae (Sphingidae), for example, tomato hornworm (Manduca quinquemaculata), tobacco hornworm (Manduca sexta) of Manduca spp.

(R) Moths of the family Stathmopodidae, for example, Kakinotameta (Stathmopoda masinissa);
(S) moths of the family Trichoidea (Tineidae), for example, moth (Tinea translucens);
(T) A moth of the family Tortricidae (Tortricidae), such as, for example, an Adoxophys spp., A chamomile (Adoxophys honmai), an apple cockerel (Adoxophys orana), for example, an Altipus sp. Of the apple snail (Archips breviplicanus), midarek syllabary (Archips fuscocupreanus); other, the rhubarbs (Choristoneura fumiferana), the codling moth (Cydia pomonella), the grape hosohamaki (Eupoecilia ambiguella), the snail ), Hamam (Homona magnanima), Mameshiniga (Leguminivora glycinivorella), Hosoba Himeji (Lobesia botrana), Mame hysteriae (Matsumuraeses phaseoli), Tobihamaki (Pandemis heparana), Tenguhamaki (Sparganothis pilleriana);
(U) A moth of the Sedaceae family (Yponomeutidae), for example, an apple clover (Argyresthia conjugella).

(2) Thysamiptera (Thysanoptera) pests (a) of the family Phlaeothripidae, for example, perennial thrips (Ponticulothrips diospyrosi);
(B) Of the Thripidae (Thripidae), such as, for example, of the flower of the genus Thripidae (Frankliniella spp.), The flowering thrips (Frankliniella intonsa), the flowering thrips (Frankliniella occidentalis); Thrips (Thrips palmi), New Zealand thrips (Thrips tabaci); and the other Croton thrips (Heliothrips haemorrhoidalis), the tea thrips (Scirtothrips dorsalis).

(3) Pests of the Hemiptera (Hemiptera) (A) Brachysera (Archaeorrhyncha)
(A) For the planthopper family (Delphacidae), for example, night-leaved planthopper (Laodelphax striatella), tree-footed planthopper (Nilaparvata lugens), black-footed planthopper (Perkinsiella saccharicida), tree-tailed loach (Sogatella furcifera).

(B) Cervix suborder (Clypeorrhyncha)
(A) Of the leafhopper family (Cicadellidae), for example, of the Empoasca spp. Phytohypticus (Empoasca sakaii); Other, Phytohyperglyphus (Arboridia apicalis), Midorhydlowy (Balclutha saltuella), Phytohyperglyphus (Epiacanthus stramineus), Hymenopythofops (Macrosteles striifrons), ).

(C) Hemiptera: Heteroptera
(A) of the family Alydidae, for example, the family Riptortus clavatus;
(B) of the family Helicidae (Coreidae), for example, Crustus punctiger, spider beetles (Leptocorisa chinensis);
(C) of the family of Lymphidae (Lygaeidae), such as, for example, the Red-backed Bug (Blissus leucopterus), the Yellow-backed Bug (Cavelerius saccharivorus), the Yellow-backed Bug (Togo hemipterus);
(D) For example, black-tailed snail (Halticus insularis), snail's snail (Lygus lineolaris), cotton-free hopper (Psuedatomoscelis seriatus), scutellaris (Steinoma sibiricum), red-tailed snail (Stenotus rubibitus) ), Trichonotylus caelestialium;

(E) of the Pentatomidae (Pentatomidae), such as, for example, Nezara spp. , Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, and others, Dolycoris baccarum, Eurydema rugosum, Blossy bugs Halyomorpha halys), P. pipisodorus hybneri, P. japonicus (Plautia crossota), S. japonicus (Scotinophora lurida);
(F) of the family of Pyrophocoridae (Pyrrhocoridae), for example, Dysdercus cingulatus;
(G) of the family Rhopalidae, for example, the red locust (Rhopalus msculatus);
(H) of the family Scutelleridae, eg, the wheat bug (Eurygaster integrateds);
(I) Of the family Gingambiidae (Tingidae), for example, Nassinbai (Stephanitis nashi).

(D) Rooster (Sternorrhyncha)
(A) Of the Aphididae (Adelgidae), for example, Larch Aphid (Adelges laricis);
(B) Whitefly family (Aleyrodidae), for example, Silversea whitefly (Bemisia argentifolii), B. tabaci (Bemisia tabaci) of Bemisia spp .; citri), the whitefly (Trialeurodes vaporariorum);
(C) Aphididae (Aphididae), for example, Aphis species (Aphis spp.), Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii , European apple aphids (Aphis pomi), Shrimp Aphids (Aphis sambuci), Aphid spiky aphids (Aphis spiraecola); eg, Rhopalosiphum spp. For example, Diosphis spp., Diosphis plantaginea, Dysphis radicola; eg, Macrossifum spp., Aphis gossypii (Macrosiphum avenae), (Macrosiphum euphorbiae); For example, of the genus Mizuzu sp. (Myzus spp.), Shrimp aphid (Myzus cerasi), green-billed aphid (Myzus persicae), Shrimp aphid (Myzus varians); and other Pea aphids (Acyrthosiphon pisum), potatoes Aphids (Aulachothum solani), Brystalgia aphid (Brachycaudus helichrysi), Japanese radish aphid (Brevicoryne brassicae), strawberry Psyllid aphid (Chaetosiphon fragaefolii), Momok's Burabug (Hyalopterus pruni) Lipaphis erysimi), Broad bean aphid (Megoura viciae), Mugius loaf aphid (Metopolophium dirhodum), Lettuce aphid (Nasonovia ribis-nigri), Hop's boar aphid (Phorodon humuli), boletus aphid (Schizaphis graminum), Aphid aphid (Sitobion avenae), Komikan aphid (Toxoptera aurantii);

(D) of the family Coccidae (Coccidae), for example of the Ceroplastus species (Ceroplastes spp.);
(E) Anchovy species (Pseudaulacaspis spp.) Of the Marukaididae (Diaspididae), a scaleworm (Pseudaulacaspis pentagona), a scaleworm (Pseudaulacaspis prunicola); for example, Unaspis spp. Of the mealybug (Unaspis euonymi), the mealybug (Unaspis yanonensis); and the other mealybugs (Aonidiella aurantii), the mealworm (Comstockaspis perniciosa), the mealworm (Fiorinia theae); );
(F) Of the cotton meal scale (Margarodidae), for example, a large scale scale beetle (Drosicha corpulenta), an Iceria scale beetle (Icerya purchasi);
(G) of the family Aphididae (Phylloxeridae), for example, the grapevine aphid (Viteus vitifolii);
(H) of the family Pseudococcidae, for example of the genus Planococcal sp. (Planococcus spp.); , Quackworm (Pseudococcus comstocki);
(I) Psyllididae (Psylllidae), for example, Psylla spp., Psylla mali, Psylla pyrisuga; and others, Psylla pyrisuga;

(4) Insect pests of the beetle order (Polyphaga) (a) For example, tobacco beetles (Lasioderma serricorne) of the family Anobiidae (Anobiidae);
(B) of the family Attelabidae, for example, Byctiscus betulae, Rhynchichis heros;
(C) of the family Bostrichidae, eg, Lyctus brunneus;
(D) of the family Brentidae (Brentidae), for example, Cylas formicarius;
(E) of the family Buprestidae (Buprestidae), for example, Agrillus sinuatus;
(F) Of the family of Cerambycididae (Cerambycidae), for example, Anodlophora malasiaca, Pinus longicornus (Monochamus alternatus), Pterocarpus longiflorum (Psacothea hilaris), Grapevine longhorned beetle (Xylotrechus pyrrhoderus);
(G) Of the family Chrysomelidae (Chrysomelidae), for example, of the species Burchus spp., Pea weevil (Bruchus pisorum), psyllid weevil (Bruchus rufimanus); eg, of the species Diabrotica sp. (Diabrotica spp.), Northern corn Root worm (Diabrotica barberi), Southern corn root worm (Diabrotica undecimpunctata), Western corn root worm (Diabrotica virgifera); eg, Phyllotreta sp. ;; Other, ground beetle (Aulacophora femoralis), azuki bean beetle (Callosobruchus chinensis), camphor leaf beetle (Cassida nebulosa), brown leaf beetle (Chaetocnema concinna), Colorado potato beetle (Leptinotarsa decemlineata), nematode leaf beetle (Oulema oryza,) Nagas nutbi ham Si (Psylliodes angusticollis);

(H) Of the ladybird family (Coccinellidae), for example, of the Epilacna sp. (Epilachna spp.), Green bean (Epilachna varivestis), red-winged ladybird (Epilachna vigintioctopunctata);
(I) Of the weevil family (Curculionidae), for example of the species Anthonomus spp. , Granary weevil (Sitophilus granarius), Scorpion beetles (Sitophilus zeamais); Other, Echinocnemus squameus, Eusphaerus (Euscepes postfasciatus), Pinus auris beetles (Hylobius abietis), Alfalfa tabaci Lissohoptrus oryzophilus), Anchovy weevil (Otiorhynchus sulcatus), Red-billed Weevil (Sitona lineatus), Weevil Weevil (Sphenophorus venatus);
(J) For example, Maranotus sp. (Melanotus spp.), Of the click beetle family (Elateridae), Maranotus fortnumi, Maranotus tamsuyensis;
(K) of the family Kitokiidae (Nitidulidae), for example, Epuraea domina;
(L) Of the Scarabaeidae (Scarabaeidae), for example, of the Anomala species (Anomala spp.), Anomala cuprea, Anomala rufocuprea; Other, Cetonia aurata; ), Nagachagane (Heptophylla picea), European Crayflower (Melonontha melolontha), Red-handed Bean (Popillia japonica);
(M) of the bark Beetle family (Scolytidae), for example, the spiny cub (Ips typographus);
(N) of the family Staphylinidae, for example, ascidian (Paederus fuscipes);
(O) For example, of the beetle family (Tenebrionidae), for example, Tenebrio molitor, Tricholium castaneum;
(P) of the family Kogroustidae (Trogossitidae), for example Kochnost (Tenebroides mauritanicus).

(5) Pests of the fly (Diptera) (A) The fly (Brachycera)
(A) of the family Agromyzidae, for example of the species Liriomyza spp., Liriomyza bryoniae; Other, the leafminer fly (Chromatomyia horticola), the rice leafminer fly (Agromyza oryzae);
(B) Seed fly (Delia platura), cabbage fly (Delia radicum) of, for example, Delia species (Delia spp.) Of Anthomyiidae;
(C) of the Drosophila family, for example, of the genus Drosophila (Drosophila spp.), Drosophila melanogaster, Drosophila melanogaster (Drosophila suzukii);
(D) of the family Ephydridae, for example, the rice leafminer fly (Hydrellia griseola);
(E) For example, Carrot fruit fly (Psila rosae) of the family Hameoleidae (Psilidae);
(F) Tephritidae (eg, Bactrocera spp.), A fruit fly (Bactrocera cucurbitae), a fruit fly (Bactrocera dorsalis); eg, a species of Lagoletis sp. Rhagoletis cerasi), Lyngfish fly (Rhagoletis pomonella); Other, fruit fly (Ceratitis capitata), olive fruit fly (Dacus oleae).

(B) mosquitoes (Nematocera)
(A) For example, soybean seed fly (Asphondylia yushimai), sorghum head fly (Contarinia sorghicola), red-spotted fly (Mayetiola destructor), and red-tailed fly (Sitodiplosis mossellana) of the family Cididomyiidae.

(6) Pests of the order of the locust (Orthoptera) (a) For example, of the locust family (Acrididae), for example of the Schistocerca spp., Schistocerca americana, Schistocerca gregaria; and others Australian Tobibata (Chortoicetes terminifera), Moroccan locust (Dociostaurus maroccanus), Tonosada grasshopper (Locusta migratoria), Brown locust (Locustana pardalina), Red Spotted grasshopper (Nomadacris septemfasciata), Kobane inago (Oxya yezoensis)
(B) of the cricket family (Gryllidae), for example, the European cricket (Acheta domestica), the empress (Teleogryllus emma);
(C), for example, of the family of Grilotalpidae, such as Grilotalpa orientalis;
(D), for example, a clavule (Tachycines asynamorus) of the family Tettigoniidae.

(7) Mites (Acari)
(A) Acarididae (Acaridida)
(A) Acaridae (Acaridae) mites such as, for example, Rhizoglyphus spp., Red mites (Rhizoglyphus echinopus), Robin mites (Rhizoglyphus robini); (Tyrophagus neiswanderi), Digella sativa (Tyrophagus perniciosus), Digella sativa (Tyrophagus putrescentiae), Spinach Psyllidago mite (Tyrophagus similis); Other, Acarus sicosa (Acarus siro), Acygnalogus

(B) Prestigmata (Prostigmata) mite mites (Actinedida)
(A) Ticks of the spider mite family (Tetranychidae), for example, the clover spider mite (Bryobia praetiosa), the false clover spider mite (Bryobia rubrioculus) of the species Briobia spp. Of the red-handed spider mite (Eotetranychus asiaticus), the horned spider mite (Eotetranychus boreus), the green-footed spider mite (Eotetranychus celtis), the giant-skinned spider mite (Eotetranychus geniculatus), the orange-footed spider mite (Eotetranychus kankitus) (Eotetranychus smithi), Suginami spider mite (Eotetranychus suginamensis), Walnut spider mite (Eotetranychus uncatus); Ma Red spider mite (Oligonychus mangiferus), sugar cane spider mite (Oligonychus orthius), red-tailed spider mite (Oligonychus perseae), red-spotted spider mite (Oligonychus pustulosus), green spider mite (Oligonychus shinkajii), todo matsuite , Red spider mite (Panonychus citri), black-tailed spider mite (Panonychus mori), apple red spider mite (Panonychus ulmi); , Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Tetranychus vinetnosis; eg, Aponichus sp. Yellow-spotted spider mite (Aponychus firmianae); for example, the spider spider mite (Sasanychus spp.) Of the spider spider mite (Sasanychus akitanus), the spider spider spider mite (Sasanychus pusillus); ), Scutellaris gossus longus (Shizotetranychus longus), Susukisgogo spider spider mite (Shizotetranychus miscanthi), Red-spotted spider mite (Shizotetranychus recki), Red-spotted spider mite (Shizotetranychus recki), Red-winged spider mite (Shizotetranychus recki), Willow spider mite (Shizotetranychus schizopus snails); sapporensis);

(B) Mite mites (Tenuipalpidae) mites such as, for example, Brevipulpus species (Brevipalpus spp.), Grapevine red spider mite (Brevipalpus lewisi), channoid spider mite (Brevipalpus obovatus), red haired spider mite (Brevipalpus phoenicis), cactus spider lice (Brevipalpus) russulus), red-spotted spider mite (brevipalpus californicus); such as, for example, the genus Tenipalpus sp. (Tenuipalpus spp.), the spider red mite (Tenuipalpus pacificus), the oyster spider mite (Tenuipalpus zhizhilashviliae);
(C) Acarid mites (Eriophyidae) mites, such as Aceria spp., Aceria diospyri, Ficus mondas (Aceria ficus), Clifs mite (Aceria japonica), Monascus mites (Aceria kuko), Carnations Eriophyes chibaensis (Aceria paradianthi), Aceria tiyingi, Tulip rust mite (Aceria tulipae), Sherrisome mite (Aceria zoysiea); eg, Eriophyes spp. emarginata); for example of the species Acrops spp., tomato snail mite (Aculops lycopersici), e.g. Aculops pelekassi; e.g. of the species Aculus spp. schlechtendali); Other, Acaphyll a theavagrans), mangrove mite (Calacarus carinatus), grape leafminus mite (Colomerus vitis), grapevine snail (Calepitrimerus vitis), navy rust mite (Epitrimerus pyri), goldfish mite (Paraphytoptus kikus), spiny mite (Paracalacarus podocarpumiw) citri);
(D) Tick mites (Transonemidae) mites, such as, for example, the tarsonemus spp. );
(E) Mite mites (Penthaleidae) mites, such as, for example, Penthaleus erythrophalus of the genus Pentareus sp. (Penthaleus spp.), And green mites (Penthaleus major).

The insecticides or acaricides of the present invention are other active ingredients such as fungicides, insecticides / acaricides, nematocides, soil pests and the like; plant regulators, herbicides, synergists, fertilizers, soil improvement It may be used in combination or in combination with an agent, animal feed and the like.
Combinations of the compound of the present invention and other active ingredients can be expected to have a synergistic effect on insecticidal, acaricidal and nematicidal activity. The synergistic effect can be confirmed according to a standard method by Colby's formula (Colby. SR; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, pp. 20-22, 1967).

  Specific examples of an insecticide / acaricide, a nematocide, a soil insecticide / acaricide, an insecticide, etc. that can be used in combination or in combination with the insecticide or acaricide of the present invention are shown below.

(1) Acetylcholinesterase inhibitors:
(A) Carbamate system: Alanicarb, aldiocarb, benzocarb, benfracarb, butoboxoxime, butoxy carboxime, carbaryl, carbofuran, carbosulfan, carbohephan, ethiophene carb, fenobucarb, formetanate, furaiocarb, isocarb, methiocarb, mesomil, oximi, piromicarb, propoxal, Thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb, phenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, alixicarb, aminocarb, bufencarb, cloetocarb, metame sodium, promecarb;

(B) Organophosphorus: Acephate, azamethyphos, azinphos-ethyl, azinphos-methyl, kazzaphos, chlorethoxyphos, chlorphenphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demetone-S-methyl, diazinon, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylphosphine, Disulfoton, EPN, Ethion, Ethoprophos, Pham Fool, Fenamiphos, Fenitrothion, Fenthione, Fosciate, Heptenophos, Imicifoss, Isophenphos, Isocarbophos, Isoxathion, Malathion, Mecarbammethizophos Methiomethone, Monocrotophos, Naredo, Omethoate, Oxydimethone-Methyl, Parathion, Parathion-Methyl, Fent And phorate, hosalone, phosmet, phosphamidone, phoximidone, pyrimiphos-methyl, propenophos, propetamphos, prothiophos, pyraclophos, pyridafenthion, quinalphos, sulfotep, tebupillinphos, temephos, terbuphos, tetrachlorvinphos, thiomethone, triazolophos, trichlorphos, trisodium phosphide, Bromophos Ethyl, BRP, Carbophenothione, Cyanophenphos, CYAP, Demetone-S-Methylsulfone, Diariphos, Diclofenthion, Dioxabenzophos, Etriphos, Fensulfothion, Flupirazophos, Honophos, Formothion, Phosmethyrane, Isazophos, Iodophenphos, Methacrylophos, pyrimiphos-ethyl, phosphocarb, propaphos, protoate, sulpropos.

(2) GABA-agonizing chloride ion channel antagonists: acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprol, pyriprole, campechlor, heptachlor, dienochlor.
(3) Sodium channel modulators: acrolinathrin, d-cis-trans arethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- Cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cypophothrin [(1R) -trans isomer], deltamethrin, enpentrin [(EZ)-( 1R) -isomer], esfenvalerate, etofenprox, fenpropatrin, fenvalerate, flucithinate, flumethrin, tau-fluvalinate, halfenprox, imi Lythrin, Cadesulin, Permethrin, Phenothrin [(1R) -trans isomer], Praretrin, pyrethrum, resmethrin, silafluofen, tefluthrin, tetramethrin [(1R) -isomer], tralomethrin, transfluthrin, allethrin, pyrethrin, pyrethrin I, Pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, phenpyritrin, flubrositrinate, flufenprox, metfluthrin, protrifenbuto, pyrethmethrin, terraretrin.

(4) Nicotinic acetylcholine receptor agonists: Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyrazifron.
(5) Nicotinic acetylcholine receptor allosteric modulators: spinetoram, spinosad.
(6) Chloride channel activators: Abamectin, emamectin benzoate, lepimectin, milbemectin, ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, nemadectin.
(7) Juvenile hormone-like substances: hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen, diofenolan, epofenonan, triprene.
(8) Other nonspecific inhibitors: methyl bromide, chlorpicrin, sulfuryl fluoride, borax, tartaric acid.
(9) Homoptera order selective antifeedants: flonicamide, pimetrodine, pyrifluquinazone.

(10) Acaricide growth inhibitors: clofenthezin, difrobidazine, hexythiazox, etoxazole.
(11) Microorganisms derived from insect midgut inner membrane disrupter: Bacillus thuringiensis subsp. Islaerensis, Bacillus sphaericus, Bacillus thuringiensis subsp. Eiwai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. Teneburionis, Bt Crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.
(12) Mitochondrial ATP biosynthetic enzyme inhibitor: diafenthiuron, azocyclotin, cyhexatin, phenbutatin oxide oxidized, propargite, tetradiphone.
(13) Oxidative phosphorylation uncoupling agent: chlorfenapyr, sulframide, DNOC; binapakryl, dinobuton, dinocup.
(14) Nicotinic acetylcholine receptor channel blocker: bensultap, cartap hydrochloride, nereistoxin, thiosultap monosodium salt, thiocyclam.
(15) Chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxlon, flufenoxuron, hexaflumuron, lufenuron, novallon, noviflumuron, teflubenzurone, triflumuron, buprofezin, fluazulon.
(16) Diptera molt-disrupting agents: cyromazine.
(17) Molting hormone receptor agonists: Chromafenozide, halofenozide, methoxyfenozide, tebufenozide.
(18) Octopamine receptor agonists: amitraz, demiditraz, chlordimeform.
(19) Mitochondrial electron transport complex III inhibitor: acequinosyl, fluacripyrim, hydramethylnon.
(20) Mitochondrial electron transport complex I inhibitor: phenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrade, tolfenpyrade, rotenone.

(21) Voltage-gated sodium channel blockers: indoxacarb, metaflumizone.
(22) Acetyl CoA carboxylase inhibitor: spirodiclofen, spiromesifen, spirotetramat.
(23) Mitochondrial electron transport complex IV inhibitor: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide.
(24) Mitochondrial electron transport complex II inhibitor: sienopyrafen, ciflumethofen, piflubumide.
(25) Ryanodine receptor modulators: chloranthraniliprole, cyantraniprole, flubendiamide, cyclaniliprole, tetraniliprole.
(26) Mixed Function Oxidase Inhibitor Compound: Piperonyl butoxide.
(27) Latrophin receptor agonist: Depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside.
(28) Other agents (the mechanism of action is unknown): azadirachtin, benzoxmate, biphenazate, bromopropilate, quinomethionate, cryolite, dicophor, pyridoryl, benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, Phenylsobromolate, benzomate, methaldehyde, chlorobenzylate, crothiazobene, dicyclanyl, phenoxacrim, phentrifanyl, flubenziamine, fluphenadine, gossypua, japonirua, methoxadiazon, petroleum, potassium oleate, tetrasul, triaracene, afidopyropene ), Flomethoquin, flufiprole, fluensulphone, meperflusulline, tetramethylfursulline, tralopyril, dimeflusulline, methyl Neodecanamide, fluralanel, afoxolanel, fluxamethamide, 5- [5- (3,5-dichlorophenyl) -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] -2- (1H-1,2,6 4-Triazol-1-yl) benzonitrile (CAS: 943137-49-3), brofuranilide, and other metadiamides.

(29) Antiparasitic agent:
(A) Benzimidazole: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxendazole, perbendazole, flubendazole; febantel, netobimine, thiophanate, thiabendazole, cambendazole;
(B) salicylanilides: closantel, oxyclosanide, lafoxanide, niclosamide;
(C) substituted phenols: nitroxynil, nitroskenate;
(D) pyrimidines: pyrantel, morantel;
(E) imidazothiazole system: levamisole, tetramisole;
(F) tetrahydropyrimidines: praziquantel, epsiprantel;
(G) Other anthelmintic agents: cyclodienes, lyanias, chlorthrone, metronidazole, demiditraz; piperazine, diethyl carbamazine, dichlorophen, monetantel, tribenzimidin, amidanter; thiacetalsamide, merolsamine, arsenamide

Specific examples of the bactericide which can be used in combination or in combination with the pest control agent of the present invention are shown below.
(1) Nucleic acid biosynthesis inhibitors:
(A) RNA polymerase I inhibitors: Benalaxil, Benalaxyl-M, fralaxyl, metalaxyl, metalaxyl-M, oxadixyl, cloziracone, off-race;
(B) adenosine deaminase inhibitors: bupirimate, dimethymol, ethylimol;
(C) DNA / RNA synthesis inhibitors: hymexazole, octilinone;
(D) DNA topoisomerase II inhibitor: oxophosphate.

(2) Mitotic proliferation inhibitors and cytostatics:
(A) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate methyl, dietofencarb, zoxamide, etaboxam;
(B) cell division inhibitors: penciclone;
(C) Delocalization inhibitors of spectrin-like protein: fluopicolide.

(3) Respiratory inhibitor:
(A) Complex I NADH oxidoreductase inhibitor: diflumetrim, tolfenpyrad;
(B) Complex II succinate dehydrogenase inhibitors: benodanyl, flutolanil, mepronil, isofetamide, fluopyram, fenfuram, flumeclox, carboxin, oxycarboxin, thifluzamide, benzobin diflupyr, bixafen, fluxapiroxade , Flumetopyr, isopyrazam, penflufen, penthiopyrade, sedaxane; boscalid;
(C) Complex III Ubiquinol Oxidase Qo Inhibitor: Azoxystrobin, spiderxystrobin, cumoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyraxtrobin, pyraclostrobin, Pyramethostrobin, triclopyricarb, cresoxim-methyl, trifloxystrobin, dimoxystrobin, phenaminstrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, phenamidone, pyribencarb;
(D) Complex III ubiquinol reductase Qi inhibitors: Cyazofamid, amisulblom;
(E) Oxidative phosphorylation uncouplers: vinapacryl, meptylizino cup, dino cup, fluazinam, ferimsone;
(F) Oxidative phosphorylation inhibitors (inhibitors of ATP synthetase): phentin acetate, phentin chloride, phentin hydrochloride;
(G) ATP production inhibitor: silthiofam;
(H) Complex III: Qx (unknown) inhibitor of thyrochrome bc1 (ubiquinone reductase): Amethocrazine.

(4) Amino acid and protein synthesis inhibitors (a) Methionine biosynthesis inhibitors: Andprim, cyprodinil, mepanipyrim, pyrimethanyl;
(B) Protein synthesis inhibitors: Blasticidin-S, Kasugamycin, Kasugamycin hydrochloride, streptomycin, oxytetracycline.

(5) Signal transduction inhibitors:
(A) Signal transduction inhibitors: quinoxyfene, proquinazide;
(B) MAP-histidine kinase inhibitors in osmotic signaling: fenpicronil, fludioxonil, clozolimate, iprodione, procymidone, vinclozolin.

(6) Lipid and cell membrane synthesis inhibitors:
(A) Phospholipid biosynthesis, methyl transferase inhibitors: Edifenphos, iprovenphos, pyrazophos;
(B) lipid peroxides: biphenyl, chloroneb, dichlorane, quindozen, technazen, tolclophos methyl; etordiazole;
(C) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb bosecetate, prothiocarb;
(D) Microorganisms that disrupt pathogen cell membranes: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain;
(E) Agents that disrupt cell membranes: extracts of Goseika Jupte (tea tree).

(7) Sterol biosynthesis inhibitor of cell membrane:
(A) Demethylation inhibitors at C14 position in sterol biosynthesis: Trifolin; pyriphenox, pyriisoxazole; phenarimol, flurprimidol, nualimol; Triflumizole, biniconazole;
Azaconazole, vitertanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinonazole, flusilazole, flutriaazole), fluconazole, fluconazole- Cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, quinconazole, cimeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole;
(B) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis:
Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidine, piperaline, spiroxamine;
(C) 3-Keto reductase inhibitors at C4 demethylation of sterol biosynthesis system: fenhexamid, fenpyrazamine;
(D) Squalene epoxidase inhibitors of sterol biosynthesis system: pyributycarb, naftifene, terbinafine.

(8) Cell wall synthesis inhibition (a) Trehalase inhibitor: Validamycin;
(B) Chitin synthetase inhibitors: polyoxins, polyoxolims;
(C) Cellulose synthetase inhibitors: dimethomorph, flumorph, pymorph, bench abariculum, iprobicarb, tolprocarb, varifenalate; mandipropamide.

(9) Melanin biosynthesis inhibitor (a) Reductase inhibitor of melanin biosynthesis: fushalide, pyroxolone, tricyclazole;
(B) Inhibitors of melanin biosynthesis: Carpropamide, diclocimet, phenoxanyl.

(10) Host plant resistance inducer:
(A) Agents that act on the salicylic acid synthesis pathway: acibenzolar-S-methyl;
(B) Others: Probenazole, Thiazinyl, Isotianil, Laminarin, Oitadori extract.

(11) Agents with unknown activity: Shimoxanyl, fosetylaluminum, phosphoric acid (phosphate), teclophthalam, triazoloxide, flusulfamide, diclomedin, metasulfocarb, cyfluphenamide, metraphenone, pyrofenone, dodine, dodine free base, flutianil.

(12) Agents having multiple action points: copper (copper salt), Bordeaux solution, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, faram, mancozeb, maneb) , Mankappa, methylam, polycarbamate, propineb, thiram, zineb, ziram, captan, captaphor, captophor, phorpet; chlorothalonil, diclofluanid, tolylfluanid, gazatine, iminoctadine triacetate, iminoctadine albesylate ( iminoctadine trialbesilate), anilazine, dithianone, quinomethionate, fluorimide.

(13) Other agents: DBEDC, fluorophorpet, gazatine acetate, bis (8-quinolinolato) copper (II), propamidine, chloropicrin, ciprofram, agrobacteria, betoxazine, diphenylamine, methylisothianate (MITC ), Mildeomycin, Capsaicin, Kuflaneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophen, Diphenzoquat, Diphenzoquat Methylsulfonate, Flumethobel, Fosetyl Calcium, Fosetyl Sodium, Irumamycin, Natamycin, Nitrotal Isopropyl , Oxamocarb, propamocin sodium, pyrrolnitrin, tebufloquine, tornifanide, zalliramide, algophase, amicarthiazole (Amicarthiazol), oxalic Apipurorin (Oxathiapiprolin), metiram zinc, benches azole, trichlamide, uniconazole, mill Deo mycin, oxyphencyclimine Ji-in (Oxyfenthiin), Pical -but Ratho box (picarbutrazox).

Specific examples of plant regulators which can be used in combination or in combination with the insecticides or acaricides of the present invention are shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorphenuron, thidiazuron, chlorphenuron, dihydrozeatin, gibberellin A4, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (alias: abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothiol, 1 -Naphthylacetamide, ethychlozate, croxifonac, maleic acid hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+) -Deo Cysts Rigoru, (+) - Orobankoru, (+) - Sorugorakuton, 4-oxo-4- (2-phenylethyl) amino acid, ethephon, chlormequat, mepiquat chloride, benzyl adenine, 5-aminolevulinic acid.

[Ectoparasite control agent]
The ectoparasite control agent of the present invention comprises at least one selected from the fused heterocyclic compounds of the present invention as an active ingredient. The fused heterocyclic compound of the present invention is excellent in the control effect of ectoparasites which harm animals.

The ectoparasites include mites, lice, fleas, mosquitoes, sand flies, and rickets.
Host animals to be treated with the agent for controlling ectoparasites of the present invention include companion animals such as dogs and cats; pet birds; domestic animals such as cattle, horses, pigs and sheep; warm-blooded animals such as poultry; Be Other examples include bees, stag beetles and beetles.
The ectoparasite infests in and on host animals, particularly warm-blooded animals. More specifically, it infests the back of the host animal, underarms, lower abdomen, inner crotch, etc., and ingests and ingests nutrient sources such as blood and dandruff from the animal.

  The ectoparasite control agent of the present invention can be applied by known veterinary methods (topical, oral, parenteral or subcutaneous administration). As a method thereof, a method of orally administering to an animal by tablet, capsule, feed mixing, etc .; a method of administering to an animal by immersion fluid, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal etc.); A method of topically administering an aqueous solution by spraying, pour-on, spot-on, etc .; extrinsic agent for controlling ectoparasites in resin; shaping the mixture into a suitable shape such as a collar, ear tags, etc. Method of wearing and local administration; and the like.

  Specific examples of ectoparasites that can be controlled by the ectoparasite control agent of the present invention are shown below.

(1) Mites (Acari)
Acarid (Dermanyssidae) tick, Macrocarpus snail (Macronys sidae) tick, Scutellaris mite (Laelapidae) mite, Acarididae (Varroidae) mite, Acarididae (Argasidae) mite, Acaridae (Ixodidae) tick (Psoroptidae) mites, Sarcoptidae mites, Trichodermid mites (Knemidokoptidae) ticks, Phytoseiids (Demodixidae) ticks, Trichodermids (Trombiculidae) ticks, insect pests such as stag beetles .
(2) Lice (Phthiraptera)
Lice of the lice of the family Haematopinidae, lice of the family Linognidae, lice of the family Leptocoridae (Menoponidae), the flies of the family Leptophyte family (Philopteridae), the flea of the family Trichodiidae (Trichodictidae).
(3) Flea eyes (Siphonaptera)
Human fleas (Pulicidae) fleas, such as the dog flea species (Ctenocephalides spp.), The dog flea (Ctenocephalides canis), the cat flea (Ctenocephalides felis);
A flea of Tungidae (Tungidae), a flea of Ceramophyllidae (Ceratophyllidae), and a flea of Leptopsyllidae.
(4) Hemiptera (Hemiptera).
(5) Mosquitoes of the order Culicidae of the order Diptera (Bulicidae), the flies of the family of Simuliidae, the pupa of the family Ceratopononidae, the flies of the family of Taberidae (Tabanidae), the flies of the family of housefly (Muscidae) Glossinidae Shepherd fly, Nikfly fruit fly (Nipidae), Flyfly (Hippoboscidae) fly, Calliphoridae fly (Calliphoridae) fly, Ophitriidae fly (Oestridae).

[Internal parasite control or control agent]
The endoparasite control or control agent of the present invention contains at least one selected from the fused heterocyclic compounds of the present invention as an active ingredient.

  The parasites targeted by the endoparasite control or control agent of the present invention infest the host animal, particularly warm-blooded animals and fish (endoparasites). Host animals effective as the endoparasite control or control agent of the present invention are humans, domestic mammals (eg, cows, horses, pigs, sheep, goats, etc.), experimental animals (eg, mice, rats, gerbils, etc.) , Companion animals (eg, hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), mammals in wild and zoos (eg, monkeys, foxes, deer, buffalo), poultry (eg, turkeys, ducks, chickens, quails) Warm-blooded animals such as geese, goose birds, pet birds (eg, pigeons, parrots, nine-legged birds, literary birds, parrots, cane pines, canaries, etc.); or fish such as salmon, trout, or Nishikigoi. By controlling and controlling parasites, parasite-mediated parasitic diseases can be prevented or treated.

The parasites to be controlled or eliminated include the following.
(1) Nematode (Dioctophymatidae) nematode (a) Nematode (Dioctophymatidae) nematode, such as, for example, Dioctophyma renale of Dioctophyma spp.
(B) Nematodes of Soboliphymatidae, such as Sobliphyme abei of Sobliphyme sp. (Soboliphyme spp.), Sobliphyme baturini.

(2) A nematode of the Trichoderma (Trichocephalida) (a) A Trichinella of the Trichinelladidae (Trichinellidae), for example, a Trichinella spiralis of a Trichinella sp. (Trichinella spp.);
(B) Helminthias (Trichuridae), for example, Capillaria annulata, Capillaria contorta, Hepatic capillary nematode (Capillaria annulata) of Capillaria spp. Capillaria hepatica), Capillaria perforans, Capillaria plica, Porcine nematode (Capillaria suis); Trichuris spp., Doguris (Trichuris vulpis), Cattle Worm (Trichuris discolor), rickets (Trichuris ovis), Trichuris scrjabini (Trichuris skrjabini), swine worm (Trichuris suis).

(3) Nematodes of the order Rhabditida Feces Nematoda of the family Nematode (Strongyloididae), for example, papillary nematodes (Strongyloides papillosus) of fecal nematode species (Strongyloides spp.), Cat feces Nematode (Strongyloides planiceps), Pig feces Nematode (Strongyloides ransomi), Pig feces Nematode (Strongyloides suis), Fecal nematode (Strongyloides stercoralis), American cat fecal nematode (Strongyloides tumefaciens), Rat fecal nematode (Strongyloides ratti) .

(4) Nematodes of the order Nematode of Strongylida (Strongylida), such as angilostoma species (Ancylostomatidae), for example, a Brazilian helminth (Ancylostoma braziliense), a dog helminth (Ancylostoma caninum) of a species of Ancylostoma spp. (Ancylostoma duodenale), Nematophagia (Ancylostoma tubaeforme); Uncinaria spenocephala's, Uncinaria stenocephala's (Uncinaria stenocephala); Benostomum spp. Bunostomum trigonocephalum).

(5) Nematodes of the order Nematode (Strongylida) (a) Nematodes of the family Nematode (Angiostrongylidae), for example, cat catworm (Aelurostrongylus abtrusus) of a species of the genus Nematoda (Aelurostrongylus spp.); Schistosoma species (Angiostrongylus spp.), Schistosoma japonicum (Angiostrongylus vasorum), Guangdong schistosomiasis (Angiostrongylus cantonesis);
(B) Nematodes of the Crenosomadidae family (eg Crenosoma spp.), Lung capillary nematodes (Crenosoma aerophila), fox lungworms (Crenosoma vulpis);
(C) Nematodes of Filaroides (Filaroididae), for example, canine lungworms (Filaroides hirthi) of Filaroides sp. (Filaroides spp.), Filaroides osleri (Filaroides)
osleri);
(D) Lungworms of the Lungworm family (Metastrongylidae), for example pig lungworm species (Metastrongylus spp.), Swine lungworm (Metastrongylus apri), Metastrongil asymmetrics (Metastrongylus asymmetricus), Metastrongil pudende techtus (Metastrongylus spri.) Metastrongylus pudendotectus), Metastrongils salmi (Metastrongylus salmi);
(E) Open worms of the family Syngamidae, for example, water bird lungworm (Cyathostoma bronchialis) of the species Cyathostoma spp .; Scripjabin of the genus Syngamus (Syngamus spp.) Syngamus skrjabinomorpha), chicken open wormworm (Syngamus trachea).

(6) Nematodes of the order of the genus Nematode (Molineidae) of the order Nematode (Strongylida), for example, Nematodirus filicollis of the species Nematodirus sp. (Nematodirus spp.), Nematodils spa Tiger (Nematodirus spathiger);
(B) Nematodes of the Dictyocaulidae family, such as, for example, Dictyocaulus filaria, Dictyocaulus viviparus of the Dictyocaulus spp.
(C) Nematodes of the Tortoiseriidae (Haemonchidae), such as the Tortoise gastropods (Haemonchus contortus) of the genus Haemonchus (Haemonchus spp.); Cattle Tortoises of the genus Mexistocirrus spp. (Mecistocirrus digitatus);
(D) A nematode of Haemonchidae (Haemonchidae), such as, for example, Ostertagia ostertagi, of a species of the genus Gastomies (Ostertagia spp.);
(E) A nematode of the family Heligmoneridae (Heligmonellidae), for example, a murine roundworm (Nippostrongylus braziliensis) of a species Nippotolongylus sp. (Nippostrongylus spp.);
(F) Nematodes of Trichostrongylidae, for example, Trichostrongylus spp., Trichostrongylus axei, Trichostrongylus colubriformis, Trichostrongylus spp. ), Trichostrongylus tenuis; of the Hyostronhis sp. (Hyostrongylus spp.), Hyostrongylus rubidus of the Genus Hyostrongylus spp .; Obeliscoides cuniculis of the Obeliscoides sp. ).

(7) Nematodes of the order of the order of the genus Strongylida (a) Nematodes of the Chabertiridae (Chabertiidae), for example sheep-reduced nematodes (Chabertia ovina) of the species Chabertia spp. Nodule (Oesophagostomum spl. Sp.), Nodule (Oesophagostomum brevicaudatum), Columbia Enteric Nodule (Oesophagostomum columbianum), Pork Nodule Oe Enteric nodule (Oesophagostomum maplestonei), Enteric nodule (pig) (Oesophagostomum quadrispinulatum), Bovine Intestine Nodule (Oesophagostomum radiatum), Goat Intestine Nodule (Oesophagostomum venulosum), Intestinal nodule (Warbler) (Oesophagostomum watanabei)
(B) Nematodes of the Porcine Nematode family (Stephanuridae), for example, the porcine nematode of the Stephanurus spp. (Stephanurus dentatus);
(C) C. elegans (Strongyllidae) nematodes, such as, for example, of the genus Streptomyces sp. (Strongylus spp.), Donkeys roundworm (Strongylus asini), roundworm (Strongylus edentatus), equid roundworm (Strongylus equinus) , Common roundworm (Strongylus vulgaris).

(8) Nematodes of the order Oxirida (Oxyryda) Nematodes of the family Oxirididae (Oxyuidae), for example, chimpanzees (Enterobius anthropopitheci) of the species Enterobius spp., Enterobius vermicularis; spp., Oxyuris equi; Passalurus spp., Rabbit helminth (Passalurus ambiguus).

(9) Ascaridida nematode (a) Nematode of Ascaridiidae, eg, Ascaridia galli of Ascaridia spp.
(B) A nematode of the family Ceteridae (Heterakidae), such as Heterakis beramporia of Heterakis spp., Heterakis beramporia, Heterakis brevispiculum, chicken ceria (Heterakis gallinarum) Heterakis pusilla, Heterakis putaustralis;
(C) A nematode of the family Anisakida (Anisakida), for example, Anisakis nematode (Anisakis simplex) of the species Anisakis spp.
(D) Nematodes of Ascarididae, such as, for example, Ascaris spp., Human Ascaris (Ascaris lumbricoides), Ascaris suum; Ascaris spum; (Parascaris equation);
(E) Nematodes of the Toxocaridae family (eg, Toxocara spp., Toxocara canis), Toxocara canis, Toxicara leonina, Toxicarasuum, Toxicara vitulorum (Toxocara vitulorum) ), Ascaris cat (Toxocara cati).

(10) A nematode of the Nematode of the Rotiferoid order (Spirurida) (a) A nematode of the Onchocercidae, such as, for example, Brugia malayi of the Brugia spp., Brugia pahangii (Brugia pahangi), Brugia patei; Dipetalonema sp. (Dipetalonema spp.), Dipetalonema reconditum (Dipetalonema reconditum); Dirofilaria sp. (Dirofilaria spp.), Dirofilaria (Dirofilaria) immitis; Filaria spp., Filaria oculi; Onchocerca spp., Onchocerca spp., Onchocerca cervicalis, Gibson Onchocerca gibsoni, Pharyngeal filamentous Insect (Onchocerca gutturosa);
(B) Nematodes of the Setariidae (Setariidae), for example, Setaria digitata, Setaria equina of the Setaria spp., Lipia papiliata (Setaria labiatopapillosa) , Marshal filaria (Setaria marshalli); Bancroft filaria (Wuchereria bancrofti) of Buchereria sp. (Wuchereria spp.);
(C) Nematodes of the family Filaridae (Filariidae), such as, for example, the multi-papillaris Parafilaria (Parafilaria multipapillosa) of the species Parafilaria spp .; Encystis (Stephanofilaria assamensis), Stefanophilalia dedoesi (Stephanofilaria dedoesi), Stefanophilalia caerii (Stephanofilaria kaeli), Okinawan flatworm (Stephanofilaria okinawaensis), Stefanofilaria stilisi (Stephanofilaria stilesi).

(11) Nematodes of the Nematode of the Rotifer (Spirurida) (a) Nematodes of the Genus Gnathostomatidae (Gnathostomatidae), for example, Gnathostoma doloresi of the Genus Gnathostoma sp. (Gnathostoma spp.) , Spiny jawworm (Gnathostoma spinigerum);
(B) Nematodes of the family Habronematidae (eg Habronema spp., Habronema majus, Habronema microstoma, Habronema muscae) Horse-tailed bug (Draschia megastoma) of the genus (Draschia spp.);
(C) Nematodes of the family Physalopteridae (Physalopteridae), for example, dog gastropods (Physaloptera canis) of the family of Physaloptera spp. Ferididis (Physaloperta felidis), Egyptian cat gastropod (Physaloptera gemina), Physaloptera papilloradiata (Physaloptera papilloradiata), Cat gastropod (Physaloptera praeputialis), Physioptera pseudopraerutialis (Physalopterae pseudopraerutialis), Geralciola (Physalaptera) rara), Physaloptera sibirica, Physaloptera vulpineus;
(D) Nematodes of the family Gongylonematidae, for example, beautiful esophagus (Gongylonema pulchrum) of the species Gongylonema spp.
(E) Nematodes of the family Spirocercidae (Spirocercidae), for example, the circular pig stomachworm (Ascarops strongylina) of the species Ascarops spp.
(F) Nematodes of Thelaziaceae (Thelaziidae), such as, for example, Thelazia callipaeda, Thelazia gulosa of Thelazi spp., Thelazia gulosa, Thelazia lacrymalis, Lodesia eyes Bug (Thelazia rhodesi), Scryabin Eyeworm (Thelazia skrjabini).

[Control agent for other harmful organisms]
In addition, the control effect of pests that have poisoned needles and venom, which cause damage to animals, pests that mediate various pathogens and pathogens, and pests that cause human discomfort (toxic pests, hygiene pests, unpleasant pests, etc.) Excellent.
Below, the example is shown.
(1) Bees of the Hymenoptera (Hymenoptera), bees of the Hymenoptera (Argidae), bees of the Hymenoptera (Cynipidae), wasps of the Hymenoptera (Diprionidae), Anes of the Antidae (Formicidae), bees of the Ariidae (Mutililidae) Wasp of the hornets (Vespidae).

(2) Other pest cockroaches (Blattodea), termites (termite), arachnids (Araneae), centipedes (cetipede), cuttlefish (millipede), crustaceans (Crustacea), and worms (Cimex lectularius).

[Formulation prescription]
Although some formulations of the pest control agent, insecticide or acaricide, ectoparasite control agent or endoparasite control or control agent of the present invention are shown, additives and addition rates should be limited to these examples. It is possible to make a wide range of changes. Parts in the formulation indicate parts by weight.

  The following shows formulations for agriculture and horticulture and for rice.

(Formulation 1: wettable powder)
40 parts of the fused heterocyclic compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfuric acid ester, and 3 parts of alkyl naphthalene sulfonate are uniformly mixed and finely ground to obtain a wettable powder of 40% active ingredient obtain.

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

(Formulation 3: granules)
5 parts of the condensed heterocyclic compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and finely ground to obtain particles of 0.5 to 1.0 mm in diameter Granulate into 5% active ingredient granules.

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

(Formulation 5: suspension agent)
10 parts of the fused heterocyclic compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 parts of xanthan gum and 73.8 parts of water are mixed, and the particle size is 3 Wet grinding to submicron size to obtain a suspension of 10% active ingredient.

  The formulation formulation of an ectoparasiticide, or an endoparasite control or repellent is shown below.

(Formulation 6: granules)
5 parts of the fused heterocyclic compound according to the invention are dissolved in an organic solvent to obtain a solution, the solution is sprayed on 94 parts of kaolin and 1 part of white carbon and then the solvent is evaporated under reduced pressure. Granules of this type can be mixed with animal feed.

(Formulation 7: Injection)
0.1 to 1 part of the fused heterocyclic compound of the present invention and 99 to 99.9 parts of peanut oil are uniformly mixed, and then filter-sterilized with a sterilizing filter.

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

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

(Formulation 10: Spray)
One part of the fused heterocyclic compound of the present invention, 10 parts of propylene glycol and 89 parts of isopropanol are uniformly mixed to obtain a spray.

  Next, compound examples will be shown to explain the present invention more specifically. However, the present invention is not limited at all by the following compound examples.

Example 1
2- (6- (ethylsulfonyl) -2- (trifluoromethyl) imidazo [1,2-a] pyridin-7-yl) -3-methyl-6- (trifluoromethyl) -3H-imidazo [4 ,. 5-b] pyridine [2- (6- (ethylsulfonyl) -2- (trifluoromethyl) imidazo [1,2-a] pyridine-7-yl) -3-methyl-6- (tri- fluoromethyl) -3H-imidazo [4 , 5-b] Pyridine] (Compound No. 4)

反応容器において２−クロロ−５−フルオロピリジン（２．０ｇ）をテトラヒドロフラン（６１ｍｌ）に溶解させ、該反応容器を窒素で置換し、その後−７０℃に冷却した。これにｎ−ブチルリチウム（２．６５Ｍ ｎ−ヘキサン溶液，７．０ｍｌ）を滴下し、−７０℃で３０分間撹拌した。これに砕いたドライアイス（適当量）を加え、−７０℃で３０分間撹拌した。得られた液を２M塩酸に注ぎ、ジエチルエーテルで抽出した。得られた有機層を無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた濃縮物をクロロホルムで洗浄することによって目的物１．１１ｇ（収率４２％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR（400 MHz, DMSO-d₆）: δ 8.63 （s, 1H）, 7.84 （s, 1H）. (Step 1) Synthesis of 2-chloro-5-fluoroisonicotinic acid [2-chloro-5-fluoroisonicotinic acid]

In a reaction vessel 2-chloro-5-fluoropyridine (2.0 g) was dissolved in tetrahydrofuran (61 ml) and the reaction vessel was flushed with nitrogen and then cooled to -70 ° C. To this was added n-butyllithium (2.65 M n-hexane solution, 7.0 ml) dropwise and stirred at -70 ° C for 30 minutes. Crushed dry ice (appropriate amount) was added to this and stirred at -70 ° C for 30 minutes. The resulting solution was poured into 2 M hydrochloric acid and extracted with diethyl ether. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the obtained concentrate was washed with chloroform to obtain 1.11 g (yield 42%) of the desired product.
The ¹ H-NMR of the desired product obtained is shown below.
¹ H-NMR (400 MHz, DMSO-d ₆ ): δ 8.63 (s, 1 H), 7.84 (s, 1 H).

２−クロロ−５−フルオロイソニコチン酸（０．８２ｇ）をピリジン（５．７ｍｌ）に溶解させ、室温で撹拌した。これにＮ²−メチル−５−（トリフルオロメチル）ピリジン−２，３−ジアミン（０．５０ｇ）、１−（３−ジメチルアミノプロピル）−３−エチルカルボジイミド塩酸塩（０．９８ｇ）、および１−ヒドロキシベンゾトリアゾール（０．０５８ｇ）を加え、６０℃で１８時間撹拌した。得られた液を飽和塩化アンモニウム水溶液に注ぎ、クロロホルムで抽出した。得られた有機層を無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた濃縮物をシリカゲルカラムクロマトグラフィーで精製することによって目的物０．９１ｇ（収率９２％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR（400 MHz, CDCl₃）: δ 8.49 （d, 1H）, 8.42 （s, 1H）, 8.03 （d, 1H）, 7.93 （d, 1H）, 7.73 （s, 1H）, 4.90 （s, 1H）, 3.07 （s, 3H）. (Step 2) 2-chloro-5-fluoro-N- (2- (methylamino) -5- (trifluoromethyl) pyridin-3-yl) isonicotinamide [2-chloro-5-fluoro-N- ( Synthesis of 2- (methylamino) -5- (trifluoromethyl) pyridine-3-yl) isonicotinamide

2-Chloro-5-fluoroisonicotinic acid (0.82 g) was dissolved in pyridine (5.7 ml) and stirred at room temperature. These were N ² -methyl-5- (trifluoromethyl) pyridine-2,3-diamine (0.50 g), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (0.98 g), and 1-hydroxybenzotriazole (0.058 g) was added and stirred at 60 ° C. for 18 hours. The resulting solution was poured into saturated aqueous ammonium chloride solution and extracted with chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the obtained concentrate was purified by silica gel column chromatography to obtain 0.91 g (yield 92%) of the desired product.
The ¹ H-NMR of the desired product obtained is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 8.49 (d, 1 H), 8.42 (s, 1 H), 8.03 (d, 1 H), 7. 93 (d, 1 H), 7.73 (s, 1 H), 4.90 (4 s, 1 H), 3.07 (s, 3 H).

２−クロロ−５−フルオロ−Ｎ−（２−（メチルアミノ）−５−（トリフルオロメチル）ピリジン−３−イル）イソニコチンアミド（０．９０ｇ）を酢酸（１０ｍｌ）に溶解させ、加熱還流下で７時間撹拌した。得られた液を室温まで放冷し、溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物０．６６ｇ（収率７７％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR（400 MHz, CDCl₃）: δ 8.79 （d, 1H）, 8.53 （s, 1H）, 8.38 （d, 1H）, 7.76 （d, 1H）, 3.95 （s, 3H）. (Step 3) 2- (2-chloro-5-fluoropyridin-4-yl) -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine [2- (2-) Synthesis of chloro-5-fluoropyridine-4-yl) -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine]

Dissolve 2-chloro-5-fluoro-N- (2- (methylamino) -5- (trifluoromethyl) pyridin-3-yl) isonicotinamide (0.90 g) in acetic acid (10 ml) and heat to reflux It stirred below for 7 hours. The obtained solution was allowed to cool to room temperature, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.66 g (yield 77%) of the desired product.
The ¹ H-NMR of the desired product obtained is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 8.79 (d, 1 H), 8.53 (s, 1 H), 8.38 (d, 1 H), 7.76 (d, 1 H), 3.95 (s, 3 H).

２−（２−クロロ−５−フルオロピリジン−４−イル）−３−メチル−６−（トリフルオロメチル）−３Ｈ−イミダゾ［４，５−ｂ］ピリジン（７．７ｇ）をＮ，Ｎ−ジメチルホルムアミド（１１６ｍｌ）とテトラヒドロフラン（２３３ｍｌ）の混合溶媒に溶解させ、室温で撹拌した。これにエチルメルカプタンナトリウム（８０％，２．５７ｇ）を加え、室温で３．５時間撹拌した。得られた液を水に注ぎ、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた濃縮物を酢酸エチルとヘキサンの混合溶媒で結晶化させることによって目的物３．７５ｇ（収率４３％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR（400 MHz, CDCl₃）: δ 8.77 （d, 1H）, 8.53 （s, 1H）, 8.36 （d, 1H）, 7.46 （s, 1H）, 3.83 （s, 3H）, 2.89 （q, 2H）, 1.25 （t, 3H）. (Step 4) 2- (2-chloro-5- (ethylthio) pyridin-4-yl) -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine [2- ( Synthesis of 2-chloro-5- (ethylthio) pyridine-4-yl) -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine]

2- (2-chloro-5-fluoropyridin-4-yl) -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine (7.7 g) was N, N- It was dissolved in a mixed solvent of dimethylformamide (116 ml) and tetrahydrofuran (233 ml) and stirred at room temperature. Ethyl mercaptan sodium (80%, 2.57 g) was added to this, and it stirred at room temperature for 3.5 hours. The resulting solution was poured into water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the obtained concentrate was crystallized with a mixed solvent of ethyl acetate and hexane to obtain 3.75 g (yield 43%) of the desired product.
The ¹ H-NMR of the desired product obtained is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 8.77 (d, 1 H), 8.53 (s, 1 H), 8.36 (d, 1 H), 7.46 (s, 1 H), 3.83 (s, 3 H), 2.89 (2. q, 2H), 1.25 (t, 3H).

２−（２−クロロ−５−（エチルチオ）ピリジン−４−イル）−３−メチル−６−（トリフルオロメチル）−３Ｈ−イミダゾ［４，５−ｂ］ピリジン（４００ｍｇ）をジクロロメタン（１０ｍｌ）に溶解させ、０℃で撹拌した。これにメタクロロ過安息香酸（７０％，５８０ｍｇ）を加え、室温で３時間撹拌した。得られた液を飽和炭酸水素ナトリウム水溶液と飽和チオ硫酸ナトリウム水溶液の混合溶液へ注ぎ、クロロホルムで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、２−（２−クロロ−５−（エチルスルホニル）ピリジン−４−イル）−３−メチル−６−（トリフルオロメチル）−３Ｈ−イミダゾ［４，５−ｂ］ピリジンを含む濃縮物を得た。 (Step 5) 2- (2-chloro-5- (ethylsulfonyl) pyridin-4-yl) -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine [2- Synthesis of (2-chloro-5- (ethylsulfonyl) pyridine-4-yl) -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine]

2- (2-chloro-5- (ethylthio) pyridin-4-yl) -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine (400 mg) in dichloromethane (10 ml) And stirred at 0.degree. To this was added metachloroperbenzoic acid (70%, 580 mg) and stirred at room temperature for 3 hours. The obtained solution was poured into a mixed solution of saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution, and extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure and 2- (2-chloro-5- (ethylsulfonyl) pyridin-4-yl) -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine A concentrate containing was obtained.

工程５で得られた２−（２−クロロ−５−（エチルスルホニル）ピリジン−４−イル）−３−メチル−６−（トリフルオロメチル）−３Ｈ−イミダゾ［４，５−ｂ］ピリジンを含む濃縮物をＮ，Ｎ−ジメチルホルムアミド（５ｍｌ）に溶解させ、０℃で撹拌した。これに４−メトキシベンジルアミン（１６３ｍｇ）、および炭酸セシウム（４５６ｍｇ）を添加し、室温で一晩撹拌した。得られた液を水に注ぎ、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、５−（エチルスルホニル）−N−（４−メトキシベンジル）−４−（３−メチル−６−（トリフルオロメチル）−３Ｈ−イミダゾ［４，５−ｂ］ピリジン−２−イル）ピリジン−２−アミンを含む濃縮物を得た。 (Step 6) 5- (ethylsulfonyl) -N- (4-methoxybenzyl) -4- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl ) Pyrimidin-2-amine [5- (ethylsulfonyl) -N- (4-methoxybenzyl) -4- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine-2-yl) Synthesis of [pyridin-2-amine]

2- (2-chloro-5- (ethylsulfonyl) pyridin-4-yl) -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine obtained in step 5 The concentrate containing was dissolved in N, N-dimethylformamide (5 ml) and stirred at 0 ° C. To this was added 4-methoxybenzylamine (163 mg) and cesium carbonate (456 mg) and stirred at room temperature overnight. The resulting solution was poured into water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, and 5- (ethylsulfonyl) -N- (4-methoxybenzyl) -4- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine- A concentrate containing 2-yl) pyridin-2-amine was obtained.

工程６で得られた５−（エチルスルホニル）−N−（４−メトキシベンジル）−４−（３−メチル−６−（トリフルオロメチル）−３Ｈ−イミダゾ［４，５−ｂ］ピリジン−２−イル）ピリジン−２−アミンを含む濃縮物をトリフルオロ酢酸（５ｍｌ）に溶解させ、加熱還流下で３時間撹拌した。得られた液を室温まで放冷し、溶媒を減圧留去した。残渣を飽和炭酸水素ナトリウム水溶液で中和した。その後、クロロホルムで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた濃縮物をシリカゲルカラムクロマトグラフィーで精製することによって目的物３００ｍｇ（収率７２％，３工程）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR（400 MHz, CDCl₃）: δ 8.78 （1H, s）, 8.74 （1H, d）, 8.28 （1H, d）, 6.53 （1H, s）, 5.29 （2H, s）, 3.78 （3H, s）, 3.29 （2H, q）, 1.27 （3H, t）. (Step 7) 5- (ethylsulfonyl) -4- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl) pyridin-2-amine [5- Synthesis of (ethylsulfonyl) -4- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine-2-yl) pyridine-2-amine]

5- (ethylsulfonyl) -N- (4-methoxybenzyl) -4- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine-2 obtained in Step 6 The concentrate containing (-yl) pyridin-2-amine was dissolved in trifluoroacetic acid (5 ml) and stirred under heating reflux for 3 hours. The resulting solution was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was neutralized with saturated aqueous sodium hydrogen carbonate solution. Then, it extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the obtained concentrate was purified by silica gel column chromatography to obtain 300 mg of the desired product (yield 72%, 3 steps).
The ¹ H-NMR of the desired product obtained is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 8.78 (1 H, s), 8. 74 (1 H, d), 8. 28 (1 H, d), 6.53 (1 H, s), 5. 29 (2 H, s), 3. 78 (5 3H, s), 3.29 (2H, q), 1.27 (3H, t).

マイクロウェーブ合成用反応容器に５−（エチルスルホニル）−４−（３−メチル−６−（トリフルオロメチル）−３Ｈ−イミダゾ［４，５−ｂ］ピリジン−２−イル）ピリジン−２−アミン（８０ｍｇ）と３−ブロモ−１，１，１−トリフルオロアセトン（４００ｍｇ）とアセトン（１ｍｌ）を加え、マイクロウェーブを照射し、１２０℃で２時間反応させた。得られた液を室温まで放冷し、溶媒を減圧留去した。残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物２６ｍｇ（収率２６％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR（400 MHz, CDCl₃）: δ 9.10 （1H, s）, 8.79 （1H, d）, 8.32 （1H, d）, 8.21 （1H, s）, 7.87 （1H, s）, 3.82 （3H, s）, 3.62 （2H, q）, 1.34 （3H, t）. (Step 8) 2- (6- (ethylsulfonyl) -2- (trifluoromethyl) imidazo [1,2-a] pyridin-7-yl) -3-methyl-6- (trifluoromethyl) -3H- Imidazo [4,5-b] pyridine [2- (6- (ethylsulfonyl) -2- (trifluoromethyl) imidazo [1,2-a] pyridine-7-yl) -3-methyl-6- (trifluoromethyl) -3H Synthesis of -imidazo [4,5-b] pyridine]

5- (ethylsulfonyl) -4- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl) pyridin-2-amine in a reaction vessel for microwave synthesis (80 mg), 3-bromo-1,1,1-trifluoroacetone (400 mg) and acetone (1 ml) were added, and the mixture was irradiated with microwaves and reacted at 120 ° C. for 2 hours. The resulting solution was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 26 mg (yield 26%) of the desired product.
The ¹ H-NMR of the desired product obtained is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 9.10 (1 H, s), 8. 79 (1 H, d), 8.32 (1 H, d), 8.21 (1 H, s), 7.87 (1 H, s), 3.82 ( 3H, s), 3.62 (2H, q), 1.34 (3H, t).

  Examples of the fused heterocyclic compounds of the present invention prepared in the same manner as in the above examples are shown in Table 1. Physical property data of the compound was entered in the "physical properties" column. As physical property data, properties and melting points (mp) were described.

[Biological test]
The following test examples show that the fused heterocyclic compound of the present invention is useful as an active ingredient of a pest control agent. "Parts" is by weight.

(Preparation of emulsion for test)
An emulsion (I) of 5% active ingredient was prepared by mixing and dissolving 5 parts of the condensed heterocyclic compound of the present invention, 93.6 parts of dimethylformamide and 1.4 parts of polyoxyethylene alkyl aryl ether.
As a control, Emulsion (II) was prepared by mixing and dissolving 93.6 parts of dimethylformamide and 1.4 parts of polyoxyethylene alkyl aryl ether.

The insecticidal rate and the control rate were calculated by the following formula.
Insecticidal rate (%) = (number of dead insects / number of tested insects) x 100

(Test Example 1) Efficacy Test on Millet Fructus 0.8 g of a commercially available artificial feed (Insector LFS, manufactured by Nippon Agro-Industrial Co., Ltd.) and 1 μl of emulsion (I) were mixed well to obtain a test feed.
The test feed was packed in a plastic test container (1.4 ml in volume) at 0.2 g per treatment area. Then, two chicks for 2nd instar larvae were inoculated per treatment area. The test vessel was sealed with a plastic lid. It was placed in a constant temperature room at 25 ° C., and on the fifth day, the insecticidal rate and food consumption were examined. The test was performed in duplicate.

  As a control, the insecticidal rate and food consumption were examined in the same manner as in Test Example 1 except that the emulsion (I) was changed to the emulsion (II).

  The compounds No. 2, 3 and 4 were tested for efficacy against the carob. Each compound had an insecticidal rate of 100% or an intake of 10% or less of that in the control relative to the ascidian. It is understood that the fused heterocyclic compound of the present invention is effective to the carob tree.

(Test Example 2) Efficacy test against diamond moth Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. The cabbage leaves were immersed in the diluted solution for 30 seconds. The cabbage leaves were placed in a petri dish, and five P. moth larvae were released. The petri dish was placed in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 60%. When 3 days have passed since the helminth, life and death judgments were made and the insecticidal rate was calculated. The test was performed in duplicate.

  The compound No. 4 was tested for efficacy against diamondback moth. Both compounds showed an insecticidal rate of 80% or more against diamondback moth.

(Test Example 3) Efficacy test against Klebsi bean leafhopper Emulsion (I) was diluted with water to a concentration of 125 ppm of the compound of the present invention to prepare a test solution. The medicinal solution for the test was sprayed on a seedling of Qing ginseng planted in a 3-inch pot (7th true leaf development period) and air-dried. Thereafter, the bok choy seedling was placed in a plastic cup, and 10 adults of Phyllotreta striolata were released. They were stored in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 65%, and after 7 days from the helminth, their life and death were judged, and the insecticidal rate was calculated. The test was performed in duplicate.

  The compound No. 2, 3 and 4 were tested for efficacy against Kishinomihamushi. Each of the compounds showed an insecticidal rate of 80% or more against K. ginseng.

Test Example 4 Efficacy Test Against Bean Aphid A cowpea was raised in a 3 inch pot, and bean aphid nymphs were inoculated on primary leaves. The emulsion (I) was diluted with water to 125 ppm of the compound of the present invention, and the diluted solution was sprayed on a cowpea which is infested with aphid nymphs. The cowpea was placed in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 60%. After 4 days from the spraying, the aphids were alive and dead, and the insecticidal rate was calculated. The test was performed in duplicate.

  The compound No. 4 was tested for efficacy against bean aphid. Both compounds showed an insecticidal rate of 80% or more against bean aphid.

Test Example 5 Efficacy Test for Tobiirounka Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Rice seedlings were immersed in the diluted solution for 30 seconds and allowed to air dry. After that, it was put in a plastic case, and five 2nd instar larvae of Tobilirounka were released. They were stored in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 65%, and after 7 days from inoculation, their viability was judged to calculate an insecticidal rate. The test was performed in duplicate.

  The compound No. 2, 3 and 4 were tested for efficacy against Tobiirounka. All compounds showed an insecticidal rate of 80% or more.

  The condensed heterocyclic compounds of the present invention, including compounds that could not be exemplified, are pests, since those selected at random among the fused heterocyclic compounds of the present invention exhibit the effects as described above. It can be understood that it is a compound having an effect such as control, in particular acaricidal, insecticidal and the like. In addition, it can be understood that the compound has an effect also on parasites harmful to humans and animals such as ectoparasites.

Claims (5)

The compound or its salt represented by a formula (I).

(In the formula (I),
A ¹ is N or CH,
A ² is N or CR ² ,
R ¹ is a C1-6 alkyl group,
R ² and R ³ each independently represent a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, Substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C1-6 alkoxycarbonyl group, formyl group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted Or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-8 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted 3 to 6 membered heterocyclyl group, substituted or unsubstituted C 6-10 aryloxy group, substituted or unsubstituted 5-6 membered heteroaryloxy group, substituted Or unsubstituted amino group, substituted or unsubstituted aminocarbonyl group, substituted or unsubstituted hydrazinyl group, nitro group, cyano group or halogeno group, and Q is a group represented by formula (Q-1) It is.

(In the formula (Q-1), * represents a bonding position,
R ⁵ is C1~6 alkyl group and R ⁶ is a substituted or unsubstituted C1~6 alkyl group, a substituted or unsubstituted C1~6 alkoxy group, a substituted or unsubstituted C1~6 alkylthio group, Substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted 5-6 membered heteroaryl group, nitro group A cyano group, a halogeno group, a trifluoromethylsulfonyloxy group or a pentafluorosulfanyl group. )))   A pest control agent containing, as an active ingredient, at least one selected from the group consisting of the compound according to claim 1 and a salt thereof.   An insecticidal or acaricidal agent which contains at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.   An ectoparasiticide containing at least one member selected from the group consisting of the compound according to claim 1 and salts thereof as an active ingredient.   The endoparasite control or control agent which contains at least 1 chosen from the group which consists of a compound of Claim 1, and those salts as an active ingredient.