WO2019022002A1 - 1-heterodiene compound and pest control agent - Google Patents

Abstract

A compound represented by formula (I) or a salt thereof. (In formula (I), Q1 represents an (un)substituted C6-10 aryl group; Q2 represents an (un)substituted C1-6 alkyl group, an (un)substituted C6-10 aryl group, or a five- to ten-membered, (un)substituted heteroaryl group; R1 represents a hydrogen atom; A represents an oxygen or sulfur atom; B represents an oxygen or sulfur atom; D represents an (un)substituted methylene group, a carbonyl group, or an oxygen atom; and E represents an (un)substituted benzene ring.)

Description

1-heterodiene compound and pest control agent

The present invention relates to 1-heterodiene compounds and pest control agents. More specifically, the present invention provides a 1-heterodiene compound which has excellent insecticidal and / or acaricidal activity, is excellent in safety, and can be industrially advantageously synthesized, and a pest control agent containing this as an active ingredient It relates to the agent.
Priority is claimed on Japanese Patent Application No. 201-144806, filed July 26, 2017, the content of which is incorporated herein by reference.

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.

WO2010 / 070910A

An object of the present invention is to provide a 1-heterodiene compound which is excellent in pest control activity, in particular, insecticidal activity and / or acaricidal activity, is excellent in safety, and can be industrially advantageously synthesized. Another object of the present invention is to provide a pest control agent, an insecticidal or acaricidal agent, an ectoparasite control agent, or a pesticidal composition containing a 1-heterodiene compound as an active ingredient.

As a result of examining in order to solve the above-mentioned subject, it came to complete the present invention including the following forms.
[1] A compound represented by the formula (I) or a salt thereof.

Wherein (I), Q ¹ represents a substituted or unsubstituted C6 ~ 10 aryl group, Q ² represents a substituted or unsubstituted C1 ~ 6 alkyl group, a substituted or unsubstituted C6 ~ 10 aryl group, or, R ⁵ represents a hydrogen atom, A represents an oxygen atom or a sulfur atom, B represents an oxygen atom or a sulfur atom, and D represents a substituted or unsubstituted 5- to 10-membered heteroaryl group. Or E represents an unsubstituted methylene group, a carbonyl group, or an oxygen atom, and E represents a substituted or unsubstituted benzene ring.

[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 which comprises at least one member selected from the group consisting of the compounds described in the above [1] and salts thereof as an active ingredient.

[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 agent for preventing the adhesion of a pest to a fishing net or a ship bottom, which comprises as an active ingredient at least one member selected from the group consisting of the compounds according to the above [1] and salts thereof.

The 1-heterodiene compound of the present invention can control pests that cause agricultural and hygiene problems. In particular, agricultural pests and mites can be effectively controlled at lower concentrations. Furthermore, it can effectively control ectoparasites that harm humans and animals. Furthermore, adhesion of adhering pests such as barnacles can be prevented.

[1-heterodiene (1-heterodiene) Compound]
The 1-heterodiene 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 "C1-6" indicate that the number of carbon atoms of the 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, etc. 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 C2-6 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 C 3-8 cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cuvanyl group;
A C 6-10 aryl group 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 to 6 membered heterocyclyl C 1-6 alkyl group;

Hydroxyl group;
C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and the like;
A C 2-6 alkenyloxy group such as a vinyloxy group, an allyloxy group, a propenyloxy group, a butenyloxy group;
A C2-6 alkynyloxy group such as ethynyloxy group, propargyloxy group;
A C 6-10 aryloxy group such as phenoxy group and naphthoxy group;
C 6-10 aryl C 1-6 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;
A C1-6 alkylcarbonyl group such as an acetyl group and a propionyl group;
Formyloxy group;
A C1-6 alkylcarbonyloxy group such as an acetyloxy group, a propionyloxy group and the like;
A C 6-10 arylcarbonyl group 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 alkoxycarbonyloxy groups such as methoxycarbonyloxy group, ethoxycarbonyloxy 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;
A C 1-6 haloalkyl group 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;
C2-6 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;
C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group, 3-bromobutenyloxy group;
C 1-6 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 group, naphthylamino group;
C 6-10 aryl C 1-6 alkylamino groups such as benzylamino group, phenethylamino group and the like;
Formylamino group;
A C 1-6 alkylcarbonylamino group such as an acetylamino group, a propanoylamino group, a butyrylamino group, an i-propylcarbonylamino group;
A C 1-6 alkoxycarbonylamino group 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;
A C 1-6 alkyl substituted aminocarbonyloxy group such as ethylaminocarbonyloxy group, dimethylaminocarbonyloxy group and the like;

Mercapto group;
A C1-6 alkylthio group such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group and the like;
A C 1-6 haloalkylthio group such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group;
A C 6-10 arylthio group such as phenylthio group and naphthylthio group;
5- to 6-membered heteroarylthio groups such as thiazolylthio group, pyridylthio group and the like;

C1-6 alkylsulfinyl groups such as methylsulfinyl, ethylsulfinyl and t-butylsulfinyl;
A C 1-6 haloalkylsulfinyl group such as trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group;
A C 6-10 arylsulfinyl group such as a phenylsulfinyl group;
5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl group, pyridylsulfinyl group and the like;

A C 1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group and the like;
A C 1-6 haloalkylsulfonyl group such as a trifluoromethylsulfonyl group, a 2,2,2-trifluoroethylsulfonyl group;
A C 6-10 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 group such as methylsulfonyloxy group, ethylsulfonyloxy group, t-butylsulfonyloxy group and the like;
A C 1-6 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 triphenyl silyl group;
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. As the “substituent” in that case, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, a nitro group and the like can be mentioned.

In addition, the above-mentioned "3 to 6-membered heterocyclyl group" contains 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as ring constituent 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, a 5 to 6-membered partially unsaturated heterocyclyl group and the like.

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

[Q ¹ ]
Q ¹ represents a substituted or unsubstituted C6-10 aryl group.
Examples of the “C 6-10 aryl group” in Q ¹ include a phenyl group and a naphthyl group. Of these, phenyl is preferred.

The substituent on the “C 6-10 aryl group” in Q ¹ is preferably a halogeno group such as fluoro, chloro, bromo or iodo; methyl, ethyl, n-propyl or i-propyl C 1-6 alkyl group such as n-butyl group, s-butyl group, i-butyl group, t-butyl group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group And C1-6 alkoxy groups such as s-butoxy group, i-butoxy group and t-butoxy group; C1-6 haloalkyl groups such as 2-chloro-n-propyl group, 2,3-dichlorobutyl group and trifluoromethyl group Group; C1-6 haloalkoxy group such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group etc .; cyano group; nitro group; And xy groups. Among them, fluoro, halogeno such as chloro, C1-6 alkyl such as methyl, C1-6 alkoxy such as methoxy, C1-6 haloalkyl such as trifluoromethyl, methylenedioxy Is preferred.

[Q ² ]
Q ² represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 10-membered heteroaryl group. Among these, a substituted or unsubstituted C6-10 aryl group and a substituted or unsubstituted 5-10 membered heteroaryl group are preferable.

"C1 ~ 6 alkyl group" in Q ² are may be linear, may be branched as long as three or more carbon atoms. As the alkyl group, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group And i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like. Of these, n-pentyl is preferred.

As specific examples of "C1-6 alkyl group having a substituent",
Fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trifluoro Ethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1 -C1-6 haloalkyl group such as -trifluoromethylethyl group, perfluoropropan-2-yl group, (perfluorobutyl) methyl group, perfluorohexyl group, perchlorohexyl group, 2,4,6-trichlorohexyl group ;

Hydroxy C 1-6 alkyl groups such as hydroxymethyl group, hydroxyethyl group;
C1 to C4 such as methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group and the like 6 alkoxy C1-6 alkyl groups;
C6-10 aryl C1-6 alkyl groups such as benzyl group, phenethyl group and the like;
And C3-8 cycloalkyl C1-6 alkyl groups such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, 2-cyclooctylethyl group and the like. Among these, C1-6 haloalkyl groups such as (perfluorobutyl) methyl group are preferable.

The substituent on the "C1-6 alkyl group" for Q ² 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, an i-propoxy group And C1-6 alkoxy groups such as n-butoxy, s-butoxy, i-butoxy and t-butoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy and the like And C1-6 haloalkoxy groups; cyano groups; Among these, halogeno groups such as fluoro groups are preferable.

Examples of the “C 6-10 aryl group” in Q ² include the same as those specifically exemplified in Q ¹ .
As "5- to 10-membered heteroaryl group" in Q ^2, a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group Member, 5-membered heteroaryl group such as tetrazolyl group, 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, etc. indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, indazolyl group, benzoimidazolyl group -Membered heteroaryl group such as a group, benzoxazolyl group, benzoisoxazoolyl group, benzothiazolyl group, benzisothiazolyl group; quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl Group, quinazolinyl group, 10-membered heteroaryl group, such as Kinokisaniru group; and the like. Among these, 6-membered heteroaryl groups such as pyridyl and pyrimidinyl are preferable.

Examples of substituents on the “C 6-10 aryl group” in Q ² include the same as those specifically exemplified in Q ¹ above.
Examples of the substituent on the “5 to 10-membered heteroaryl group” in Q ² include the same as those specifically exemplified in Q ¹ above.

[R ¹ ]
R ¹ represents a hydrogen atom.

[A, B]
A represents an oxygen atom or a sulfur atom. B represents an oxygen atom or a sulfur atom, preferably a sulfur atom.

[D]
D represents a substituted or unsubstituted methylene group, a carbonyl group or an oxygen atom. Among these, a substituted or unsubstituted methylene group is preferable.
The substituent on the "methylene group" in D is, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, etc. And C1-6 alkyl groups can be mentioned. Of these, methyl is preferred.

[E]
E represents a substituted or unsubstituted benzene ring.
The substituent on the "benzene ring" in E is preferably a halogeno group such as fluoro, chloro, bromo or iodo; methyl, ethyl, n-propyl, i-propyl, n-butyl C1-C6 alkyl group such as s-butyl group, i-butyl group and t-butyl group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group C1-C6 alkoxy groups such as i-butoxy group and t-butoxy group; C1-6 haloalkyl groups such as 2-chloro-n-propyl group, 2,3-dichlorobutyl group and trifluoromethyl group; 2- And C 1-6 haloalkoxy groups such as chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, etc .; cyano group; nitro group; Among these, fluoro groups, halogeno groups such as chloro groups, and C1-6 alkyl groups such as methyl groups are preferable.

The crossed carbon-carbon double bond in the formula (I) has stereoisomerism due to the carbon-carbon double bond in E form, Z form, or a mixture of E form and Z form, or stereoisomerism Indicates that is not specified. In the present invention, examples of the stereoisomer include a compound represented by Formula (I-1) or a compound represented by Formula (I-2). In formulas (I-1) and (I-2), Q ¹ , Q ² , A, B, D, E, and R ¹ have the same meanings as in formula (I).

Among the above, preferred is a compound having a steric structure represented by the formula (I-1). That is, the carbon-carbon double bond moiety is preferably a compound which is an E-form.

The 1-heterodiene compound of the present invention is preferably a compound represented by the formula (Ia) shown below (hereinafter sometimes referred to as compound (I)) or a salt of the compound (Ia). The compound represented by the formula (Ia) is a compound in which B is a sulfur atom, and D is a substituted or unsubstituted methylene group and is in an E form.
Here, Q ¹ , Q ² and A have the same meaning as those in formula (I). R ^a represents a hydrogen atom or a C1-6 alkyl group. X represents a halogeno group, a C1-6 alkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, a cyano group or a nitro group, and a halogeno group, a C1-6 alkyl group Is preferred. n is an integer of 0 to 4, preferably 0 or 1.

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; and salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine and hydrazine.

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) can be obtained by a known production method described in Examples and the like. In addition, the salt of compound (I) can be obtained from compound (I) by a known method.

The 1-heterodiene compound of the present invention (hereinafter referred to as the present compound) is excellent in the control effect of various agricultural pests and pests such as mites which affect the growth of plants.
In addition, the compound of the present invention is a highly safe substance because it has low phytotoxicity to crops and low toxicity 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 compounds of the present invention show excellent control effects not only on susceptible lines, but also on pests of various resistant lines, and also on mites of acaricide-resistant lines.

The compounds of the present invention are excellent in the control effect of ectoparasites that cause harm to 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 ectoparasites or an anti-adherent agent of adherent pests.

In addition, the compound of the present invention shows efficacy at all developmental stages of the organism to be controlled, and exhibits excellent control effect on, for example, ticks, eggs such as insects, nymphs, larvae, moths and adults.

[Pest control agent, insecticide or acaricide]
The pest control agent, or insecticidal or acaricidal agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the pest control agent of the present invention, or the insecticidal or acaricidal agent is not particularly limited as long as the pest, agricultural pest or mite controlling effect is exhibited.

The pest control agent of the present invention, or an insecticidal or acaricidal agent, is grains, vegetables, root vegetables, potatoes, florets, fruits, house plants, tea, coffee, trees such as cocoa, grasses; It is preferable to use for plants such as turf; cotton.
For application to plants, the pest control agent, or insecticidal or acaricidal agent of the present invention is any of leaves, stems, handles, flowers, buds, fruits, seeds, sprouts, roots, tubers, tubers, shoots, cuttings, etc. It may be used at the site of
Also, the pest control agent, or insecticidal or acaricidal agent of the present invention is not particularly limited by the species of plant to which it is applied. Examples of the plant species include original species, varieties, improved varieties, cultivars, mutants, hybrids, genetically modified organisms (GMO) and the like.

The pest control 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 pest control agent of the present invention are shown below.

(1) A butterfly of the order Lepidopteran (Lepidoptera) or a moth (a) a moth of the family Arctiidae, such as Hyphantria cunea, 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 leafminer moth (Diaphania nitidalis); No. 1 (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), azukinomeiga (Ostrinia scapulalis); others, Chiropodella moth (Cnaphalocrocis medinalis), Monocoma calamari gobetiles veil Diatraea grandiosella), Glyphodes pyloalis, Hyalunella (Hellula undalis), Shibatoga (Parapediasia teterrella);
(E) moths of the family Gelechiidae, such as, for example, immature bug (Helcystogramma triannulella), cotton bedbug (Pectinophora gossypiella), potato leafhopper (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 Lacasiocampidae (Lasiocampidae), such as Malacosoma neustria;
(J) moths of the family Lymantriidae, for example, of the species Lymantria spp., Lymantria dispar, Lymantria monacha; Other, Euproctis pseudoconspersa, Orgyia thyellina);

(K) moths of the family Molyrigidae (Lyonetidae), such as, for example, Lyonetia clerkella, of the species Lionetia sp. (Lyonetia spp.), Glymone Haemoglyca (Lyonetia prunifoliella malinella);
(L) A moth of Noctidae (eg, Spodoptera spp.), Spodoptera depravata, Southern armyworm (Spodoptera eridania), Spodoptera exigua, Spodoptera frugiperda ), African Spurge (Spodoptera littoralis), Spodoptera litura; eg, Autographa spp., Autographa gamma, Autographa nigrisigna; eg, Agrotis spp. (Agrotis spp.) ), Agrotis ipsilon, Agrotis segetum; eg Helicoverpa spp., Helicoverpa armigera, Helicoverpa assulta, cotton ball worm (Helicoverpa zea); Cottontail of Heliothis sp. (Heliothis spp.) Other moths (Heliothis armigera), fake American tobacco moth (Heliothis virescens); Other, Aedia leucomames, Citnoplusia agnata, Eudocima tyrannus, ト ウ br Mamestra brassica, White-tailed pokemon (Naranga aenescens), Japanese pine moth (Panolis japonica), Western-tailed snail (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 Archips sp. (Archips spp. Of the apple snail (Archips breviplicanus), midarek syllabary (Archips fuscocupreanus); other, the rhubarb (Choristoneura fumiferana), the codling moth (Cydia pomonella), the grape hosohamaki (Eupoecilia ambiguella), the nasi himi ), Chamon (Homona magnanima), bean legume (Leguminivora glycinivorella), scallop (Lobesia botrana), green-spotted moth (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 flower thrips (Frankliniella intonsa), the leaf thrush (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, the night-wing plant (Laodelphax striatella), the black-footed planthopper (Nilaparvata lugens), the black-footed planthopper (Perkinsiella saccharicida), the white-tailed deer (Sogatella furcifera).

(B) Cervix suborder (Clypeorrhyncha)
(A) Of the leafhopper family (Cicadellidae), for example, of the Empoasca spp., The potato leafhopper (Empoasca fabae), the leafhopper leafhopper (Empoasca nipponica), the leafhopper leafhopper (Empoasca onukii), 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) For example, the bug of the bug of the family Lygaeidae (Lygaeidae) (Blissus)
leucopterus), anchovy bug (Cavelerius saccharivorus), and a dipper bug (Togo hemipterus);
(D) For example, black-tailed snail (Halticus insularis), snail's snail (Lygus lineolaris), cotton-free hopper (Psuedatomoscelis seriatus), scutellaris (Steodema sibiricum), red-tailed snail (Stenotus rubibitus) ), Trichonotylus caelestialium;

(E) Of the Pentatomidae (Pentatomidae), for example, of the Nezara species (Nezara spp.), Green-streated bug (Nezara antennata), South- American stink bug (Nezara viridula); , Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, and others, Dolycoris baccarum, Eurydema rugosum, and Bryophytes 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, for example, the wheat bug (Eurygaster)
integraleps);
(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), elder tree aphids (Aphis sambuci), aphid snail aphids (Aphis spiraecola); 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 Aphid aphid (Chaetosiphon fragaefolii), Momokoburaphis (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 sp. (Ceroplastes ceriferus), ruby (Ceroplastes rubens);
(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 Planococcus sp. (Planococcus spp.); , Quackworm (Pseudococcus comstocki);
(I) Of the family Psyllididae, 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), 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), Nij.
(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 leafworm 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 the family Anthomyiidae; other sugar beet (Pegomya cunicularia);
(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 spp.) 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-spotted fly (Sitodiplosis mossellana) of the family Cididomyiidae.

(6) Pests of the order of the locust (Orthoptera) (a) 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 locust (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 Psyllium congenus (Tyrophagus similis); Others, Acarus sicosa (Acarus siro), Acygalis aus

(B) Prestigmata (Prostigmata) mite mites (Actinedida)
(A) Ticks of the spider mite family (Tetranychidae), such as the clover spider mite (Bryobia praetiosa), the false clover spider mite (Bryobia rubrioculus) of the species Briobia spp., For example, the species Eotetranychus 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 matsuuchi , Red spider mite (Panonychus citri), black-tailed spider mite (Panonychus mori), apple red mite (Panonychus ulmi); ), Acinonia red spider mite (Tetranychus ludeni), Citrus red spider mite (Tetranychus quercivorus), Sagami spider mite (Tetranychus phaselus), Nami spider mite (Tetranychus urticae), Red spider mite (Tetranychus viennensis); Of the red-spotted spider mite (Aponychus corpuzae), the red-spotted spider mite (Aponychus firmianae); Of the spider spider mite (Shizotetranychus celarius), the spider spider spider mite (Shizotetranychus longus), the spider crab spider mite (Shizotetranychus miscanthi), the spider spider spider mite (Shizotetranychus recki), the willow spider spider mite (Shizotetra chytich dithiotacitium) Red spider mite (Tuckerella pavoniformis), Yellow spider mite (Yezonychus 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 safflower (Aceria tulipae), Shefamphid 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. a species of the species Aculus sp. (Aculus spp.), snail (Aculus fockeui), apple snail schlechtendali); Other, Acaphyll a theavagrans), mangrove mite (Calacarus carinatus), grapevine mite (Colomerus vitis), grapevine snail (Calepitrimerus vitis), snail mite (Epitrimerus pyri), goldfish mite (Paraphytoptus kikus), giant scallop mite (Paracalacarus podocarpumiw) citri);
(D) ticks of the family Pcarididae (Transonemidae), such as, for example, the tarsonemus sp. );
(E) Mite mites (Penthaleidae) mites, such as, for example, Penthaleus erythrophalus of the genus Pentareus sp. (Penthaleus spp.), And green mites (Penthaleus major).

The pest control agents 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 conditioners And animal feed may be used together or in combination.
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 pest control agent of the present invention are shown below.

(1) Acetylcholinesterase inhibitors:
(A) Carbamate system: Alanicarb, aldiocarb, benzocarb, benfracarb, butocarboxim, butoxy carboxim, carbaryl, carbofuran, carbosulfan, carbohephan, ethiophene carb, fenobucarb, formetanate, furaiocarb, isocarb, methiocarb, methoyl, oxamyl, 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, Fenthion, Fosciate, Heptenophos, Imicifoss, Isophenphos, Isocarbophos, Isoxathion, Malathion, Mecarbammetizophos Methiomethone, Monocrotophos, Naredo, Omethoate, Oxydimethone-Methyl, Parathion, Parathion-Methyl, Fent Eate, Folate, Phosalone, Phosmet, Phosphamidone, Hoximme, Pirimiphos-Methyl, Propenophos, Propetamphos, Prothiophos, Pyracophos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupillinphos, Temephos, Terchuphos, Tetrachlorvinphos, Thiometone, Triazophos, Trichlorphos, Bromophos;・ Ethyl, BRP, carbophenothion, cyanophenphos, demeton-S-methylsulfone, diariphos, diclofenthion, dioxabenzophos, etlyrphos, fensulfothion, flupirazophos, phonophos, formothion, phosmethilane, isazophos, iodophenphos, methaphis, pyrimiphos -Ethyl, phosphocarb, propaphos, protoate, sulprofos.

(2) GABA-agonizing chloride ion channel antagonist: 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 Rothrin, 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, methoprene, 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, sulflumid, 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, bifenazate.
(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, spiropidione.
(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: chlorantranilipurol, cyantraniriprol, flubenziamide, cyclaniliprol, tetraniliprol.
(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, bromopropilate, cryolite, dicofol, pyridalyl; benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromo Rate, benzomate, methaldehyde, chlorbenzylate, crothiazobene, dicyclanyl, phenoxacrim, phentrifanyl, flufenzamine, fluphenadine, gossypua, japoniale, methoxadiazon, petroleum, sodium oleate, tetrasul, triaracene; , Flufiprole, fluensulphone, meperflusulline, tetramethylfursulline, tralopyril, dimeflusulline, methyl neodecanamide; fluralane , Afoxolanel, fluxamethamide, 5- [5- (3,5-dichlorophenyl) -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] -2- (1H-1,2,4-triazole- 1-yl) benzonitrile (CAS: 943137-49-3), brofuranilide, triflumesopyrim, dichloro-mesothiaz, oxazosulphyl, and other metadiamides.

(29) Antiparasitic agent:
(A) Benzimidazole: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, 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;

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 inhibitor: 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, flumecyclox; carboxin, oxycarboxin; thifluzamide; benzobin diflupyr, bixafen, fluxapiroxade , Flumetopyr, isopyrazam, penflufen, penthiopyrade, sedaxane; boscalid, pyradiflumid;
(C) complex III ubiquinol oxidase Qo inhibitors: azoxystrobin, spiderxystrobin, quaxitostrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyraxtrobin; pyraclostrobin, Crayoxime-methyl, trifloxystrobin; dimoxystrobin, phenaminstrobin, metominostrobin, orysastrobin; famoxadone; fluoxastrobin; phenamidone; pyribencarb, mandestrobin;
(D) Complex III ubiquinol reductase Qi inhibitors: Cyazofamid; amisulbrom;
(E) Uncoupling agent for oxidative phosphorylation: vinapacryl, meptylizino cup, dino cup; fluazinam; ferimzone;
(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, vinclozoline.

(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 position C14 in sterol biosynthesis: Trifolin; pyriphenox, pilisoxazole; phenarimol, flulprimidol, nualimol; imazaryl, imazalil sulfate, oxosconazole, peflazoate, prochloraz, triflumisole , Biniconazole;
Azaconazole, biteltanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinonazole, flusilazole, flutriaazole, fluconazole, fluconazole-cis , Hexaconazole, imibenconazole, ipconazole, metconazole, microbutanil, penconazole, propiconazole, quinconazole, cimeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole; prothioconazole, voriconazole, mephene Trifluconazole (mefentrifluconazole);
(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, pirimorph; bench abariculum, iprobicarb, tolprocarb, varifenalate; mandipropamide.

(9) Melanin Biosynthesis Inhibitor (a) Reductase Inhibitor of Melanin Biosynthesis: Phthalide; Pyroquirone; Tricyclazole;
(B) Dehydratase inhibitor 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;

(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 product, calcium polysulfide; faram, mancozeb, maneb) , Man kappa, methylam, polycarbamate, propineb, tilam, zineb, ziram; captan, captaphor, phorpet; chlorothalonil; diclofluanid, tolylfluanid; gazatine, iminoctadine triacetate, iminoctadine albesylate ( iminoctadine trialbesilate); anilazine; dithianone; quinomethionate;

(13) Other agents: DBEDC, fluorophorpet, gazatine acetate, bis (8-quinolinolato) copper (II), propamidine, chloropicrin, ciprofram, agrobacteria, betoxazine, diphenylamine, methylisothianate ), 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), oxachite Piproline (Oxathiapiprolin), methylam zinc, benzazole, trichlamide, uniconazole, mildeomycin, Oxyfenthiin, picarbutrazox, fenpicoxamide, dichlobentiazox , Quinoferin (Quinofumelin).

Specific examples of the plant regulator which can be used in combination or in combination with the pest control agent of the present invention are shown below.
1-Methylcyclopropene, 2,3,5-triiodobenzoic acid, IAA, IBA, MCPA, MCPB, 4-CPA, 5-aminolevulinic acid hydrochloride, 6-benzylaminopurine, abscisic acid, abiglycine hydrochloride, ansimi Dool, butoralin, calcium carbonate, calcium chloride, calcium formate, calcium peroxide, calcium sulfur, calcium sulfate, calcium chloride, chlormequat chloride, chloroprofam, choline chloride, cloprop, cyanamide, cyclanilide, daminozide, decyl alcohol, dichlorprop , Dikeglac, dimethypine, diquat, ethephon, ethiclosate, flumetraline, flurprimidol, forchlorphenuron, gibberellin A, gibberellin A3, hymexazole, inabenfide, isoprothiolane, chi Tin, maleic acid hydrazide, mefluidide, mepiquat chloride, oxidized glutathione, paclobutrazol, pendimethalin, prohexadione calcium, prohydrojasmone, pyraflufen ethyl, syntophen, sodium 1-naphthaleneacetate, cyanic acid Sodium, streptomycin, thidiazuron, triapentenol, tribphos, trinexapac ethyl, uniconazole P, 1-naphthylacetamide.

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

Host animals to be treated with the ectoparasitic agent of the present invention include companion animals such as dogs and cats; pet birds; domestic animals such as cattle, horses, pigs and sheep; poultry; warm blooded animals such as And fish such as trout, puffer fish, carp and goldfish, and insects such as bees, stag beetles and beetles.

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.

Ectoparasites infect the body and skin of host animals, particularly warm-blooded animals and fish. 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. As ectoparasites, ticks, lice, fleas, flies, lice and the like can be mentioned. Specific examples of ectoparasites that can be controlled by the ectoparasite control agent of the present invention are shown below.

The following pests may be mentioned as mites (Acari).
(1) Acarids (mite) of the middle snail (Mesostigmata)
(a) Ticks of the family Wakamo (Dermanyssidae), for example Wakamo (Dermanyssus gallinae) of the Wakamo species (Dermanyssus spp.);
(b) Mite mites (Macronyssidae) mites, such as, for example, the mites species (Ornithonyssus spp.), Eurasian mite (Ornithonyssus sylviarum), Nerytris oryzae (Ornithonyssus bursa), house mite (Ornithonyssus bacoti);
(c) Tick mites (Laelapidae) mites, such as the solitary mites (Laelaps echidninus) of the mite species (Laelaps spp.), the black-spotted mite (Laelaps jettmari)
(2) Ticks (ticks) of the posterior order
(a) ticks of the family Aphididae (Argasidae), for example of the long haired mite species (Argas spp.), of the long haired mite (Argas persicus), Argus reflexus (Argas reflexus); eg of the flowering mite species (Ornithodoros spp.) Mouvata (Ornithodorus moubata);
(b) Haemaphysalis concina, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cymbalinas, Haemaphysalis cinctata, of the tick family Ixodidae, such as the tick species (Haemaphysalis spp.) Haemaphysalis otophila, Haemaphysalis leachi, Haemaphysalis longicornis, Haemaphysalis tick (Haemaphysalis mageshimaensis), Trichoderma japonicum, Utaphysalis, Gl, Gl, Gl, Gl, Gl, Gl, Gl, Gl, Gl, Gl, Gl, Gl, Gl, Gl ), Haemaphysalis megaspinosa, Haemaphysalis japonica, Hagella japonica (Haemaphysalis douglasi); such as, for example, Amblyomma spp. Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma heebraeum, Ambalitechitimates Of the tick species (Ixodes spp.), Ticks (Ixodes ricinus), Ixodes hexagonas (Ixodes hexagonus), Ixodes canisga (Ixodes canisuga), Ixodes pilosus, Ixodes rubicundus (Ixodes rubicundus), Scapularis (Ixodes scapularis), Ixodes holocyclus, Ixodes tick (Ixodes persulcatus), Tanegatama tick (Ixodes nipponensis); Subgenus species (Boophilus spp.): Red tick (Rhipicephalus (Boophilus) microplus), Lipicepharus (Boophilus), Decolorata (Rhipicephalus (Boophilus) decoloratus), Lipicephorus (Boophilus), Annularus (Rhipicephalus (Boophilus) annulus), A.) Cerceratus (Rhipicephalus (Boophilus) calceratus), such as, for example, Rhipicephalus spp. Of Rhipicephalus evertsi, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Ripicephalus capillusus For example, Dermacentor marginatas (Dermacentor reticulatus), Dermacentor marginatas (Dermacentor reticulatus), of the species Dermacentor spp. (Dermacentor pictus), Dermacentor albipictus (Dermacentor albipictus), Dermacentor Andersoni (Dermacentor andersoni), Dermacentor Barrier Squirrel (Dermacentor variabilis);
(3) Acarididae (Acaridida)
(a) mites of the family Psoroptidae (Psoroptidae), such as Psoroptidae spp., Psoroptes ovis, Psoroptes cuniculi, Psoroptes equine (Psoroptes equi) Chorioptes spp., Chorioptes bovis; Otodectes spp., Otodectes cynotis;
(b) Scarpidae mites, such as Sarcopidae sp. (Sarcoptes spp.), Spermatophora japonicus (Sarcoptes scabiei), Spermatophora japonicus Sarcoptes canis) ovis), Sarcoptes rupicaprae, Sarcoptes equi (Sarcoptes equi), Sarcoptes suis (eg Sarcoptes suis); eg, Notoeds sp. (Notoedres spp.), Scutellariae (Notoedres cati);
(c) Acarid of the Trichodermidae (Knemidokoptidae), such as Trichothema tick (Knemidokoptes mutans) of the Trichophyton species (Knemidokoptes spp.);
(4) Prestigmata (Prostigmata) mite mites (Actinedida)
(a) Mite mites (Demodixidae) mites, such as Deixox species (Demodex spp.), Bite mites (Demodex canis), Bovine Bite (Demodex bovis), Ovine Bite (Demodex ovis), Goat Bite (Demodex caprae), Sea urchin mite (Demodex equi), Demodex caballi (Demodex caballi), scorpionfish mite (Demodex suis), cat snail (Demodex cati);
(b) Acarididae (Trombiculidae) mites, such as, for example, Trombicula alfreddugesi, of the species Azalea (Trombiculidae spp.), Trombicula akamushi;

The following pests may be mentioned as lice (Phthiraptera).
(1) The lice (louse) of the lice (Anoplura)
(a) lice of the family Haematopinidae, such as the lice (Haematopinus asini), the cow lice (Haematopinus eurysternus), the pig lice (Haematopinus suis) of the lice species (Haematopinus spp.);
(b) Lice of the family Linognathidae (Linognathidae), for example, the species Linognathus spos. of the species Linognathus spp. Linognathus pedalis (Linognathus pedalis), goat lice (Linognathus stenopsis); such as, for example, Solenopotes spp., Solenopotes capillatus;
(2) Bugs of the order Amblycera (biting louse)
(a) Hotheads of the family Tanopakidae (Menoponidae), for example, chicken fly flea (Menacanthus stramineus) of the species Genacantha sp. (Menacanthus spp.); Genus species (Menopon spp.), Chicken fowl (Menopon gallinae);
(3) Whiteheads (biting louse) of the order Suborder (Ischnocera)
(a) Psyllid (Philopteridae) psyllids, such as those of the genus Corumbicola sp. (Columbicola spp.), Psyllium persica (Columbicola columbae); such as, for example, Klucrotogaster spp. for example, Goniodes spp., Goniodes dissimilis, Goniodes gigas, Goniodes gallinae; eg Lipeurus spp. caponis);
(b) Psyllid family Trichodectidae, such as Bovicola bovis, Bovicola ovis, Bovicola limbata, Bovicola caprae of Bovicola spp. Horseflies (Bovicola equi); for example of the leafminer species (Trichodectes spp.), Dogflies (Trichodectes canis); for example of a felicola species (Felicola spp.), Catflies (Felicola subrostrata);

The following pests may be mentioned as fleas (Siphonaptera).
(a) A flea of the family Tungidae (Tungidae), for example, a species of Tuna species (Tunga spp.), a species of Tunidae (Tunga penetrans);
(b) Human fleas (Pulicidae) fleas, such as the dog flea species (Ctenocephalides spp.), dog flea (Ctenocephalides canis), feline flea (Ctenocephalides felis); e.g. Eg, of the species of the genus Flea species (Xenopsylla spp.), Oriental flea (Xenopsylla cheopis), for example of the species of the human flea species (Pulex spp.), Human flea (Pulex irritans); Fleas (Echidnophaga gallinacea);
(c) Flea species (Ceratophyllidae) flea, such as Ceratophyllus spp., Ceratophyllus gallinae, Ceratophyllus anisus flea; such as Nosopsularus spp. (Nosopsyllus fasciatus),
(d) Fleas of the family Holophidae (Leptopsyllida), such as the horned flea (Leptopsylla segnis) of the species Holophossy (Leptopsylla spp.);

The pests of the flies (Diptera) include the following pests.
(1) Stigmata (Nematocera)
(a) Mosquitoes of the family Culicidae, such as Culex spp., Culex quinquefasciatus, Culex pipiens pallens, Culex tarsalis, Culex pipiens molestus , Culex pipiens fatigans, Culex tritaeniorhynchus cumulosus; for example, Armigeres spp., Armigeres subalbatus; Anopheles maculipennis, Anopheles sinensis, Anopheles lesteri; eg, Aedes aegypti, Aedes spic. (Aedes taeniorhynchus), To Gouyabuka (Aedes togoi), Kin'iroyabuka (Aedes vexans nipponii);
(b) Simuliidae (Simuliidae) purpura, for example, Simulium spp., Simulium reptans, Simulium ornatum, Simulium venustum, Simulium salopiense For example Prosimulium sp., Prosimulium yezoense;
(c) Nukaka of Ceratopogonidae, for example of the species of the genus Culicoides sp. oxystoma), Japanese nukaka (Culicoides nipponensis), Hoshinukaka (Culicoides punctatus), Miyamanukaka (Culicoides maculatus), Matsuzawakakaka (Culicoides matsuzawai);
(2) short corner eyes
(a) Tabanidus (Tabanidae), eg, Tabanus sp., Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudicacus (Tabanus spp.) Tabanus sudeticus), Bovine fly (Tabanus trigonus), Red-billed fly (Tabanus chrysurus), White-faced fly (Tabanus trigeminus), Kis's fly (Tabanus fulvimedioides), Yoyoshiroobiabe (Tabanus iyoensis); caecutiens), Chrysops relictus, Chrysops suavis, Chrysops japonicus;
(e) flies of the housefly family (Muscidae), for example, housefly species (Musca domestica), house fly (Musca bezzii), house fly (Musca hervei), house fly (Musca conducens), house fly Musca stabulans), for example of the genus Streptomyces sp. (Stomoxys spp.), Of the species Strepoxys calcitrans, for example of the species of the genus Haematobia spp. , Hematobia stimulation (Haematobia stimulans); Hemneids species (Fannia spp.), Of the Hymenae fly (Fannia canisularis);
(c) Sheshfly species (Glossina spp.) of the family Glossinidae;
(flies of the family Elipidae (Hippoboscidae), such as the lice fly (Melophagus ovinus) of Melophagus sp. (Melophagus spp.);
(e) Fly fly (Calliphoridae) flies, such as the fly fly species (Calliphora), the fly fly (Calliphora lata); for example the fly fly species (Lucilia spp.), the sheep fly fly (Lucilia (Phaenicia) cuprina) Phaenicia) sericata), green leaf fly (Lucilia illustris); such as the spiny fly (Chrysomya hominivorax), chrysomya chloropyga, chrysomya chloromyga, chrysomya veveana (Chrysomya sph.)
(f) A fly of the sheep fly family (Oestridae), for example, a rabbit fly species (Cuterebra spp.) of the family of the family Flyfly Subfamily (Cuterebrinae); such as a fly of the genus Bovine fly (Hypoderma spp.); (Hypoderma bovis), Hydoderma lineatum; for example of the family Flyfish (Gasterophilina sp.), Even of the genus Flyfly (Gasterophilus spp.), The dry fly (Gasterophilus intestinalis), the fresh fly (Gasterophilus haemorroidalis), Gasterophilus (H.) Gasterophilus inermis), Red-necked Fly (Gasterophilus nasalis), Gastrophilus nigricornis (Gasterophilus nigricornis), Red-spotted Fly (Gasterophilus pecorum); Oestrus ovis);

In addition to the above, the compound of the present invention has poisoned needles and venom, and causes harmful insect pests, pests that mediate various pathogens and pathogens, and harmful insect pests (toxic pest insect pests and harmful insect pests Etc.) are 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).

[Pest control agent]
The pest control agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the pest control agent of the present invention is not particularly limited as long as it exhibits the pest control effect of pests.
The adherent pests to be controlled are crustaceans represented by barnacles (barnacles). It is industrially useful to control adherent organisms of the amphipods, in particular barnacles, stag mussels, kamenotes, in particular barnacles, which are harmful to underwater structures.

The above-mentioned underwater structure means an artificial structure which is submerged or almost always in contact with water. For example, revetment in ports, waterways, shipyards, etc .; underwater facilities; water conduits; facilities and equipment in contact with water in power plants, factories etc .; equipment in contact with cooling towers, cooling water or heat transfer water; Ships, especially bottoms, ballast tanks and equipment attached to them; fishing reefs; equipment such as fishing nets used underwater in fishery etc .; buoys;
As a practically effective method, it is used as a composition containing the compound of the present invention. Specifically, the composition may be added as it is to water in which the pests hide, for example, ballast water of ships, heat medium water such as cooling water used in various devices, etc. By applying, injecting, or impregnating the surface of an underwater structure installed in a lake, river water, etc.).

[Formulation prescription]
Although some formulations of the pest control agent, insecticidal or acaricidal agent, ectoparasitic agent, or pest 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 compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfuric acid ester, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely ground to obtain a wettable powder with an active ingredient of 40%.

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

(Formulation 3: granules)
5 parts of the 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 pulverized, and then granulated into particles of 0.5 to 1.0 mm in diameter Granules of 5% active ingredient are obtained.

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

(Formulation 5: suspension agent)
10 parts of the 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 to obtain a particle size of 3 microns or less Wet grinding to obtain a 10% suspension of the active ingredient.

The following shows the formulation for controlling ectoparasites.

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

(Formulation 7: Injection)
0.1 to 1 part of the 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 compound of the present invention, 10 parts of myristic ester, and 85 parts of isopropanol.

(Formulation 9: Spot-on agent)
10 to 15 parts of the compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol are uniformly mixed to obtain a spot-on agent.

(Formulation 10: Spray)
One part of the 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.

[Reference Example 1]
Synthesis of 3- (2-iodo-3-methylphenyl) -N- (p-tolyl) propanethioamide

1- (bromomethyl) -2-iodo-3-methylbenzene was synthesized by the method described in Non-Patent Document 1.
N- (p-tolyl) ethanethioamide (8.5 g) was dissolved in tetrahydrofuran (170 mL) and cooled to -78.degree. After that, n-butyllithium (2.65 mol / L, 39 mL) was added dropwise, the temperature was raised to 0 ° C., and the mixture was stirred for 1 hour. It was again cooled to -78 ° C. Thereafter, 1- (bromomethyl) -2-iodo-3-methylbenzene (16.1 g) was added, and the mixture was stirred at -78 ° C for 2 hours and then at room temperature for 2 hours. The resulting solution was added to aqueous ammonium chloride solution, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 6.5 g of the desired product. The NMR data of the desired product is shown below.
¹ H-NMR (CDCl ₃ ) δ ppm: 2.31 (s, 3 H), 2.49 (s, 3 H), 3.06 (t, 2 H), 3. 35 (t, 2 H), 7.03-7. 19 (m, 5 H), 7.35 (m , 2H).

Reference Example 2
Synthesis of (Z) -8-methyl-N- (p-tolyl) thiochroman-2-imine

Copper iodide (0.63 g), 1,10-phenanthroline (0.62 g), and potassium phosphate (7 g) were added to a solution of thioamide (6.5 g) obtained in Reference Example 1 in N-methylpyrrolidone (33 mL). 1 g) was added and stirred at 100 ° C. for 1 hour. The resulting solution was added to aqueous ammonium chloride solution, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 3.0 g of the desired product. The NMR data of the desired product is shown below.
¹ H-NMR (CDCl ₃ ) δ ppm: 2.17 (s, 3 H), 2.36 (s, 3 H), 2.91 (t, 2 H), 3.05 (t, 2 H), 6.83 (d, 2 H), 7.03-7.09 (m , 3H), 7.16 (d, 2H).

[Reference Example 3]
Synthesis of 8-methyl-2- (p-tolylamino) -4H-thiochromene-3-carbaldehyde

Lithium diisopropylamide (1.5 mol / L, 15 mL) was added to a tetrahydrofuran solution (37 mL) of the imine (3.0 g) obtained in Reference Example 2 at −10 ° C., and the mixture was stirred for 1 hour. Ethyl formate (1.8 mL) was added to the obtained solution, and the mixture was stirred at room temperature for 3 hours. The resulting solution was then added to aqueous ammonium chloride solution, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 1.4 g of the desired product. The NMR data of the desired product is shown below.
¹ H-NMR (CDCl ₃ ) δ ppm: 2.27 (s, 3 H), 2.37 (s, 3 H), 3.56 (s, 2 H), 7.03-7. 19 (m, 7 H), 9.09 (s, 1 H).

Example 1
Synthesis of (2Z, 3E) -8-methyl-3-(((6-methylpyrimidin-4-yl) thio) methylene) -N- (p-tolyl) thiochroman-2-imin

Triethylamine (0.48 mL) and methanesulfonyl chloride (0.09 mL) were added to a tetrahydrofuran solution (2 ml) of the aldehyde (0.17 g) obtained in Reference Example 3 at 0 ° C., and stirred at room temperature for 1 hour did. It was then cooled to 0 ° C. Thereafter, 6-methylpyrimidine-4-thiol (0.075 g) was added to the obtained solution, and stirred at room temperature for 1 hour. Then, the obtained solution was added to ice water and extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 0.06 g of the desired product. The NMR data of the desired product is shown below.
¹ H-NMR (CDCl ₃ ) δ ppm: 2.18 (s, 3 H), 2.37 (s, 3 H), 2.48 (s, 3 H), 3.86 (s, 2 H), 6.92 (d, 2 H), 7.19 (m, 7 H) ), 8.10 (s, 1 H).

[Reference Example 4]
Synthesis of (2Z, 3E) -3- (chloromethylene) -8-methyl-N- (p-tolyl) thiochroman-2-imine

To an N, N-dimethylformamide solution (16 mL) of the aldehyde (1.4 g) obtained in Reference Example 3 was added triethylamine (1.0 mL) and methanesulfonyl chloride (0.6 mL) at 0 ° C., and room temperature It stirred below for 1 hour. The obtained solution was added to ice water and extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 1.0 g of the desired product. The NMR data of the desired product is shown below.
¹ H-NMR (CDCl ₃ ) δ ppm: 2.18 (s, 3 H), 2.37 (s, 3 H), 3.88 (s, 2 H), 6.85 (d, 2 H), 7.03-7.20 (m, 6 H).

Example 2
Synthesis of (2Z, 3E) -8-methyl-3- (phenoxymethylene) -N- (p-tolyl) thiochroman-2-imine

To a toluene solution (3 mL) of the imine (0.25 g) obtained in Reference Example 4, phenol (0.09 g), tris (dibenzylideneacetone) dipalladium (0.15 g), 2-di-t-butylphos Fino-2 ′, 4 ′, 6′-triisopropylbiphenyl (0.07 g) and cesium carbonate (0.26 g) were added and stirred at 70 ° C. for 1 hour. The obtained solution was added to ice water and extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 0.085 g of the desired product. The NMR data of the desired product is shown below.
¹ H-NMR (CDCl ₃ ) δ ppm: 2.19 (s, 3 H), 2.36 (s, 3 H), 3.87 (s, 2 H), 6.87 (d, 2 H), 7.04-7.36 (m, 10 H), 7.76 (s) , 1 H).

Table 1 shows examples of the compounds of the present invention prepared in the same manner as the above examples. Table 1 shows the substituent of the compound represented by formula (I-a). The compound represented by the formula (Ia) is a compound in which B is a sulfur atom and D is a substituted or unsubstituted methylene group and is in an E form.

The melting point (mp), the refractive index (nD), or the properties thereof are described in the column of "physical properties" in Table 1. In Table 1, Me represents a methyl group and Ph represents a phenyl group.

The NMR data of the compound described as viscous oil or amorphous in the column of "Physical properties" of Table 1 is shown below.
Compound number (a-5): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 3.82 (s, 3 H), 3.89 (s, 2 H), 6. 92 (m, 4 H), 7.09-7. 25 (m, 6 H), 7.32-7.41 (m, 3H), 7.68 (s, 1H).
Compound number (a-6): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 2.38 (s, 3 H), 2.51 (s, 3 H), 3. 85 (s, 2 H), 6. 92 (d, 2 H), 7.12- 7.31 (m, 7 H), 8.31 (s, 1 H), 8.43 (d, 1 H).
Compound number (a-9): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 2.37 (s, 3 H), 2.49 (s, 3 H), 3.81 (s, 2 H), 6.85-7.10 (m, 6 H), 7.20 (d, 2 H), 8.34 (s, 1 H), 8.42 (d, 1 H).
Compound number (a-10): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 2.37 (s, 3 H), 2.49 (s, 3 H), 3.80 (s, 2 H), 6.82-6. 89 (m, 4 H), 7.20-7.25 (m, 4H), 8.32 (s, 1 H), 8.42 (d, 1 H).
Compound number (a-16): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 2.19 (s, 3 H), 2. 35 (s, 3 H), 2. 48 (s, 3 H), 3. 85 (s, 2 H), 6. 80 ( d, 1H), 6.91 (d, 1H), 7.03-7.18 (m, 5H), 7.30 (m, 1H), 8.40-8.44 (m, 2H).
Compound number (a-18): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 2.17 (s, 3H), 2.34 (s, 3H), 3.85 (s, 2H), 6.77 (d, 1H), 7.04- 7.15 (m, 6H), 7.30 (m, 1 H), 8.34 (s, 1 H), 8. 57 (d, 1 H).
Compound number (a-19): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 2.16 (s, 3 H), 2.31 (s, 3 H), 2.33 (s, 3 H), 3.80 (s, 2 H), 6.74 ( d, 1 H), 6.84-6. 90 (m, 3 H), 7.00-7.05 (m, 2 H), 7.12 (s, 1 H), 7. 25 (m, 1 H), 8.21 (s, 1 H), 8.34 (d, 1 H) .
Compound number (a-27): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 1.48 (d, 3 H), 2.35 (s, 3 H), 2.37 (s, 3 H), 4.54 (q, 1 H), 6.87 6.93 (m, 4 H), 7.08-7. 29 (m, 8 H), 7.52 (s, 1 H).
Compound number (a-42): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 1.48 (d, 3 H), 4.56 (q, 1 H), 6.79-6.93 (m, 3 H), 7.08-7.44 (m, 11 H) ), 7.56 (s, 1 H).
Compound number (a-48): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 2.13 (s, 3 H), 2.33 (s, 3 H), 3.84 (s, 2 H), 6. 76 (d, 1 H), 7.01- 7.31 (m, 8 H), 7.56 (t, 1 H), 8. 19 (d, 1 H), 8. 49 (d, 1 H).
Compound number (a-49): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 2.14 (s, 3 H), 2.36 (s, 3 H), 3.89 (s, 2 H), 6.86 (d, 1 H), 7.15 7.52 (m, 11 H).

Subsequently, Table 2 also shows examples of the compounds of the present invention.

[Biological test]
The following test examples show that the compounds of the present invention are useful as active ingredients of pest control agents. Parts are by weight.

(Preparation of emulsion for test)
5 parts of the compound of the present invention, 93.6 parts of dimethylformamide and 1.4 parts of polyoxyethylene alkyl aryl ether were mixed and dissolved to prepare an emulsion (I) of 5% of the active ingredient.

The insecticidal rate was calculated by the following equation.
Insecticidal rate (%) = (number of dead insects / number of tested insects) x 100

Test Example 1 Efficacy test against Mythimna separata Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Corn leaves were soaked in the dilution for 30 seconds. The corn leaves were air dried and placed in a petri dish, and 5 second instar larvae of the 2nd instar 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 6 days passed from the helminth, the life and death judgment was performed and the insecticidal rate was calculated. The test was performed in duplicate.

The compounds of the numbers shown in Table 3 were tested for efficacy against the carob. Each of the compounds showed an insecticidal rate of 80% or more against the ascidian.

Test Example 2 Efficacy test against Spodoptera litura Emulsion (I) was diluted with water to a concentration of the compound of the present invention of 125 ppm. The cabbage leaves were immersed in the diluted solution for 30 seconds. The cabbage leaves were air-dried and placed in a petri dish, and 5 second instar larvae of the lotus root were released. The petri dish was placed in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 60%. When 6 days passed from the helminth, the life and death judgment was performed and the insecticidal rate was calculated. The test was performed in duplicate.

The compounds of the numbers shown in Table 4 were tested for efficacy against Hessonia sinensis. Each of the compounds showed an insecticidal rate of 80% or more against the lotus cutlet.

Test Example 3 Efficacy Test Against Psyllium (Plutella xylostella) Emulsion (I) was diluted with water to a concentration of the compound of the present invention of 125 ppm. The cabbage leaves were immersed in the diluted solution for 30 seconds. The cabbage leaves were air-dried and 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 compounds of the numbers shown in Table 5 were tested for efficacy against diamondback moth. Both compounds showed an insecticidal rate of 80% or more against diamondback moth.

(Test Example 4) Efficacy test against cotton aphid (Aphis gossypii) Cucumber seeds were sown in a 3 inch bowl, and adult cotton aphid was released when 10 days had passed after germination. One day after the helminth, adults were removed, leaving only the 1st instar larvae delivered. The emulsion (I) was diluted with water to obtain a test solution adjusted to a predetermined concentration of the compound of the present invention. The test solution was sprayed on the cucumber. Thereafter, the cucumber was placed in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 60%. Six days after that, life and death of cotton aphid were examined, and the insecticidal rate was calculated. The test was performed in duplicate.

The compounds of the numbers shown in Table 6 were tested for efficacy against cotton aphid at a compound concentration of 125 ppm. All compounds showed an insecticidal rate of 80% or more.

Test Example 5 Efficacy Test against Bemisia tabaci Emulsion (I) was diluted with water so that the compound of the present invention was 125 ppm, and the diluted solution was sprayed on tomato seedlings and air-dried. On the day of spraying, B. tabaci type B adults were released and allowed to lay eggs. The number of parasitic larvae was counted 12 days after spraying. The efficacy of the compounds was evaluated by the control rates shown below. The test was performed in duplicate.
Control rate = 100-[(Nt / Nc) x 100]
Nt: Number of parasites in the scatter treatment area Nc: Number of parasites in the untreated area

The compounds of the numbers shown in Table 7 were tested for efficacy against B. tabaci. All compounds showed a control rate of 80% or more against B. tabaci.

(Test Example 6) Efficacy test against Thrips palmi (Thrips palmi) Seeds of cucumber were seeded in a three-sized bowl, and after 10 days from germination, adults of thistle was released. The emulsion (I) was diluted with water to obtain a test solution adjusted to a predetermined concentration of the compound of the present invention. One day after the release, the test solution was sprayed onto the cucumber. Thereafter, the cucumber was placed in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 60%. Two days after that, the life and death of the adult thrips palmatee were examined, and the kill rate was calculated. The test was performed in duplicate.

The compounds of the numbers shown in Table 8 were tested for efficacy against South African thrips at a compound concentration of 125 ppm. All compounds showed an insecticidal rate of 80% or more.

(Experimental example 7) Efficacy test against the red spider mite (Tetranychus urticae) The green beans were raised in a three inch bowl, and eight primary adult female spider mites from Aomori were inoculated on primary leaves. Emulsion (I) was diluted with water to a concentration of 125 ppm of the compound of the present invention. The diluted solution was sprayed on the beans. The beans were placed in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 65%. Three days after the application, the life and death of adult mite females were examined. The test was performed in duplicate.

The compounds of the numbers shown in Table 9 were tested for efficacy against two-spotted spider mite. All compounds showed an insecticidal rate of 90% or more.

Test Example 8 Contact Effect Test on Rhipicephalus microplus A DMSO solution of the compound of the present invention was diluted with water to obtain 100 ppm of a test solution. This drug solution was dropped into a container containing 20 larvae of bullfrog tick and incubated in a temperature-controlled room at a temperature of 28 ° C. and a humidity of 80%. Life and death of the larvae were judged 24 hours after the drug solution was dropped. The test was performed in duplicate.

The compounds of the numbers shown in Table 10 were subjected to a contact effect test on the tick. All compounds showed an insecticidal rate of 90% or more.

Test Example 9 Contact Effect Test on Cat Flea (Ctenocephalides felis) A DMSO solution of the compound of the present invention was diluted with water to obtain 100 ppm of a test solution. This drug solution was dropped onto a filter paper in a container containing 10 adult cat fleas and incubated in a temperature-controlled room at a temperature of 28 ° C. and a humidity of 80%. Life and death of adults were determined 24 hours after the drug solution was dropped. The test was performed in duplicate.

The compounds of the numbers shown in Table 11 were subjected to a contact effect test on cat fleas. All compounds showed an insecticidal rate of 90% or more.

Test Example 10 Contact / Feeding Effect Test for Larvae of the Sheep Flyfly (Lucilia cuprina) A DMSO solution of the compound of the present invention was mixed with horse meat to obtain a mixture of 1000 ppm. Twenty sheep flyfly larvae were introduced into test tubes with the mixture. It was incubated in a temperature-controlled room at a temperature of 28 ° C. and a humidity of 80%. Life and death of the larvae were determined 48 hours after the start of the incubation. The test was performed in duplicate.

When the compound shown in Table 12 was subjected to a contact / feeding effect test on sheep flyfly larvae, it showed an insecticidal rate of 90% or more.

Test Example 11 Contact / Feeding Effect Test for Aedes aegypti Larvae The DMSO solution of the compound of the present invention was diluted with water to obtain a 100 ppm diluted solution. Ten 1 N. 1st instar larvae were placed in each well of a 96-well microtiter plate along with the breeding fluid. To this was added 1/10 volume of the diluted solution to adjust the final concentration to 10 ppm. It was incubated in a temperature-controlled room at a temperature of 28 ° C. and a humidity of 80%. Life and death of the larvae were determined 48 hours after the start of the incubation. The test was performed in duplicate.

The contact / feeding effect test was carried out on P. pipiens larvae for the compounds of the numbers shown in Table 13. All compounds showed an insecticidal rate of 90% or more.

Test Example 12 Pesticidal Effect on Guinea Pigs Rhipicephalus sanguineus The guinea pig (Cavia porcellus) was randomly assigned to a drug-treated group and a control (untreated) group. Each group consisted of 3 guinea pigs. One guinea pig was infected with about 120 nymphs of Rhipicephalus sanguineus, one guinea pig one day prior to drug treatment.
On the day of the test, 30 mg of the test compound was dissolved in 15 ml of dimethylformamide, and 285 ml of ion exchanged water was added and mixed well to prepare 300 ml of a test solution of 100 ppm.
The guinea pig infected with the aforementioned tick was immersed for 2 minutes using 100 ml of the test solution per guinea pig for external treatment.

Drug treatment On the second, third, sixth and seventh days, each group of engorged tick nymphs and tick nymphs wicked and detached from guinea pigs were counted (eN), and the effect of drug treatment was calculated according to the following formula.

In this test, compound a-25 showed 100% tick repellent effect. In addition, no side effects were observed during the test period.

Since compounds selected at random among the compounds of the present invention exert the effects as described above, the compounds of the present invention, including compounds that could not be exemplified, are pest control, in particular acaricidal, insecticidal, ectoparasitic It can be understood that the compound has an effect such as insect control, does not cause phytotoxicity on plants, and is a compound having little toxicity to humans and animals and environmental impact.

It is possible to provide a 1-heterodiene 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. In addition, it is possible to provide a pest control agent, an insecticidal or acaricidal agent, an ectoparasite control agent, or a pesticidal agent containing a 1-heterodiene compound as an active ingredient.

Claims (5)

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

   

   (In the formula (I),
   Q ¹ represents a substituted or unsubstituted C 6-10 aryl group,
   Q ² represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 10-membered heteroaryl group,
   R ¹ represents a hydrogen atom,
   A represents an oxygen atom or a sulfur atom,
   B represents an oxygen atom or a sulfur atom,
   D represents a substituted or unsubstituted methylene group, a carbonyl group or an oxygen atom,
   E represents a substituted or unsubstituted benzene ring. )
2. 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.
3. An insecticide or acaricide comprising at least one member selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.
4. An ectoparasiticide containing at least one member selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.
5. An anti-pesticidal agent for fishing nets or ship bottoms, which comprises at least one member selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.