JP2020158393A - 1-heterodiene compound and pest control agent - Google Patents

Abstract

To provide a 1-heterodiene compound which is excellent in safety and insecticidal and/or acaricidal activity and can be industrially advantageously synthesized.SOLUTION: The invention provides 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, or the like; R1 represents H; A and B each independently represent O or S; D represents an (un)substituted methylene group, a carbonyl group, or O; and E represents an (un)substituted benzene ring.)SELECTED DRAWING: None

Description

The present invention relates to 1-heterodiene compounds and pest control agents. More specifically, the present invention has excellent insecticidal and / or acaricidal activity, is excellent in safety, and can be synthesized industrially advantageously. 1-Heterodiene compound and pest control containing the same as an active ingredient. Regarding agents.

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

By the way, Patent Document 1 discloses a compound represented by the formula (A) and the like.

WO2010 / 070910A

An object of the present invention is 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 synthesized industrially advantageously. Another object of the present invention is to provide a pest control agent, an insecticide or acaricide, a ectoparasite control agent, or a pest adhesion preventive agent containing a 1-heterodiene compound as an active ingredient.

As a result of studies for solving the above problems, the present invention including the following forms has been completed.
[1] A compound represented by the formula (I) or a salt thereof.

In formula (I), Q ¹ represents a substituted or unsubstituted C6 to 10 aryl group, and Q ² is a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C6 to 10 aryl group, or Substituted or unsubstituted 5- to 10-membered heteroaryl groups, R ¹ indicates a hydrogen atom, A indicates an oxygen atom or a sulfur atom, B indicates an oxygen atom or a sulfur atom, and D indicates a substituted atom. Alternatively, it 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 at least one selected from the group consisting of the compound according to the above [1] and a salt thereof as an active ingredient.

[3] An insecticide or acaricide containing at least one selected from the group consisting of the compound according to the above [1] and a salt thereof as an active ingredient.

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

[5] An agent for preventing pests from adhering to fishing nets or the bottom of a ship, which contains at least one selected from the group consisting of the compound according to the above [1] and a salt thereof as an active ingredient.

The 1-heterodiene compound of the present invention can control pests that pose a problem in terms of crops and hygiene. In particular, agricultural pests and mites can be effectively controlled at lower concentrations. Furthermore, ectoparasites that harm humans and animals can be effectively controlled. Furthermore, it is possible to prevent the adhesion of adherent pests such as barnacles.

[1-heterodiene compound]
The 1-heterodiene compound of the present invention is a compound represented by the formula (I) (hereinafter, may be referred to as compound (I)) or a salt of compound (I).

In the present invention, the term "unsubstituted" means that it is only a parent group. When there is no description of "substitution" and only the name of the parent group is described, it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that any hydrogen atom of the parent group is substituted with a group (substituent) having the same or different structure as the mother nucleus. Therefore, a "substituent" is another group attached to the parent group. The substituent may be one or two or more. The two or more substituents may be the same or different.
Terms such as "C1 to 6" indicate that the number of carbon atoms of the parent group is 1 to 6 or the like. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.

The "substituent" is chemically acceptable and is not particularly limited as long as it has the effect of the present invention. The groups that can be "substituents" are illustrated 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. 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. C2-6 alkenyl groups;
C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group;

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

Hydroxy 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;
C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group;
C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group;
C6-10 aryloxy groups such as phenoxy groups and naphthoxy groups;
C6-10 aryl C1-6 alkoxy groups such as benzyloxy group and phenethyloxy group;
5- to 6-membered heteroaryloxy groups such as thiazolyloxy groups and pyridyloxy groups;
5-6 membered heteroaryl C1-6 alkyloxy groups such as thiazolylmethyloxy group, pyridylmethyloxy group;

Holmil group;
C1-6 alkylcarbonyl groups such as acetyl group, propionyl group;
Formyloxy group;
C1-6 alkylcarbonyloxy groups such as acetyloxy groups and propionyloxy groups;
C6-10 arylcarbonyl groups such as benzoyl groups;
C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group;
C1-6 alkoxycarbonyloxy groups such as methoxycarbonyloxy group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group, i-propoxycarbonyloxy group, n-butoxycarbonyloxy group, t-butoxycarbonyloxy group;
Carboxylic group;

Halogeno groups such as fluoro group, chloro group, bromo group, iod group;
C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group;
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 group, 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group;
C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group, 3-bromobutenyloxy group;
C1-6 haloalkylcarbonyl groups such as chloroacetyl groups, trifluoroacetyl groups, trichloroacetyl groups;

Amino group;
C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group, diethylamino group;
C6-10 arylamino groups such as anilino group and naphthylamino group;
C6-10aryl C1-6 alkylamino groups such as benzylamino group, phenethylamino group;
Formylamino group;
C1-6 alkylcarbonylamino groups such as acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group;
C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group;
Aminocarbonyl group having an unsubstituted or substituent 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) -Imino) N-hydroxyimino C1-6 alkyl group substituted or unsubstituted such as ethyl group;
Aminocarbonyloxy group;
C1-6 alkyl-substituted aminocarbonyloxy groups such as ethylaminocarbonyloxy group, dimethylaminocarbonyloxy group;

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

C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group;
C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl groups, 2,2,2-trifluoroethylsulfinyl groups;
C6-10 arylsulfinyl groups such as phenylsulfinyl groups;
5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl groups, pyridylsulfinyl groups;

C1-6 alkylsulfonyl groups such as methylsulfonyl groups, ethylsulfonyl groups, t-butylsulfonyl groups;
C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl groups, 2,2,2-trifluoroethylsulfonyl groups;
C6-10 arylsulfonyl groups such as phenylsulfonyl groups;
5-6 member heteroarylsulfonyl groups such as thiazolylsulfonyl groups, pyridylsulfonyl groups;
C1-6 alkylsulfonyloxy groups such as methylsulfonyloxy groups, ethylsulfonyloxy groups, t-butylsulfonyloxy groups;
C1-6 haloalkylsulfonyloxy groups such as trifluoromethylsulfonyloxy groups, 2,2,2-trifluoroethylsulfonyloxy groups;

Tri-C1-6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
Tri-C6-10 aryl substituted silyl groups such as triphenylsilyl groups;
Cyano group; Nitro group;

Further, in these "substituents", any hydrogen atom in the substituent may be substituted with a group having a different structure. Examples of the "substituent" in this case include 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.

The above-mentioned "3- to 6-membered heterocyclyl group" includes 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms as ring constituent atoms. The heterocyclyl group may be monocyclic or polycyclic. The polycyclic heterocyclyl group may have any of a saturated alicyclic ring, an unsaturated alicyclic ring, and an aromatic ring as long as at least one ring is a heterocyclic ring. Examples of the "3- to 6-membered heterocyclyl group" include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.

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

Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group. Can be done.
Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, a triazinyl group and the like.

[Q ¹ ]
Q ¹ represents a substituted or unsubstituted C6-10 aryl group.
Examples of the "C6 to 10 aryl group" in Q ¹ include a phenyl group and a naphthyl group.

The substituent on "C6~10 aryl group" in Q ^1, preferably fluoro, chloro, bromo group, a halogeno group such as iodo groups; methyl, ethyl, n- propyl, i- propyl , N-butyl group, s-butyl group, i-butyl group, t-butyl group and other C1-6 alkyl groups; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group , S-butoxy group, i-butoxy group, t-butoxy group and other C1-6 alkoxy groups; 2-chloro-n-propyl group, 2,3-dichlorobutyl group, trifluoromethyl group and other C1-6 haloalkyl Groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; cyano group; nitro group; methylenedioxy group;

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

"C1~6 alkyl group" in Q ² are may be linear, may be branched as long as three or more carbon atoms. Alkyl groups include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group and t-butyl group. , I-Pentyl group, Neopentyl group, 2-Methylbutyl group, 2,2-dimethylpropyl group, i-Hexyl group and the like.

As a specific example of the "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 -Trifluoromethylethyl group, 1,1,1,3,3,3-hexafluoropropan-2-yl group, perfluoropropan-2-yl group, perfluorohexyl group, perchlorohexyl group, 2,4 , C1-6 haloalkyl groups such as 6-trichlorohexyl groups;

Hydroxy C1-6 alkyl groups such as hydroxymethyl group and hydroxyethyl group;
C1 to methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group, etc. 6 alkoxy C1-6 alkyl groups;
C6 to 10 aryl C1 to 6 alkyl groups such as benzyl group and phenethyl group;
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 can be mentioned.

The substituent on "C1~6 alkyl group" in Q ^2, preferably fluoro, chloro, bromo group, a halogeno group such as iodo group; methoxy group, ethoxy group, n- propoxy group, i- propoxy , N-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and other C1-6 alkoxy groups; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group and the like. C1-6 haloalkoxy group; cyano group; can be mentioned.

Examples of the "C6 to 10 aryl groups" in Q ² include the same ones specifically exemplified in Q ¹ .
The "5-10 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 , 5-membered heteroaryl group such as tetrazolyl group; 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, triazinyl group; indrill group, isoindryl group, benzofuranyl group, benzothienyl group, indazolyl group, benzoimidazolyl group Nine-membered heteroaryl groups such as groups, benzoxazolyl groups, benzoisooxaozolyl groups, benzothiazolyl groups, benzoisothiazolyl groups; quinolinyl groups, isoquinolinyl groups, synnolinyl groups, phthalazinyl groups, quinazolinyl groups, quinoxanyl groups and the like. 10-membered heteroaryl group; and the like.

Examples of the substituent on the “C6 to 10 aryl group” in Q ² include the same ones specifically exemplified in Q ¹ above.
Examples of the substituent on the "5- to 10-membered heteroaryl group" in Q ² include the same ones 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.

[D]
D represents a substituted or unsubstituted methylene group, carbonyl group, or oxygen atom.
Substituents on the "methylene group" in D include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group and the like. C1-6 alkyl groups; can be mentioned.

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

In the crossed carbon-carbon double bond in the formula (I), the stereoisomerism due to the carbon-carbon double bond is E-form, Z-form, or a mixture of E-form and Z-form, or stereoisomerism. Indicates that is an unspecified item. In the present invention, examples of the stereoisomer include a compound represented by the formula (I-1) and a compound represented by the formula (I-2). Wherein (I-1) and formula ^{(I-2), Q 1} , Q 2, A, B, D, E, and R ¹ has the same meaning as each of the formula (I).

Among the above, it is preferable that the compound has a solid represented by the formula (I-1). That is, the carbon-carbon double bond moiety is preferably an E-form compound.

The salt of compound (I) is not particularly limited as long as it is an horticulturally acceptable salt. Examples of the salt of 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 soils such as calcium and magnesium. Salts of similar metals; Salts of transition metals such as iron and copper; Salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine and hydrazine can be mentioned.

The compound (I) or the salt of the compound (I) is not particularly limited depending on the production method thereof. For example, compound (I) or a salt of compound (I) can be obtained by a known production method described in Examples and the like. Further, 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 compound of the present invention) is excellent in controlling harmful organisms such as various agricultural pests and mites that affect the growth of plants.
In addition, the compound of the present invention is a highly safe substance because it causes less phytotoxicity to crops and has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of insecticides or acaricides.
Furthermore, in recent years, resistance to various existing drugs has developed in many pests such as diamondback moth, planthopper, leafhopper, and aphid, causing a problem of insufficient efficacy of these drugs, and a drug effective against pests of resistant strains is desired. ing. The compound of the present invention exhibits an excellent control effect not only on susceptible strains but also on pests of various resistant strains and mites of acaricide-resistant strains.

The compound of the present invention is excellent in controlling ectoparasites that are harmful to humans and animals. In addition, it is a highly safe substance because it has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of a ectoparasite control agent or an adhesion preventive agent for adherent pests.

In addition, the compound of the present invention is effective at all developmental stages of the organism to be controlled, and exhibits an excellent control effect on, for example, eggs such as mites and insects, nymphs, larvae, pupae, and adults.

[Pest control agents, insecticides or acaricides]
The pest control agent, insecticide or acaricide of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. The amount of the pest control agent of the present invention or the compound of the present invention contained in the insecticide or acaricide is not particularly limited as long as it shows the control effect of pests, agricultural pests or mites.

The pest control agent, insecticide or acaricide of the present invention includes grains; vegetables; root vegetables; potatoes; flowers; fruit trees; foliage plants, tea, coffee, cacao and other trees; grasses; Turbs; preferably used for plants such as cotton.
In application to plants, the pest control agent, or insecticide or acaricide of the present invention may be any of leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, stalks, stalks, shoots, shoots, cuttings, etc. It may be used for the site of.
Further, the pest control agent, insecticide or acaricide of the present invention is not particularly limited depending on the species of the plant to which it is applied. Examples of plant species include original species, varieties, improved varieties, cultivars, mutants, hybrids, genetically modified organisms (GMOs) and the like.

The pest control agent of the present invention can be used for seed treatment, foliage spraying, 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) Lepidoptera butterflies or moths (a) Moths of the tiger moth (Arctiidae), such as the fall webworm (Hyphantria cunea) and mulberry moth (Lemyra imparilis);
(B) Moths of the Bucculatricidae family, such as Bucculatrix pyrivorella;
(C) Sinkiga family (Carposinidae), for example, peach Sinkiga (Carposina sasakii);
(D) Moths of the Crambidae family, such as the genus Diaphania spp., Diaphania indica, Diaphania nitidalis; for example, the genus Ostrinia spp. , Awanomeiga (Ostrinia furnacalis), European cornballer (Ostrinia nubilalis), Azukinomeiga (Ostrinia scapulalis); Others, Nikameiga (Chilo suppressalis), Cobnomeiga (Cnaphalocrocis medinalis), Momonogomadaranomeiga (Conaphalocrocis medinalis) Diatraea grandiosella), Kwanomeiga (Glyphodes pyloalis), Hymadalanomeiga (Hellula undalis), Shibatuga (Parapediasia teterrella);
(E) Moths of the family Twirler moth (Gelechiidae), such as caterpillar (Helcystogramma triannulella), cotton bollworm (Pectinophora gossypiella), potato moth (Phthorimaea operculella), and angoumois grain moth (Sitotroga cerealella);
(F) Moths of the Geometridae family, such as Ascotis selenaria;
(G) Moths of the leaf miner moth (Gracillariidae), such as Chanohosoga (Caloptilia theivora), Citrus unshiu (Phyllocnistis citrella), Phyllonorycter ringoniella;
(H) Butterflies of the Skipper family (Hesperiidae), such as Parnara guttata;
(I) Moths of the family Lappet moth (Lasiocampidae), such as Lackey moth (Malacosoma neustria);
(J) Moths of the tussock moth (Lymantriidae), such as Lymantria spp., Gypsy moth (Lymantria dispar), Nonnemaimai (Lymantria monacha); Others, Chadokuga (Euproctis pseudoconspersa), Orgyia thyellum thyellina);

(K) Moths of the family Lyonetiidae, such as the genus Lyonetia spp., Lyonetia clerkella, Lyonetia prunifoliella malinella;
(L) Moths of the family Noctuidae, such as the genus Spodoptera spp., Spodoptera depravata, Southern army worm (Spodoptera eridania), Spodoptera exigua, Fall armyworm Spodoptera exigua, Fall armyworm. ), African Noctuidae (Spodoptera littoralis), Hasmon Noctuidae (Spodoptera litura); For example, Autographa spp., Gamakin uwaba (Autographa gamma), Tamanagin uwaba (Autographa nigrisigna); For example, Agrotis sp. Noctuidae (Agrotis ipsilon), Noctuidae (Agrotis segetum); For example, Helicoverpa spp., Helicoverpa armigera, Helicoverpa assulta, Cotton ball worm (Helicoverpa zea); Species (Heliothis spp.), Watakibaga (Heliothis armigera), Fake American tobacco moth (Heliothis virescens); Others, Nakajiroshitaba (Aedia leucomelas), Mitsumonkin uwaba (Ctenoplusia agnata), Akebikonoha (Eudocima tyrannus) ), Awayoto (Mythimna separata), Futaobikoyaga (Naranga aenescens), Matsukiriga (Panolis japonica), Nisetama nayaga (Peridroma saucia), Soibean looper (Pseudoplusia includens), Irakusagin uwaba (Trichoplusia ni)
(M) Moths of the family Nolidae, such as Earias insulana;
(N) Pieridae (Pieridae) butterflies, such as the large white butterfly (Pieris brassicae) and the pieris (Pieris rapae crucivora) of the genus Pieris spp.
(O) Plutellidae moths, such as the Acrolepiopsis spp., Acrolepiopsis sapporensis, Acrolepiopsis suzukiella; and other diamondback moths (Plutella xylostella);
(P) Moths of the family Pyralidae, such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Greater wax moth;
(Q) Moths of the family Sphingidae, such as the Manduca spp. Tomato hornworm (Manduca quinquemaculata), Tobacco hornworm (Manduca sexta);

(R) Moths of the family Stahtmopodidae, such as the Stahmopoda masinissa;
(S) Moths of the family Tineidae, such as Tinea translucens;
(T) Moths of the Tortrix moth family (Tortricidae), such as the Adoxophyes spp., Adoxophyes honmai, Adoxophyes orana; for example, the Archips spp. ), Ringomonhamaki (Archips breviplicanus), Midarekakumonhamaki (Archips fuscocupreanus); Others, Tohinoshintomehamaki (Choristoneura fumiferana), Kodriinga (Cydia pomonella), Grape Hosohamaki (Eupoecilia ambiguella) ), Chahamaki (Homona magnanima), Mameshiniga (Leguminivora glycinivorella), Hosobahimehamaki (Lobesia botrana), Mamehimesayamushiga (Matsumuraeses phaseoli), Tobihamaki (Pandemis heparana), Tenguhamaki (Sparganothis pill)
(U) Moths of the Ermine moth family (Yponomeutidae), such as the apple fruit moth (Argyresthia conjugella).

(2) Thripidae (Thysanoptera) pests (a) Thripidae (Phlaeothripidae), for example, Thripidae (Ponticulothrips diospyrosi);
(B) Thripidae, eg Frankliniella spp., Thripidae thripidae, Thripidae thripidae, Frankliniella occidentalis; for example, Thrips spp. Thrips palmi, Thrips tabaci; Others, Thripidae (Heliothrips haemorrhoidalis), Chanokiiro thrips (Scirtothrips dorsalis).

(3) Pests of the order Hemiptera (A) Auchenorrhyncha (Archaeorrhyncha)
(A) Delphacidae, such as Himetobiunka (Laodelphax striatella), Brown planthopper (Nilaparvata lugens), Croftsnounka (Perkinsiella saccharicida), Segatella furcifera.

(B) Auchenorrhyncha
(A) Leafhoppers (Cicadellidae), for example, Empoasca spp., Potato leafhoppers (Empoasca fabae), Leafhoppers (Empoasca nipponica), Chanomidorihimeyokobai (Empoasca onukii), Maeno Leafhopper (Empoasca sakaii); Others, Leafhopper (Arboridia apicalis), Empoasca (Balclutha saltuella), Leafhopper (Epiacanthus stramineus), Leafhopper (Macrosteles striifrons), Cinc ).

(C) Heteroptera
(A) Riptortus clavatus of the family Riptortus pedestrianis (Alydidae);
(B) Of the leaf-footed bug family (Coreidae), for example, the leaf-footed bug (Cletus punctiger), the spider stink bug (Leptocorisa chinensis);
(C) For example, Chinch bug (Blissus) of the family Malcidae (Lygaeidae)
leucopterus), Cavelerius saccharivorus, Togo hemipterus;
(D) For example, black-spotted bugs (Halticus insularis), sabiiro-kasumi-turtle (Lygus lineolaris), cotton-free hopper (Psuedatomoscelis seriatus), nagamugi-kasumi-turtle (Stenodema sibiricum), lygus (Akasujikasumi) ), Rice Hosomidori Kasumi turtle (Trigonotylus caelestialium);

(E) Stink bugs (Pentatomidae), eg, Nezara spp., Stink bug (Nezara antennata), Southern green stink bug (Nezara viridula); for example, Stink bug genus (Eysarcoris spp.) , Stink bug (Eysarcoris aeneus), Stink bug (Eysarcoris lewisi), Stink bug (Eysarcoris ventralis), Others, Stink bug (Dolycoris baccarum), Stink bug (Dolycoris baccarum), Stink bug (Dolycoris baccarum), Stink bug (Eurydema rugo) Halyomorpha halys), stink bug (Piezodorus hybneri), stink bug (Plautia crossota), stink bug (Scotinophora lurida);
(F) Of the red bug family (Pyrrhocoridae), for example, the red bug (Dysdercus cingulatus);
(G) Of the family Riptortus pedestrianis (Rhopalidae), for example, the red-footed bug (Rhopalus msculatus);
(H) For example, the wheat arma custos (Eurygaster) of the family Scutelleridae.
integriceps);
(I) Of the Tingidae family, for example, Stephanitis nashi.

(D) Sternorrhyncha
(A) Adelgidae, for example, Larch aphid (Adelges laricis);
(B) Whitefly family (Aleyrodidae) For example, Bemisia spp., Silver leaf whitefly (Bemisia argentifolii), Tobacco whitefly (Bemisia tabaci); Other whitefly (Aleurocanthus spiniferus), Whitefly (Di) citri), whitefly (Trialeurodes vaporariorum);
(C) Aphididae, for example, Aphis spp., Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii. , European apple aphid (Aphis pomi), chicken aphid (Aphis sambuci), Yukiyanagi aphid (Aphis spiraecola); for example, corn aphid (Rhopalosiphum spp.), Corn aphid (Rhopalosiphum maidis), wheat aphid (Rhopalosiphum maidis), wheat aphid For example, the genus Aphididae (Dysaphis spp.), Aphididae (Dysaphis plantaginea), Aphididae (Dysaphis radicola); for example, the genus Macrosiphum (Macrosiphum spp.), Aphididae (Macrosiphum avenae), Tulip (Macrosiphum euphorbiae); for example, of the genus Myzus spp., Myzus cerasi, Myzus persicae, Myzus varians; Other, Aphididae, Actho pisum), potato aphid (Aulacorthum solani), wheat aphid (Brachycaudus helichrysi), daikon aphid (Brevicoryne brassicae), strawberry aphid (Chaetosiphon fragaefolii), peach aphid (Chaetosiphon fragaefolii), peach aphid (Haetosiphon fragaefolii) , Fake aphid (Lipaphis erysimi), Aphididae (Megoura viciae), Mugius aphid (Metopolophium dirhodum), Lettuce aphid (Nasonovia ribis-nigri), Hot Phorodon humuli, Schizaphis graminum, Sitobion avenae, Toxoptera aurantii;

(D) Coccidae, for example, Ceroplastes spp., Ceroplastes ceriferus, Ceroplastes rubens;
(E) Diaspididae, Pseudaulacaspis spp., Pseudaulacaspis pentagona, Pseudaulacaspis prunicola; for example, Unaspis spp. Of the scale insects (Unaspis euonymi), the scale insects (Unaspis yanonensis); and others, the scale insects (Aonidiella aurantii), the scale insects (Comstockaspis perniciosa), the scale insects (Fiorinia theae), and the scale insects (Fiorinia theae). );
(F) Icerya scale insects (Margarodidae), for example, Owaraji scale insect (Drosicha corpulenta), Iceria scale insect (Icerya purchasi);
(G) Phylloxeridae, for example, Viteus vitifolii;
(H) Pseudococcidae, for example, Planococcus spp., Planococcus citri, Planococcus kuraunhiae; Other, Phenacoccus sol , Pseudococcus comstocki;
(I) Psyllidae, for example, Psylla spp., Psylla mali, Psylla pyrisuga; and other Diaphorina citri.

(4) Pests of the suborder Polyphaga (a) Anobiidae, for example, Lasioderma serricorne;
(B) Of the Attelabidae family, for example, Byctiscus betulae, Rhynchites heros;
(C) Lyctus brunneus of the family Nagasink beetle (Bostrichidae);
(D) Of the family Cylas formicarius, for example, Cylas formicarius;
(E) Of the jewel beetle family (Buprestidae), for example, the jewel beetle (Agrilus sinuatus);
(F) Longhorn beetle (Cerambycidae), for example, Citrus long-horned beetle (Anoplophora malasiaca), Longhorn beetle (Monochamus alternatus), Psacothea hilaris, Grape tiger longhorn beetle (Xylotrechus pyrrhoderus)
(G) Chrysomelidae, for example, Bruchus spp., Bruchus pisorum, Broad bean weevil (Bruchus rufimanus); for example, Diabrotica spp., Northern corn. Root worm (Diabrotica barberi), Southern corn root worm (Diabrotica undecimpunctata), Western corn root worm (Diabrotica virgifera); For example, Phyllotreta spp., Phyllotreta nemorum, Phyllotreta nemorum, Phyllotte leaf beetle. ); Others, Aulacophora femoralis, Callosobruchus chinensis, Cassida nebulosa, Chaetocnema concinna, Colorado leaf beetle (Leptinotarsa decemlineata), Inekubihosohamushi (Leptinotarsa decemlineata) Nagasnetobi beetle (Psylliodes angusticollis);

(H) Coccinellidae, for example, Epilacna spp., Mexican bean beetle (Epilachna varivestis), Henosepilachna vigintioctopunctata;
(I) Curculionidae, eg, Anthonomus spp., Watamizoumushi (Anthonomus grandis), Nashihanazoumushi (Anthonomus pomorum); for example, Sitophilus spp. , Granary Weevils (Sitophilus granarius), Sitophilus (Sitophilus zeamais); Others, Weevils (Echinocnemus squameus), Imozoumushi (Euscepes postfasciatus), Matsuana Akizoumushi (Hylobius abietis), Alfalfa weevil (Hylobius abietis) Lissohoptrus oryzophilus), Sitophilus weevil (Otiorhynchus sulcatus), Red-spotted weevil (Sitona lineatus), Sitophilus weevil (Sphenophorus venatus);
(J) Click beetles (Elateridae), for example, Melanotus spp., Melanotus fortnumi, Melanotus tamsuyensis;
(K) Sap beetle (Nitidulidae), for example, Sap beetle (Epuraea domina);
(L) Scarabaeidae, for example, Anomala spp., Anomala cuprea, Anomala rufocuprea; Others, Cetonia aurata, Gametis jucunda ), Nagachakogane (Heptophylla picea), European scarabaeoidea (Melolontha melolontha), Mamekogane (Popillia japonica);
(M) Of the bark beetle family (Scolytidae), for example, the spruce bark (Ips typographus);
(N) Staphylinidae, for example, Paederus fuscipes;
(O) Tenebrionidae, for example, Tenebrio molitor, Red flour beetle (Tribolium castaneum);
(P) Of the family Red flour beetle (Trogossitidae), for example, the red flour beetle (Tenebroides mauritanicus).

(5) Flies (Diptera) pests (A) Flies (Brachycera)
(A) Agromyzidae, for example, Agromyzidae (Liriomyza spp.), Agromyzidae (Liriomyza bryoniae), Agromyzidae (Liriomyza chinensis), Tomato leafminer (Liriomyza sativae), Agromyzidae (Liriomyza sativae) Others, Agromyzidae (Chromatomyia horticola), Agromyzidae (Agromyza oryzae);
(B) Anthomyiidae, eg, Delia spp., Delia platura, Delia radicum; and other sugar beet, Pegomya cunicularia;
(C) Drosophilidae, for example, fruit fly species (Drosophila spp.), Drosophila melanogaster, fruit fly (Drosophila suzukii);
(D) Of the family Ephydridae, for example, Hydrollia griseola;
(E) From the family Psilidae, for example, the carrot fly (Psila rosae);
(F) Of the family Tephritidae, for example, the genus Bactrocera spp., The melon fly (Bactrocera cucurbitae), the fruit fly (Bactrocera dorsalis); for example, the genus Rhagoletis spp. Rhagoletis cerasi), Ringo fly (Rhagoletis pomonella); Others, Chichukai mibae (Ceratitis capitata), Olive mibae (Dacus oleae).

(B) Nematocera
(A) Cecidomyiidae, for example, Soybean Sayama fly (Asphondylia yushimai), Sorghum tama fly (Contarinia sorghicola), Hessian fly (Mayetiola destructor), Mugia katama fly (Sitodiplosis mosellana).

(6) Orthoptera pests (a) Acrididae, eg, Schistocerca spp., American locusts (Schistocerca americana), Sabactobibatta (Schistocerca gregaria); Australian locusts (Chortoicetes terminifera), Moroccan locusts (Dociostaurus maroccanus), Tonosama locusts (Locusta migratoria), Brown locusts (Locustana pardalina), Akato locusts (Nomadacris septemfasciata), Kobaneinago (Oxya yezoensis)
(B) Cricket family (Gryllidae), such as European house cricket (Acheta domestica), cricket (Teleogryllus emma);
(C) Mole cricket (Gryllotalpidae), for example, mole cricket (Gryllotalpa orientalis);
(D) Of the Bush cricket family (Tettigoniidae), for example, Tachycines asynamorus.

(7) Mites (Acari)
(A) Acaridida of the order Astigmata
(A) Acaridae mites, such as Rhizoglyphus spp., Rhizoglyphus echinopus, Rhizoglyphus robini; for example, Tyrophagus spp. (Tyrophagus neiswanderi), Tyrophagus putrescenti, Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; Others, Acarus siro, Tyrophagus putrescentiae, Acarus siro, Tyrophagus putrescentiae

(B) Prostigmata prostigmata (Actinedida)
(A) Spider mite (Tetranychidae) mites, such as Bryobia spp., Clover spider mite (Bryobia praetiosa), fake clover spider mite (Bryobia rubrioculus); for example, Eotetranychus spp. , Eotetranychus asiaticus, Anzu spider mite (Eotetranychus boreus), Eotetranychus celtis, Michinoku spider mite (Eotetranychus geniculatus), Miyake spider mite (Eotetranychus geniculatus), Miyake spider mite (Eotetranychus kankitus), Eotetranychus kankitus (Eotetranychus smithi), Suginami spider mite (Eotetranychus suginamensis), walnut spider mite (Eotetranychus uncatus); for example, Oligonychus spp., Oligonychus hondoensis, Oligonychus hondoensis, Chibicob spider mite Mango spider mite (Oligonychus mangiferus), sugar cane spider mite (Oligonychus orthius), avocado spider mite (Oligonychus perseae), Ezosugi spider mite (Oligonychus pustulosus), rice spider mite (Oligonychus shinkajii), rice spider mite (Oligonychus shinkajii), genus Todomatsu spider mite , Mikan spider mite (Panonychus citri), quail spider mite (Panonychus mori), apple spider mite (Panonychus ulmi); for example, Tetranychus spp., Nisenami spider mite (Tetranychus cinnabarinus), Kanzawa spider mite (Tetranychus cinnabarinus) ), Mizunara spider mite (Tet) ranychus quercivorus), Sagami spider mite (Tetranychus phaselus), Nami spider mite (Tetranychus urticae), Oto spider mite (Tetranychus viennensis); For example, Aponychus spp., Itomaki spider mite (Aponychus spp.) Midori spider mite (Sasanychus spp.), Midori spider mite (Sasanychus akitanus), Himemidori spider mite (Sasanychus pusillus); for example, Shizotetranychus spp., Takesugomori spider mite (Shizotetranychus celarius) ), Shizotetranychus miscanthi, Shizotetranychus recki, Shizotetranychus schizopus; Others, Tetranychina harti, Tetranychus harti, Tuckerella pavoniformis, Tuckerella pavoniformis

(B) Tick of the family Tenuipalpidae, for example, Brevipalpus spp., Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Brevipalpus phoenicis, Brevipalpus phoenicis russulus), Brevipalpus californicus; For example, Tenuipalpus spp., Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; Others, pineapple zhizhilashviliae;
(C) Eriophyidae mites, for example, Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, carnation. Aceria paradianthi, Aceria tiyingi, Aceria tulipae, Aceria zoysiea; for example, Eriophyes spp., Eriophyes chibaensis, Eriophyes chibaensis, Eriophyes chibaensis. emarginatae); for example, Aculops spp., Tomato sabi mite (Aculops lycopersici), Mikan sabi mite (Aculops pelekassi); for example, Aculus spp., Momosa sabi mite (Aculus fockeui), apple sabi mite (Aculus fockeui). schlechtendali; Others, Acaphylla theavagrans, Calacarus carinatus, Colomerus vitis, Calepirimerus vitis, Epitrimerus pyri, Epitrimerus pyri, Epitrimerus pyrai podocarpi), Ryukyu mites (Phyllocotruta citri);
(D) Tarsonemidae mites, such as Tarsonemus spp., Tarsonemus bilobatus, Tarsonemus waitei; and other Cyclamen mite (Phytonemus pallidus), Chano dust mites (Polyphago). );
(E) Penthaleidae mites, such as Penthaleus spp., Penthaleus erythrocephalus, and Penthaleus major.

The pest control agents of the present invention are other active ingredients such as fungicides, insecticides / acaricides, nematode pesticides, soil pesticides; plant growth regulators, herbicides, synergists, fertilizers, soil conditioners. , May be mixed or used in combination with animal feed and the like.
The combination of the compound of the present invention and another active ingredient can be expected to have a synergistic effect on insecticidal, acaricidal, and nematode activity. The synergistic effect can be confirmed by Colby's formula (Colby.SR; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, pp. 20-22, 1967) according to a conventional method.

Specific examples of insecticides / acaricides, nematodes, soil pesticides, anthelmintics and the like that can be mixed or used in combination with the pest control agent of the present invention are shown below.

(1) Acetylcholinesterase inhibitor:
(A) Carbamate: Aranicarb, Aldicarb, Bengiocarb, Benfracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiophenacarb, Phenoccarb, Formetanate, Frathiocarb, Isoprocarb, Methiocarb, Methomyl, Oxamil, Pyrimicarb, Propoxal. Thiodicarb, thiofanox, triazamate, trimetacarb, XMC, xylylcarb; phenothiocarb, MIPC, MPMC, MTMC, aldicarb, alixicalve, aminocarb, butocarboxim, chlorocarb, metam sodium, promecarb;

(B) Organophosphorus: acephate, azamethifos, azinephos-ethyl, azinephos-methyl, kazusaphos, chlorethoxyphos, chlorphenbinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, bearphos, cyanophos, demeton-S-methyl, diazinone, Dichlorvos / DDVP, Dichlorvos, Dimethoate, Dimethylbinphos, Disulfoton, EPN, Ethion, Etoprophos, Famfur, Fenamiphos, Fenitrothione, Fention, Hostizate, Heptenophos, Imiciaphos, Isophenphos, Isocarbhos, Isoxathion, Malathion, Mecarbamme, Metaphos Monochrometophos, Nared, Omethoate, Oxydimethoate-Methyl, Palathion, Palatin-Methyl, Fentate, Holate, Hosalon, Hosmet, Phosphamide, Hoxim, Pyrimiphos-Methyl, Prophenofus, Propetamphos, Prothiophos, Pyraclophos, Pyridafenthion, Kinalphos, Sulfotep Temephos, terbuphos, tetrachlorvos, thiometon, triazophos, trichlorphon, bamidthione; bromophos ethyl, BRP, carbophenothione, cyanophenphos, CYAP, demeton-S-methylsulfos, dichlorphos, dichlorphenthione, dioxabenzophos, ethis , Fensulfothione, flupyrazophos, honophos, formotione, phosmethilan, isazophos, iodophenphos, methacryphos, pyrimiphos-ethyl, phosphocarbs, propaphos, protoate, sulprophos.

(2) GABA-operated chloride channel antagonists: acetoprol, chlordane, endosulfan, ethiprol, fipronil, pilafprowl, pilafrol; camfechlor, heptachlor, dienochlor.
(3) Sodium channel modulators: acrinathrin, d-cis-trans-allethrin, d-trans-allethrin, bifentrin, bioallethrin, bioarethrin S-cyclopentyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyfluthrin, lambda- Sihalothrin, Gamma-Cihalothrin, Cipermethrin, Alpha-Cipermethrin, Beta-Cipermethrin, Theta-Cipermethrin, Zeta-Cipermethrin, Ciphenothrin [(1R) -Trans-isomer], Deltamethrin, Empentrin [(EZ)-( 1R)-isomer], esphenvalerate, etofenprox, fenpropatrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halphenprox, imiprithrin, cadesrin, permethrin, phenothrin [(1R) -trans Heterogeneous], prarethrin, pyrethrum, lesmethrin, cyfluthrin, tefluthrin, tetramethrin [(1R) -isomer], tralomethrin, transfluthrin; allethrin, pyrethrin, pyrethrin I, permethrin II, profluthrin, dimefluthrin, bioetanomethrin Permethrin, transpermethrin, fenfluthrin, fenpyritrin, flubrocitrinate, flufenprox, methfurthrin, protrifenbut, pyrethrin, terraretrin.

(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradiflon.
(5) Nicotinic acetylcholine receptor allosteric modulators: spinetram, spinosad.
(6) Chloride channel activator: abamectin, emamectin benzoate, repimectin, milbemectin; ivermectin, selamectin, dramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, nemadetin.
(7) Juvenile hormone-like substances: hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen; diophenolan, epophenonan, triprene.
(8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, liquor stone.
(9) Diptera selective feeding inhibitors: Fluoricamide, Pymetrodin, Pyrifluquinazone.

(10) Mite growth inhibitors: clofentezine, difluorovidazine, hexitiazox, etoxazole.
(11) Microbial-derived insect mid-intestinal membrane-destroying agent: Bacillus thuringiensis subspecies Isla Elenshi, Bacillus thuringiensis subspecies Isla Elenshi, Bacillus thuringiensis subspecies Isawai, Bacillus thuringiensis subspecies Kurstaki, Bacillus thuringiensis subspecies Teneblionis, Bt Crop protein: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.
(12) Mitochondrial ATP biosynthetic enzyme inhibitor: diafentiurone, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradiphon.
(13) Oxidative phosphorylation decoupling agent: chlorfenapyr, sulfamide, DNOC; binapacryl, dinobutone, dinocup.
(14) Nicotinic Acetylcholine Receptor Channel Blocker: Bensultap, Cartap Hydrochloride; Nelystoxin; Thiosultap Monosodium Salt, Thiocyclum.
(15) Chitin synthesis inhibitors: bistrifluron, chlorflubenzuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumron, lufenuron, novalron, nobiflumron, teflubenzuron, triflubenzuron, buprofezin, fluazuron.
(16) Diptera molting disturber: Cyromazine.
(17) Moulting hormone receptor agonists: chromaphenozide, halophenozide, methoxyphenozide, tebufenozide.
(18) Octopamine receptor agonists: Amitraz, Demiditraz, Chlordimeform.
(19) Mitochondrial electron transport chain complex III inhibitor: acequinosyl, fluacripirim, hydramethylnon.
(20) Mitochondrial electron transport chain complex I inhibitor: phenazakin, phenpyroximate, pyrimidiphen, pyridaben, tebufenpyrado, tolfenpyrad, rotenone.

(21) Voltage-gated sodium channel blockers: indoxacarb, metaflumisone.
(22) Acetyl-CoA carboxylase inhibitors: spirodiclophen, spiromesiphen, spirotetramato.
(23) Mitochondrial electron transport chain complex IV inhibitor: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide.
(24) Mitochondrial electron transport chain complex II inhibitor: sienopyraphen, siflumethofen, pifrubmid.
(25) Ryanodine receptor modulators: chloranthraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, tetraniliprole.
(26) Mixed Function Oxidase Inhibitor Compound: Piperonyl butoxide.
(27) Latrophilin receptor agonists: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside.
(28) Other agents (mechanism of action unknown): azadilactin, benzoximate, biphenazate, bromopropilate, quinomethionate, cryolite, dicoform, pyridalyl; bencrothias, sulfur, amidoflumet, 1,3-dichloropropene, DCIP , Phenisobromolate, benzomate, metaldehyde, chlorbenzylate, clothiazoben, disiccranyl, phenoxacrim, fentrifanyl, flubenzimine, flufenazine, gossiplua, japonilua, metoxadiazone, petroleum, potassium oleate, tetrasul, triarasen; afidopyropen), fromotkin, flufiprole, fluensulphon, meperfluthrin, tetramethylfluthrin, traropyryl, dimefluthrin, methylneodecanamide; flularanel, afoxolanel, fluxamethamide, 5- [5- (3,5-dichlorophenyl) -5-tri Fluoromethyl-4,5-dihydroisoxazole-3-yl] -2- (1H-1,2,4-triazole-1-yl) benzonitrile (CAS: 943137-49-3), brofuranilide, and other metaldehydes Kind.

(29) Anthelmintic:
(A) Benzimidazole system: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole; fevantel, netobimin, thiophanate; thiabendazole, cambendazole;
(B) Salicylanilide system: closantel, oxyclozanide, lafoxanide, niclosamide;
(C) Substituted phenolic system: nitroxynyl, nitroscanate;
(D) Pyrimidines: Pyrantel, Morantel;
(E) Imidazothiazole type: levamisole, tetramisole;
(F) Tetrahydropyrimidines: Praziquantel, Epsiprantel;
(G) Other anthelmintics: cyclodiene, liania, chlorthrone, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophene, monepantel, tribendimidine, amidantel; thiacetalsamide, merolsamine, arsenamide.

Specific examples of the fungicide that can be mixed or used in combination with the pest control agent of the present invention are shown below.
(1) Nucleic acid biosynthesis inhibitor:
(A) RNA polymerase I inhibitor: Benalaxil, Benalaxil-M, Flaluxil, Metalaxil, Metalaxil-M; Oxadixil; Crodilacon, Offrace;
(B) Adenosine deaminase inhibitors: bupirimate, dimethyrimole, etilimol;
(C) DNA / RNA synthesis inhibitors: himexazole, octinenone;
(D) DNA topoisomerase II inhibitor: oxolinic acid.

(2) Mitotic and fission inhibitors:
(A) β-tubulin polymerization inhibitor: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; dietofencarb; zoxamide; etaboxam;
(B) Cell division inhibitor: pencyclon;
(C) Inhibitor of spectrin-like protein delocalization: fluoricolide.

(3) Respiratory inhibitor:
(A) Complex I NADH Oxidoreductase Inhibitor: Diflumetrim; Torphenpyrad;
(B) Complex II succinate dehydrogenase inhibitors: benodanyl, flutranyl, mepronil; isofetamide; fluopirum; fenfuram, flumecyclox; carboxyne, oxycarboxyne; thyfluzamide; benzobindiflupill, bixaphen, fluxapyroxado , Flametopil, isopyrazam, penflufen, penthiopyrado, sedaxan; boscalid;
(C) Complex III Ubiquinol Oxidase Qo Inhibitors: Azoxystrobin, Spiderxtrobin, Kumethoxystrobin, Enokistrobin, Fluphenoxystrobin, Pycoxystrobin, Pyraoxystrobin; Pyrametostrobin, triclopyricalve; cresoxime-methyl, trifloxystrobin; dymoxystrobin, phenaminestrobin, metminostrobin, orythastrobin; famoxadon; fluoroxastrobin; fenamiden;
(D) Complex III Ubiquinol Reductase Qi Inhibitor: Ciazofamide; Amisulbrom;
(E) Oxidative phosphorylation decoupling agents: binapacryl, meptyldinocup, dinocup; fluazinum; ferlimzone;
(F) Oxidative phosphorylation inhibitor (inhibitor of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide;
(G) ATP production inhibitor: silthiofam;
(H) Complex III: Qx (unknown) inhibitor of tyrochrome bc1 (ubiquinone reductase): amethoctrazine.

(4) Amino acid and protein synthesis inhibitors (a) Methionine biosynthesis inhibitors: andprim, cyprodinyl, mepanipyrim, pyrimethanyl;
(B) Protein synthesis inhibitor: Blasticidin-S; casugamycin, casugamycin hydrochloride; streptomycin; oxytetracycline.

(5) Signal transduction inhibitor:
(A) Signal transduction inhibitors: quinoxyphen, proquinazide;
(B) MAP-histidine kinase inhibitors in osmotic signaling: fenpicronyl, fludioxonyl; clozolimate, iprodion, procymidone, vinclozoline.

(6) Lipid and cell membrane synthesis inhibitor:
(A) Phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenphos, pyrazophos; isoprothiolane;
(B) Lipid oxidizers: biphenyl, chloroneb, dichlorane, kinden, technazen, turquophosmethyl; etridiazole;
(C) Agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb hosetylate, prothiocarb;
(D) Pathogens Microorganisms that disrupt cell membranes: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain;
(E) Agent that disturbs cell membranes: Extract of Gosei Kayupte (tea tree).

(7) Cell membrane sterol biosynthesis inhibitor:
(A) Demethylation inhibitor at position C14 in sterol biosynthesis: trifoline; pyriphenox, pyriisoxazole; phenalimol, furluprimidol, nuarimol; imazalyl, imazalyl sulfate, oxpoconazole, pefrazoate, prochloras, Triflumizole, biniconazole;
Azaconazole, bitertanol, bromconazole, cyproconazole, diclobutrazole, diphenoconazole, diniconazole, diniconazole-M, epoxyconazole, etaconazole, fenbuconazole, flukinconazole, flucilazole, flutriahole), fluconazole, fluconazole- Sis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, quinconazole, simeconazole, tebuconazole, tetraconazole, triazimefone, triazimenol, triticonazole; prothioconazole, boriconazole;
(B) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis:
Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidine, piperarin; spiroxamine;
(C) 3-Ket reductase inhibitor in C4 demethylation of sterol biosynthesis system: fenhexamide; fenpyrazamine;
(D) Sterol biosynthetic squalene epoxydase inhibitor: pyribuchicarb; naphthifen, terbinafine.

(8) Inhibition of cell wall synthesis (a) Trehalase inhibitor: Validamycin;
(B) Chitin synthase inhibitors: polyoxine, polyoxolim;
(C) Cellulose Synthetic Enzyme Inhibitors: Dimethmorph, Fulmorph, Pyrimorph; Bench Avaricarb, Iprovaricarb, Torprocarb, Varifenalate; Mandipropamide.

(9) Melanin biosynthesis inhibitor (a) Melanin biosynthesis reductase inhibitor: fusalide; pyrokyron; tricyclazole;
(B) Dehydratase inhibitor for melanin biosynthesis: calpropamide; diclosimet; phenoxanyl.

(10) Host plant resistance inducer:
(A) Agent acting on the salicylic acid synthesis pathway: Acibenzolar-S-methyl;
(B) Others: probenazole; thiazinyl; isothianil; laminarin; Reynoutria sachalinensis extract.

(11) Agents of unknown activity: simoxanyl, Josetylaluminum, phosphate (phosphate), tecrophthalam, triazoxide, flusulfamide, dichromedin, metasulfocarb, ciflufenamide, metrafenone, pyriophenone, dodine, dodine free base, fluthianyl.

(12) Agents with multiple points of action: copper (copper salt), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; ferbum, mancozeb, maneb) , Mancopper, Methylam, Polycarbamate, Propineb, Tiram, Dineb, Dyram; Captan, Captahole, Folpet; Chlorotaronyl; Diclofluanide, Trillflunide; Guazatin, iminoctadine triacetate, Iminoctadine albesilate ( iminoctadine trialbesilate); anilazine; dithianone; quinomethionate; fluorimide.

(13) Other agents: DBEDC, fluorofolpet, oxadiazole acetate, bis (8-quinolinolato) copper (II), propamidin, chloropyrrolnitrin, cyprofram, agrobacterium, betoxazine, diphenylamine, methylisothianate (MITC) ), Mildeomycin, Capsaicin, Cufraneb, Ciprosulfamide, Dazomet, Devacarb, Dichlorophene, Diphenzoquat, Difenzoquat Methylsulfonate, Flumetbel, Josetil Calcium, Josetyl Sodium, Irmamycin, Natamicin, Nitrotal Isopropyl , Oxamocarb, Propamosin Sodium, Pyrrolnitrin, Tebuflokin, Tornifanide, Zariramid, Algophase, Amicarthiazol, Oxathiapiprolin, Methylamzinc, Benchazole, Triclamid, Uniconazole, Mildeo Mycin, Oxyfenthiin, picarbutrazox.

Specific examples of plant growth regulators that can be mixed or used in combination with the pest control agent of the present invention are shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorphenurone, tidiazulone, chlorphenurone, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as abscisic acid), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indol-3-butyric acid, gibberellin, phenothiol, 1 -Naphtylacetamide, ethicrozeto, cloxyhonac, hydrazide maleate, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+) -Deoxystrigor, (+)-Orovancol, (+)-Solgolactone, 4-oxo-4- (2-phenylethyl) aminobutyric acid; etephon, chlormecoat, mepicote chloride, benzyladenin, 5-aminoleverellin.

[Pest 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 the ectoparasite control effect.

The host animals to be treated with the ectoparasite control agent of the present invention include pet animals such as dogs and cats; pet birds; domestic animals such as cows, horses, pigs and sheep; poultry; and other warm-blooded animals and salmon. , Fish such as trout, puffer, carp, goldfish, and insects such as honeybees, stag beetles, and beetles.

The ectoparasite control agent of the present invention can be applied by a known veterinary method (topical, oral, parenteral or subcutaneous administration). The method is to administer it orally to animals by mixing tablets, capsules, feed, etc .; to administer it to animals by dipping solution, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); oily or A method of locally administering an aqueous solution by spraying, pore-on, spot-on, etc .; Kneading an ectoparasite control agent into a resin, molding the kneaded product into an appropriate shape such as a collar or ear tag, and applying it to an animal. A method of wearing and locally administering; etc. can be mentioned.

Ectoparasites parasitize the body and skin of host animals, especially warm-blooded animals and fish. Specifically, it parasitizes the back, armpits, lower abdomen, inner thighs, etc. of the host animal and inhabits by obtaining nutrient sources such as blood and dandruff from the animal. Examples of ectoparasites include mites, lice, fleas, mosquitoes, stable flies, flesh flies, and worms. Specific examples of ectoparasites that can be controlled by the ectoparasite control agent of the present invention are shown below.

(1) Mites (Acari)
Dermanyssidae mites, Macronyssidae mites, Laelapidae mites, Varroidae mites, Argasidae mites, Ixodidae mites, cucumber mites Insect-parasitic mites such as family (Psoroptidae) mites, mites of the family Sarcoptidae, mites of the family Knemidokoptidae, mites of the family Demodixidae, mites of the family Trombiculidae, and mites of mulberry. ..
(2) Louse eyes (Phthiraptera)
Louse of the family Haematopinidae, louse of the family Linognathidae, mallophaga of the family Menoponidae, mallophaga of the family Philopteridae, mallophaga of the family Mammal chewing (Trichodectida).
(3) Flea eyes (Siphonaptera)
Human fleas (Pulicidae) fleas, such as dog fleas (Ctenocephalides spp.), Dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis);
Fleas of the family Chigoe flea (Tungidae), fleas of the family Ceratophyllidae, fleas of the family Ceratophyllidae (Leptopsyllidae).
(4) Hemiptera.
(5) Diptera mosquitoes, Culicidae mosquitoes, Simuliidae mosquitoes, Ceratopogonidae mosquitoes, Tabanidae mosquitoes, Muscidae flies, Glossinidae Glossinidae, Glossinidae flies, Hipboscidae flies, Calliphoridae flies, and Botfly Oestridae flies.

The compound of the present invention also has poisonous needles and poisonous liquids, pests that damage human animals, pests that transmit various pathogens and pathogens, and pests that cause discomfort to humans (toxic pests, sanitary pests, and unpleasant pests). Etc.) is excellent in control effect.

A specific example is shown below.
(1) Hymenoptera pests, velvet ants (Argidae), velvet ants (Cynipidae), pine bees (Diprionidae), ants (Formicidae), ants (Mutillidae), A bee of the family Vespidae.

(2) Other pests Cockroaches (Blattodea), termites (termite), spiders (Araneae), mucades (cetipede), millipedes (millipede), crustacea (crustacea), Nanjing insects (Cimex lectularius).

[Pest adhesion inhibitor]
The pest biofouling inhibitor 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 adhesion inhibitor of the present invention is not particularly limited as long as it exhibits the pest adhesion prevention effect.
Adhesive pests to be controlled are crustaceans represented by barnacles (barnacles). Barnacle-attached organisms, specifically barnacles, lepas anatifers, and capitulum mitella, are of great harm to aquatic structures, and their control is industrially beneficial.

The underwater structure means an artificial structure that is submerged in water or is in contact with water almost all the time. For example, shore protection in ports, waterways, shipyards, etc .; underwater facilities; water pipes; facilities and equipment in contact with water in power plants, factories, etc .; equipment in contact with cooling towers, cooling water or heat medium; water supply facilities; water purification Fields, sewage treatment plants; ships, especially bottoms, ballast tanks and equipment attached to them; fishing reefs; equipment such as fishing nets used underwater in fishing industries; buoys; underwater facilities such as oil drilling facilities; etc.
As a practically effective method, it is used as a composition containing the compound of the present invention. Specifically, the composition is added as it is to water in which harmful organisms lie, for example, ballast water in ships, heat medium such as cooling water used in various devices, or water in which harmful organisms lie (seawater). , Lake water, river water, etc.) by applying, injecting, or impregnating the surface of an underwater structure installed.

[Formulation prescription]
Some formulations of the pest control agent, insecticide or acaricide, ectoparasite control agent, or pest control agent of the present invention are shown, but the additives and addition ratios should be limited to these examples. It is possible to change it over a wide range. The part during formulation indicates the part by weight.

The formulation formulas for agriculture and horticulture and paddy rice are shown below.

(Formulation 1: wettable powder)
40 parts of the compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate ester, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely pulverized to obtain a wettable powder having 40% of the active ingredient.

(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 alkyl allyl ether are mixed and dissolved to obtain an emulsion containing 30% of the 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 granules having a diameter of 0.5 to 1.0 mm. Obtain granules with 5% active ingredient.

(Formulation 4: Granules)
5 parts of the compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of sodium dioctyl sulfosuccinate, and 1 part of potassium phosphate were pulverized and mixed well, water was added and kneaded well, and then granulated and dried. Obtain granules with 5% active ingredient.

(Formulation 5: Suspension)
10 parts of the compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of sodium polycarboxylic acid salt, 10 parts of glycerin, 0.2 part of xanthan gum, and 73.8 parts of water are mixed to reduce the particle size to 3 microns or less. Wet grind to obtain a suspension of 10% active ingredient.

The formulation for controlling ectoparasites is shown below.

(Formulation 6: Granules)
Five parts of the compound of the present invention are dissolved in an organic solvent to obtain a solution, the solution is sprayed onto 94 parts of kaolin and 1 part of white carbon, and then the solvent is evaporated under reduced pressure. This type of granule can be mixed with animal food.

(Formulation 7: Injectable)
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 sterilized by filtration through a sterilization filter.

(Formulation 8: Poaon agent)
5 parts of the compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol are uniformly mixed to obtain a poreon agent.

(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)
A spray agent is obtained by uniformly mixing 1 part of the compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol.

Next, a compound example will be shown, and the present invention will be described in more detail. However, the present invention is not limited 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 Bulletin of the Chemical Society of Japan, 1996, 69, 6, 1679.
N- (p-trill) ethanethioamide (8.5 g) was dissolved in tetrahydrofuran (170 mL) and cooled to −78 ° C. Then, 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 cooled to −78 ° C. again. Then, 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 obtained solution was added to an aqueous ammonium chloride solution, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 6.5 g of the target product. The NMR data of the target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δppm: 2.31 (s, 3H), 2.49 (s, 3H), 3.06 (t, 2H), 3.35 (t, 2H), 7.03-7.19 (m, 5H), 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) were added to the N-methylpyrrolidone solution (33 mL) of thioamide (6.5 g) obtained in Reference Example 1. .1 g) was added, and the mixture was stirred at 100 ° C. for 1 hour. The obtained solution was added to an aqueous ammonium chloride solution, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 3.0 g of the target product. The NMR data of the target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δppm: 2.17 (s, 3H), 2.36 (s, 3H), 2.91 (t, 2H), 3.05 (t, 2H), 6.83 (d, 2H), 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 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. Then, the obtained liquid was added to an aqueous ammonium chloride solution, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 1.4 g of the target product. The NMR data of the target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δppm: 2.27 (s, 3H), 2.37 (s, 3H), 3.56 (s, 2H), 7.03-7.19 (m, 7H), 9.09 (s, 1H).

[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 the mixture was stirred at room temperature for 1 hour. did. Then it was cooled to 0 ° C. Then, 6-methylpyrimidine-4-thiol (0.075 g) was added to the obtained solution, and the mixture was stirred at room temperature for 1 hour. Then, the obtained liquid was added to ice water, extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 0.06 g of the target product. The NMR data of the target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δppm: 2.18 (s, 3H), 2.37 (s, 3H), 2.48 (s, 3H), 3.86 (s, 2H), 6.92 (d, 2H), 7.19 (m, 7H) ), 8.10 (s, 1H).

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

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

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

In a toluene solution (3 mL) of 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 the mixture was stirred at 70 ° C. for 1 hour. The obtained solution was added to ice water, extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 0.085 g of the target product. The NMR data of the target product is shown below.
^{1 1} H-NMR (CDCl ₃ ) δppm: 2.19 (s, 3H), 2.36 (s, 3H), 3.87 (s, 2H), 6.87 (d, 2H), 7.04-7.36 (m, 10H), 7.76 (s , 1H).

Table 1 shows an example of the compound of the present invention produced by the same method as in the above-mentioned Examples. Table 1 shows the substituents of the compound represented by the formula (Ia). The compound represented by the formula (Ia) is a compound in which B is a sulfur atom, D is a substituted or unsubstituted methylene group, and it is an E form.

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

The NMR data of the compounds described as viscous oil or amorphous in the "Physical properties" column of Table 1 are shown below.
Compound No. (a-5): ¹ H-NMR (400MHz, CDCl ₃ ) δppm: 3.82 (s, 3H), 3.89 (s, 2H), 6.92 (m, 4H), 7.09-7.25 (m, 6H), 7.32-7.41 (m, 3H), 7.68 (s, 1H).
Compound No. (a-6): ¹ H-NMR (400MHz, CDCl ₃ ) δppm: 2.38 (s, 3H), 2.51 (s, 3H), 3.85 (s, 2H), 6.92 (d, 2H), 7.12- 7.31 (m, 7H), 8.31 (s, 1H), 8.43 (d, 1H).
Compound No. (a-9): ¹ H-NMR (400MHz, CDCl ₃ ) δppm: 2.37 (s, 3H), 2.49 (s, 3H), 3.81 (s, 2H), 6.85-7.10 (m, 6H), 7.20 (d, 2H), 8.34 (s, 1H), 8.42 (d, 1H).
Compound No. (a-10): ¹ H-NMR (400MHz, CDCl ₃ ) δppm: 2.37 (s, 3H), 2.49 (s, 3H), 3.80 (s, 2H), 6.82-6.89 (m, 4H), 7.20-7.25 (m, 4H), 8.32 (s, 1H), 8.42 (d, 1H).
Compound No. (a-16): ¹ H-NMR (400MHz, CDCl ₃ ) δppm: 2.19 (s, 3H), 2.35 (s, 3H), 2.48 (s, 3H), 3.85 (s, 2H), 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 No. (a-18): ¹ H-NMR (400MHz, CDCl ₃ ) δppm: 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, 1H), 8.34 (s, 1H), 8.57 (d, 1H).
Compound No. (a-19): ¹ H-NMR (400MHz, CDCl ₃ ) δppm: 2.16 (s, 3H), 2.31 (s, 3H), 2.33 (s, 3H), 3.80 (s, 2H), 6.74 ( d, 1H), 6.84-6.90 (m, 3H), 7.00-7.05 (m, 2H), 7.12 (s, 1H), 7.25 (m, 1H), 8.21 (s, 1H), 8.34 (d, 1H) ..
Compound No. (a-27): ¹ H-NMR (400MHz, CDCl ₃ ) δppm: 1.48 (d, 3H), 2.35 (s, 3H), 2.37 (s, 3H), 4.54 (q, 1H), 6.87- 6.93 (m, 4H), 7.08-7.29 (m, 8H), 7.52 (s, 1H).
Compound No. (a-42): ¹ H-NMR (400MHz, CDCl ₃ ) δppm: 1.48 (d, 3H), 4.56 (q, 1H), 6.79-6.93 (m, 3H), 7.08-7.44 (m, 11H) ), 7.56 (s, 1H).
Compound No. (a-48): ¹ H-NMR (400MHz, CDCl ₃ ) δppm: 2.13 (s, 3H), 2.33 (s, 3H), 3.84 (s, 2H), 6.76 (d, 1H), 7.01- 7.31 (m, 8H), 7.56 (t, 1H), 8.19 (d, 1H), 8.49 (d, 1H).
Compound No. (a-49): ¹ H-NMR (400MHz, CDCl ₃ ) δppm: 2.14 (s, 3H), 2.36 (s, 3H), 3.89 (s, 2H), 6.86 (d, 1H), 7.15- 7.52 (m, 11H).

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

[Biological test]
The following test examples show that the compound of the present invention is useful as an active ingredient of a pest control agent. The "part" is based on weight.

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

The insecticidal rate was calculated by the following formula.
Insecticide rate (%) = (number of dead insects / number of test insects) x 100

(Test Example 1) Emulsion test for Mythimna separata Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. The corn leaves were immersed in the diluent for 30 seconds. The corn leaves were air-dried and placed in a petri dish, and five second-instar armyworm larvae were released. The petri dish was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. When 6 days had passed since the insect was released, the life or death was judged and the insecticidal rate was calculated. The test was performed in two iterations.

The compounds with the numbers shown in Table 3 were tested for efficacy against Mythimna separata. Both compounds showed an insecticidal rate of 80% or more with respect to armyworm.

(Test Example 2) Emulsion test against Spodoptera litura (Spodoptera litura) The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. The cabbage leaves were immersed in the diluted solution for 30 seconds. The cabbage leaves were air-dried and placed in a petri dish, and five Hasmontou 2nd instar larvae were released. The petri dish was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. When 6 days had passed since the insect was released, the life or death was judged and the insecticidal rate was calculated. The test was performed in two iterations.

The compounds with the numbers shown in Table 4 were tested for efficacy against Spodoptera litura. Both compounds showed an insecticidal rate of 80% or more with respect to Spodoptera litura.

(Test Example 3) Emulsion test against diamondback moth (Plutella xylostella) Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. The cabbage leaves were immersed in the diluted solution for 30 seconds. The cabbage leaves were air-dried and placed in a petri dish, and five second-instar diamondback moth larvae were released. The petri dish was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. A life or death judgment was made when 3 days had passed since the insect was released, and the insecticidal rate was calculated. The test was performed in two iterations.

The compounds with the numbers shown in Table 5 were tested for efficacy against diamondback moth. Both compounds showed an insecticidal rate of 80% or more with respect to diamondback moth.

(Test Example 4) Efficacy test against Aphis gossypii Cucumber seeds were sown in a 3 inch pot, and adult cotton aphids were released 10 days after germination. One day after release, the adults were removed, leaving only the first-instar larvae that were born. The emulsion (I) was diluted with water to obtain a test drug solution adjusted to a predetermined compound concentration of the present invention. The test drug solution was sprayed on the cucumber. Then, the cucumber was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. Six days later, the life and death of the cotton aphid was examined, and the insecticidal rate was calculated. The test was performed in two iterations.

The compounds with the numbers shown in Table 6 were subjected to an efficacy test against Aphis gossypii at a compound concentration of 125 ppm. Both compounds showed an insecticidal rate of 80% or more.

(Test Example 5) Emulsion test against whitefly (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, adult tobacco whiteflies typeB were released and spawned. The number of parasitic larvae was counted 12 days after spraying. The efficacy of the compound was evaluated by the control rate shown below. The test was performed in two iterations.
Control rate = 100-[(Nt / Nc) x 100]
Nt: Number of parasites in the spray treatment area
Nc: Number of parasites in untreated plot

The compounds with the numbers shown in Table 7 were tested for efficacy against tobacco whiteflies. Both compounds showed a control rate of 80% or more against tobacco whiteflies.

(Test Example 6) Efficacy test against Thrips palmi Cucumber seeds were sown in a 3 inch pot, and adult Thrips palmi Karny was released 10 days after germination. The emulsion (I) was diluted with water to obtain a test drug solution adjusted to a predetermined compound concentration of the present invention. One day after the release of the insects, the test drug solution was sprayed on the cucumbers. Then, the cucumber was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. Two days later, the life and death of adult Thrips palmi Karny was examined, and the insecticidal rate was calculated. The test was performed in two iterations.

The compounds with the numbers shown in Table 8 were subjected to an efficacy test on Thrips palmi Karny at a compound concentration of 125 ppm. Both compounds showed an insecticidal rate of 80% or more.

(Test Example 7) Efficacy test against Tetranychus urticae Green beans were raised in a 3-inch pot, and eight female adults of Tetranychus urticae from Aomori Prefecture were inoculated on the primary leaves. Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. The diluted solution was sprayed on the green beans. The green beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. The life and death of adult mite females were investigated 3 days after spraying. The test was performed in two iterations.

The compounds with the numbers shown in Table 9 were tested for efficacy against spider mites. Both compounds showed an insecticidal rate of 90% or more.

(Test Example 8) Contact effect test against Rhipicephalus microplus The DMSO solution of the compound of the present invention was diluted with water to obtain a test drug solution of 100 ppm. This chemical solution was dropped into a container containing 20 larvae of Rhipicephalus thunder and incubated in a constant temperature room at a temperature of 28 ° C. and a humidity of 80%. The life or death of the larva was determined when 24 hours had passed from below the drug droplet. The test was performed in two iterations.

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

(Test Example 9) Contact effect test on cat flea (Ctenocephalides felis) The DMSO solution of the compound of the present invention was diluted with water to obtain a test drug solution of 100 ppm. This chemical solution was dropped onto a filter paper in a container containing 10 adult cat fleas and incubated in a constant temperature room at a temperature of 28 ° C. and a humidity of 80%. When 24 hours had passed from below the drug droplet, the life or death of the adult was determined. The test was performed in two iterations.

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

(Test Example 10) Contact / feeding effect test on larvae of 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 Lucilia cuprina larvae were introduced into test tubes with the mixture. Incubation was carried out in a homeothermic chamber having a temperature of 28 ° C. and a humidity of 80%. The larvae were determined to be alive or dead 48 hours after the start of incubation. The test was performed in two iterations.

The compounds shown in Table 12 were subjected to a contact / feeding effect test on larvae of Lucilia cuprina, and showed an insecticidal rate of 90% or more.

(Test Example 11) Contact / feeding effect test on Aedes aegypti larvae The DMSO solution of the compound of the present invention was diluted with water to obtain a diluted solution of 100 ppm. Ten first-instar larvae of Aedes aegypti were placed in each well of a 96-well microtiter plate together with the breeding solution. 1/10 of the diluted solution was added thereto to adjust the final concentration to 10 ppm. Incubation was carried out in a homeothermic chamber having a temperature of 28 ° C. and a humidity of 80%. The larvae were determined to be alive or dead 48 hours after the start of incubation. The test was performed in two iterations.

The compounds with the numbers shown in Table 13 were tested for contact / feeding effect on Aedes aegypti larvae. Both compounds showed an insecticidal rate of 90% or more.

Randomly selected compounds of the present invention exert the above-mentioned effects. Therefore, the compounds of the present invention, including compounds that could not be exemplified, control pests, especially acaricide, insecticide, and ectoparasite. It can be understood that it is a compound that has effects such as insect control, does not cause chemical damage to plants, and has little toxicity to humans, livestock and fish, and has little effect on the environment.

Claims (5)

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

(In formula (I),
Q ¹ represents a substituted or unsubstituted C6 to 10 aryl group.
Q ² represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C6 to 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, carbonyl group, or oxygen atom.
E represents a substituted or unsubstituted benzene ring. ) A pest control agent containing at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient. An insecticide or acaricide containing at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient. An ectoparasite control agent containing at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient. An agent for preventing pests from adhering to a fishing net or a ship bottom, which contains at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.