WO2017104692A1

WO2017104692A1 - Termite control agent

Info

Publication number: WO2017104692A1
Application number: PCT/JP2016/087173
Authority: WO
Inventors: 優介村瀬; 亮堀越; 保道小野▲崎▼
Original assignee: ＭｅｉｊｉＳｅｉｋａファルマ株式会社
Priority date: 2015-12-15
Filing date: 2016-12-14
Publication date: 2017-06-22
Also published as: JPWO2017104692A1

Abstract

A termite control agent which contains at least one substance selected from the group consisting of iminopyridine derivatives represented by general formula (1) and salts thereof. (In formula (1), Ar represents a pyridyl group or a pyrimidyl group, which may be substituted by a halogen atom, a C1-C4 alkyl group which may be substituted by a halogen atom, an alkyloxy group which may be substituted by a halogen atom, a hydroxyl group, a cyano group or a nitro group; R1 represents a hydrogen atom or a C1-C6 alkyl group; Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-C6 alkyl group which may be substituted by a halogen atom, a C1-C6 alkyloxy group which may be substituted by a halogen atom, a cyano group, a formyl group or a nitro group; and R2 represents a C1-C6 alkyl group which is substituted by a halogen atom.)

Description

Termite control agent

The present invention relates to a termite control agent, and more particularly to a termite control agent containing an iminopyridine derivative and having a high controllability, and a termite control method using the same.

Termites are generated from temperate regions to tropical regions and are feared as wood pests that cause great damage to wooden buildings such as houses. As this termite control agent, organophosphorus compounds, carbamate compounds, pyrethroid compounds, neonicotinoid compounds, and phenylpyrazole compounds have been developed, but those that are satisfactory in both extermination and prevention effects. It cannot be said that it has been obtained. In addition, there are many compounds whose use scenes are limited in terms of safety against human livestock and safety against non-target organisms. Under such circumstances, there is an urgent need for new drugs that can be used in a variety of situations, such as building materials in the home where termites are a problem and treatment on soil, and that are highly safe against non-target organisms. ing.

International Publication No. 2012/029672 (Patent Document 1) describes that an amine derivative represented by the general formula (Ie ′) exhibits an insecticidal effect, and EP-A-268915 ( Patent Document 2) describes the insecticidal activity of an amine derivative having a structure similar to that of the amine derivative. Furthermore, International Publication No. 2013/129692 (Patent Document 3) discloses a controlling effect on termites of amine derivatives having a structure similar to that of the amine derivative.

However, there is no specific disclosure of the effect of the amine derivative represented by the general formula (Ie ') on termites.

International Publication No. 2012/029672 European Patent Application Publication No. 268915 International Publication No. 2013/129692

An object of the present invention is to provide a novel termite control agent having high practicality and a termite control method using the same.

As a result of intensive studies to solve the above problems, the present inventors have found that the compound represented by the following general formula (1) and / or a salt thereof has high safety for animals. As a result, the present invention was completed by finding that it has an extremely high termite control effect compared with existing agents.

That is, the aspects of the present invention are as follows.

[1] A termite control agent containing at least one selected from the group consisting of an iminopyridine derivative represented by the following general formula (1) and a salt thereof.

[In the formula (1), Ar is a halogen atom, a C1-C4 alkyl group optionally substituted by a halogen atom, an alkyloxy group optionally substituted by a halogen atom, a hydroxyl group, a cyano group, or a nitro group. An optionally substituted pyridyl group; or a halogen atom, a C1-C4 alkyl group optionally substituted by a halogen atom, an alkyloxy group optionally substituted by a halogen atom, a hydroxyl group, a cyano group, or a nitro group Represents an optionally substituted pyrimidyl group;
R1 represents a hydrogen atom or a C1-C6 alkyl group,
Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-C6 alkyl group optionally substituted by a halogen atom, a C1-C6 alkyloxy group optionally substituted by a halogen atom, a cyano group, a formyl group, or a nitro group. Group, and
R2 represents a C1-C6 alkyl group substituted by a halogen atom. ].

[2] The termite control agent according to [1], wherein in the general formula (1), Y is a hydrogen atom or a halogen atom.

[3] The iminopyridine derivative represented by the general formula (1) is N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2 -Trifluoroacetamide, N- [1-((6-chloro-5-fluoropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N -[1-((6-fluoropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N- [1-((6-bromopyridine- 3-yl) methyl) pyridin-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N- [1- (1- (6-chloropyridin-3-yl) ethyl) pyridine-2 (1H) -Ilidene] -2,2,2-to Fluoroacetamide, N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2-difluoroacetamide, 2-chloro-N- [1 -((6-chloropyridin-3-yl) methyl) pyridin-2 (1H) -ylidene] -2,2-difluoroacetamide, N- [1-((2-chloropyrimidin-5-yl) methyl ) Pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, and N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] The termite control agent according to [1], which is at least one selected from the group consisting of -2,2,3,3,3-pentafluoropropanamide.

[4] The iminopyridine derivative represented by the general formula (1) is N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2 The termite control agent according to [1], which is trifluoroacetamide.

[5] A termite control method using the termite control agent according to any one of [1] to [4].

[6] The termite control method according to [5], comprising a step of applying the termite control agent to a termite or a termite growing place.

[7] The termite control method according to [5], including a step of applying the termite control agent to a surface of wood or a step of injecting the same inside.

[8] The method according to [5], including at least one step selected from the group consisting of a step of spraying the termite control agent on the surface of soil, a step of injecting into the soil, and a step of mixing with soil. Termite control method.

[9] including a step of treating the termite control agent in a place where at least one termite enters from a group consisting of a rising periphery of the building foundation, a concrete surface of the building foundation, and a building outer periphery. Termite control method according to [5].

[10] The termite control method according to [5], comprising a step of bringing the termite control agent into contact with or eating the termite.

The termite control agent of the present invention has a high control effect on termites. A high termite control effect can be obtained by bringing such termite control agents into contact with and / or ingesting termites. Moreover, the damage by the termite of a to-be-processed object can also be prevented by eating of the to-be-processed object processed by the said termite control agent.

The termite control agent of the present invention has the following general formula (1) as an active ingredient:

And at least one selected from the group consisting of salts thereof.

In the general formula (1), Ar is a halogen atom, a C1-C4 alkyl group optionally substituted by a halogen atom, an alkyloxy group optionally substituted by a halogen atom, a hydroxyl group, a cyano group, or a nitro group. A pyridyl group optionally substituted by: a halogen atom, a C1-C4 alkyl group optionally substituted by a halogen atom, an alkyloxy group optionally substituted by a halogen atom, a hydroxyl group, a cyano group, or a nitro The pyrimidyl group which may be substituted by group is shown. R1 represents a hydrogen atom or a C1-C6 alkyl group.

Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-C6 alkyl group optionally substituted by a halogen atom, a C1-C6 alkyloxy group optionally substituted by a halogen atom, a cyano group, a formyl group, or a nitro group. Indicates a group. R2 represents a C1-C6 alkyl group substituted with a halogen atom.

In the “optionally substituted pyridyl group” and “optionally substituted pyrimidyl group” represented by Ar, the optionally substituted substituent is a halogen atom or a C1 optionally substituted by a halogen atom. A C4 alkyl group, an alkyloxy group optionally substituted by a halogen atom, a hydroxyl group, a cyano group, a nitro group and the like. Among them, a preferred substituent is a halogen atom.

Here, in the general formula (1), examples of the “halogen atom” include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. In the general formula (1), the “C1-C4 alkyl group optionally substituted by a halogen atom” specifically includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group. Group, difluoromethyl group, trifluoromethyl group, chloromethyl group, 2-trifluoroethyl group, 2-chloroethyl group and the like. Furthermore, in the general formula (1), examples of the “alkyloxy group optionally substituted by a halogen atom” include a methoxy group, an ethoxy group, a trifluoromethyloxy group, a difluoromethyloxy group, and the like. It is done.

In the compound represented by the general formula (1), preferred examples of Ar include a 3-pyridyl group, a 6-chloro-3-pyridyl group, a 5-chloro-2-thiazolyl group, and a 5-chloro-4-thiazolyl group. 6-chloro-5-fluoro-3-pyridyl group, 6-bromo-3-pyridyl group, 6-fluoro-3-pyridyl group, 5,6-dichloro-3-pyridyl group, 6-trifluoromethyl-3 -Pyridyl group, 2-chloro-5-pyrimidyl group. Among them, 6-chloro-3-pyridyl group, 6-fluoro-3-pyridyl group, 6-chloro-5-fluoro-3-pyridyl group, 6-bromo-3-pyridyl group, 2-chloro-5 are preferable. -Pyrimidyl group and the like.

Examples of the “C1 to C6 alkyl group” represented by R1 include chain, branched, cyclic, or combinations thereof having 1 to 6 carbon atoms. When the branched or cyclic alkyl group is included, the number of carbon atoms is 3 or more. Specific examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and a cyclopropyl group. Among them, preferred are a methyl group, an ethyl group and the like.

Specific examples of the “C1-C6 alkyl group optionally substituted with a halogen atom” represented by Y include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an n-pentyl group, Examples include a difluoromethyl group, a trifluoromethyl group, a chloromethyl group, a 2,2,2-trifluoroethyl group, and a 2-chloroethyl group.

Specific examples of the “C1-C6 alkyloxy group optionally substituted by a halogen atom” represented by Y include a methoxy group, an ethoxy group, a trifluoromethyloxy group, a difluoromethyloxy group, and an isopropyloxy group. Is mentioned.

The “C1-C6 alkyl group substituted by a halogen atom” represented by R2 is a chain, branched, cyclic, or combination thereof having one or more hydrogen atoms substituted with a halogen atom in a C1-C6 alkyl group The upper limit of the number of substituted hydrogen atoms is the number of hydrogen atoms of the alkyl group. When the branched or cyclic alkyl group is included, the number of carbon atoms is 3 or more. Specific examples of the “C1-C6 alkyl group substituted by a halogen atom” include a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, Examples include 2,2-difluoroethyl group, dichloroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, 2,2-difluorocyclopropyl group, 2,3-difluorocyclopropyl group and the like. Among them, preferably a trifluoromethyl group, a trichloromethyl group, a dichloromethyl group, a difluoromethyl group, a difluorochloromethyl group, a chloromethyl group, a pentafluoroethyl group, more preferably a trifluoromethyl group, a difluoromethyl group, A difluorochloromethyl group, a chloromethyl group and a pentafluoroethyl group;

Among the iminopyridine derivatives represented by the general formula (1), a more preferable compound is N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2, 2,2-trifluoroacetamide, N- [1-((6-chloro-5-fluoropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroaceta N- [1-((6-Fluoropyridin-3-yl) methyl) pyridin-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N- [1-((6- Bromopyridin-3-yl) methyl) pyridin-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N- [1- (1- (6-chloropyridin-3-yl) ethyl) Pyridine-2 (1H) -ylidene -2,2,2-trifluoroacetamide, N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2-difluoroacetamide, 2 -Chloro-N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2-difluoroacetamide, N- [1-((2-chloro Pyrimidin-5-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide and N- [1-((6-chloropyridin-3-yl) methyl) pyridine- 2 (1H) -ylidene] -2,2,3,3,3-pentafluoropropanamide is at least one compound selected from the group consisting of N- [1-(( 6-chloropyridin-3-yl) Le) pyridine -2 (IH) - ylidene] -2,2,2 a trifluoroacetamide.

The iminopyridine derivative represented by the general formula (1) can be synthesized by the method described in International Publication No. 2012/029672, International Publication No. 2013/031671, or International Publication No. 2015/137216, etc. For example, N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide is disclosed in WO2013 / 031671 or It can be synthesized by the method described in International Publication No. 2015/137216.

In the termite control agent of the present invention, the salt of the iminopyridine derivative represented by the general formula (1) is preferably a pharmaceutically acceptable acid addition salt. Examples include hydrochloride, nitrate, sulfate, phosphate, acetate, and the like.

The termite control agent of the present invention is not particularly limited as long as it contains the iminopyridine derivative represented by the general formula (1) and / or a salt thereof as an active ingredient, and any one of the iminopyridine derivative and a salt thereof. It may be composed of a single composition or a mixture thereof, and may be composed of a composition composed by mixing with other components as long as the characteristics of the iminopyridine derivative and / or salt thereof are not impaired. There may be. Such other components include other active ingredients (other termite control ingredients, insecticide ingredients, antibacterial ingredients, etc.) other than the iminopyridine derivative represented by the general formula (1) and salts thereof, and pharmaceutically acceptable. Examples include carriers and additives.

Examples of other termite control components and insecticidal components that can be mixed with the iminopyridine derivative represented by the general formula (1) and / or a salt thereof (hereinafter sometimes simply referred to as “iminopyridine derivative and / or a salt thereof”) Carbamate compounds (fenobcarb, xylylcarb, metorcarb, carbaryl, isoprocarb, propoxur, methoxadiazone, bassa, propoxer, etc.), organophosphorus compounds (foxime, chlorpyrifos, fenitrothion, malathion, pyridafenthion, isofenphos, dichlorvos, etc.), phenylpyrazole compounds ( Fipronil, pyriprole, etc.), pyrethroid compounds (aresulin, cyfluthrin, permethrin, tralomethrin, cypermethrin, d-phenothrin, halfenprox, Emparerate, etofenprox, bifenthrin, acrinathrin, transfluthrin, ciphenothrin, silafluophene, pyrethrin, imiprotolin, praretrin, phthalthrin, resmethrin, phenpropatoline, transfluthrin, methfluthrin, profluthrin, etc., amidoflumethrin ), Neonicotinoid compounds (such as nitenpyram, acetamiprid, clothianidin, imidacloprid, thiamethoxam, dinotefuran, thiacloprid), mesoionic compounds (such as triflumezopyrim, dichloromezothiaz), benzoylphenylurea compounds (bistrifluron), Macrolide compounds (Ebamectin, Abamectin, Emamectin, Nemadectin, Spino ), Juvenile hormone analogs (such as pyriproxyfen), boron compounds (such as boric acid and sodium borate), aryl pyrrole compounds (such as chlorfinapir), nereistoxin compounds (such as bensultap), dia Cyluhydrazine compounds (chromaphenozide, tebufenozide, methoxyphenozide, etc.), amidinohydrazone compounds (hydramethylnon, etc.), voltage-dependent sodium channel blockers (indoxacarb, metaflumizone, etc.), diamide compounds (fulbendiamide, chlorantranilip) Oxazoline compounds (such as etoxazole), higher alcohols (such as tridecanol, hexadecanol), chitin biosynthesis inhibitors (hexaflumuron, diflubenzuron, flufenoxuron, Examples include lufenuron, chlorfluazuron, diafenthiuron, novallon, fluazuron, triflumuron, teflubenzuron, and buprofezin, GABA agonists (such as floxamethamide), and juvenile hormone-like compounds (such as metoprene and hydroprene). In addition, fatty acids (decanoic acid, octanoic acid, etc.), natural product-derived components (obacnon, berberine, Pfaffia, Kawa species, Licopodium, Whitania, Gomfrena, Amphrantes) (Achylanthes), an extract from a plant belonging to the genus Cocos or Elaeis; mint oil; lemongrass oil; geranium oil; lemon eucalyptus oil; hiba oil and the like) and other compounds (diet (N, N-diethyl-m-toluamide), p-menthane-3,8-diol, dimethyl phthalate, dibutyl phthalate, MGK-11 (2,3,4,5-bis- (δ-butylene) -tetrahydrofurfural) MGK-326 (Isocinco Ron di -n- propyl), L-menthol, cineole, alpha-pinene, citronellal, camphor, linalool, etc. Azadirachtin), natural enemy microorganisms (Beauveria, Metarhizium, etc. Beruchishiriumu) can also be mentioned. These other termite control components and insecticidal components can be used alone or in combination of two or more.

The mixing ratio of these other termite control components and insecticidal components can be selected from 0 to 100 parts by weight with respect to 100 parts by weight of the iminopyridine derivative and / or salt thereof, for example, 0.1 to 80 parts by weight. Parts, preferably 1 to 50 parts by weight.

Antibacterial components that can be mixed with the iminopyridine derivative and / or salt thereof include, for example, organic iodo compounds (3-bromo-2,3-diiodo-2-propenylethyl carbonate, 3-iodo-2-propynylbutylcarbamate ( IPBC), 2,3,3-triiodoallyl alcohol, parachlorophenyl-3-iodopropargyl formal, etc.), benzimidazole and benzothiazole compounds (2- (4-thiazolyl) benzimidazole, 2-thiocyanomethylthiobenzothiazole Etc.), triazole compounds (1- (2- (2 ′, 4′-dichlorophenyl) -1,3-dioxolan-2-ylmethyl) -1H-1,2,4-triazole, 1- (2- (2 , 4-Dichlorophenyl) -4-propyl-1,3-dioxola -2-ylmethyl) -1H-1,2,4-triazole (generic name: propiconazole), α- (2- (4-chlorophenyl) ethyl) -α- (1,1-dimethylethyl) -1H- 1,2,4-triazole-1-ethanol (generic name: tebuconazole), natural products (4-isopropyltropolone (common name: hinokitiol), borax, etc.), antibacterial metals (silver compounds (for example, metallic silver) Silver halides such as AgCl, AgF and AgF ₂ ; oxides such as Ag ₂ O and AgO; sulfides such as Ag ₂ S; Ag ₂ SO ₄ , Ag ₂ CrO ₄ , Ag ₃ PO ₄ , Ag ₂ CO ₃ , Oxyacid salts such as Ag ₂ SiO ₃ ), copper compounds, and zinc compounds). These antibacterial components can be used alone or in combination of two or more.

The mixing ratio of these antibacterial components can be selected from a ratio of 0 to 2000 parts by weight, preferably 50 to 1000 parts by weight, and more preferably 100 to 500 parts per 100 parts by weight of the iminopyridine derivative and / or salt thereof. Parts by weight.

The pharmaceutically acceptable carrier can be appropriately selected from a liquid carrier, a gel carrier, a solid carrier, a semi-solid carrier and the like according to the dosage form of the termite control agent of the present invention described later.

Examples of the liquid carrier include oily liquid carriers such as silicone oil, animal fats and oils, and vegetable oils (eg, rapeseed oil); aqueous solvents; organic solvents and the like.

Examples of the aqueous solvent and the organic solvent include water, alcohols (lower aliphatic alcohols such as ethanol and isopropanol; (poly) alkylene glycols such as ethylene glycol and diethylene glycol; aliphatic polyhydric alcohols such as glycerin), ethers, and the like. (Chain ethers such as diethyl ether; cyclic ethers such as tetrahydrofuran; carbitols such as carbitol and diethylene glycol dimethyl ether), ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), cellosolves (alkyl such as methyl cellosolve) Cellosolve), esters (fatty acid esters such as ethyl acetate and diisononyl adipate), hydrocarbons (hydrocarbon solvents based on naphthene; hexane, etc.) Aliphatic hydrocarbons; Alicyclic hydrocarbons such as cyclohexane; Aromatic hydrocarbons such as toluene and xylol; Halogenated hydrocarbons such as methylene chloride and chloroform), Amides (such as dimethylformamide), Nitriles (acetonitrile) Etc.) and sulfoxides (dimethyl sulfoxide, etc.). These solvents can be used alone or in combination of two or more. Of these solvents, water or water-soluble organic solvents (lower aliphatic alcohols, (poly) alkylene glycols, aliphatic polyhydric alcohols, acetone, etc.) are often used. Among the solvents, a highly volatile solvent (for example, a lower aliphatic alcohol such as ethanol, acetone, acetonitrile, short chain ether, etc.) may be used.

Examples of the gel carrier include resins such as alginic acids, cellulose or derivatives thereof, and polyethylene glycol.

Examples of the solid carrier and the semi-solid carrier include powdery carriers widely used for agricultural chemicals, horticultural preparations and the like. For example, clay minerals (zeolite, sepiolite, attapulgite (also known as palygorskite)), synthetic zeolite, charcoal (charcoal, bamboo charcoal, etc.), talc (talc powder, wax stone powder, etc.), clays (fine powder clay, etc.), pumice (Rhyolite natural glass, perlite, etc.), mineral powder (silica sand, vermiculite, mica, calcium carbonate, etc.), metal oxide (titanium oxide, etc.), sulfur powder, urea powder, vegetable powder Products (peat moss, wood flour, etc.); sugars such as starch and dextrin (polysaccharides, etc.); synthetic polymers such as carboxyvinyl polymer and crosslinked polyvinylpyrrolidone; cellulose ethers; metal soaps; (Wax, solid paraffin, long chain fatty acid ester, higher alcohol, higher fatty acid, etc.).

These carriers can be used alone or in combination of two or more.

Examples of the pharmaceutically acceptable additive include conventional additives such as emulsifiers (for example, various surfactants such as anionic, cationic, nonionic, and amphoteric surfactants), dispersants, and additives. Sticky agent, pH adjuster, binder, stabilizer (antioxidant, UV absorber, etc.), spreading agent, wetting agent, penetrating agent, flow aid, anti-caking agent, flocculant, desiccant, deodorant Agents, coloring agents, antifungal agents, antifoaming agents, antifreezing agents and the like. These additives can be used alone or in combination of two or more.

In the termite control agent of the present invention, the content of the iminopyridine derivative and / or salt thereof (in the case of a mixture, the total content thereof, the same shall apply hereinafter) may be appropriately selected according to the use and dosage form. Although not particularly limited, it is preferably 0.00001 to 95% by weight, more preferably 0.001 to 90% by weight, still more preferably 0.01 to 85% by weight, particularly based on the total weight of the termite control agent. Preferably, it is 0.1 to 80% by weight.

For example, when the termite control agent of the present invention is provided as the following liquid preparation, the content of the iminopyridine derivative and / or salt thereof is in the range of 0.00001 to 50% by weight with respect to the total weight of the preparation. It can be selected, and is preferably 0.001 to 40% by weight, more preferably 0.01 to 30% by weight, and still more preferably 0.1 to 20% by weight.

In addition, when the termite control agent of the present invention is provided as the following solid preparation, the content of the iminopyridine derivative and / or salt thereof is in the range of 0.01 to 95% by weight with respect to the total weight of the preparation. It can be selected, preferably 0.1 to 90% by weight, more preferably 1 to 85% by weight, still more preferably 40 to 80% by weight.

The termite control agent of the present invention is a liquid preparation (solution, suspension, emulsion, EW agent, oil, lotion, microcapsule, microsphere, flowable, etc.), solid preparation (powder, granule, wettable powder). , Granule wettable powders, tablets, foaming agents, ant-proof sheets, ant-proofing films, etc.), semi-solid preparations (pastes, creams, mousses, gels, etc.), optional agents such as sprays or aerosols Can be provided in mold. Moreover, according to these dosage forms, the said support | carrier and additive can be selected suitably, and can be used. For example, when a liquid preparation such as a solution or an emulsion is used, a liquid carrier such as the above solvent, an emulsifier, a pH adjuster, or the like may be used in appropriate combination.

Further, the termite control agent of the present invention may be in a form in which the liquid preparation and an appropriate solid diluent (for example, the solid carrier) are mixed and dried if necessary. The said solid diluent can be used individually or in combination of 2 or more types. As the solid diluent, mineral powder such as talc and silica sand, vegetable powder such as wood powder, and the like are generally used. In such a form, the ratio (weight ratio) between the solid diluent and the liquid preparation is, for example, solid diluent / liquid preparation = 100/1 to 1/5, preferably 50/1 to 1/3. More preferably, it is 30/1 to 1/2 (especially 10/1 to 1/1).

Furthermore, the termite control agent of the present invention may be in the form of a bait agent for feeding termites. The bait preparation may be in the form of a liquid preparation, but is usually provided in the form of a solid preparation (powder, granule, tablet, etc.) or a semi-solid preparation (paste etc.). The bait preparation usually contains termite foods and termite favorite foods. Examples of the termite diet and the termite favorite food include celluloses (for example, wood flour (such as pine wood flour), decayed wood, plant fine slices (such as sawdust, bark shredded material, paper, etc.), Sugars (monosaccharides (mannose, galactose, rhamnose, etc.)), oligosaccharides (lactose, raffinose, etc.), sugar alcohols (mannitol, xylitol, etc.), cyclic sugar alcohols (inositol, etc.), polysaccharides (julan gum, xanthan gum, etc.) Etc.). These termite foods and termite favorite foods can be used alone or in combination of two or more. Of these termite diets or termite favorite products, pine wood flour, mannose, galactose, mannitol, dulan gum and the like are preferable. In the bait preparation, the ratio of the termite diet and / or the termite preference (the total amount in the case of a mixture) is 100 parts by weight of the iminopyridine derivative and / or salt thereof. For example, 0.1 to 1000 parts by weight, preferably 1 to 500 parts by weight, and more preferably 5 to 200 parts by weight.

The termite control method (termite control method and termite prevention method) using the termite control agent of the present invention includes a method in which the termite control agent is applied directly to a termite, and a termite damages the termite control agent of the present invention. Possible treated areas (termite growth or breeding places) or treated objects (soil, wood parts such as wood, concrete surface, foundation insulation, building floor bottom, building ceiling, building foundation, building foundation The method is applicable to places where termites can pass and invade in the surrounding area of the rise and the outer periphery of the building; street trees; ant roads;

The termite control agent of the present invention may be applied to a target object by mixing the termite control agent and the target object in advance, for example, depending on the form of the target object, and manufactured. You may apply the said termite control agent to the surface of a to-be-processed object by apply | coating, injecting, and / or treating in a mousse form.

For example, as an aspect of the termite control method of the present invention (application method of the termite control agent of the present invention), a method of directly treating the termite control agent on a wood part such as wood, and the termite control agent to prevent the entry of termites May be a method of constructing a barrier layer by treating soil, a method of indirectly preventing damage to wood by mixing or spraying the termite control agent on a basic heat insulating material, and the like.

Further, as another aspect of the termite control method of the present invention, for the purpose of treatment inside and outside the house, the method of embedding the termite control agent of the present invention in the form of the bait agent or the like, or the termite control agent is used. The method may be applied to plywood, laminated timber, wood board, etc. by mixing with an adhesive.

Furthermore, as another aspect of the termite control method of the present invention, the termite control agent of the present invention is retained by coating, impregnation, kneading, etc. on a sheet or film-like substrate such as a synthetic resin sheet, paper or cloth. A method may be used in which a sheet agent is prepared, and this sheet agent is placed on or pasted on a termite entry point or occurrence point, a termite damage part, or the like. The termite control method of the present invention includes a method for preventing the entry or occurrence of these termites.

As another aspect of the termite control method of the present invention, a method of feeding termites to the termite control agent of the present invention may be used. For example, the termite control agent of the present invention may be applied as the bait agent, and may be applied as the following xylem treating agent in the form of the liquid preparation. Usually, the termite is in the form of the solid preparation or the semisolid preparation. It can be applied by placing it in a place where it can pass (soil surface, concrete surface under the building floor, surrounding area of the foundation of the building; outer periphery of the building, etc.).

The termite control agent of the present invention is particularly useful for treating soil, xylem and the like. Moreover, by bringing the termite control agent of the present invention into contact with or feeding on the termites through these treatments, the termites can be effectively killed or weakened, and a high termite control effect can be achieved.

When the termite control agent of the present invention is used for soil treatment (when used as a soil treatment agent), it is sprayed (for example, sprayed onto the soil surface, sprayed into grooves formed in the soil) or injected into the soil. The termite control agent can be applied to soil by a method, a method of mixing with soil, or the like. Further, in such applications, when the termite control agent is applied by spraying or mixing, the termite control agent dosage forms include solid preparations such as powders and granules, liquid preparations, liquid preparations and the powdered granules. A mixture with a carrier is preferred. The soil may contain silica sand and the like.

Further, when the termite control agent of the present invention is used for treating xylem (when used as a xylem treatment agent), the termite control agent is usually applied to the xylem (preferably wood by application, impregnation, injection, spraying, etc. Applicable to the surface or the inside). Therefore, the dosage forms of the termite control agent may be liquid preparations (emulsions, oils using the oily liquid carrier, etc.), semi-solid preparations, sprays (liquids, sprays using powders, etc.), etc. Good. In addition, the termite control agent of the present invention can be applied to a place where termites may cause harm, and in particular, a place where termites are likely to be generated or invaded, for example, the lower part of a water floor such as a kitchen, a bathroom, and a toilet. It is preferably applied to a living room, a corner of a floor, a ceiling, a base, a pillar, a wall, and a wooden product such as furniture.

In the termite control method of the present invention, the effective amount of the termite control agent of the present invention with respect to termites is not particularly limited, but the amount of the iminopyridine derivative and / or salt thereof (the total amount in the case of a mixture, the same applies hereinafter). ) Is preferably 0.001 to 25 μg / animal, more preferably 0.01 to 5 μg / animal, and most preferably 0.1 to 1 μg / animal.

Further, when the termite control agent of the present invention is applied to a termite growing place, its effective amount is not particularly limited, but the amount of the iminopyridine derivative and / or salt thereof is preferably 0.02 to 125 g / m ^2. 0.1 to 25 g / m ² is more preferable, and 0.5 to 5 g / m ² is most preferable.

In addition, when the termite control agent of the present invention is used for soil treatment, its effective amount is not particularly limited. However, in the case of band-like spraying on the soil surface, the amount of the iminopyridine derivative and / or salt thereof is 0.02 ˜125 g / m ² is preferred, 0.1 to 25 g / m ² is more preferred, and 0.5 to 5 g / m ² is most preferred. In the case of planar spraying, 0.012 to 75 g / m ² is preferable, 0.06 to 15 g / m ² is more preferable, and 0.3 to 3 g / m ² is most preferable. When mixed with soil or injected into soil, 0.0001 to 25 mg / g is preferable, 0.001 to 5 mg / g is more preferable, and 0.1 to 1 mg / g is most preferable.

Further, when the termite control agent of the present invention is used for the treatment of xylem, the effective amount is not particularly limited. However, when treating the surface or inside of wood by coating or spraying, the iminopyridine derivative and / or salt thereof as the amount of, preferably 0.4 ~ 1200mg / ^{m 2,} more preferably ² ~ 600mg / ^m 2, and most preferably 10 ~ 300mg / ^{m 2.}

Further, in the case where the termite control agent of the present invention is brought into contact with or eaten by termites, when it is used for an object to be treated other than the soil and xylem, the effective amount of the termite control agent is not particularly limited, but the iminopyridine derivative and / or as the amount of a salt thereof, preferably from 0.001 ~ 25 [mu] g / cm ^2, more preferably 0.01 ~ 5 [mu] g / cm ^2, and most preferably 0.1 ~ 1μg / cm ^2.

The termite control agent of the present invention provides a high control effect against various termites. Examples of such termites include insects belonging to the order of the termites, for example, the genus Mastotermidae: the genus Mastotermes, etc .; the termite family (Thermopsidae): the genus Zootermopsis, the genus Archoptomopsis, the genus Hodotermopsis ), Etc.), Porotermes genus, Strotermes genus; Kalotemitidae: Kalotermes genus, Neotermes genus (Neotermes koshunensis, etc.), Cryptomer genus (Dikopoxy territory) Cyptotermes brevis, etc.) Glypoptermes kodamai), Kushimoto termites (Glypoptermes kushimensis, etc.); Hawoptermitidae: Hodometerites, Microhodometers, Anacanthomer Genus; groove-headed termites Department (Rhinotermitidae): Reticulitermes genus (. Yamato termite (Reticulitermes speratus), Amami termites (Reticulitermes miyatakei), R. flavipes (Reticulitermes flaviceps amamianus), Kang Mont termites (Reticulitermes sp), etc.), Heterotermes spp, Coptotermes Genus (such as Coptermes formosanus, Coptermes guangzhoensis, Philippine termites vatotor), Schedorhin Serteritidae; Termitidae: Amitermes, Drepanotermes, Hopitateremes, Tritervitermes, Macrotermes, Odontotermes, etc. Termites (Nasuittermestaskasagoensis, etc.), Pericapritermes genus (Peritapriterme nitobei, etc.), Anoprotermes genus, Globitemes genus, Sinocapitator es genus belonging to (warrior termites (Sinocapritermes mushae), etc.) and the like. Preferred are the genus Coptothermes, the genus Reticulites, and the genus Incitermes, more preferably the termites (Copttermes formosanus), the termites termites (Reticulitermes supertus), and the American termites minor (Incitermites minor).

Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited to these examples.

Synthesis Example 1: N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide (Compound 1: Structure of the present invention) Formula (2))

Compound 1 of the present invention represented by the above formula (2) was synthesized by the production method described in International Publication No. 2015/137216. The yield was 84%.
1H-NMR (CDC13, δ, ppm): 5.54 (2H, s), 6.88 (1H, td), 7.34 (1H, d), 7.79 (1H, td), 7.87 (2H, m), 8.46 (1H, s), 8.55 (1H, dd).

Further, the compounds of comparative examples used in the following test examples were synthesized with reference to the production methods described in European Patent Application Publication No. 268915 and International Publication No. 2013/129692 respectively. The structural formulas of the compounds of the comparative examples are shown in Table 1 below.

Test Example 1 Efficacy Test by Filter Paper Treatment A chemical solution of the compound 1 of the present invention or the compound 1 of the comparative example prepared so as to have a predetermined concentration with acetone was treated as 0.005 and 0.05 μg / cm respectively as the treatment amount of each compound. ² soaked in filter paper. After sufficiently air-drying, filter papers were placed in a plastic petri dish, and five ants of the termites ( Coptothermes formosanus ) were released. Then, it was left in a constant temperature room at 25 ° C. Five days after the release, termite mortality and bitter melon were evaluated, and the mortality rate of dead ants was calculated according to the following formula. Three replicates were evaluated for each compound.
Death bitter worm rate (%) = (number of dead insects + number of bitter worms) / number of worms x 100
The results of test examples using each compound are shown in Table 2. Compound 1 of the present invention was confirmed to have a high control effect on termites.

Test Example 2 Efficacy Test by Soil Treatment Compound 1 of the present invention and the compound of the comparative example shown in Table 3 below were mixed with the soil dried after sterilization to a concentration of 0.2 ppm (0.0002 mg / g). did. 20 g of these soils and untreated soil were each filled in a plastic petri dish (diameter 85 mm, height 15 mm) and dried at room temperature for 1 day. After drying, 5 mL of distilled water was added per petri dish, and 10 ants of the termites ( Coptothermes formosanus ) were released per petri dish. On the 4th day after the release, termite mortality and bitter melon were evaluated, and the rate of dead ant worms was calculated according to the following formula. Three replicates were evaluated for each compound.
Death bitter worm rate (%) = (number of dead insects + number of bitter worms) / number of worms x 100
The results of test examples using each compound are shown in Table 3. On the 4th day after the release, Compound 1 of the present invention had a death morbidity rate of 100%, which was higher than that of the compound of Comparative Example. Therefore, it was confirmed that the compound 1 of this invention has a high control effect with respect to a termite.

Test Example 3 Efficacy Test by Wood Piece Treatment On the surface of a piece of wood (raw material: cedar, woodworking surface: 20 mm × 20 mm × height 10 mm) dried at 60 ° C. for 2 days, the concentration of Compound 1 of the present invention is 1000 ppm. Each chemical solution in which the same compound was dissolved in 10% acetone water was applied to 110 ± 10 g / m ² (0 to 110 ± 10 mg / m ² as the treatment amount of Compound 1 of the present invention). About 20 g of silica sand was filled in a plastic petri dish (diameter 85 mm, height 15 mm), and a piece of wood was placed on the silica sand. Distilled water was added to the silica sand as appropriate during the test period. Among them, 10 ants of the termite ( Coptothermes formosanus ) were released. Seven days after the release, the life and death of termites were evaluated, and the death rate of the ants was calculated according to the following formula. Three replicates were evaluated for each concentration.
Death bitter worm rate (%) = (number of dead insects + number of bitter worms) / number of worms x 100
As a result of the test, the death torrent rate of Compound 1 of the present invention at 7 days after the release was 100% at 1000 ppm, and Compound 1 of the present invention showed a high rate of death torrent. Therefore, it was confirmed that the compound 1 of this invention has a high control effect with respect to a termite.

The termite control agent of the present invention is useful for controlling termites.

Claims

A termite control agent comprising at least one selected from the group consisting of an iminopyridine derivative represented by the following general formula (1) and a salt thereof.

[In the formula (1), Ar is a halogen atom, a C1-C4 alkyl group optionally substituted by a halogen atom, an alkyloxy group optionally substituted by a halogen atom, a hydroxyl group, a cyano group, or a nitro group. An optionally substituted pyridyl group; or a halogen atom, a C1-C4 alkyl group optionally substituted by a halogen atom, an alkyloxy group optionally substituted by a halogen atom, a hydroxyl group, a cyano group, or a nitro group Represents an optionally substituted pyrimidyl group;
R1 represents a hydrogen atom or a C1-C6 alkyl group,
Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-C6 alkyl group optionally substituted by a halogen atom, a C1-C6 alkyloxy group optionally substituted by a halogen atom, a cyano group, a formyl group, or a nitro group. Group, and
R2 represents a C1-C6 alkyl group substituted by a halogen atom. ]
The termite control agent according to claim 1, wherein Y in the general formula (1) is a hydrogen atom or a halogen atom.
The iminopyridine derivative represented by the general formula (1) is N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroa Cetamide, N- [1-((6-chloro-5-fluoropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N- [1 -((6-Fluoropyridin-3-yl) methyl) pyridin-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N- [1-((6-Bromopyridin-3-yl ) Methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N- [1- (1- (6-chloropyridin-3-yl) ethyl) pyridine-2 (1H) -Ilidene] -2,2,2-Triflu Roacetamide, N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2-difluoroacetamide, 2-chloro-N- [1-(( 6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2-difluoroacetamide, N- [1-((2-chloropyrimidin-5-yl) methyl) pyridine- 2 (1H) -ylidene] -2,2,2-trifluoroacetamide, and N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2, The termite control agent according to claim 1, which is at least one selected from the group consisting of 2,3,3,3-pentafluoropropanamide.
The iminopyridine derivative represented by the general formula (1) is N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroa The termite control agent according to claim 1, which is cetamide.
Termite control method using the termite control agent according to any one of claims 1 to 4.
The termite control method according to claim 5, comprising a step of applying the termite control agent to a termite or a termite growing place.
The termite control method according to claim 5, comprising a step of applying the termite control agent to a surface of wood or a step of injecting the same inside.
The termite control according to claim 5, comprising at least one step selected from the group consisting of a step of spraying the termite control agent on the surface of the soil, a step of injecting the termite control agent into the soil, and a step of mixing with the soil. Method.
Treating the termite control agent in a place where at least one termite selected from the group consisting of a rising periphery of a building foundation, a concrete surface of the building foundation, and a building outer periphery can enter. Item 7. The termite control method according to Item 5.
The termite control method according to claim 5, comprising a step of bringing the termite control agent into contact with or eating a termite.