TW201304680A - Benzamide derivative or its salt, and insecticide, miticide, nematicide or soil pesticide containing it - Google Patents

Abstract

For many years, many insecticides, miticides, nematicides or soil pesticides have been used, but many of them have various problems such that the effects are inadequate, their use is restricted as insects, etc. have acquired resistance, etc. Accordingly, it is desired to develop a novel insecticide, miticide, nematicide or soil pesticide substantially free from such problems. Therefore, the present invention is to provide a novel insecticide, miticide, nematicide or soil pesticide having a very high controlling effect against insects, mites, nematodes or soil pests at a low dose. The present invention provides an insecticide, miticide, nematicide or soil pesticide containing a benzamide derivative represented by the formula (I) or its salt, as an active ingredient: wherein R1 is a hydrogen atom or C1-3 alkyl, and R2 is C2-8 alkyl or C3-8 cycloalkyl.

Description

Benzylamine derivatives or salts thereof, and insecticides, acaricides, nematicides or soil-killing insecticides containing the same

The present invention relates to a benzamide derivative or a salt thereof, and an insecticide, acaricide, nematicide or soil-killing insecticide containing these as an active ingredient.

Patent Document 1 describes that a specific benzamide derivative is suitable as a herbicide. However, the use of benzamidine derivatives as insecticides, acaricides, nematicides or soil-killing insecticides is not described in this document. Further, there is no specific description of the benzamidine derivative represented by the following formula (I). On the other hand, Patent Document 2 and Patent Document 3 disclose the use of a benzamide derivative having a specific chemical structure as a nematicide. However, the chemical structures of these compounds are different from the compounds of the present invention.

[Previous Technical Literature]

[Patent Document 1] International Publication WO2001/091558

[Patent Document 2] U.S. Patent No. 4840969

[Patent Document 3] European Patent Gazette No. 323637

A large number of insecticides, acaricides, nematicides, or soil-killing insecticides have been used for many years, but there are not many cases in which various effects such as insufficient efficacy or resistance to pests and the use restrictions are caused. Therefore, it is desirable to develop novel insecticides, acaricides, nematicides or soil-killing insecticides which have few disadvantages.

The inventors of the present invention conducted various studies on benzamidine derivatives in order to find more excellent insecticides, acaricides, nematicides, or soil-killing insecticides. As a result, it has been found that the benzamide derivative represented by the following formula (I) has an extremely high control effect against nematodes at a low dose, and at the same time, has a natural enemies for crops, pests, or the like, or a mammal. The safety is completed and the present invention has been completed.

That is, the present invention relates to a formula (I):

[wherein, R ¹ is a hydrogen atom or a C ₁ -C ₃ alkyl group; R ² is a C ₂ -C ₈ alkyl group or a C ₃ -C ₈ cycloalkyl group] is a benzamide derivative or a salt thereof . Further, the present invention relates to an insecticide, an acaricide, a nematicide or a soil-killing insecticide containing the benzamide derivative of the above formula (I) or a salt thereof as an active ingredient, and the application thereof A method of pests, mites, nematodes or soil pests.

The insecticide, acaricide, nematicide or soil-killing insecticide of the benzamide derivative of the above formula (I) or a salt thereof as an active ingredient is low-dose to pests, mites, nematodes or soil pests. Extremely high control effect.

The alkyl group in the above formula (I) may be either a linear chain or a branched form, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group. C _1-8 such as a tertiary butyl group, a pentyl group, a hexyl group, a heptyl group or an octyl group.

The cycloalkyl group in the above formula (I) may, for example, be a C _3-8 such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group or a cyclooctyl group.

The salt of the benzamide derivative in the above formula (I) may contain any salt as long as it is permissible in the technical field, however, for example, dimethylammonium salt, for example, An ammonium salt such as an ethylammonium salt; an inorganic acid salt such as a hydrochloride, a perchlorate, a sulfate or a nitrate; an organic acid salt such as an acetate or a methanesulfonate.

In the benzamide derivative of the above formula (I), an isomer is present, and in the present invention, both of the isomer and the mixture of isomers are contained. Examples of the isomer of the benzamide derivative of the above formula (I) include stereoisomers such as a mirror image isomer and a non-image isomer, and among them, R ¹ and R ² are preferred. Different formula (Ia):

Wherein R ^1-a is C ₁ -C ₃ alkyl; R ^2-a is C ₂ -C ₈ alkyl or C ₃ -C ₈ cycloalkyl, and R ^1-a and R ^2-a are mutually The compound represented by the same formula, and the mirror image isomer of the methine carbon-based asymmetric center to which R ¹ and R ² in the above formula (Ia) are bonded. In the mirror image isomer, there are an R type and an S type, but among them, the S type is preferable. In the present specification, the isomer is described as a mixture unless otherwise specified. Further, the present invention also encompasses various isomers other than those described above within the scope of the technical knowledge in the technical field. Further, depending on the type of the isomer, there are cases in which the chemical structure is different from the above formula (I). However, as long as the person skilled in the art can fully understand the relationship of these lines to the isomer, it is apparent that the system is It is within the scope of the invention.

The benzamide derivative of the above formula (I) or a salt thereof (hereinafter, simply referred to as a compound of the present invention) can be produced according to the following production method [1] and a general method for producing a salt, but is not limited thereto. These methods.

System of law [1]

In the above formula, R ¹ and R ² are as described above, and Z is a hydroxyl group, an alkoxy group or a halogen. Examples of the halogen include each atom of fluorine, chlorine, bromine or iodine. The salt of the compound of the formula (II) may be any salt as long as it is permissible in the technical field, and examples thereof include, for example, inorganic acid salts such as hydrochlorides and sulfates; An organic acid salt such as methanesulfonate.

The reaction of the process [1] can be generally carried out in the presence of a base and a solvent. As the base, for example, an alkali metal such as sodium or potassium; an alkali metal alkoxide such as sodium methoxide, sodium ethoxide or potassium pentoxide; a carbonate such as sodium carbonate or potassium carbonate; sodium bicarbonate or potassium bicarbonate; Equivalent bicarbonate; metal hydroxide such as sodium hydroxide or potassium hydroxide; metal hydride such as sodium hydride or potassium hydride; amine such as monomethylamine, dimethylamine or triethylamine; pyridine, 4- One or two or more kinds of pyridines such as dimethylaminopyridine are appropriately selected.

The solvent is not particularly limited as long as it can be reacted, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; and aliphatic hydrocarbons such as hexane, heptane, petroleum ether, light gasoline, and cyclohexane. Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, dichloroethane, trichloroethane, chlorobenzene; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane ; esters such as methyl acetate, ethyl acetate; polar aprotic solvents such as dimethyl hydrazine, cyclobutyl hydrazine, dimethyl acetamide, dimethylformamide, N-methylpyrrolidone; acetonitrile, Nitriles such as propionitrile; ketones such as acetone and methyl ethyl ketone; water; and the like are appropriately selected one or more. Further, in addition to the above, an amine or a pyridine may be used among the above-mentioned bases.

The reaction of the process [1] can be carried out in the presence of a dehydrating condensing agent as needed. As the dehydrating condensing agent, one or two kinds can be appropriately selected, for example, from N,N'-dicyclohexylcarbodiimide, chlorosulfonyl isocyanate, N,N'-carbonyldiimidazole, trifluoroacetic anhydride or the like. the above.

The reaction temperature of the preparation method [1] is generally from 0 to 100 ° C, preferably from 0 to 50 ° C, and the reaction time is usually from about 0.1 to 48 hours, preferably from about 0.5 to 24 hours.

The compound of the formula (II) which is the starting material of the above Process [1] can be produced, for example, according to the production method [A] shown below.

System of law [A]

In the above formula, R ¹ and R ² are as described above.

The reduction reaction of the process [A] is a reaction of a compound of the formula (IV) with a reducing agent. As the reduction reaction, for example, a contact hydrogenation reaction shown below or a reduction reaction by a metal hydride can be used to produce a compound of the formula (II) by any reaction.

[contact hydrogenation reaction]

As the reducing agent to be used in the contact hydrogenation reaction, one type or two or more types can be appropriately selected, for example, from hydrogen, formic acid, ammonium formate or the like.

The contact hydrogenation reaction can generally be carried out in the presence of a catalyst and a solvent. As the catalyst, one type or two or more types can be appropriately selected, for example, from platinum, platinum oxide, platinum black, nickel nickel, palladium, palladium-carbon, ruthenium, osmium-alumina or the like.

The solvent is not particularly limited as long as it can be reacted, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; and aliphatic hydrocarbons such as hexane, heptane, petroleum ether, light gasoline, and cyclohexane; Ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; esters such as methyl acetate and ethyl acetate; dimethylacetamide, dimethylformamide, N-methylpyrrolidone The acid amides; alcohols such as methanol, ethanol, propanol and butanol; water; and the like are appropriately selected one or more.

The reaction temperature for the hydrogenation reaction is generally -100 to 150 ° C, preferably -10 to 100 ° C, and the reaction time is usually about 0.5 to 96 hours, preferably about 1 to 48 hours.

[Reduction reaction by metal hydride]

Examples of the reducing agent used in the reduction reaction of the metal hydride include metal hydrides such as sodium borohydride and lithium aluminum hydride. The reduction reaction of the metal hydride can be carried out in the presence of titanium tetrachloride, molybdenum oxide or the like as needed.

The reduction by metal hydride can generally be carried out in the presence of a solvent. The solvent is not particularly limited as long as it can be reacted, and examples thereof include ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; and alcohols such as methanol, ethanol, propanol, and butanol; Water; etc., one or two or more are appropriately selected.

The reaction temperature by the reduction reaction of the metal hydride is usually -100 to 150 ° C, preferably -10 to 100 ° C, and the reaction time is usually about 0.5 to 96 hours, preferably about 1 to 48 hours.

The compound of the formula (IV) which is the starting material of the above Process [A] can be produced, for example, by the production method [B] shown below.

System of law [B]

In the above formula, R ¹ and R ² are as described above. As the salt of NH ₂ OH, any salt may be contained as long as it is permissible in the technical field, and examples thereof include inorganic acid salts such as hydrochlorides and sulfates; for example, acetates and methanesulfonic acids. An organic acid salt such as a salt.

The reaction of Process [B] can be carried out in the presence of a base as needed. As the base, for example, an alkali metal such as sodium or potassium; an alkali metal alkoxide such as sodium methoxide, sodium ethoxide or tertiary potassium oxychloride; a carbonate such as sodium carbonate or potassium carbonate; for example, sodium bicarbonate; a bicarbonate such as potassium bicarbonate; a metal hydroxide such as sodium hydroxide or potassium hydroxide; a metal hydride such as sodium hydride or potassium hydride; such as monomethylamine, dimethylamine, triethylamine, etc. An amine; a pyridine such as pyridine or 4-dimethylaminopyridine; an acetate such as sodium acetate or potassium acetate; or the like, one or more of them are appropriately selected.

The reaction of the process [B] can be carried out in the presence of a catalytic amount of hydrochloric acid, sulfuric acid, p-toluenesulfonic acid or the like as needed.

The reaction of Process [B] can generally be carried out in the presence of a solvent. The solvent is not particularly limited as long as it can be reacted, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; and aliphatic hydrocarbons such as hexane, heptane, petroleum ether, light gasoline, and cyclohexane. Such as ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; such as methyl acetate, ethyl acetate and other esters; such as dimethyl hydrazine, cyclobutyl hydrazine, dimethyl a polar aprotic solvent such as guanamine, dimethylformamide or N-methylpyrrolidone; a nitrile such as acetonitrile or propionitrile; an alcohol such as methanol, ethanol, propanol or butanol; water; Choose one or two or more. Further, among the above-mentioned bases which can be used in the reaction of the process [B], an amine or a pyridine may be used as a solvent.

The reaction temperature of the method [B] is generally 20 to 150 ° C, preferably 50 to 100 ° C, and the reaction time is usually about 0.5 to 96 hours, preferably about 1 to 48 hours.

Preferred embodiments of the insecticide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention are described below. The insecticide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention can be used as a control agent for pests, mites, nematodes or soil pests, for example, in the field of agriculture and horticulture, or animal parasitism a pest or a control agent for cockroaches.

The insecticide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention can be used in the field of agriculture and horticulture as described above. Specifically, it can effectively control aphids such as green peach aphid (Myzus persicae) and cotton aphid (Aphis gossypii); diamondback moth (Plutella xylostella), cabbage armyworm (cabbage armyworm) (Mamestra brassicae)), common cutworm (Spodoptera litura), codling moth (Cydia pomonella), bollworm (Heliothis Zea), tobacco budworm (Heliothis) Virescens)), gypsy moth (Lymantria dispar), rice leafroller (Cnaphalocrocis medinalis), smalller tea tortrix (Adoxophyes sp.), colorado potato beetle (colorado potato beetle) Leptinotarsa decemlineata)), cucurbit leaf beetle (Aulacophora femoralis), boll weevil (Anthonomus grandis), planthoppers, leafhoppers, scale insects ( Scales), bugs, whiteflies, thrips, grasshoppers, anthomyiid flies, scarabs, black cutworm (A Grotis ipsilon)), cutworm (Agrotis segetum), ants and other agricultural pests; such as sputum (slugs), snail (snail) and other gastropods; such as tropical rat mite (Ornithonyssus bacoti), Hygienic pests such as cockroaches, housefly (Musca domestica), house mosquito (Culex pipiens); such as angiomois grain moth (Sitotroga cerealella), mung bean (adzuki bean weevil (Callosobruchus chinensis) )), red flour beetle (Tribolium castaneum), aphid (mealworms) and other pests; casemaking clothes moth (Tinea pellionella), carpet 鲣 (black carpet beetle (Attagenus) Japonicus)) genus pests; termites and other house pests; and other pests such as two-spotted spider mite (Tetranychus urticae), carmine spider mite (Tetranychus cinnabarinus), and sacred Kanzawa spider mite (Tetranychus kanzawai), citrus red mite (Panonychus citri), European red mite (Panonychus ulmi), broad mite (Polyphagotarsone) Music mites (pin citrus rust mite (Aculops pelekassi)), bark mite (Rhizoglyphus echinopus) and other plant parasitic mites; such as rot (sold mite (Tyrophagus putrescentiae), Dust mites (Dermatophagoides farina), Chelacaropsis moorei, and other house dust mites; isobaric, root-knot nematodes, cyst nematodes, root rot nematodes (root- Lesion nematodes), such as white-tip nematode (Aphelenchoides besseyi), strawberry bud nematode (Nothotylenchus acris), pine wood nematode (Bursaphelenchus xylophilus) and other plant parasitic nematodes Classes; equipotential worms, such as rat worms (pillbugs (Armadillidium vulgare, Porcellio scaber, etc.) and other foot; and other soil pests. Among them, it is particularly effective in the control of plant parasitic mites, agricultural pests, plant parasitic nematodes, etc., and exhibits superior effects in the control of agricultural pests and plant parasitic nematodes, and is therefore very suitable for use as Insecticides or nematicides. In addition, the insecticide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention is resistant to various agents such as organophosphorus agents, carbamate agents, pyrethroids, neonicotine agents and the like. The pest control is also effective. Further, since the compound of the present invention has excellent permeation transmissibility, it can be harmful to the soil by treating the soil by using the insecticide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention. Insects, mites, nematodes, gastropods, and etc., as well as pests in the stems and leaves.

As another preferred embodiment of the insecticide, acaricide, nematicide or soil-killing insecticide in the agricultural and horticultural field containing the compound of the present invention, comprehensively controlling the above-mentioned plant parasitic mites and agriculture can be cited. Insecticides, acaricides, nematicides or soil-killing insecticides for pests, plant parasitic nematodes, gastropods, soil pests, etc.

An insecticide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention, generally, the compound is mixed with various agricultural adjuvants, and is formulated into a powder, a granule, and a granule wettable A powder, a wettable powder, an aqueous suspension, an oily suspension, an aqueous solvent, an emulsion, a liquid, a sizing agent, an aerosol, a microdispersing agent, and the like, but as long as it is suitable for the purpose of the present invention It can be formed into various preparation forms generally used in the field. As the adjuvant used in the preparation, there may be mentioned, for example, diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, carbonic acid. Solid support such as sodium hydrogen, mirabilite, zeolite, starch; such as water, toluene, xylene, solvent petroleum brain, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, a solvent such as dimethyl hydrazine, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone or an alcohol; such as a fatty acid salt, a benzoate, Alkyl sulfosuccinate, dialkyl sulfosuccinate, polycarboxylate, alkyl sulfate, alkyl sulfate, alkyl aryl sulfate, alkyl glycol ether sulfate, alcohol sulfuric acid Esters, alkyl sulfonates, alkyl aryl sulfonates, aryl sulfonates, lignosulfonates, alkyl diphenyl ether disulfonates, polystyrene sulfonates, alkyl phosphates Salt, alkyl aryl phosphate, styryl aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aromatic ether sulfate, polyoxyethylene alkyl Anionic surfactant such as oleyl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl aryl phosphate, naphthalene sulfonate formaldehyde condensate; such as sorbitan fatty acid ester, glycerin Fatty acid ester, fatty acid polyglyceride, fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl aromatic ether, polyoxyethylene benzene Vinyl aromatic ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hardened castor oil Nonionic surfactants such as polyoxypropylene fatty acid esters; such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, yellow Vegetable oil or mineral oil such as soybean oil, rapeseed oil, linseed oil, tung oil, liquid paraffin; The components of the auxiliary agents may be appropriately selected from one or two or more kinds as long as they do not deviate from the object of the present invention. Further, in addition to the above-mentioned auxiliary agents, it may be appropriately selected from those known in the art, and for example, an extender, a tackifier, a sedimentation inhibitor, a freeze preventing agent, a dispersion stabilizer, and a drug may also be used. A variety of adjuvants commonly used for reducing agents, anti-mold agents, and the like. The blending ratio (weight ratio) of the compound of the present invention and various adjuvants is from 0.001:99.999 to 95:5, preferably from 0.005:99.995 to 90:10. When these preparations are actually used, they can be used as they are, or diluted with a diluent such as water to a predetermined concentration, and if necessary, various extenders (surfactant, vegetable oil, mineral oil, etc.) are added and used.

The application of the insecticide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention cannot be made according to the meteorological conditions, the form of the preparation, the application period, the place of application, the type or occurrence of the pest, and the like. It is completely specified, however, generally, it is carried out at an active ingredient concentration of 0.05 to 800,000 ppm, preferably 0.5 to 500,000 ppm, and the application amount per unit area is 0.05 to 50,000 g per 1 hectare of the compound of the present invention. It is preferably from 1 to 30,000 g. Further, in the present invention, a method for controlling pests, mites, nematodes or soil pests, particularly plant parasitic mites, agricultural pests, and plant parasitic nematodes, by such an application method, is also included.

The preparation of the insecticide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention, or the application of the dilution, can usually be carried out by a commonly used application method, that is, dispersion (for example, spraying) , misting, atomizing, shot, surface application, etc., soil application (mixing, infusion, etc.), surface application (coating, powder coating, coating, etc.), impregnation of baits, etc. Further, the above-mentioned active ingredient may be mixed into the feed and fed to the livestock, and the excretion inhibits the occurrence and growth of pests, particularly harmful insects. Furthermore, it can also be applied by the so-called ultra low volume application method. In this method, the active ingredient may be included in 100%.

Further, the insecticide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention may be mixed with or used in combination with other pesticides, fertilizers, phytotoxicity reducing agents, etc., in which case, sometimes, it is shown More excellent effects and efficiencies. Examples of other pesticides include herbicides, insecticides, acaricides, nematicides, soil-killing insecticides, bactericides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, and the like. In particular, the insecticidal composition, the acaricidal composition, the nematicidal composition, or the soil-killing pest of the compound of the present invention and one or more of the active ingredient compounds of other agricultural chemicals are used in combination or in combination. The composition can be improved in a preferable direction in terms of its application range, period of chemical treatment, and control activity. Further, the compound of the present invention and the active ingredient compound of another agricultural chemical may be used in the case where they are dispersed, or may be used together. In the present invention, the insecticidal composition, the acaricidal composition, the nematicidal composition, or the soil-killing pest composition are also included.

The mixing ratio (weight ratio) of the compound of the present invention and the active ingredient compound of other agricultural chemicals cannot be completely specified depending on the meteorological conditions, the form of the preparation, the application period, the place of application, the type of the pest or the occurrence state, and the like. Generally speaking, it is 1:300~300:1, preferably 1:100~100:1. Further, the appropriate amount to be applied is 0.1 to 50,000 g, preferably 1 to 30,000 g, per 1 hectare of the total amount of the active ingredient compound. In the present invention, the method for controlling pests, mites, nematodes or soil pests by the method for applying the insecticidal composition, the acaricidal composition, the nematicidal composition or the soil-killing pest composition is also included .

As an active ingredient compound (general name; part of the application, or the Japanese Plant Epidemic Prevention Association experiment code) of the above-mentioned other pesticides, such as insecticides, acaricides, nematicides or soil-killing pesticides, for example, , profenofos, dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, Acephate, prothiofos, fosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, acesulfame (ethion), etrimfos, quinalphos, dimethylvinphos, dimethoate, sulprofos, thiometon, sylvestris (vamidothion), pyraclofos, pyridaphthion, pirimiphos-methyl, propaphos, phosalone, formothion, malathion, music Tetrachlorvinphos, chlorfensone Fenvinphos), cyanophos, trichlorfon, methidathion, phenthoate, ESP, azinphos-methyl, fenthion, Feida Heptophophos, methoxychlor, parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos, (imicyafos), parathion-methyl, terbufos, phosphamidon, phosmet, phorate, and other organophosphate compounds; Carbaryl), propoxur, aldicarb, carbofuran, thiodicarb, methodyl, oxamyl, ethiofencarb ), pirimicarb, fenobucarb, carbosulfan, benfuracarb, bendiocarb, furathiocarb, extinction Carbamate compounds such as isoprocarb, metolcarb, xylylcarb, XMC, and fenothiocarb; (cartap), thiocyclam, bensultap, thiosultap-sodium, etc. Neilistoxin derivatives; dicofol, tetradifon, sulfur Organochlorine compounds such as endosulfan, dienochlor, and dieldrin; organometallic compounds such as fenbutatinoxide and cyhexatin; fenvalerate, Permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, ethofenprox, flufenprox , cyfluthrin, fenpropathrin, flucythrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrum Pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin ), alpha-cypermethrin, allethrin, gamma cylonine (gam Ma-cyhalothrin), theta-cypermethrin, tau-fluvalinate, tralmethrin, profluthrin, beta-cypermethrin , pyrethroid compounds such as beta-cyfluthrin, metofluthrin, phenothrin, flumethrin, etc.; Diflubenzuron), chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron ), bistrifluron, noviflumuron, fluzuron and other benzammonium compounds; metoprene, pyriproxyfen, fennock Young hormone-type compounds such as (fenoxycarb) and diofenolan; pyridazinone compounds such as pyridaben; fenpyroximate, fipronil, and desfens Tebufenpyrad), ethiprole, tolfenpyrad, (acetoprole), (pyrafluprole), (pyriprole) And other pyrazole-based compounds; imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, New nicotine compounds such as nidinotefuran, dinotefuran, and nithiazine; tebufenozide, methoxyfenozide, chromafnozide, (halofenozide), etc. Amine compounds; pyridine compounds such as Pyridalyl and flonicamid; cyclic ketones such as spirodiclofen, spiromesifen, and spirotetramat- An olefinic compound; a strobilurin compound such as fluacrypyrim; a pyrimidine amine compound such as flufenerim; a dinitro compound; an organic sulfur compound, a urea compound, and a triazabenzene compound; Lanthanide compounds, in addition, as other compounds, buprofezin, hexythiazox, amitraz, chlordimeform, silafluofen, triazamate , pymetrozine, 毕Pyrimidifen, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, cyromazine, 1,3-dichloropropene , diafenthiuron, (benclothiaz), bifenazate, propargite, clofentezine, metaflumizone, flubendiamide, 赛芬螨(cyflumetofen), chlorantraniliprole, (cyenopyrafen), (pyrifluquinazon), fenazaquin, (amidoflumet), sulfluramid, hydramethylnon, metaldehyde, a compound such as cyantraniliprole, ryanodine, verbutin, (sulfoxaflor), (cypropene); Furthermore, it can be combined with a crystalline protein toxin, an entomopathogenic virus agent, an entomopathogenic filamentous fungus, a nematode pathogen, such as Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis or Bacillus thuringiensis. Microbial pesticides such as avermectin, emamectin Benzoate, milbemectin, milbemycin, spinosad, ivermectin ), (lepimectin), DE-175, abamectin, emamectin, spinetoram, and other anti-biomass and semi-synthetic antibiotics; such as azadirachtin, vine Natural substances such as (rotenone); repellents such as deetamine; etc.; mixed or used together.

As an active ingredient compound (general name; part of the application, or the Japanese Plant Epidemic Prevention Association experimental code) of the above-mentioned other pesticides, for example, mepanipyrim and pyrimethanil may be mentioned. An anilinopyrimidine compound such as cyprodinil; 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1, 2,4]triazolopyrimidine compound such as triazolo[1,5-a]pyrimidine; pyridinamine compound such as fluazinam; triadimefon, bitertanol ), triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole, Tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, oxpoconazole fumarate, Sipconazole), (prothioconazole), tritaimenol, flutriafol, diknoconazol e), fluquinconazole, fenbuconazole, bromuconazole, diniconazole, tricyclazole, probenazole, simeconazole, An azole compound such as pefurazoate, ipconazole or imibenconazole; a quinoxaline compound such as quinomethionate; manne, zincine (zineb) , dithiocarbamate compounds such as mancozeb, polycarbamate, metiram, propineb, thiram, etc.; (fthalide), organochlorine-based compounds such as chlorothalonil and quintozene; benomyl, cyazofamid, thiophanate-methyl , imidazole-based compounds such as carbendazim, thiabendazole, (fuberiazole); cyanoacetamide-based compounds such as cymoxanil; metalaxyl, metalaxyl-M ), mefenoxam, oxadixyl, ofurace, bental (benalax) Yl), Benbenxyl-M (alias kiralaxyl, chiralaxyl), furalaxyl, cyprofuram, carboxin, oxycarboxin, thifluzamide , aniline compounds such as boscalid, isotianil, (bixafen), tiadinil, sedaxane, and sulfonamide compounds such as dichlofluanid ; copper compound such as cupric hydroxide or oxine copper; isoxazole compound such as hymexazol; fosetyl-Al, tolclofos- Methyl), S-benzyl-O, O-diisopropylphosphorothioate, O-ethyl-S, S-diphenyldithiophosphate (O -ethyl S, S-diphenylphosphorodithioate), aluminum ethylhydrogen phosphonate, edifenphos, iprobenfos and other organophosphorus compounds; captan, tetrachlordane (captafol), folpet (folpet) and other imine compounds; procymidone, iprodione, vincline Dioxoquinone-based compound such as ozolin); benzamidine anilide compound such as Flutolanil or mepronil; penthiopyrad, 3-(difluoromethyl)-1- Methyl-N-[(1RS,4SR,9RS)-1,2,3,4-tetrahydro-9-isopropyl-1,4-methane-5-naphthyl]pyrazole-4-carboxamide (3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9RS)-1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl]pyrazole-4- Carboxamide) with 3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9SR)-1,2,3,4-tetrahydro-9-isopropyl-1,4-methane a mixture of -5-naphthyl]pyrazole-4-carboxamide, (isopyrazam), silthiopham, fenoxanil, etc.; (fluopyram), saponin ( Zoxamidamide-based compound; piperazine-based compound such as triforine; pyridine-based compound such as pyrifenox; carbinol-based compound such as fenarimol; a piperidine compound such as (fenpropidin); a phenanthrene compound such as fenpropimorph or Tridmorph; fentin hydroxide, fentin acetate, etc. a tin-based compound; a urea compound such as pencycuron; a cinnamic acid compound such as dimethomorph or flumorph; or a phenyl carbamate compound such as diehofencarb; Cyanpyrrole-based compounds such as fludioxonil and fenpiclonil; azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, Stortby compounds such as picoxystrobin, oryzastrobin, dimoxystrobin, pyraclostrobin, fluoxastrobin, and oxazolinone such as famoxadone a compound; a thiazolcarbamide compound such as ethaboxam; a valinamide compound such as (iprovalicarb) or benthiavalicarb-isopropyl; methyl-N-(isopropyl isopropoxide) Alkylamino)-L-Amidino-yl-(3RS)-3-(4-chlorophenyl)-β-alanine (valiphenalate) and the like hydrazino-based acid compound; imidazolidone (fenamidone) and the like Iridazolinone compound; hydroxyaniline system such as fenhexamid a benzenesulfonamide compound such as flusulfamide; an oxime ether compound such as cyflufenamid; an anthraquinone compound; a butenoic acid compound; validamycin, kasugamycin (kasugamycin), anti-biomass such as polyoxins; lanthanide compounds such as iminoctadine and dodine; 6-tertiary butyl-8-fluoro-2,3-dimethyl Quinoline-based compound such as quinoline-4-yl acetate (tebufloquin); (Z)-2-(2-fluoro-5-(trifluoromethyl)phenylsulfanyl)-2-(3-(2-A) Tetrahydrothiazole-based compound such as oxyphenyl)tetrahydrothiazole-2-ylidene) acetonitrile; as other compounds, pyribencarb, isoprothiolane, pyroquilon , diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin, dazomet, metam-sodium, nicofifen , metrafenone, UBF-307, diclocymet, (proquinazid), amesulbrom (alias amberromdole), (pyriofenone), mandipropamid, flubenz (fl Uopicolide), carpropamid, meptyldinocap, ferimzone, spiroxamine, S-2188 (fenpyrazamine), S-2200, ZF-9646, BCF-051 , BCM-061 and BCM-062, etc.

Further, as the pesticide which can be used in combination with or in combination with the compound of the present invention, for example, there is an active ingredient compound of a herbicide as described in The Pesticide Manual (15th Edition), particularly a soil treatment type.

The insecticide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention is also suitable as a control agent for pests or cockroaches which are parasitic as described above. Specifically, it is harmful to external parasites that are parasitic on the surface of the host animal (back, underarm, lower abdomen, inner thigh, etc.) or parasitic in the host animal (stomach, intestine, lung, palpitations, liver palsy, The control of harmful internal parasites of blood vessels, subcutaneous, lymphoid tissues, etc. is effective, but it is effective in controlling external parasites.

Examples of the external parasite include, for example, mites or mites which are parasitic in animals. There are many types, and it is difficult to list them all, so the following examples are given.

Examples of the parasitic mites of animals include, for example, Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, and scorpion head. Bloody (Haemaphysalis campanulata), Haemaphysalis concinna, Haemaphysalis japonica, Haemaphysalis kitaokai, Haemaphysalis ias, Ixodes ovatus, Japanese hard palate (Ixodes nipponensis), Ixodes persulcatus, Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, Dermacentor taiwanesis, etc. Class; Dermanyssus gallinae; (Ornithonyssus sylviarum), tropical fowl (Ornithonyssus bursa) and other fowl mites; Eutrombicula wichmanni, Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, Europe Ot (Neotrombicula autumnalis), American locust (Eutrombicula alfreddugesi), (Helenicula miyagawai) and other aphids; canine 螨 螨 (Cheyletiella yasguri), rabbit meat 螨 (Cheyletiella parasitivorax), cat meat 螨 (Cheyletiella blakei) and other meat Aphids; Aphids such as Psoroptes cuniculi, Chorioptes bovis, Otodectes cynotis, Sarcoptes scabiei, Notoedres cati; Demodex (Demodex canis) and other blister wall mites. Among them, it is particularly effective for the control of mites and the like.

Examples of the parasitic mites of the animal include, for example, an external parasitic wingless insect belonging to the order of Siphonaptera, and more specifically, a genus belonging to the genus Pulicidae, Ceratephyllus, or the like. class. Examples of the genus belonging to the family Aphididae include: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga gallinacea, Xenopsylla cheopis, Leptopsylla segnis, Nosopsyllus fasciatus, Monopsyllus anisus, etc. Among them, the control agent for pests or mites which are parasitic in animals containing the compound of the present invention is effective for the control of mites belonging to the family Aphididae, particularly canine lice, cat mites and the like.

Examples of other external parasites include, for example, Haematopinus eurysternus, Haematopinus asini, Alpaca, Linognathus vituli, Pediculus capitis, and the like; Trichodectes canis); such as the genus Tabanus trigonus, Culicoides schultzei, Simulium ornatum, and other blood-sucking Diptera pests. Further, examples of the internal parasite include, for example, a lungworm, a whipworm, a tuberous worm, a gastric parasite, a mites, a filamentous worm, and the like; a Spirometra erinacei , such as the genus Echinococcus granulosus, Echinococcus granulosus, Echinococcus multilocularis, etc.; the trematode such as schistosomiasis, liver sputum, etc.; coccidia , malaria protozoa, intestinal sarcocyst (intestinal sarcocyst), toxoplasma, cryptosporidium and other protozoa.

Examples of the host animal include various pet animals, livestock, poultry, and the like, and more specifically, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, scorpions, ferrets, and birds (for example, , pigeons, parrots, caskets, birds, long-tailed parrots, white-backed birds, canaries, etc.), cattle, horses, pigs, sheep, ducks, chickens, etc. Among them, the control agent for pests or mites which are parasitic in animals containing the compound of the present invention is effective for the control of pests or mites which are parasitic on pet animals or livestock. Among pet animals or domestic animals, it is particularly effective for dogs, cats, cattle or horses.

When the compound of the present invention is used as a control agent for animal parasitic pests or mites, it can be used as it is, and it can also be formulated into a powder, granule, lozenge, powder, capsule together with a suitable adjuvant. It can be used in various forms such as liquid, emulsion, aqueous suspension, and oily suspension. Further, in addition to the above-described form of the preparation, various preparation forms which are generally used in the field can be formed as long as it is suitable for the purpose of the present invention. Examples of the auxiliary agent to be used in the preparation include an anionic surfactant or a nonionic interface exemplified as an adjuvant for preparation of the above-mentioned agricultural and horticultural insecticide, acaricide, nematicide or soil-killing insecticide. Active agent; cationic surfactant such as hexadecyltrimethylammonium bromide; water, acetone, acetonitrile, N-methylacetamide, N,N-dimethylacetamide, N,N-dimethyl Base amide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethyl b Glycol, liquid polyoxyethylene glycol, butanediol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol n-butyl ether, propylene glycol monomethyl ether, propylene glycol n-butyl ether Equivalent solvents; butyl hydroxyanisole, butyl hydroxytoluene, ascorbic acid, sodium metabisulfite, propyl gallate, sodium thiosulfate and other antioxidants; polyvinylpyrrolidone, polyvinyl alcohol, vinyl acetate a film forming agent such as a copolymer of an ester and vinylpyrrolidone; exemplified as the above-mentioned agricultural and horticultural killing Vegetable oil or mineral oil for the preparation of agents, acaricides, nematicides or soil-killing pesticides; lactose, sucrose, glucose, starch, wheat flour, corn flour, soybean oil, defatted rice bran, calcium carbonate, other municipalities A carrier such as a feed ingredient sold; The components of the auxiliary agents may be appropriately selected from one or two or more kinds as long as they do not deviate from the object of the present invention. Further, in addition to the above-mentioned auxiliary agent, it may be appropriately selected from those known in the art, and may be appropriately selected from various adjuvants and the like used in the above-mentioned agricultural and horticultural field. .

The blending ratio (weight ratio) of the compound of the present invention and various adjuvants is generally from about 0.1:99.9 to about 90:10. When these preparations are actually used, they can be used as they are, or diluted with a diluent such as water to a predetermined concentration, and if necessary, various extenders (surfactant, vegetable oil, mineral oil, etc.) are added and used.

Administration of the compounds of the invention to a host animal is carried out by oral or parenteral administration. Examples of the oral administration method include a method of administering a tablet, a liquid preparation, a capsule, a muffin, a biscuit, a minced meat, and other feeds containing the compound of the present invention. Examples of the parenteral administration method include, for example, a method in which the compound of the present invention is prepared into an appropriate preparation, and then introduced into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration or the like; a method of applying a surface to a body by spot-on treatment, pour-on treatment, spray treatment, or the like; a method of embedding a resin sheet containing the compound of the present invention, etc. under the skin of a host animal; .

The amount of the compound of the present invention administered to the host animal varies depending on the administration method, the purpose of administration, the symptoms of the disease, and the like. However, generally, the appropriate ratio is 0.01 mg to 100 g per 1 kg of the body weight of the host animal. The ratio is preferably 0.1mg~10g.

In the present invention, a method for controlling pests or mites which are parasitic by a method or a given amount of animals as described above, particularly a method for controlling external parasites or internal parasites, is also included.

Further, in the present invention, various diseases caused by host animals of the parasites can be prevented or treated in some cases by controlling harmful animal parasites as described above. As described above, the present invention also includes a prophylactic or therapeutic agent for a parasitic causative animal disease containing the compound of the present invention as an active ingredient, and a method for preventing or treating a parasitic causative animal disease.

When the compound of the present invention is used as a control agent for animal parasitic pests or mites, it can be used together with adjuvants, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents. , fungicides, colorants, fragrances, preservatives, etc., mixed or used together. In addition, as needed, it can be mixed with other various animal drugs or pesticides, for example, insect repellents, anticoccidial agents, insecticides, acaricides, acaricides, nematicides, fungicides, antibacterial agents, etc. In combination, in this case, sometimes it will show more excellent results. In the present invention, the composition for controlling an animal parasite according to the above-mentioned various components is used in combination or in combination, and a method for controlling an animal parasite using the composition, particularly an external parasite or an internal parasite, is also included. Prevention method.

Examples of preferred aspects of the invention are described below, but the invention is not limited to the aspects.

(1) A benzamide derivative represented by the above formula (I) or a salt thereof.

(2) A benzoguanamine derivative or a salt thereof as described in (1), wherein the R ² is a C ₃ -C ₈ cycloalkyl group.

(3) A benzoguanamine derivative or a salt thereof as described in (1), wherein the R ² is a C ₂ -C ₈ alkyl group.

(4) A benzoguanamine derivative or a salt thereof as described in (1), wherein the R ¹ is a hydrogen atom; and the R ² is a C ₃ -C ₈ cycloalkyl group.

(5) A benzoguanamine derivative or a salt thereof as described in (1), wherein the R ¹ is a hydrogen atom; and the R ² is a C ₂ -C ₈ alkyl group.

(6) R ¹ -based C ₁ -C ₃ alkyl group; R ² -based C ₂ -C ₈ alkyl group or C ₃ -C ₈ cycloalkyl group; the benzamide derivative described in (1) or a salt thereof .

(7) A benzoguanamine derivative or a salt thereof as described in (1), wherein R ¹ is a C ₁ -C ₃ alkyl group; and R ² is a C ₃ -C ₈ cycloalkyl group.

(8) A benzoguanamine derivative or a salt thereof as described in (1), wherein R ¹ is a C ₁ -C ₃ alkyl group; and R ² is a C ₂ -C ₈ alkyl group.

(9) R ¹ is a C ₁ -C ₃ alkyl group; R ² is a C ₂ -C ₈ alkyl group or a C ₃ -C ₈ cycloalkyl group (however, R ² is a cyclopropyl group when R ¹ is a methyl group) The benzoguanamine derivative or a salt thereof as described in (6).

(10) a benzoguanamine derivative described in (1), wherein R ¹ is a hydrogen atom or a C ₁ -C ₃ alkyl group; R ² is a C ₂ -C ₅ alkyl group or a C ₃ -C ₆ cycloalkyl group; Its salts.

(11) A benzoguanamine derivative or a salt thereof as described in (10), wherein the R ¹ is a hydrogen atom or a C ₁ alkyl group.

(12) A stereoisomer of the benzamide derivative or a salt thereof as described in (1) to (3) or (6) to (11).

(13) A stereoisomer according to (12), wherein the stereoisomer is a mirror image isomer or a non-image isomer.

(14) A mirror image isomer of the benzamide derivative or a salt thereof as described in (1) to (3) or (6) to (11).

(15) A mirror image isomer of the benzamide derivative or a salt thereof according to (14), wherein the compound of the above formula (I) is a formula (Ia) in which R ¹ and R ^{2 are} different. ):

Wherein R ^1-a is C ₁ -C ₃ alkyl; R ^2-a is C ₂ -C ₈ alkyl or C ₃ -C ₈ cycloalkyl, and R ^{1-a is} related to R ^2-a The compound represented by the same formula, and the methine carbon-based asymmetric center to which R ^1-a and R ^2-a are bonded in the formula (I).

(16) The mirror image isomer according to (14) or (15), which is characterized in that it is an S type.

(17) (S)-N-(1-Cyclopropylethyl)-2,6-difluorobenzamide.

(18) The mirror image isomer according to (14) or (15), which is characterized in that it is an R type.

(19) (R)-N-(1-Cyclopropylethyl)-2,6-difluorobenzamide.

(20) An insecticide, an acaricide, a nematicide or a soil-killing insecticide containing the benzamide derivative (I) or a salt thereof as described in (1) to (19) as an active ingredient.

(21) A nematicide containing the benzamide derivative or a salt thereof as described in (1) to (19) as an active ingredient.

(22) Insecticides for controlling pests, mites, nematodes or soil pests which cause problems in the field of agriculture and horticulture, containing the benzamide derivatives (1) to (19) or salts thereof as active ingredients Agents, acaricides, nematicides or soil-killing agents.

(23) An insecticide or acaricide for controlling animal parasitic pests or mites containing the benzamidine derivative or a salt thereof as described in (1) to (19) as an active ingredient.

(24) A method of administering an effective amount of a benzamide derivative or a salt thereof as described in (1) to (19) to control pests, mites, nematodes or soil pests.

(25) A method of controlling an effective amount of a benzamide derivative or a salt thereof as described in (1) to (19) to control a nematode.

[Examples]

The embodiments of the present invention are described below, but the present invention is not limited to the embodiments. First, a synthesis example of the compound of the present invention will be described.

Synthesis Example 1 Synthesis of (S)-N-(1-cyclopropylethyl)-2,6-difluorobenzamide (Compound No. 2)

A mixed solution of 0.21 g of 2,6-difluorobenzylhydrazine chloride and 5 mL of tetrahydrofuran was added to a mixed solution of 0.13 g of (S)-1-cyclopropylethaneamine and 0.15 g of triethylamine and 5 mL of tetrahydrofuran. The reaction was allowed to proceed for 1 hour at room temperature. After the completion of the reaction, the reaction mixture was added to water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After the anhydrous sodium sulfate was separated by filtration, the oxime was added and the solvent was concentrated under reduced pressure, and the obtained residue was purified by hexane column chromatography (eluent: n-hexane/ethyl acetate = 9/1 to 7) /3) Purification to obtain 0.20 g of a desired compound as a white solid. ¹ H-NMR data thereof [by ¹ H- nuclear magnetic resonance spectroscopy (Nuclear Magnetic Resonance Spectroscopy) measured. δ is a chemical shift value. ]as follows. ¹ H-NMR (solvent: CDCl ₃ /300 MHz) δ (ppm): 7.38-7.28 (1H, m), 6.95-6.88 (2H, m), 5.87 (1H, br), 3.69-3.57 (1H, m) , 1.35 (3H, d), 0.93-0.82 (1H, m), 0.58-0.37 (3H, m), 0.33-0.26 (1H, m).

Synthesis Example 2 Synthesis of N-(4,4-dimethylpentan-2-yl)-2,6-difluorobenzamide (Compound No. 7)

(1) A mixed solution of 1.14 g of 4,4-dimethyl-2-pentanone and 0.83 g of hydroxylamine hydrochloride and 0.64 g of sodium carbonate and 20 mL of ethanol was heated under reflux for 2 hours. After the reaction was completed, the reaction mixture was concentrated under reduced pressure and water was evaporated. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give crude 4,4-dimethyl-2-pentanone oxime 0.96 g.

(2) A mixed solution of 1.18 g of titanium tetrachloride and 10 mL of 1,2-dimethoxyethane was ice-cooled, and 0.47 g of sodium borohydride was added little by little. After stirring the reaction mixture for 15 minutes under ice cooling, 0.4 g of crude 4,4-dimethyl-2-pentanone oxime obtained in (1) and 6 mL of 1,2-dimethoxyethane were added dropwise. mixture. Then, the reaction mixture was allowed to warm to room temperature, stirred for 16 hours, and then cooled with ice. A mixed solution of 3.1 g of potassium hydroxide, 3.3 g of sodium acetate, and 20 mL of water was added to the reaction mixture to make it alkaline. Thereafter, the reaction mixture was filtered through Celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and then evaporated to dryness.

(3) A mixed solution of 0.30 g of triethylamine and 5 mL of tetrahydrofuran was added to the mixed solution of the crude 4,4-dimethyl-2-pentylamine obtained in (2) and 5 mL of tetrahydrofuran at room temperature. A mixed solution of 0.14 g of 2,6-difluorobenzylhydrazine chloride and 5 mL of tetrahydrofuran was added. After the reaction mixture was stirred at room temperature for 45 minutes, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was evaporated, and the solvent was concentrated under reduced pressure, and the obtained residue was subjected to a gel column chromatography (eluent: n-hexane / acetic acid The ester = 9/1 to 7/3) was purified to obtain the object compound (0.10 g). The ¹ H-NMR data is as follows. ¹ H-NMR (solvent: CDCl ₃ /300 MHz) δ (ppm): 7.38-7.29 (1H, m), 6.96-6.89 (2H, m), 5.67 (1H, br), 4.39-4.30 (1H, m) , 1.42 (2H, d), 1.26 (3H, d), 0.98 (9H, s).

Representative examples of the compounds of the above formula (I) are listed in Table 1. These compounds can be produced in accordance with the above Synthesis Examples 1 to 2 or the above various production methods. In Table 1, No. represents a compound No., Me represents a methyl group, Et represents an ethyl group, n-Pr represents a n-propyl group, i-Pr represents an isopropyl group, c-Pr represents a cyclopropyl group, and c-Bu represents an Cyclobutyl, t-Bu represents a tertiary butyl group, n-Penty1 represents a n-pentyl group, and c-Hexy1 represents a cyclohexyl group, and the temperature as a physical property is a melting point. In addition, the R/S system is represented by which mirror image isomer.

【Table 1】

The experimental examples are described below.

Experimental Example 1 Effect on southern root-knot nematode (Meloidgyne incognita)

In 400 mL of the southern root nodule contaminated soil, 7 mL of the chemical solution of the present invention was adjusted to a concentration of 400 ppm of the drug solution, and then mixed to uniformly disperse the drug. After the treated soil was filled in a flower pot (9 cm in diameter and 8 cm in height), tomato seedlings of 2 leaf age were transplanted and placed in a greenhouse. After 3 to 4 weeks of tomato transplantation, the degree of epiphysis formed in the root nodules was determined according to the nodule index shown in Table 2. As a result, the above compounds No. 1, 2, 4, 7 and 19 showed a high control effect of a nodule index of 1 or less.

【Table 2】

Experimental Example 2 Effect on Cobb root-lesion nematode (Pratylenchus penetrans)

In 400 mL of the northern root rot nematode contaminated soil, 7 mL of the chemical solution of the present invention was adjusted to a concentration of 400 ppm of the drug solution, and then mixed to uniformly disperse the drug. After the treated soil was filled in a flower pot (diameter 9 cm, height 8 cm), 10 burdock seeds were sown and placed in a greenhouse. About 2 months after the seeding of the burdock seed, the degree of damage to the root was determined according to the damage index shown in Table 3. As a result, the above Compound Nos. 1 and 2 showed a high control effect of a damage index of 1 or less.

【table 3】

Experimental Example 3 The effect of stun (overturning) and killing effect on long-horned blood stasis

1 mL (concentration: 10 mg/mL, 1 mg/mL, 0.1 mg/mL, 0.01 mg/mL, 0.001 mg/mL) of the acetone solution of the compound of the present invention was dropped on a filter paper set in a petri dish by a micropipette In. After the filter paper was dried, 100 cubs (long-horned blood clams) were placed in a petri dish and sealed with a polyethylene foil. The number of stunned pups was recorded at 10, 30, 60, and 240 minutes from the time the pup was placed. Further, the number of dead pups was recorded after 24, 48 and 72 hours from the time of placing the pups. The experiment was repeated twice.

Experimental Example 4 Using the effect of dogs on long-horned blood stasis

A gelatin capsule containing 10 mg/kg of the compound of the present invention is administered to a dog (Miglu dog, 8 months old), and immediately after the dog's auricle is placed into a long-horned blood clam, about 50 Artificial parasitic. After the treatment, the number of parasites, the number of falls, and the life and death of the fallen long-horned blood stasis were observed. As a result, the compound of the present invention causes parasitic longhorn blood stasis to fall or kill.

Experimental Example 5 Experiment on the efficacy of dogs against cat lice

A gelatin capsule containing 10 mg/kg of the compound of the present invention was administered to a dog (Miglu dog, 8 months old), and immediately about 100 eggs of the cat mites were placed on the back coat to artificially parasitize . After the treatment, the cat mites were recovered using a mites comb and the number of the ticks was calculated. As a result, the compounds of the present invention inhibit the parasitism of meerkats.

The formulation examples are described below.

Formulation Example 1

(1) 20 parts by weight of the compound of the present invention

(2) clay 70 parts by weight

(3) White carbon 5 parts by weight

(4) sodium polycarboxylate 3 parts by weight

(5) sodium alkylnaphthalenesulfonate 2 parts by weight

The above components are uniformly mixed to form a wettable powder.

Formulation Example 2

(1) The compound of the present invention 5 parts by weight

(2) talc 60 parts by weight

(3) calcium carbonate 34.5 parts by weight

(4) Flowing paraffin 0.5 parts by weight

The above ingredients are uniformly mixed to form a powder.

Formulation Example 3

(1) 20 parts by weight of the compound of the present invention

(2) N,N-dimethylacetamide 20 parts by weight

(3) polyoxyethylene tristyrylphenyl ether 10 parts by weight

(4) calcium dodecylbenzenesulfonate 2 parts by weight

(5) xylene 48 parts by weight

The above components are uniformly mixed and dissolved to form an emulsion.

Formulation Example 4

(1) clay 68 parts by weight

(2) sodium lignosulfonate 2 parts by weight

(3) polyoxyethylene alkyl aryl sulfate 5 parts by weight

(4) White carbon 25 parts by weight

A mixture of the above components and the compound of the present invention were mixed in a weight ratio of 4:1 to form a wettable powder.

Formulation Example 5

(1) The compound of the present invention 50 parts by weight

(2) Sodium alkylnaphthalene sulfonate formaldehyde condensate 2 parts by weight

(3) anthrone oil 0.2 parts by weight

(4) water 47.8 parts by weight

Further added to the stock solution in which the above components are uniformly mixed and pulverized

(5) sodium polycarboxylate 5 parts by weight

(6) anhydrous sodium sulfate 42.8 parts by weight

The particles are uniformly mixed, granulated, and dried to form a particulate wettable powder.

Formulation Example 6

(1) The compound of the present invention 5 parts by weight

(2) polyoxyethylene octyl phenyl ether 1 part by weight

(3) Polyoxyethylene alkyl ether phosphate 0.1 parts by weight

(4) Granular calcium carbonate 93.9 parts by weight

(1) to (3) were uniformly mixed in advance, diluted with an appropriate amount of acetone, sprayed onto (4), and acetone was removed to form a granule.

Formulation Example 7

(1) 2.5 parts by weight of the compound of the present invention

(2) N,N-dimethylacetamide 2.5 parts by weight

(3) Soybean oil 95.0 parts by weight

The above components were uniformly mixed and dissolved to form an ultra low volume formulation.

Formulation Example 8

(1) 40 parts by weight of the compound of the present invention

(2) Polyoxyethylene tristyrylphenyl ether potassium phosphate 4 parts by weight

(3) anthrone oil 0.2 parts by weight

(4) Sanxianjiao 0.1 parts by weight

(5) ethylene glycol 5 parts by weight

(6) water 50.7 parts by weight

The above components are uniformly mixed and pulverized to form an aqueous suspension.

Formulation Example 9

(1) 10 parts by weight of the compound of the present invention

(2) Diethylene glycol monoethyl ether 80 parts by weight

(3) polyoxyethylene alkyl ether 10 parts by weight

The above ingredients are uniformly mixed to form a liquid preparation.

Claims (14)

A benzepidine derivative or a salt thereof, which is represented by the formula (I): [wherein R ¹ is a hydrogen atom or a C ₁ -C ₃ alkyl group; R ² is a C ₂ -C ₈ alkyl group or a C ₃ -C ₈ cycloalkyl group]. The benzamide derivative or a salt thereof according to the first aspect of the invention, wherein R ² is a C ₃ -C ₈ cycloalkyl group. The benzamide derivative or a salt thereof according to the first aspect of the invention, wherein R ² is a C ₂ -C ₈ alkyl group. The benzamide derivative or a salt thereof according to the first aspect of the invention, wherein R ¹ is a hydrogen atom; and R ² is a C ₃ -C ₈ cycloalkyl group. The benzamide derivative or a salt thereof according to the first aspect of the invention, wherein R ¹ is a C ₁ -C ₃ alkyl group; R ² is a C ₂ -C ₈ alkyl group or a C ₃ -C ₈ cycloalkyl group; . The benzamide derivative or a salt thereof according to the first aspect of the invention, wherein R ¹ is a C ₁ -C ₃ alkyl group; and R ² is a C ₃ -C ₈ cycloalkyl group. The benzamide derivative or a salt thereof according to the first aspect of the invention, wherein R ¹ is a C ₁ -C ₃ alkyl group; and R ² is a C ₂ -C ₈ alkyl group. The benzamide derivative or a salt thereof according to the first aspect of the invention, wherein R ¹ is a C ₁ -C ₃ alkyl group; R ² is a C ₂ -C ₈ alkyl group or a C ₃ -C ₈ cycloalkyl group; (However, the case where R ² is a cyclopropyl group when R ¹ is a methyl group) is excluded. A mirror image isomer of a benzamide derivative or a salt thereof, which is a mirror image isomer of a benzamide derivative or a salt thereof according to claim 1 of the patent application, which is characterized in that: The compound of the formula (I) of the ^first aspect is a compound represented by the formula (Ia) in which R ¹ and R ² are different from each other: Wherein R ^1-a is C ₁ -C ₃ alkyl; R ^2-a is C ₂ -C ₈ alkyl or C ₃ -C ₈ cycloalkyl, and R ^1-a and R ^2-a are mutually Iso], and the methine carbon (*) to which R ^1-a and R ^2-a are bonded is an asymmetric center. A mirror image isomer of a benzamide derivative or a salt thereof according to claim 9 of the patent application, which is in the S form. An insecticidal, acaricidal, nematicidal or soil-killing insecticide containing the benzamidine derivative or a salt thereof as the active ingredient as in the first aspect of the patent application. A nematicide containing the benzamide derivative of the first aspect of the patent application or a salt thereof as an active ingredient. A method for controlling pests, mites, nematodes or soil pests, which comprises administering an effective amount of a benzamide derivative or a salt thereof as claimed in claim 1 to control pests, mites, nematodes or soil pests. A method for controlling nematodes, which comprises administering an effective amount of a benzamide derivative or a salt thereof as claimed in claim 1 to control nematodes.