JP2012072120A - Benzamide derivative or its salt, and insecticide, miticide, nematocide or soil vermicide containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel insecticide, miticide, nematocide or soil vermicide having very high control effect on vermins, mites, nematodes or soil vermins in a low chemical dosage, since the novel insecticide, miticide, nematocide or soil vermicide not exhibiting such defects and not a few problems that although a large number of insecticides, miticides, nematocides or soil vermicides are used over long years, the effects are insufficient and vermins and the like acquire resistivity to thereby limit the chemical usage, and otherwise.SOLUTION: There are provided an insecticide, miticide, nematocide or soil vermicide containing as an active component a benzamide derivative represented by formula (I) (wherein Ris a hydrogen atom or a 1-3C alkyl; Ris a 2-8C alkyl or a 3-8C cycloalkyl) or its salt.

Description

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

  Patent Document 1 describes that a specific benzamide derivative is useful as a herbicide. However, there is no mention of the use of benzamide derivatives as insecticides, acaricides, nematicides or soil-killing pesticides. Further, there is no specific description of the benzamide derivative represented by the following formula (I). On the other hand, Patent Literature 2 and Patent Literature 3 disclose the use of a benzamide derivative having a specific chemical structure as a nematicide. However, these compounds differ in chemical structure from the compounds of the present invention.

International Publication WO 2001/091558 US Pat. No. 4,840,969 European Patent Publication No. 323637

  Over the years, many insecticides, acaricides, nematicides or soil pesticides have been used, but their effectiveness is insufficient, pests gain resistance and their use is limited. There are many that have the problem of. Therefore, it is desired to develop a novel insecticide, acaricide, nematicide or soil insecticide with few such disadvantages.

  The present inventors have made various studies on benzamide derivatives in order to find better insecticides, acaricides, nematicides or soil insecticides. As a result, the benzamide derivative represented by the following formula (I) has an extremely high control effect especially against nematodes at a low dose, and has safety against natural enemies such as crops and pests or mammals. As a result, the present invention was completed.

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

[Wherein, R ¹ is a hydrogen atom or C ₁ -C ₃ alkyl; R ² is C ₂ -C ₈ alkyl or C ₃ -C ₈ cycloalkyl], or a salt thereof. Further, an insecticide, acaricide, nematicide or soil insecticide containing the benzamide derivative of the formula (I) or a salt thereof as an active ingredient, and a pest, mite, nematode or soil by applying them The present invention relates to a method for controlling pests.

  The insecticide, acaricide, nematicide or soil pesticide containing the benzamide derivative of the formula (I) or a salt thereof as an active ingredient is low in dose, against pests, mites, nematodes or soil pests. Has a very high control effect.

The alkyl in the formula (I) may be linear or branched, and specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, pentyl, hexyl, heptyl, octyl. And those having C _1-8 such as
Examples of the cycloalkyl in the formula (I) include C _3-8 such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

  Examples of the salt of the benzamide derivative in the formula (I) include any salt as long as it is acceptable in the art. For example, ammonium salts such as dimethylammonium salt and triethylammonium salt; Examples thereof include inorganic acid salts such as perchlorate, sulfate and nitrate; organic acid salts such as acetate and methanesulfonate.

The benzamide derivative in the formula (I) may have isomers, but the present invention includes both isomers and isomer mixtures. Examples of the isomers of the benzamide derivative of the formula (I) include stereoisomers such as enantiomers and diastereomers, among which R ¹ and R ² are different from each other in the 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 And an enantiomer in which the methine carbon to which R ¹ and R ^{2 in} Formula (Ia) are bonded is an asymmetric center. Enantiomers include R and S isomers, with the S isomer being preferred. In the present specification, unless otherwise specified, isomers are described as a mixture. The present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field. Depending on the type of isomer, there may be a chemical structure different from that of the formula (I). However, since those skilled in the art can fully recognize that they are related to isomers, the scope of the present invention. It is clear that it is within.

The benzamide derivative of the above formula (I) or a salt thereof (hereinafter abbreviated as the compound of the present invention) can be produced according to the following production method [1] and usual salt production methods, but is limited to these methods. It is not something.
Manufacturing method [1]

In the above formula, R ¹ and R ² are as described above, and Z is hydroxy, alkoxy or halogen. Examples of halogen include each atom of fluorine, chlorine, bromine or iodine. The salt of the compound of formula (II) includes any salt that is acceptable in the art, but includes, for example, inorganic acid salts such as hydrochlorides and sulfates; acetates and methanesulfonates. Organic acid salt; and the like.

  The reaction of the production process [1] can usually be performed in the presence of a base and a solvent. Examples of the base include alkali metals such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide; carbonates such as sodium carbonate and potassium carbonate; sodium bicarbonate, Bicarbonates such as potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine and triethylamine 1 type, or 2 or more types can be suitably selected from pyridines such as pyridine and 4-dimethylaminopyridine;

  The solvent is not particularly limited as long as the reaction proceeds. For example, aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; chloroform Halogenated hydrocarbons such as dichloromethane, carbon tetrachloride, dichloroethane, trichloroethane, chlorobenzene; ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; esters such as methyl acetate, ethyl acetate; dimethyl sulfoxide, Polar aprotic solvents such as sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone; Nitriles such as acetonitrile and propiononitrile; Ketos such as acetone and methyl ethyl ketone S; water; suitably selected one or more from such. In addition to these, amines or pyridines may be used among the above-mentioned bases.

The reaction of the production method [1] can be carried out in the presence of a dehydration condensing agent, if necessary. As the dehydrating condensing agent, for example, one or two or more kinds can be appropriately selected from N, N′-dicyclohexylcarbodiimide, chlorosulfonyl isocyanate, N, N′-carbonyldiimidazole, trifluoroacetic anhydride and the like.
The reaction temperature of the production method [1] is usually 0 to 100 ° C., preferably 0 to 50 ° C., and the reaction time is usually about 0.1 to 48 hours, preferably about 0.5 to 24 hours.

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

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

The reduction reaction of the production method [A] is a reaction between the compound of formula (IV) and a reducing agent. Examples of the reduction reaction include the following catalytic hydrogenation reaction or reduction reaction with a metal hydride, and the compound of formula (II) can be produced by any reaction.
[Catalytic hydrogenation reaction]

  As the reducing agent used in the catalytic hydrogenation reaction, for example, one or two or more kinds can be appropriately selected from hydrogen, formic acid, ammonium formate, and the like.

  The catalytic hydrogenation reaction can usually be performed in the presence of a catalyst and a solvent. As a catalyst, 1 type (s) or 2 or more types can be suitably selected from platinum, platinum oxide, platinum black, Raney nickel, palladium, palladium-carbon, rhodium, rhodium-alumina, etc., for example.

  The solvent is not particularly limited as long as the reaction proceeds. For example, aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; dioxane Ethers such as tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; acid amides such as dimethylacetamide, dimethylformamide and N-methylpyrrolidone; methanol, ethanol, propanol and butanol 1 type (s) or 2 or more types can be suitably selected from such alcohols; water;

The reaction temperature of the catalytic hydrogenation reaction 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.
[Reduction reaction with metal hydride]

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

  The reduction reaction with a metal hydride can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; alcohols such as methanol, ethanol, propanol and butanol; water; Or 2 or more types can be selected suitably.

  The reaction temperature of the reduction reaction with 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. is there.

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

In the above formula, R ¹ and R ² are as described above. NH ₂ OH salts include any salt that is acceptable in the art, but include, for example, inorganic acid salts such as hydrochlorides and sulfates; organic salts such as acetates and methanesulfonates. Acid salt; and the like.

  Reaction of a manufacturing method [B] can be performed in presence of a base as needed. Examples of the base include alkali metals such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide; carbonates such as sodium carbonate and potassium carbonate; sodium bicarbonate, Bicarbonates such as potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine and triethylamine 1 type or 2 types or more can be suitably selected from pyridines such as pyridine and 4-dimethylaminopyridine; acetates such as sodium acetate and potassium acetate;

  The reaction of the production method [B] can be carried out in the presence of a catalytic amount of hydrochloric acid, sulfuric acid, para-toluenesulfonic acid or the like, if necessary.

  The reaction of the production method [B] can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; dioxane Ethers such as tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide and N-methylpyrrolidone; acetonitrile Nitriles such as propiononitrile; alcohols such as methanol, ethanol, propanol and butanol; water; In addition to these, amines or pyridines can be used as a solvent among the above bases that can be used in the reaction of the present production method [B].

  The reaction temperature of the production method [B] is usually 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.

  Desirable embodiments of the insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention will be described below. Insecticides, acaricides, nematicides or soil pesticides containing the compounds of the present invention include, for example, pests, mites, nematodes or soil pests that are problematic in the field of agriculture and horticulture, and animal parasitic agents. Useful as a pest or mite control agent.

  The insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention is useful in the field of agriculture and horticulture as described above. Specifically, aphids such as peach aphid, cotton aphid, etc .; longhorn beetle, weevil, lotus moth, codling moth, ball worm, tobacco bad worm, maiigaiga, kobinomeiga, chanocokakumonhamaki, colorado beetle, cucumber potato beetle, ball weevil Pests such as slugs, maimai, etc .; planthoppers, leafhoppers, scale insects, stink bugs, whiteflies, thrips, grasshoppers, fly flies, scarabs, snails, cabbage moths, ants, etc .; Hygiene pests such as house dust mites, cockroaches, house flies, and mosquitoes; storage pests such as stag beetles, azuki beetles, bark beetles, bark beetles, etc .; clothing pests such as burrows, swordworms, termites, etc. House pests in Pests, worm spider mites, spider mites, kanzawa spider mites, citrus spider mites, apple spider mites, citrus dust mites, citrus mites, mites, etc .; Plant parasitic nematodes such as root-knot nematodes, cyst nematodes, negaless nematodes, rice stag beetles, strawberry nematodes, pine wood nematodes, etc .; It is effective for the control of soil pests. Among them, it is particularly effective for the control of plant parasitic mites, agricultural pests, plant parasitic nematodes, etc., and it shows even better effects for controlling agricultural pests, plant parasitic nematodes, etc. It is very useful as an insecticide or nematicide. In addition, the insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention is an organic phosphorus agent, carbamate agent, synthetic pyrethroid agent, neonicotinoid agent and other various resistant insect pests. It is also effective for control. Furthermore, since the compound of the present invention has an excellent osmotic transfer property, it can be harmful to soil by treating the soil with an insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention. At the same time as controlling insects, mites, nematodes, gastropods, isopodaes, it is possible to control pests on the foliage.

  As another desirable mode of the insecticide, acaricide, nematicide or soil insecticide in the field of agriculture and horticulture containing the compound of the present invention, the plant parasitic mites, agricultural pests, plant parasitic lines described above Examples include insecticides, acaricides, nematicides or soil-killing pesticides that comprehensively control insects, gastropods, soil pests and the like.

  Insecticides, acaricides, nematicides or soil pesticides containing the compound of the present invention are usually powders, granules, granule wettable powders by mixing the compound with various agricultural adjuvants, Used in various forms such as wettable powders, aqueous suspensions, oily suspensions, aqueous solvents, emulsions, solutions, pastes, aerosols, microdispersions, etc., but suitable for the purpose of the present invention As long as it is, it can be in any formulation form commonly used in the art. Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; water , Toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, alcohol, etc. Solvent; fatty acid salt, benzoate, alkylsulfosuccinate, dialkylsulfosuccinate, polycarboxylate, alkylsulfate, alkylsulfate, alkylarylsulfate, alkyldiglycolethersulfate, alcohol Sulfate ester salt, alkyl sulfonate salt, alkyl aryl sulfonate salt, aryl sulfonate salt, lignin sulfonate salt, alkyl diphenyl ether disulfonate salt, polystyrene sulfonate salt, alkyl phosphate ester salt, alkyl aryl phosphate salt, styryl aryl Phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl aryl phosphate , Anionic surfactants such as naphthalenesulfonate formaldehyde condensate; sorbitan fatty acid ester, glycerin fatty acid ester, fatty acid polyglyceride, fat Fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxy Nonionic surfactants such as ethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid ester; olive oil, kapok oil, castor oil, palm oil , Coconut oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, Riabura, vegetable oils and mineral oils such as liquid paraffin; and the like. Each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. In addition to the above-mentioned adjuvants, it can be used by appropriately selecting from those known in the art. For example, a bulking agent, a thickening agent, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a phytotoxicity reduction. Various commonly used adjuvants such as agents, antifungal agents and the like can also be used. The compounding ratio (weight ratio) of the compound of the present invention and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10. In actual use of these preparations, use them as they are or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.

  The application of the insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention is generally based on differences in weather conditions, formulation form, application time, place of application, type of pests and occurrence, etc. Although it cannot be defined, it is generally carried out at an active ingredient concentration of 0.05 to 800,000 ppm, preferably 0.5 to 500,000 ppm. The application amount per unit area is 0.05 to 50,000 g, preferably 1 to 30,000 g of the compound of the present invention per hectare. It is. The present invention also includes a method for controlling pests, mites, nematodes or soil pests by such an application method, particularly a method for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.

  Application of various preparations or dilutions of insecticides, acaricides, nematicides or soil insecticides containing the compounds of the present invention, or dilutions thereof, is usually a commonly used application method, ie spraying (for example, Spraying, misting, atomizing, dusting, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.), immersion poison bait, etc. It is also possible to feed livestock with the above-mentioned active ingredient mixed with feed to inhibit the occurrence and growth of harmful insects, particularly harmful insects, in the excreta. It can also be applied by the so-called ultra low volume application method. In this method, it is possible to contain 100% of the active ingredient.

  Further, the insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners, etc. May show excellent effects and functionality. Other pesticides include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. It is done. In particular, an insecticidal composition, an acaricidal composition, a nematicidal composition or a composition for soil-killing insect pests in which the compound of the present invention and one or more active ingredient compounds of other agricultural chemicals are mixed or used in combination. The product can improve the application range, the timing of chemical treatment, the control activity, and the like in a preferable direction. The compound of the present invention and the other active ingredient compounds of other agricultural chemicals may be used separately by mixing them at the time of spraying, or both may be used together. The present invention includes such an insecticidal composition, an acaricidal composition, a nematicidal composition or a soil-killing insect pest composition.

  The mixing ratio (weight ratio) between the compound of the present invention and the active ingredient compound of other pesticides cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, type of pests and occurrence, etc. 1: 300 to 300: 1, preferably 1: 100 to 100: 1. In addition, the appropriate amount to be applied is 0.1 to 50,000 g, preferably 1 to 30,000 g as the total active ingredient compound amount per hectare. The present invention also includes a method for controlling pests, mites, nematodes or soil pests by the application method of such insecticidal compositions, acaricidal compositions, nematicidal compositions or soil-killing insect pests. It is.

In the above-mentioned other agricultural chemicals, as an active ingredient compound of an insecticide, acaricide, nematicide or soil pesticide (generic name; including some pending applications or Japan Plant Protection Association test code), for example Profenofos, dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiophos, prothiophos, prothiophos Fosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate ), Sulprofos, thiomethos (thiometon), bamidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl, propaphos, phosalone, formothion, malathion, tetrachlorvinphos (tetrachlorvinphos), chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate, ESP, azinphos-methyl, fenthion, heptenophos , Methoxychlor, parathion, phosphocarb, demeton-S-methyl, monocrotophos, metamidophos, imicyafos, parathion-methyl -methyl), terbufos ( terbufos), organophosphate compounds such as phosphamidon, phosmet, phorate;
Carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, fenobucarb Carbamates such as carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC, fenothiocarb Compound;
Nereistoxin derivatives such as cartap, thiocyclam, bensultap, sodium thiosultap-sodium;
Organochlorine compounds such as dicophor, tetradifon, endosulfan, dienochlor, dieldrin;
Organometallic compounds such as fenbutatin oxide and cyhexatin;
Fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, etofenprox, flufenprox, cyfluthrin , Fenpropathrin, flucytrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrin, esfenvalerate, tetramethrin (Tetramethrin), resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypemethrin (alpha-cype) rmethrin), allethrin, gamma-cyhalothrin, theta-cypermethrin, tau-fluvalinate, tralomethrin, profluthrin, beta-si Pyrethroid compounds such as per-methrin (beta-cypermethrin), beta-cyfluthrin, mettofluthrin, phenothrin, flumethrin;
Diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron, hexaflumuron Benzoylurea compounds such as (bistrifluron), nobifluuron, fluazuron;
Juvenile hormone-like compounds such as metoprene, pyriproxyfen, fenoxycarb, diofenolan;
Pyridazinone compounds such as pyridaben;
Pyrazole compounds such as fenpyroximate, fipronil, tebufenpyrad, ethiprole, tolfenpyrad, acetoprole, pyrafluprole, pyriprole;
Imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, nidinotefuran, dinotefuranit, dinotefuranit A noid compound;
Hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide, halofenozide;
Pyridine compounds such as Pyridalyl and flonicamid;
Cyclic ketoenol compounds such as spirodiclofen, spiromesifen, spirotetramat;
Strobilurin-based compounds such as fluacrypyrim;
Pyrimidinamine compounds such as flufenerim;
Dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazone compounds, and other compounds include buprofezin, hexythiazox, amitraz, chlordimeform, silafluofen ), Triazamate, pymetrozine, pyrimidifen, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, cyromazine, 1,3-dichloropropene (1,3-dichloropropene), diafenthiuron, benclothiaz, bifenazate, propargite, clofentezine, metaflumizone metaflumizone, flubendiamide, cyflumetofen, chlorantraniliprole, cyenopyrafen, pyrifluquinazon, fenazaquin, fenazaquin, amidoflumet, sulfid And compounds such as hydramethylnon, metaldehyde, cyantraniliprole, ryanodine, verbutin, sulfoxaflor, cypropene; and the like. Furthermore, Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis or crystalline protein toxins produced by Bacillus thuringiensis, entomopathogenic fungi, nematode pathogenic fungi, etc. Microbial pesticides such as: avermectin, emamectin benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin ), Antibiotics such as emamectin, spinetoram and semi-synthetic antibiotics; natural products such as azadirachtin and rotenone; repellents such as deet; etc. And mixed use It is also possible to.

In the above-mentioned other pesticides, as an active ingredient compound (generic name; including partial application or Japanese Plant Protection Association test code), for example, mepanipyrim, pyrimethanil, cyprodinil Anilinopyrimidine compounds such as
Tria such as 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine Zolopyrimidine compounds;
Pyridinamine compounds such as fluazinam;
Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole), tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, o Oxpoconazole fumarate, sipconazole, prothioconazole, triadimenol, flutriafol, difenoconazole , Fluquinconazole, fenbuconazole, bromuconazole, diniconazole, tricyclazole, probenazole, cimeconazole, pefurazoate, ipconazole, ipconazole ), Azole compounds such as imibenconazole;
Quinoxaline compounds such as quinomethionate;
Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, thiram;
Organochlorine compounds such as fthalide, chlorothalonil, quintozene;
Imidazole compounds such as benomyl, cyazofamid, thiophanate-methyl, carbendazim, thiabendazole, and fuberiazole;
Cyanoacetamide compounds such as cymoxanil;
Metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, offurace, benalaxyl, benalaxyl-M, also known as kiralaxyl, chiax ), Fluralaxyl, cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, isothianil, bixafen, tiadinil, Anilide compounds such as sedaxane;
Sulfamide-type compounds such as dichlofluanid;
Copper-based compounds such as cupric hydroxide and oxine copper;
Isoxazole compounds such as hymexazol;
Fosetyl-Al, tolclofos-Methyl, S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate, edifenphos, iprobenphos Organophosphorus compounds such as (iprobenfos);
Phthalimide compounds such as captan, captafol, folpet;
Dicarboximide compounds such as procymidone, iprodione, vinclozolin;
Benzanilide compounds such as flutolanil and mepronil;
Penthiopyrad, 3- (difluoromethyl) -1-methyl-N-[(1RS, 4SR, 9RS) -1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl ] Pyrazole-4-carboxamide and 3- (difluoromethyl) -1-methyl-N-[(1RS, 4SR, 9SR) -1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalene-5 Amide compounds such as -yl] pyrazole-4-carboxamide mixtures (isopyrazam), silthiopham, fenoxanil;
Benzamide compounds such as fluopyram and zoxamid;
Piperazine compounds such as triforine;
Pyridine compounds such as pyrifenox;
Carbinol compounds such as fenarimol;
Piperidine compounds such as fenpropidin;
Morpholine compounds such as fenpropimorph and Tridemorph;
Organotin compounds such as fentin hydroxide and fentin acetate;
Urea-based compounds such as pencycuron;
Synamic acid compounds such as dimethomorph, flumorph;
Phenyl carbamate compounds such as dietofencarb;
Cyanopyrrole compounds such as fludioxonil and fenpiclonil;
Azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin ( strobilurin compounds such as dimoxystrobin), pyraclostrobin, fluoxastrobin;
Oxazolidinone compounds such as famoxadone;
Thiazole carboxamide compounds such as ethaboxam;
Valinamide compounds such as iprovalicarb, benchthiavalicarb-isopropyl;
Acylamino acid compounds such as methyl N- (isopropoxycarbonyl) -L-valyl- (3RS) -3- (4-chlorophenyl) -β-valaniphenate;
Imidazolinone compounds such as fenamidone;
Hydroxyanilide compounds such as fenhexamid;
Benzenesulfonamide compounds such as flusulfamide;
Oxime ether compounds such as cyflufenamid;
Anthraquinone compounds;
Crotonic acid compounds;
Antibiotics such as validamycin, kasugamycin, polyoxins;
Guanidine compounds such as iminoctadine and dodine;
Quinoline compounds such as 6-tertiarybutyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate (tebufloquin)
Thiazolidines such as (Z) -2- (2-fluoro-5- (trifluoromethyl) phenylthio) -2- (3- (2-methoxyphenyl) thiazolidine-2-ylidene) acetonitrile (flutianil) Compound;
Other compounds include pyribencarb, isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin, dazomet, metam Sodium salt (metam-sodium), nicobifen, metrafenone, UBF-307, diclocymet, proquinazid, amisulbrom (aka amibromdole), pyriofenone (manipropamide) mandipropamid), fluopicolide, carpropamid, meptyldinocap, ferimzone, spiroxamine, S-2188 (fenpyrazamine), S- 2200, ZF-9646, BCF-051, BCM-061, BCM-062, and the like.

  Other pesticides that can be used in combination with or combined with the compounds of the present invention include, for example, active compound compounds of herbicides such as those described in The Pesticide Manual (15th edition), especially those treated with soil. There is.

  The insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention is also useful as an animal parasitic insect or mite control agent as described above. Specifically, harmful ectoparasites that parasitize on the host animal's body surface (back, armpit, lower abdomen, inner thigh, etc.), and host animal body (stomach, intestinal tract, lungs, heart, liver, blood vessels, It is effective for controlling harmful endoparasites that are parasitic on the subcutaneous, lymphoid tissues, etc., but is particularly effective for controlling ectoparasites.

  Examples of ectoparasites include animal parasitic mites and fleas. There are so many of these types that it is difficult to list them all.

The animal parasitic mites, for example Boophilus microplus (Boophilus microplus), Rhipicephalus sanguineus (Rhipicephalus sanguineus), Haemaphysalis longicornis (Haemaphysalis longicornis), Haemaphysalis flava (Haemaphysalis flava), Adenophora chima tick (Haemaphysalis campanulata), Isukachimadani (Haemaphysalis concinna), Yamatochimadani (Haemaphysalis japonica), H. kitaokai (Haemaphysalis kitaokai), Iyasuchimadani (Haemaphysalis ias), Ixodes ovatus (Ixodes ovatus), I. nipponensis (Ixodes nipponensis), Schulze ticks (Ixodes persulcatus), Takasago testudinarium (Amblyomma testudinarium), Ootogechimadani (Haemaphysalis megaspinosa ), tick such as Dermacentor reticulatus , Dermacentor taiwanesis ; duck ( Dermanyssus gallinae ); Shidani (Ornithonyssus sylviarum), Torisashidani, such as Southern tri sand mite (Ornithonyssus bursa); Nan iodine tsutsugamushi (Eutrombicula wichmanni), red mites (Leptotrombidium akamushi), L. pallidum (Leptotrombidium pallidum), Fuji chiggers (Leptotrombidium fuji), Tosa mites ( Leptotrombidium tosa), Europe Aki mites (Neotrombicula autumnalis), the United States chiggers (Eutrombicula alfreddugesi), chiggers, such as Miyagawa Tama chiggers (Helenicula miyagawai); Inutsumedani (Cheyletiella yasguri), rabbit Tsumedani (Cheyletiella parasitivorax), Nekotsumedani (Cheyletiella blakei) Tsumedani, such as; rabbits 9,000 mite (Psoroptes cuniculi), Ushishokuhidani (Chorioptes bovis), dog ear mites (Otodectes cynotis), mange mites (Sar coptes scabiei ), mite mites like Notoedres cati, mite mites like Demodex canis , and the like. Among them, it is particularly effective for controlling ticks and the like.

Examples of animal parasitic fleas include ectoparasite worms belonging to the order Flea ( Siphonaptera ), and more specifically, fleas belonging to the family Flea family ( Pulicidae ), Nagano family ( Ceratephyllus ) and the like. Examples of fleas belonging to the family flea family include, for example, dog fleas ( Ctenocephalides canis ), cat fleas ( Ctenocephalides felis ), human fleas ( Purex irritans ), elephant fleas ( Echidnophaga gallinacea ), keops mouse fleas ( Xenopsylla cheopis ) Leptopsylla segnis ), European mud minnow ( Nosopsyllus fasciatus ), Yamato mud mink ( Monopsyllus anisus ); and the like. Among them, the animal parasitic pest or mite control agent containing the compound of the present invention is effective for controlling fleas belonging to the family Flea, particularly dog fleas, cat fleas and the like.

  Other ectoparasites include, for example, lice such as bovine lice, foal lice, sheep lice, bovine white lice, head lice; lice such as cat lice; blood-sucking dipterous pests such as bovine abs, quail sharks, . In addition, examples of endoparasites include nematodes such as lungworm, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms; Tapeworms such as real tapeworms, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms; Japanese schistosomiasis, fluke like liver fluke; coccidium, malaria parasite, intestinal granulocyst, toxoplasma, chestnut Protozoa such as Ptosporidium, and the like.

  Examples of host animals include various pet animals, livestock, poultry, and the like. More specifically, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (eg, pigeons, parrots, (E.g., nine-bird, bird, parakeet, juvenile pine, canary, etc.), cattle, horses, pigs, sheep, ducks, chickens, etc. Among them, the animal parasitic pest or tick control agent containing the compound of the present invention is effective for controlling pests or mites that are externally parasitic on pet animals or livestock. Among pet animals or domestic animals, it is particularly effective for dogs, cats, cows or horses.

  When the compound of the present invention is used as an animal parasitic pest or mite control agent, it may be used as it is, and together with suitable auxiliary agents, powders, granules, tablets, powders, capsules, liquid agents, emulsions, It can also be formulated into various forms such as an aqueous suspension and an oily suspension. In addition to the above-mentioned preparation forms, any preparation forms used in the normal field can be used as long as the object of the present invention is met. As an adjuvant to be used in the preparation, the anionic surfactants and nonionic surfactants exemplified as the above-mentioned preparation adjuvant for agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides. Surfactant; cationic surfactant such as cetyltrimethylammonium bromide; water, acetone, acetonitrile, N-methylacetamide, N, N-dimethylacetamide, N, N-dimethylformamide, 2-pyrrolidone, N- Methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, di Solvents such as tylene glycol monoethyl ether, diethylene glycol normal butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; butylhydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium metabisulfite, propyl gallate, sodium thiosulfate Antioxidants such as: polyvinyl pyrrolidone, polyvinyl alcohol, film forming agents such as vinyl acetate and vinyl pyrrolidone copolymers; formulations of the aforementioned agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides Vegetable oils and mineral oils exemplified as adjuvants for milk; lactose, sucrose, glucose, starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, calcium carbonate, and other carriers such as commercially available feed ingredients; That. Each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. In addition to the above-mentioned adjuvants, it can be used by appropriately selecting from those known in the field, and further, selected from various adjuvants used in the above-mentioned agricultural and horticultural fields. You can also

  The blending ratio (weight ratio) of the compound of the present invention and various adjuvants is usually about 0.1: 99.9 to 90:10. In actual use of these preparations, use them as they are or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.

  Administration of the compound of the present invention to the host animal is performed orally or parenterally. Examples of the oral administration method include a method of administering tablets, liquid agents, capsules, wafers, biscuits, minced meat, and other feeds containing the compound of the present invention. As a parenteral administration method, for example, the compound of the present invention is prepared into an appropriate preparation and then taken into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, etc .; spot-on And a method of administering to the body surface by treatment, pour-on treatment, spray treatment, etc .; a method of embedding a resin piece containing the compound of the present invention under the skin of a host animal, and the like.

  The dose of the compound of the present invention to the host animal varies depending on the administration method, administration purpose, disease symptoms, etc., but is usually 0.01 mg to 100 g, preferably 0.1 mg to 10 g, relative to 1 kg body weight of the host animal. Is suitable for administration.

  The present invention also includes a method for controlling animal parasitic pests or ticks by the administration method or dosage as described above, particularly a method for controlling ectoparasites or endoparasites.

  In the present invention, by controlling harmful animal parasites as described above, various host animal diseases caused by them may be prevented or treated. Thus, the present invention includes a prophylactic or therapeutic agent for parasitic animal diseases containing the compound of the present invention as an active ingredient, and a method for preventing or treating parasitic animal diseases.

  When the compound of the present invention is used as an animal parasitic insect or mite control agent, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, fungicides, It can be mixed or used together with a coloring agent, a fragrance, a preservative and the like. In addition, if necessary, other animal drugs and agricultural chemicals such as anthelmintics, anticoccidials, insecticides, acaricides, fleas, nematicides, fungicides, antibacterials, etc. In this case, a more excellent effect may be exhibited. The present invention includes a composition for controlling animal parasites in which various components as described above are mixed or used together, and a method for controlling animal parasites using the composition, in particular, control of ectoparasites or endoparasites. A method is also included.

Next, although an example of the desirable mode of the present invention is described, the present invention is not limited to these.
(1) A benzamide derivative represented by the formula (I) or a salt thereof.
(2) The benzamide derivative or a salt thereof according to (1), wherein R ² is C ₃ -C ₈ cycloalkyl.
(3) The benzamide derivative or a salt thereof according to (1), wherein R ² is C ₂ -C ₈ alkyl.
(4) The benzamide derivative or a salt thereof according to (1), wherein R ¹ is a hydrogen atom; and R ² is C ₃ -C ₈ cycloalkyl.
(5) The benzamide derivative or a salt thereof according to (1), wherein R ¹ is a hydrogen atom; and R ² is C ₂ -C ₈ alkyl.
(6) The benzamide derivative or the salt thereof according to (1), wherein R ¹ is C ₁ -C ₃ alkyl; and R ² is C ₂ -C ₈ alkyl or C ₃ -C ₈ cycloalkyl.
(7) The benzamide derivative or a salt thereof according to (1), wherein R ¹ is C ₁ -C ₃ alkyl; and R ² is C ₃ -C ₈ cycloalkyl.
(8) The benzamide derivative or a salt thereof according to (1), wherein R ¹ is C ₁ -C ₃ alkyl; and R ² is C ₂ -C ₈ alkyl.
(9) R ¹ is C ₁ -C ₃ alkyl; R ² is C ₂ -C ₈ alkyl or C ₃ -C ₈ cycloalkyl (except when R ¹ is methyl and R ² is cyclopropyl) Benzamide derivative or a salt thereof according to (6).
(10) The benzamide derivative or a salt thereof according to (1), wherein R ¹ is a hydrogen atom or C ₁ -C ₃ alkyl; and R ² is C ₂ -C ₅ alkyl or C ₃ -C ₆ cycloalkyl.
(11) The benzamide derivative or a salt thereof according to (10), wherein R ¹ is a hydrogen atom or C ₁ alkyl.
(12) Stereoisomers of the benzamide derivatives or salts thereof according to (1) to (3) or (6) to (11).
(13) The stereoisomer according to (12), wherein the stereoisomer is an enantiomer or a diastereomer.
(14) An enantiomer of the benzamide derivative or a salt thereof according to (1) to (3) or (6) to (11).
(15) In the compound of the formula (I), R ¹ and R ² are different from each other in the formula (Ia):

〔式中、Ｒ^１−ａはＣ_１-Ｃ_３アルキルであり；Ｒ^２−ａはＣ_２-Ｃ_８アルキル又はＣ_３-Ｃ_８シクロアルキルであり、Ｒ^１−ａとＲ^２−ａは互いに異なる〕で表される化合物であり、式（Ｉ）中のＲ^１−ａとＲ^２−ａが結合するメチン炭素が不斉中心であることを特徴とする（１４）に記載のベンズアミド誘導体又はその塩のエナンチオマー。
（１６）Ｓ体であることを特徴とする（１４）又は（１５）に記載のエナンチオマー。
（１７）（Ｓ)−N−（１−シクロプロピルエチル）−２，６−ジフルオロベンズアミド。
（１８）Ｒ体であることを特徴とする（１４）又は（１５）に記載のエナンチオマー。
（１９）（Ｒ)−N−（１−シクロプロピルエチル）−２，６−ジフルオロベンズアミド。
（２０）（１）〜（１９）に記載のベンズアミド誘導体又はその塩を有効成分として含有する殺虫剤、殺ダニ剤、殺線虫剤又は殺土壌害虫剤。
（２１）（１）〜（１９）に記載のベンズアミド誘導体又はその塩を有効成分として含有する殺線虫剤。
（２２）（１）〜（１９）に記載のベンズアミド誘導体又はその塩を有効成分として含有する農園芸分野で問題となる害虫、ダニ、線虫又は土壌害虫の防除用である殺虫剤、殺ダニ剤、殺線虫剤又は殺土壌害虫剤。
（２３）（１）〜（１９）に記載のベンズアミド誘導体又はその塩を有効成分として含有する動物寄生性害虫又はダニの防除用である殺虫剤又は殺ダニ剤。
（２４）（１）〜（１９）に記載のベンズアミド誘導体又はその塩の有効量を施用して害虫、ダニ、線虫又は土壌害虫を防除する方法。
（２５）（１）〜（１９）に記載のベンズアミド誘導体又はその塩の有効量を施用して線虫を防除する方法。

[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 The benzamide derivative according to (14), wherein the methine carbon to which R ^1-a and R ^2-a in formula (I) are bonded is an asymmetric center Or an enantiomer of a salt thereof.
(16) The enantiomer according to (14) or (15), which is an S form.
(17) (S) -N- (1-cyclopropylethyl) -2,6-difluorobenzamide.
(18) The enantiomer according to (14) or (15), which is an R form.
(19) (R) -N- (1-cyclopropylethyl) -2,6-difluorobenzamide.
(20) An insecticide, acaricide, nematicide or soil insecticide containing the benzamide derivative or salt thereof according to (1) to (19) as an active ingredient.
(21) A nematicide containing the benzamide derivative or a salt thereof according to (1) to (19) as an active ingredient.
(22) An insecticide or acaricide for controlling pests, mites, nematodes or soil pests which are problematic in the field of agriculture and horticulture, containing the benzamide derivative or salt thereof according to (1) to (19) as an active ingredient Agent, nematicide or soil-killing pesticide.
(23) An insecticide or acaricide for controlling animal parasitic pests or ticks containing the benzamide derivative or salt thereof according to (1) to (19) as an active ingredient.
(24) A method for controlling pests, mites, nematodes or soil pests by applying an effective amount of the benzamide derivative or a salt thereof according to (1) to (19).
(25) A method for controlling nematodes by applying an effective amount of the benzamide derivative or a salt thereof according to (1) to (19).

  Next, examples of the present invention will be described, but the present invention is not limited thereto. First, the synthesis example of this invention compound is described.

Synthesis example 1
Synthesis of (S) -N- (1-cyclopropylethyl) -2,6-difluorobenzamide (Compound No. 2) 0.13 g of (S) -1-cyclopropylethanamine, 0.15 g of triethylamine and 5 mL of tetrahydrofuran A mixed solution of 0.21 g of 2,6-difluorobenzoyl chloride and 5 mL of tetrahydrofuran was added to the mixed solution and reacted at room temperature for 1 hour. After completion of the reaction, the reaction mixture was added to water and extracted with ethyl acetate, and then the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After anhydrous sodium sulfate was filtered off, silica gel was added and the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 9/1 to 7/3). As a result, 0.20 g of a white solid target product was obtained. Measured by The ¹ H-NMR data ^[1 H- nuclear magnetic resonance spectroscopy of this compound (Nuclear Magnetic Resonance Spectroscopy). δ is a chemical shift value. ] Is as follows.
¹ H-NMR _{(solvent: CDCl 3 / 300MHz) 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-dimethylpentan-2-one, 0.83 g of hydroxylamine hydrochloride, 0.64 g of sodium carbonate, and 20 mL of ethanol was heated to reflux for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, dried and concentrated under reduced pressure to obtain 0.96 g of crude 4,4-dimethylpentan-2-one oxime.
(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. The reaction mixture was stirred for 15 minutes under ice cooling, and then a mixed solution of 0.4 g of the crude 4,4-dimethylpentan-2-one oxime obtained in (1) and 6 mL of 1,2-dimethoxyethane was added dropwise. . The reaction mixture was then warmed to room temperature, stirred for 16 hours, and ice-cooled. The reaction mixture was made basic by adding a mixed solution of 3.1 g of potassium hydroxide, 3.3 g of sodium acetate and 20 mL of water. Thereafter, the reaction mixture was filtered through Celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then dried under reduced pressure to obtain 0.52 g of crude 4,4-dimethylpentan-2-amine.
(3) A mixed solution of 0.30 g of triethylamine and 5 mL of tetrahydrofuran was added to a mixed solution of the total amount of crude 4,4-dimethylpentan-2-amine obtained in (2) and 5 mL of tetrahydrofuran, and 2,6- A mixed solution of 0.14 g of difluorobenzoyl chloride and 5 mL of tetrahydrofuran was added. The reaction mixture was stirred at room temperature for 45 minutes, and then 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, silica gel was added, the solvent was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (eluent: n-hexane / ethyl acetate). = 9/1 to 7/3) to obtain 0.10 g of the desired product. The ¹ H-NMR data of this product are as follows.
¹ H-NMR _{(solvent: CDCl 3 / 300MHz) 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 formula (I) are listed in Table 1. These compounds can be produced based on the synthesis examples 1 to 2 or the various production methods described above. In Table 1, No. indicates the compound No., Me is methyl, Et is ethyl, n-Pr is normal propyl, i-Pr is isopropyl, c-Pr is cyclopropyl, c-Bu Represents cyclobutyl, t-Bu represents tertiary butyl, n-Pentyl represents normal pentyl, c-Hexyl represents cyclohexyl, and the temperatures shown as physical properties are melting points. R / S represents which enantiomer it is.

Next, test examples are described.
Test Example 1 Effect test on sweet potato nematode nematode In 400 mL of sweet potato nematode contaminated soil, 7 mL of a chemical solution in which the concentration of the compound of the present invention was adjusted to 400 ppm was irrigated and mixed so that the drug was uniformly dispersed. After the treated soil was packed in a pot (diameter 9 cm, height 8 cm), tomato seedlings at the 2nd leaf stage were transplanted and placed in a greenhouse. Three to four weeks after tomato transplantation, the degree of root nodule formation at the root was determined according to the root nodule index shown in Table 2. As a result, the compounds No. 1, 2, 4, 7, and 19 showed a high control effect with a root-knot index of 1 or less.

Test Example 2 Effect Test on Kitanegusu Nematode After irrigating 7 mL of a solution of the present invention with a concentration of the compound of the present invention adjusted to 400 ppm, it was mixed so that the drug was uniformly dispersed. After the treated soil was packed in a pot (diameter 9 cm, height 8 cm), 10 burdock seeds were sown and placed in a greenhouse. About two months after sowing of burdock seeds, the degree of damage to the roots was determined according to the damage index shown in Table 3. As a result, the compounds No. 1 and 2 showed a high control effect with a damage index of 1 or less.

Test Example 3 Knockdown (rollover) effect / acaricidal effect test for Phytophthora tick 1 mL of acetone solution of the compound of the present invention (concentration: 10 mg / mL, 1 mg / mL, 0.1 mg / mL, 0.01 mg) on filter paper installed in the petri dish After the filter paper has dried, place 100 juvenile ticks (spotted ticks) in a petri dish, cover with a polyethylene sheet, and seal. Record the number of ticks knocked down after 10, 30, 60, and 240 minutes over time, and record the number of ticks that died 24, 48, and 72 hours over time after placing ticks. Repeat twice.

Test Example 4 Medicinal Efficacy Test Using Dogs Against Phytophyllum Tick A dog (beagle, 8 months old) was administered a gelatin capsule containing 10 mg / kg body weight of the compound of the present invention. Let go through and artificially infest. After the treatment, observe the number of infestations, the number of drops, and the life and death of the fallen spider mites. As a result, the compound of the present invention drops or kills the parasitic spider mite.

Test Example 5 Medicinal Efficacy Test Using a Dog against a Cat Flea A gelatin capsule containing 10 mg / kg body weight of the compound of the present invention was administered to a dog (beagle, 8 months old), and immediately after that about 100 cat flea non-blood-sucking adults were covered in the back Let go on and let it infest. After the treatment, collect the cat fleas using a flea removal comb and count the number of fixings. As a result, the compound of the present invention suppresses cat flea infestation.

Next, formulation examples are described.
Formulation Example 1
(1) Compound of the present invention 20 parts by weight (2) Clay 70 parts by weight (3) White carbon 5 parts by weight (4) Sodium polycarboxylate 3 parts by weight (5) Sodium alkylnaphthalene sulfonate 2 parts by weight or more To make a wettable powder.

Formulation Example 2
(1) Compound of the present invention 5 parts by weight (2) Talc 60 parts by weight (3) Calcium carbonate 34.5 parts by weight (4) Liquid paraffin 0.5 parts by weight or more are uniformly mixed to obtain a powder.

Formulation Example 3
(1) Compound of the present invention 20 parts by weight (2) N, N-dimethylacetamide 20 parts by weight (3) Polyoxyethylene tristyryl phenyl ether 10 parts by weight (4) Calcium dodecylbenzenesulfonate 2 parts by weight (5) Xylene 48 A mixture of more than parts by weight is uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 4
(1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) White carbon 25 parts by weight A mixture of each component and the present compound Mix at a weight ratio of 4: 1 to make a wettable powder.

Formulation Example 5
(1) Compound of the present invention 50 parts by weight (2) Sodium alkylnaphthalene sulfonate formaldehyde condensate 2 parts by weight (3) Silicone oil 0.2 parts by weight (4) Water 47.8 parts by weight or more uniformly mixed (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are further added to the crushed stock solution, and the mixture is uniformly mixed, granulated and dried to obtain a granulated wettable powder.

Formulation Example 6
(1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene alkyl ether phosphate 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1 ) To (3) are uniformly mixed in advance and diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove acetone and form granules.

Formulation Example 7
(1) Compound of the present invention 2.5 parts by weight (2) N, N-dimethylacetamide 2.5 parts by weight (3) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved to give a trace amount of spray ( ultra low volume formulation).

Formulation Example 8
(1) Compound of the present invention 40 parts by weight (2) Polyoxyethylene tristyryl phenyl ether potassium phosphate 4 parts by weight (3) Silicone oil 0.2 part by weight (4) Xanthan gum 0.1 part by weight (5) Ethylene glycol 5 Part by weight (6) Water 50.7 parts by weight or more are uniformly mixed and pulverized to obtain an aqueous suspension.

Formulation Example 9
(1) Compound of the present invention 10 parts by weight (2) Diethylene glycol monoethyl ether 80 parts by weight (3) Polyoxyethylene alkyl ether 10 parts by weight or more of ingredients are mixed uniformly to obtain a liquid agent.

Claims (14)

Formula (I):

[Wherein, R ¹ is a hydrogen atom or C ₁ -C ₃ alkyl; R ² is C ₂ -C ₈ alkyl or C ₃ -C ₈ cycloalkyl], or a salt thereof. The benzamide derivative or a salt thereof according to claim 1, wherein R ² is C ₃ -C ₈ cycloalkyl. The benzamide derivative or a salt thereof according to claim 1, wherein R ² is C ₂ -C ₈ alkyl. The benzamide derivative or a salt thereof according to claim 1, wherein R ¹ is a hydrogen atom; and R ² is C ₃ -C ₈ cycloalkyl. The benzamide derivative or a salt thereof according to claim 1, wherein R ¹ is C ₁ -C ₃ alkyl; and R ² is C ₂ -C ₈ alkyl or C ₃ -C ₈ cycloalkyl. The benzamide derivative or a salt thereof according to claim 1, wherein R ¹ is C ₁ -C ₃ alkyl; and R ² is C ₃ -C ₈ cycloalkyl. The benzamide derivative or a salt thereof according to claim 1, wherein R ¹ is C ₁ -C ₃ alkyl; and R ² is C ₂ -C ₈ alkyl. R ¹ is C ₁ -C ₃ alkyl; R ² is C ₂ -C ₈ alkyl or C ₃ -C ₈ cycloalkyl (except when R ¹ is methyl and R ² is cyclopropyl) The benzamide derivative or a salt thereof according to claim 1. A compound of formula (I) according to claim 1, wherein R ¹ and R ² are different from each other in 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 The benzamide derivative according to claim 1, wherein the methine carbon (*) to which R ^1-a and R ^2-a are bonded is an asymmetric center. Salt enantiomer. The enantiomer according to claim 9, which is an S form. An insecticide, acaricide, nematicide or soil insecticide containing the benzamide derivative or salt thereof according to claim 1 as an active ingredient. A nematicide containing the benzamide derivative or salt thereof according to claim 1 as an active ingredient. A method for controlling pests, mites, nematodes or soil pests by applying an effective amount of the benzamide derivative or salt thereof according to claim 1. A method for controlling nematodes by applying an effective amount of the benzamide derivative or a salt thereof according to claim 1.