JP2018193363A - Pest control agent containing isoindolinone compound or salt thereof as active ingredient - Google Patents

Abstract

To provide a pest control agent containing an isoindolinone compound or a salt thereof as an active ingredient.SOLUTION: The present invention provides an isoindolinone compound represented by the formula or a salt thereof (R, R, R: halogen, alkyl, cycloalkyl or the like, m: an integer of 0-5, n: an integer of 1-5, p: an integer of 0-4).SELECTED DRAWING: None

Description

  The present invention relates to a pest control agent containing a novel isoindolinone compound or a salt thereof as an active ingredient.

Patent Document 1 describes that specific isoindolinone compounds are useful as insecticides. However, this compound is different from the compound of the present invention.
Patent Documents 2 and 3 describe that specific isoindolinone compounds are useful as fungicides. However, this compound differs from the compound of the present invention in that the imino group at the 3-position of the isoindolinone ring is not substituted with phenyl.
Patent Document 4 describes that a specific thienopyrrole compound is useful as an insecticide. However, this compound differs from the compound of the present invention in that the fused ring of the mother nucleus is a thienopyrrole ring.
Non-Patent Documents 1 and 2 describe specific isoindolinone compounds, but are different from the compounds of the present invention.

International Publication No. 2004/110149 JP-A-53-144570 Japanese Patent Laid-Open No. 62-22760 International Publication No. 2017/065237

Angew. Chem. Int. Ed. 2013, 52, 11879-11883 Org. Lett. Vol.13, No.6, 2011, 1429-1431

  Many pest control agents have been used for many years, but many have various problems such as insufficient efficacy, and pests gaining resistance and limiting their use. Therefore, development of a novel pest control agent with few such drawbacks is desired. An object of the present invention is to provide a compound having high activity against pests, to provide a pest control agent using the compound, and to provide a method for controlling pests by applying the compound. It is.

The present inventors have made various studies on isoindolinone compounds in order to find better pest control agents. As a result, it was found that a specific isoindolinone compound has a very high control effect against pests at a low dose, and the present invention was completed.
That is, the present invention provides a compound of formula (I):

Wherein R ¹ and R ² are each independently halogen, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, monoalkylamino optionally substituted with halogen, dialkylamino optionally substituted with halogen, alkylthio , Haloalkylthio, pentafluorosulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkoxycarbonyl, nitro, cyano, alkylcyano, phenyl optionally substituted with A, heteroaryl optionally substituted with A, A Phenoxy which may be substituted with or benzyloxy which may be substituted with A; R ³ is halogen, alkyl, cycloalkyl, haloalkyl, alkoxy, alkenyl, alkynyl, trimethylsilylalkynyl , Monoalkylamino optionally substituted with halogen, dialkylamino optionally substituted with halogen, haloalkylthio, pentafluorosulfanyl, alkylsulfinyl, haloalkylsulfinyl, haloalkylsulfonyl, formyl, alkoxycarbonyl, aminocarbonyl, dialkylaminocarbonyl , Cyano, phenyl optionally substituted with A, heteroaryl optionally substituted with A, phenoxy optionally substituted with A or benzyloxy optionally substituted with A; A is halogen, alkyl, haloalkyl M is an integer from 0 to 5, n is an integer from 1 to 5, p is an integer from 0 to 4, and when m is 2 or more, R ¹ is bonded. phenyl ring moiety, and what R ¹ may be bonded to each other to form 1,3 May form a Nzojiokisoru ring, the R ¹ moiety may be substituted by A; when n is 2 or more, the phenyl ring portion R ² is bonded, R ² if you are bonded to each other 1,3 A benzodioxole ring may be formed, and the R ² moiety may be substituted with A; when p is 2 or more, the phenyl ring moiety to which R ³ is bonded is formed by bonding R ³ to each other. A 1,3-benzodioxole ring may be formed and the R ³ moiety may be substituted with A; provided that (1) p is 1 and R ³ is halogen, alkyl, haloalkyl or alkoxy If it is, each independently R ¹ and R ^2, cycloalkyl, alkoxy, pentafluorosulfanyl, haloalkylthio, haloalkylsulfonyl, alkoxycarbonyl, nitro, cyano, alkyl cyano, be substituted by a When phenyl, heteroaryl optionally substituted with A, phenoxy optionally substituted with A, benzyloxy optionally substituted with A or 1,3-benzodioxole, and (2) when p is 2 or more , A plurality of R ³ do not simultaneously become halogen)], a pest control agent containing the compound or salt thereof as an active ingredient, and an effective amount of the compound or salt thereof The present invention relates to a method for controlling pests.

  The pest control agent comprising the compound of formula (I) or a salt thereof as an active ingredient has a very high control effect against pests with a low dose.

  Examples of the halogen atom in the compound of the formula (I) or the halogen as a substituent include each atom of fluorine, chlorine, bromine or iodine. The number of halogen atoms as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.

Examples of the alkyl or alkyl moiety in the compound of formula (I) include methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal pentyl, isopentyl, neopentyl, normal hexyl, and neohexyl. Such linear or branched C ₁ -C ₆ groups can be mentioned.
Examples of the heteroaryl in the formula (I) include pyrazole and oxadiazole.

  Salts of the compound of formula (I) include any salt that is acceptable in the art, but examples include ammonium salts such as dimethylammonium salts and triethylammonium salts; hydrochlorides, perchloric acid Examples thereof include inorganic acid salts such as salts, sulfates and nitrates; organic acid salts such as acetates, trifluoroacetates, oxalates, p-toluenesulfonates, and methanesulfonates.

  The compound of formula (I) or a salt thereof may have an isomer such as an optical isomer, but the present invention includes both the isomers and isomer mixtures. 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 compound of the formula (I) or a salt thereof (hereinafter abbreviated as the compound of the present invention) can be produced according to the following production methods and ordinary salt production methods, but is not limited to these methods. .
Manufacturing method [1]

In the production method [1], R ¹ , R ² , R ³ , m, n and p are as defined above, and Me is a methyl group.
In the reaction of the production method [1], the compound of the formula (I) can be produced by reacting the compound of the formula (II) and the compound of the formula (III) in a solvent in the presence of a transition metal catalyst.
The compound of the formula (III) is known or can be produced by reacting aniline corresponding to the compound of the formula (III) with phosgene, diphosgene or triphosgene. The compound of formula (III) can be used in an amount of 1 to 3 times, preferably 1 to 1.5 times the mol of the compound of formula (II).
Examples of transition metal catalysts include palladium compounds such as palladium acetate, dichlorobis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium, tris (dibenzylidene) dipalladium; rhenium carbonyl, bromotricarbonyl (tetrahydrofuran) rhenium dimer The rhenium compound can be selected as appropriate. The transition metal catalyst can be used in an amount of 0.001 to 1 mol, preferably 0.01 to 0.1 mol per mol of the compound of formula (II).

The solvent may be any solvent as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1,4-dioxane, dimethoxyethane; benzene, toluene, xylene, chlorobenzene, etc. Aromatic hydrocarbons; aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; nitriles such as acetonitrile and propionitrile 1 type or 2 or more types can be suitably selected from ester, such as ethyl acetate and ethyl propionate; Aliphatic hydrocarbons, such as pentane, hexane, heptane, octane, and cyclohexane;
The reaction temperature is usually 20 to 200 ° C, preferably 50 to 180 ° C.
The reaction time is usually 1 to 48 hours, preferably 10 to 30 hours.

Intermediate production method [1]
The compound of the formula (II) used in the production method [1] can be produced according to a method comprising the following first to third steps.
[First step]

In the first step, R ¹ , R ³ , m and p are as defined above.
The reaction of route A in the first step can be performed by reacting the compound of formula (VI) and the compound of formula (VII) in a solvent in the presence of a base.
The reaction of Route B in the first step can be performed by reacting the compound of formula (VIII) and the compound of formula (VII) in a solvent in the presence of a condensing agent.
The compound of the formula (VI) is a known product, or can be produced by reacting the compound of the formula (VIII) with thionyl chloride or oxalyl chloride. The compound of the formula (VIII) is a known compound or can be produced by a conventional method. The compound of the formula (VI) can be used in an amount of 1 to 3 times, preferably 1 to 1.5 times the mol of the compound of the formula (VII).
The compound of formula (VIII) can be used in an amount of 1 to 3 times mol, preferably 1 to 1.5 times mol, of the compound of formula (VII).

  Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; Alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydrides such as sodium hydride and potassium hydride; alcohol metal salts such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; triethylamine, N , N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, organic bases such as 1,8-diazabicyclo [5.4.0] -7-undecene; You can choose. The base can be used in an amount of 1 to 5 mol, preferably 1 to 3 mol per mol of the compound of formula (VII).

  Examples of the condensing agent include carbodiimide condensing agents such as 1- (3- (dimethylamino) propyl) -3-ethylcarbodiimide or a salt thereof, N, N′-dicyclohexylcarbodiimide; N, N′-carbonyldiimidazole and the like. It can be suitably selected from imidazole condensing agents; triazine condensing agents such as (4,6-dimethoxy-1,3,5-triazin-2-yl) -4-methylmorpholinium chloride; The condensing agent can be used in an amount of 1 to 5 mol, preferably 1 to 2 mol per mol of the compound of formula (VIII).

The same solvent can be used for either route A or route B. The solvent may be any solvent as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1,4-dioxane, dimethoxyethane; benzene, toluene, xylene, chlorobenzene, etc. Aromatic hydrocarbons; aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; nitriles such as acetonitrile and propionitrile 1 type or 2 or more types can be suitably selected from ester, such as ethyl acetate and ethyl propionate; Aliphatic hydrocarbons, such as pentane, hexane, heptane, octane, and cyclohexane;
The reaction temperature is usually −50 to 200 ° C., desirably −10 to 100 ° C.
The reaction time is usually 0.5 to 48 hours, preferably 1 to 24 hours.
[Second step]

In the second step, R ¹ , R ³ , m and p are as defined above.
The reaction in the second step can be carried out by reacting the compound of formula (V) with thionyl chloride or oxalyl chloride in the presence of a solvent as necessary.
The solvent may be any solvent as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1,4-dioxane, dimethoxyethane; benzene, toluene, xylene, chlorobenzene, etc. Aromatic hydrocarbons; aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; nitriles such as acetonitrile and propionitrile 1 type or 2 or more types can be suitably selected from ester, such as ethyl acetate and ethyl propionate; Aliphatic hydrocarbons, such as pentane, hexane, heptane, octane, and cyclohexane;
The reaction temperature is usually −50 to 200 ° C., desirably 20 to 100 ° C.
The reaction time is usually 0.5 to 48 hours, preferably 1 to 24 hours.
[Third step]

In the third step, R ¹ , R ³ , m and p are as defined above. Me represents a methyl group.
The reaction in the third step can be performed by reacting the compound of formula (IV) and methanol in a solvent in the presence of a base.
Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; Alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydrides such as sodium hydride and potassium hydride; alcohol metal salts such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; triethylamine, N , N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, organic bases such as 1,8-diazabicyclo [5.4.0] -7-undecene; You can choose. The base can be used in an amount of 1 to 5 mol, desirably 1 to 3 mol per mol of the compound of formula (IV).

The solvent may be any solvent as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1,4-dioxane, dimethoxyethane; benzene, toluene, xylene, chlorobenzene, etc. Aromatic hydrocarbons; aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; nitriles such as acetonitrile and propionitrile 1 type or 2 or more types can be suitably selected from ester, such as ethyl acetate and ethyl propionate; Aliphatic hydrocarbons, such as pentane, hexane, heptane, octane, and cyclohexane;
The reaction temperature is usually −50 to 200 ° C., desirably −10 to 100 ° C.
The reaction time is usually 0.5 to 48 hours, preferably 1 to 24 hours.
Manufacturing method [2]

In the production method [2], R ¹ , R ² , R ³ , m, n and p are as defined above.
In the reaction of the production process [2], the compound of the formula (I) can be produced by reacting the compound of the formula (IX) and the compound of the formula (X) in a solvent in the presence of a transition metal catalyst.
The compound of the formula (X) is a known product, or can be produced by formylating the aniline corresponding to the compound of the formula (X) and then dehydrating with phosphoryl chloride or the like. The compound of formula (X) can be used in an amount of 1 to 3 times mol, preferably 1 to 1.5 times mol, of the compound of formula (IX).

  The transition metal catalyst can be appropriately selected from palladium compounds such as palladium acetate, dichlorobis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium, and tris (dibenzylidene) dipalladium. The transition metal catalyst can be used in an amount of 0.001 to 1 mole, preferably 0.01 to 0.1 mole relative to the compound of the formula (IX).

The solvent may be any solvent as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1,4-dioxane, dimethoxyethane; benzene, toluene, xylene, chlorobenzene, etc. Aromatic hydrocarbons; aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; nitriles such as acetonitrile and propionitrile 1 type or 2 or more types can be suitably selected from ester, such as ethyl acetate and ethyl propionate; Aliphatic hydrocarbons, such as pentane, hexane, heptane, octane, and cyclohexane;
The reaction temperature is usually 20 to 200 ° C, preferably 50 to 180 ° C.
The reaction time is usually 1 to 48 hours, preferably 10 to 30 hours.

Intermediate production method [2]
The compound of the formula (IX) used in the production method [2] can be produced according to a method comprising the following first step to second step.
[First step]

In the first step, R ² , R ³ , n and p are as defined above.
The reaction in the first step can be carried out by reacting the compound of formula (XI) with sodium nitrite in the presence of an acid and then reacting with (VII).
The compound of the formula (XI) is a known product, or can be produced by reacting an acid chloride obtained by reacting the corresponding anthranilic acid with thionyl chloride or oxalyl chloride with methanol. The compound of formula (VII) can be used in an amount of 1 to 3 times mol, desirably 1 to 1.5 times mol, of the compound of formula (XI).

Examples of the acid include hydrochloric acid, acetic acid, phosphoric acid, sulfuric acid, and p-toluenesulfonic acid. The solvent may be any solvent as long as it is inert to the reaction. For example, water; alcohols such as ethanol, 2-propanol, 1-butanol; diethyl ether, butyl methyl ether, tetrahydrofuran, 1,4-dioxane , Ethers such as dimethoxyethane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, etc. Aprotic polar solvent; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; Two or more It can be selected appropriately.
The reaction temperature is usually −50 to 50 ° C., preferably −10 to 30 ° C.
The reaction time is usually 0.5 to 48 hours, preferably 1 to 24 hours.
[Second step]

In the second step, R ² , R ³ , n and p are as defined above.
The reaction in the second step can be carried out by heating the compound of the formula (XII) in the presence of a solvent and optionally in the presence of a base.
The solvent may be any solvent as long as it is inert to the reaction. For example, alcohols such as methanol and ethanol, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1,4-dioxane and dimethoxyethane; Aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; acetonitrile Nitriles such as propionitrile; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; Can
Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; Alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydrides such as sodium hydride and potassium hydride; alcohol metal salts such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; triethylamine, N , N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, organic bases such as 1,8-diazabicyclo [5.4.0] -7-undecene; You can choose.
The reaction temperature is usually −50 to 200 ° C., desirably 20 to 100 ° C.
The reaction time is usually 0.5 to 48 hours, preferably 1 to 24 hours.

  The desirable aspect of the pest control agent containing this invention compound is described below. Examples of the pest control agent containing the compound of the present invention include pests, mites, nematodes or soil pests that are problematic in the field of agriculture and horticulture, that is, agricultural and horticultural insecticides, acaricides, nematicides or Soil-killing pesticides.

  The compounds of the present invention are useful as agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides. Specifically, aphids such as peach aphids, cotton aphids, etc .; Caterpillar, Lotus moth, Codling moth, Ball worm, Tobacco bud worm, Potato moth, Cochno medulla, Chanokoku kakumonhamakiki, Colorado potato beetle, cucumber moth beetle, ball weevil, planthopper, leafhopper, scale insect, stink bug, whitefly, thrips, thrips Pests, such as slugs, cockroaches, house flies, mosquitoes; sanitary pests, such as house dust mites, cockroaches, house flies, mosquitoes, etc .; Such as weevil, beetle, beetle, etc. Pests of stored grains; clothing such as moths, swordworms, termites, etc., house pests; pests such as spider mites, spider mites, spider mites, spider mites, apple spider mites, prickly mites, citrus mites, tick mites, etc. Indoor dusty mites, such as Staghorn mite, Pleurotus mite, Southern mite, etc .; such as mites, root-knot nematodes, cyst nematodes, nesting nematodes, rice nesting nematodes, strawberry nematodes, pine wood nematodes, etc. It is effective for the control of soil pests such as plant parasitic nematodes; The pest control agent containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. Among them, it is very useful as an insecticide or acaricide because it shows a further excellent effect in controlling plant parasitic mites and agricultural pests. Moreover, the pest control agent containing the compound of the present invention is also effective in controlling various resistant pests against drugs such as organic phosphorus agents, carbamate agents, synthetic pyrethroid agents, and neonicotinoid agents. Furthermore, since the compound of the present invention has excellent osmotic transfer properties, by treating the soil with a pest control agent containing the compound of the present invention, soil harmful insects, mites, nematodes, gastropods It is possible to control pests on the foliage at the same time as the control of mosquitoes and isoppods.

  Another desirable embodiment of the pest control agent containing the compound of the present invention is a farm that comprehensively controls the aforementioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, etc. Horticultural insecticides, acaricides, nematicides or soil insecticides.

  The pest control agent containing the compound of the present invention is usually a powder, granule, granule wettable powder, wettable powder, aqueous suspension, oily suspension by mixing the compound with various agricultural adjuvants. Used in various forms, such as an agent, an aqueous granule solvent, an aqueous solvent, an emulsion, a liquid agent, a paste agent, an aerosol agent, and a microdispersion agent, as long as it meets the purpose of the present invention. It can be in any formulation form used. 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 pest control agent containing the compound of the present invention cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application place, type of pests and occurrence status, but generally 0.05 to 800,000 ppm, preferably The active ingredient concentration is 0.5 to 500,000 ppm, and 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. 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.

  The application of various preparations or dilutions of the pest control agent containing the compound of the present invention is usually performed by a commonly used application method, that is, spraying (for example, spraying, misting, atomizing, dusting, water surface). Application), soil application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.), immersion poison bait, and the like. 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.

  Moreover, the pest control agent containing the compound of the present invention can be mixed or used in combination with other agrochemicals, fertilizers, safeners, etc., and in this case, more excellent effects and actions may be exhibited. 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 a pest control composition.

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, dislufoton, 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 ( organophosphate compounds such as terbufos, phosphamidon, phosmet, phorate, phoxim, triazophos;
Carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, fenobucarb Carbamates such as carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC, fenothiocarb Compound;
Cartap, thiocyclam, bensultap, sodium thiosultap-sodium, thiosultap-disodium, monosultap, bisultap, hydrogen oxalate thiocyclam Nereistoxin derivatives such as (thiocyclam hydrogen oxalate);
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, resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypermeline (alpha-cyperme) thrin), allethrin, gamma-cyhalothrin, theta-cypermethrin, tau-fluvalinate, tralomethrin, profluthrin, beta-cypermethrin ( Pyrethroid compounds such as beta-cypermethrin, beta-cyfluthrin, mettofluthrin, phenothrin, flumethrin, decamethrin;
Diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, triflumuron, hexaflumuron, lufenuron, novaluron, novaluron, ), Bistrifluron, benzoylurea compounds such as 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, 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, spiropidion;
Strobilurin-based compounds such as fluacrypyrim;
Pyridinamine compounds such as flufenerim;
Dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazone compounds, and other compounds include flometoquin, buprofezin, hexythiazox, amitraz, chlordimeform ), Silafluofen, triazamate, pymetrozine, pyrimidifen, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, romazine , 3-dichloropropene (1,3-dichloropropene), diafenthiuron, benclothiaz, bifenazate, propargite, clofentezine (cl ofentezine), metaflumizone, flubendiamide, cyflumetofen, chlorantraniliprole, cyantraniliprole, cyclaniliprole, cyenopyrafen, cyenopyrafen (Pyrifluquinazon), fenazaquin, amidoflumet, sulfluramid, hydramethylnon, metaldehyde, ryanodine, verbutin, chlorobenzoate, thia Thiazolylcinnanonitrile, sulfoxaflor, fluenesulfone, triflumezopyrim, afidopyropen, full Radipylon (flupyradifuron), fluxametamide, tetraniliprole, fluralaner, broflanilide, pyflubumide, dicloromezotiaz, fluhexafon, ox Compounds such as fluazaindolizine, acynonapyr, benzpyrimoxan, oxazosulfyl, flupyrimin, tyclopyrazoflor; and the like; . Furthermore, crystalline protein toxins produced by Bacillus thuringiensis such as Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis, entomopathogenic fungi, nematopathogenic fungi Microbial pesticides such as avermectin, amemectin benzoate, embectin, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin ( Antibiotics and semi-synthetic antibiotics such as abamectin, emamectin, spinetoram; natural products such as azadirachtin, rotenone; repellents such as deet; Etc., mixed, combined 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 ferimzone;
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 ), Flaxaxyl, cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, bixafen, isothianil, 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, furametpyr;
Benzamide compounds such as fluopyram and zoxamide;
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;
Atraquinone compounds;
Crotonic acid compounds;
Antibiotics such as validamycin, kasugamycin, polyoxins;
Guanidine compounds such as iminoctadine and dodine;
Quinoline compounds such as tebufloquin;
Thiazolidine-based compounds such as flutianil;
Other compounds include pyribencarb, isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin, dazomet, and sodium metam Metam-sodium, nicobifen, metrafenone, UBF-307, diclocymet, proquinazid, amisulbrom; also known as amibromdole, pyriofenone of isetamid ) Mandipropamid, fluopicolide, carpropamid, meptyldinocap, spiroxamine, fenpyrazamine (fenpy) razamine), mandestrobin, 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.

  Next, some preferred embodiments of the isoindoline non-based compound or a salt thereof of the present invention will be exemplified, but these do not limit the present invention.

(1) The isoindolinone compound of the formula (I) or a salt thereof.
(2) R ¹ and R ² are each independently halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, monoalkylamino optionally substituted with halogen, dialkylamino optionally substituted with halogen, alkylthio, haloalkylthio, Alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkoxycarbonyl, nitro, cyano, phenyl optionally substituted with A, phenoxy optionally substituted with A or benzyloxy optionally substituted with A; R ³ good monoalkylamino be substituted by halogen, optionally dialkylamino optionally substituted by a halogen, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, haloalkylsulfonyl, alkoxycarbonyl, shea , Phenyl optionally substituted with A, phenoxy optionally substituted with A or benzyloxy optionally substituted with A; m and n are each independently an integer of 1 to 5, and p is 1 to 4. The compound of (1) or a salt thereof, which is an integer of 4.
(3) R ¹ and R ² are each independently substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkoxycarbonyl, cyano, phenyl optionally substituted with A or A A is halogen, alkyl or haloalkyl, R ³ is phenyl optionally substituted with dialkylamino, cyano or A, and m and n are each independently an integer of 1 to 2 There, p is an integer of 1-2, and when m is 2, the phenyl ring portion R ¹ is bonded may form was what R ¹ are bonded to each other 1,3-benzodioxole ring The R ¹ moiety may be substituted with A; when n is 2, the phenyl ring moiety to which R ² is bonded is bonded to each other by R ² A 1,3-benzodioxole ring may be formed and the R ² moiety may be substituted with A; when p is 2, the phenyl ring moiety to which R ³ is attached is such that R ³ are The compound of the above (1) or (2) or a salt thereof, which may combine to form a 1,3-benzodioxole ring, and the R ³ part thereof may be substituted with A.
(4) R ¹ and R ² are each independently halo, alkyl, haloalkyl, alkoxy, haloalkoxy, haloalkylthio, alkoxycarbonyl or phenoxy which may be substituted with A, and R ³ is substituted with cyano or A R ¹ when R is phenyl, A is halogen, alkyl or haloalkyl, m and n are each independently an integer of 1 to 2, p is an integer of 1 to 2, and m is 2. A phenyl ring moiety to which R ¹ is bonded to each other to form a 1,3-benzodioxole ring, and the R ¹ moiety may be substituted with A; when n is 2, phenyl ring portion R ² are bonded may form was what R ² are bonded to each other 1,3-benzodioxole ring, the R ² moieties may be substituted by a; p is 2 case, ^{R 3} is a bond Phenyl ring moiety is linked to what R ³ each other to form a 1,3-benzodioxole ring, the R ³ moiety may be substituted by A the compound of (1) or (2) or Its salt.

(5) A pest control agent comprising the compound or salt thereof according to (1) to (4) as an active ingredient.
(6) An insecticide, acaricide, nematicide or soil insecticide containing the compound or salt thereof according to (1) to (4) as an active ingredient.
(7) A method for controlling pests by applying an effective amount of the compound or salt thereof according to (1) to (4).

  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 6-cyano-2- (4- (trifluoromethoxy) phenyl) -3-((4- (trifluoromethoxy) phenyl) imino) isoindoline-1-one (Compound No. I-1)

(1) To a mixed solution of 2.0 g of 4-trifluoromethoxyaniline, 2.29 g of triethylamine and 25 mL of tetrahydrofuran, 2.06 g of 4-cyanobenzoyl chloride was added and reacted at room temperature for 20 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 3.46 g of 4-cyano-N- (4- (trifluoromethoxy) phenyl) benzamide.

(2) A mixed solution of 3.46 g of the compound obtained in (1) and 10 mL of thionyl chloride was heated to reflux for 22 hours. The reaction solution was distilled off under reduced pressure to obtain 3.67 g of 4-cyano-N- (4- (trifluoromethoxy) phenyl) benzimidoyl chloride.

(3) 0.36 g of methanol was added dropwise at 0 ° C. to a mixed solution of 0.45 g of sodium hydride and 15 mL of tetrahydrofuran. After stirring for 30 minutes, a mixed solution of 3.67 g of the compound obtained in (2) and 10 mL of tetrahydrofuran was added dropwise at 0 ° C. and reacted at 0 ° C. for 10 minutes and at room temperature for 19 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-heptane / ethyl acetate = 15/1, volume ratio, the same applies hereinafter) to give methyl 4-cyano-N- (4 3.17 g of-(trifluoromethoxy) phenyl) benzimidate were obtained.

(4) To a mixed solution of 63 mg of the compound obtained in (3) and 1.5 mL of toluene, 40 mg of 4- (trifluoromethoxy) phenyl isocyanate and 3.2 mg of rhenium carbonyl were added and reacted at 150 ° C. for 23 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-heptane / ethyl acetate = 10/1) to obtain the desired product (42 mg) as an oil.

Next, typical examples of the compounds of formula (I) according to the present invention are listed in Table 1. These compounds can be synthesized based on the above synthesis examples or the various production methods described above. In Table 1, the numerical values described in the physical properties column indicate melting points (° C.). The compound described as “oil” is oily, and ¹ H-NMR spectral data of the compound are listed in Table 2. In Table 1, No. indicates a compound number. Me is methyl, Ph is phenyl, PhO is phenoxy, “cyclopropyl” is cyclopropyl, “pyrazole” is pyrazole, “trimethylsilyl” is trimethylsilyl, “ethynyl” is ethynyl, “oxadiazol-3-yl” "Represents oxadiazol-3-yl, and-represents an unsubstituted case. In R ¹

Together with the phenyl ring moiety attached,

It shows that. The same applies to R ² and R ³ .
In Table 2, I-82, I-83, I-84, I-85 and I-86 use acetone-d6 as the measurement solvent, and I-132 and I-134 use DMSO-d6 as the measurement solvent. It was.

Test Example 1 Effect test on Japanese pearl moth After the compound of the present invention was dissolved in acetone containing a surfactant, cabbage leaf pieces were immersed in a chemical solution diluted with water to a concentration of 200 ppm. After the chemical solution was air-dried, the cabbage leaf pieces were placed in a Petri dish having a diameter of 9 cm, on which wet filter paper was laid. There, 10 larvae of 2 to 3 instars were released, covered and left in a constant temperature room at 25 ° C. with illumination. After 5 days of insect release, the viability of the Japanese crested damselfly was determined, and the death rate (%) was determined by the following formula. As a result, the compound no. I-2, I-4, I-5, I-6, I-9, I-12, I-13, I-21, I-23, I-24, I-25, I-26, I- 27, I-28, I-30, I-31, I-32, I-35, I-36, I-42, I-44, I-46, I-49, I-50, I-51, I-52, I-53, I-54, I-55, I-56, I-59, I-60, I-61, I-62, I-66, I-67, I-69, I- 70, I-71, I-72, I-73, I-74, I-75, I-78, I-79, I-91, I-93, I-95, I-96, I-97, I-103, I-104, I-108, I-110, I-112, I-115, I-116, I-117, I-118, I-119, I-120, I-121, I- 123, I-124, I-12 Showed I-127, I-129, I-136, I-138, I-141, I-142, I-143 and I-154 is 90% or more mortality. Death rate (%) = (Number of dead insects / Number of dead insects) × 100

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 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 (8)

Formula (I):

Wherein R ¹ and R ² are each independently halogen, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, monoalkylamino optionally substituted with halogen, dialkylamino optionally substituted with halogen, alkylthio , Haloalkylthio, pentafluorosulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkoxycarbonyl, nitro, cyano, alkylcyano, phenyl optionally substituted with A, heteroaryl optionally substituted with A, A in substituted with an optionally substituted phenoxy or A be also good benzyloxy; R ³ is halogen, alkyl, cycloalkyl, haloalkyl, alkoxy, alkenyl, alkynyl, trimethylsilyl alkyl , Monoalkylamino optionally substituted with halogen, dialkylamino optionally substituted with halogen, haloalkylthio, pentafluorosulfanyl, alkylsulfinyl, haloalkylsulfinyl, haloalkylsulfonyl, formyl, alkoxycarbonyl, aminocarbonyl, dialkylaminocarbonyl , Cyano, phenyl optionally substituted with A, heteroaryl optionally substituted with A, phenoxy optionally substituted with A or benzyloxy optionally substituted with A; A is halogen, alkyl, haloalkyl M is an integer from 0 to 5, n is an integer from 1 to 5, p is an integer from 0 to 4, and when m is 2 or more, R ¹ is bonded. phenyl ring moiety binds to how R ¹ each other 1, - may form a benzodioxole ring, the R ¹ moiety may be substituted by A; when n is 2 or more, the phenyl ring portion R ² is bonded, R ² if you are bonded to each other 1,3-benzodioxol may form a sole ring, the R ² moieties may be substituted by a; when p is 2 or more, the phenyl ring moiety R ³ is attached is, is what R ³ May be linked together to form a 1,3-benzodioxole ring, the R ³ part of which may be substituted with A; provided that (1) p is 1, R ³ is halogen, alkyl when haloalkyl or alkoxy, each independently R ¹ and R ^2, cycloalkyl, alkoxy, pentafluorosulfanyl, haloalkylthio, haloalkylsulfonyl, alkoxycarbonyl, nitro, cyano, alkyl cyano, be substituted by a Phenyl, optionally substituted heteroaryl with A, phenoxy optionally substituted with A, benzyloxy optionally substituted with A or 1,3-benzodioxole, and (2) p is 2 or more In the case, a plurality of R ³ are not simultaneously halogenated]. R ¹ and R ² are each independently halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, monoalkylamino optionally substituted with halogen, dialkylamino optionally substituted with halogen, alkylthio, haloalkylthio, alkylsulfinyl, Haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkoxycarbonyl, nitro, cyano, phenyl optionally substituted with A, phenoxy optionally substituted with A or benzyloxy optionally substituted with A; R ³ is halogen Monoalkylamino optionally substituted with dialkylamino optionally substituted with halogen, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, haloalkylsulfonyl, alkoxycarbonyl, cyano, A Phenyl which may be substituted, phenoxy which may be substituted with A, or benzyloxy which may be substituted with A; m and n are each independently an integer of 1 to 5, and p is an integer of 1 to 4 The compound according to claim 1 or a salt thereof. R ¹ and R ² are each independently substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkoxycarbonyl, cyano, phenyl optionally substituted with A or A Good phenoxy; A is halogen, alkyl or haloalkyl; R ³ is phenyl optionally substituted with dialkylamino, cyano or A; m and n are each independently an integer of 1 to 2; There is an integer of 1-2, and when m is 2, the phenyl ring portion R ¹ is bonded may form was what R ¹ are bonded to each other 1,3-benzodioxole ring, that R ¹ part may be substituted by a; when n is 2, the phenyl ring portion R ² is bonded, R ² if you are bonded to each other 1,3 May form a Nzojiokisoru ring, the R ² moieties may be substituted by A; when p is 2, the phenyl ring moiety R ³ is bonded, attached to what R ³ mutually 1,3 The compound or a salt thereof according to claim 1 or 2, which may form a benzodioxole ring, and the R ³ part thereof may be substituted with A. R ¹ and R ² are each independently halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, haloalkylthio, alkoxycarbonyl or phenoxy which may be substituted with A, and R ³ may be substituted with cyano or A When R is phenyl, A is halogen, alkyl or haloalkyl, m and n are each independently an integer of 1 to 2, p is an integer of 1 to 2, and m is 2, R ¹ is bonded. phenyl ring portion may be formed by what R ¹ are bonded to each other 1,3-benzodioxole ring, the R ¹ moiety may be substituted by a; when n is 2, R ² is In the bonded phenyl ring moiety, R ² may be bonded together to form a 1,3-benzodioxole ring, and the R ² moiety may be substituted with A; ³ is bound off Cycloalkenyl ring portion may form a R ³ if you are bound to each other 1,3-benzodioxole ring, the R ³ moiety of the compound of claim 1 or 2 may be substituted by A Or a salt thereof.   The pest control agent which contains the compound or its salt of Claims 1-4 as an active ingredient.   An agricultural and horticultural insecticide, acaricide, nematicide or soil insecticide containing the compound or salt thereof according to claim 1 as an active ingredient.   An agricultural or horticultural insecticide or acaricide containing the compound or salt thereof according to claim 1 as an active ingredient.   A method for controlling pests by applying an effective amount of the compound according to claim 1 or a salt thereof.