JP2014001199A - Pest control agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel pest control agent.SOLUTION: Compounds represented by Formula (I), wherein Rand Rare each hydrogen atom, halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy or cyano, Rare alkyl or haloalkyl, n is an integer of 0 or 1, Q is pyridyl which may be substituted, phenyl which may be substituted, 2- pyrimidinyl which may be substituted or 4-pyrimidinyl which may be substituted, or salts thereof, and pest control agents containing the same as active ingredients are provided.

Description

  The present invention relates to a pest control agent comprising a novel compound represented by the following formula (I) or a salt thereof as an active ingredient.

  Patent Document 1 describes an acaricide that contains one or more 4-nitrodiphenyl ether derivatives as active ingredients, and Patent Document 2 describes an acaricide and a herbicide. Useful phenoxypyrimidine derivatives have been described. Patent Document 3 describes a method for producing a paranitrodiphenyl ether derivative useful as an insecticide and a herbicide. However, any of them is different from the compound of the present invention represented by the following formula (I).

JP-A-48-085731 JP 54-092978 A Japanese Patent Publication No.51-047695

  Many pest control agents have been used for many years, but many have various problems such as insufficient efficacy, pests and the like acquiring 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 3-aryloxyphenyl sulfide derivatives in order to find better pest control agents. As a result, it has been found that a novel compound represented by the following formula (I) or a salt thereof has a low dose and extremely high control effect against pests, and also has safety against crops. Completed the invention.

That is, the present invention relates to the following (1) to (7).
(1) Formula (I):

〔式（Ｉ）中、Ｒ^１及びＲ^２はそれぞれ、水素原子、ハロゲン原子、アルキル、ハロアルキル、アルコキシ、ハロアルコキシ又はシアノであり；Ｒ^３はアルキル又はハロアルキルであり；ｎは０又は１の整数であり；ＱはＲ^４で置換されてもよいピリジル、Ｒ^４で置換されてもよいフェニル、Ｒ^４で置換されてもよい２−ピリミジニル又はＲ^４で置換されてもよい４−ピリミジニルであり；Ｒ^４はハロゲン原子、アルキル、ハロアルキル、アルコキシ、ハロアルコキシ、シアノ、ニトロ、ＣＯＲ^５、ＣＯ₂Ｒ^５、Ｎ（Ｒ^６)ＣＯＲ^５、Ｎ（Ｒ^６)ＣＯ₂Ｒ^５、ＮＲ^７Ｒ^８、ＣＯＮＲ^７Ｒ^８、アルキルチオ、ハロアルキルチオ、アルキルスルフィニル、ハロアルキルスルフィニル、アルキルスルホニル、又はハロアルキルスルホニルであり、Ｒ^４が２つ以上ある場合には、それらは同一であっても異なっていてもよく；Ｒ^５、Ｒ^６、Ｒ^７及びＲ^８はそれぞれ、水素原子、アルキル又はハロアルキルであり；Ｒ^７及びＲ^８がアルキル又はハロアルキルである場合、隣り合う窒素原子と共に５〜６員環を形成してもよく；但し、ＱがＲ^４で置換されてもよいフェニルであり、Ｒ^３がアルキルである場合、Ｒ^１はハロゲン原子、アルキル、ハロアルキル、アルコキシ、ハロアルコキシ又はシアノであり；但し、ＱがＲ^４で置換されてもよい２−ピリミジニル又はＲ^４で置換されてもよい４−ピリミジニルである場合、Ｒ^１が水素原子であり、Ｒ^２が水素原子又はアルキルであり、及びＲ^３がアルキルである化合物を除く〕で表される化合物又はその塩。
（２）Ｒ^１が水素原子、ハロゲン原子又はアルキルであり、Ｒ^２がハロゲン原子又はアルキルであり、Ｒ^３がアルキル又はハロアルキルであり、Ｒ^４がハロゲン原子、アルキル、ハロアルキル、アルコキシ、シアノ又はニトロである、前記（１）の化合物又はその塩。
（３）式（Ｖ）：

[In the formula (I), R ¹ and R ² are each a hydrogen atom, a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy or cyano; R ³ is alkyl or haloalkyl; n is an integer of 0 or 1 in it; Q is at has been or 4-pyrimidinyl substituted with may also be 2-pyrimidinyl, or R ⁴ that is substituted with a phenyl, R ⁴ may be substituted by pyridyl, R ⁴ be substituted with R ⁴ R ⁴ is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano, nitro, COR ⁵ , CO ₂ R ⁵ , N (R ⁶ ) COR ⁵ , N (R ⁶ ) CO ₂ R ⁵ , NR ⁷ R ^8; , CONR ⁷ R ^8, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, or haloalkylsulfenyl Is nil, when R ⁴ have two or more, they may be different even in the ^{same; R 5, R 6, R} 7 and R ⁸ each is a hydrogen atom, alkyl or haloalkyl When R ⁷ and R ⁸ are alkyl or haloalkyl, they may form a 5- to 6-membered ring with adjacent nitrogen atoms; provided that Q is phenyl optionally substituted with R ⁴ and R ³ is when it is alkyl, R ¹ is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy or cyano; provided, Q may be substituted with may be 2-pyrimidinyl, or R ⁴ that is substituted with R ⁴ 4- In the case of pyrimidinyl, a compound represented by the above or a salt thereof, except that R ¹ is a hydrogen atom, R ² is a hydrogen atom or alkyl, and R ³ is alkyl.
(2) R ¹ is a hydrogen atom, a halogen atom or alkyl, R ² is a halogen atom or alkyl, R ³ is alkyl or haloalkyl, R ⁴ is a halogen atom, alkyl, haloalkyl, alkoxy, cyano or nitro The compound of the above (1) or a salt thereof.
(3) Formula (V):

〔式（Ｖ）中、Ｒ^１はハロゲン原子又はアルキルであり；Ｒ^２はハロゲン原子又はアルキルであり；Ｒ^３はトリフルオロエチルである〕で表される化合物又はその塩。
（４）式（Ｖ）で表される前記（３）の化合物。
（５）Ｒ^１がフッ素原子、塩素原子又はアルキルであり、Ｒ^２が塩素原子又はメチルであり、Ｒ^３がトリフルオロエチルである前記（３）の化合物又はその塩。
（６）Ｒ^１がフッ素原子、塩素原子又はアルキルであり、Ｒ^２が塩素原子又はメチルであり、Ｒ^３がトリフルオロエチルである前記（３）の化合物。
（７）式（Ｉ）の化合物又はその塩を有効成分とする有害生物防除剤、該化合物又はその塩の有効量を施用して有害生物を防除する方法。

[In the formula (V), R ¹ is a halogen atom or alkyl; R ² is a halogen atom or alkyl; R ³ is trifluoroethyl] or a salt thereof.
(4) The compound of (3) represented by formula (V).
(5) The compound of (3) or a salt thereof, wherein R ¹ is a fluorine atom, a chlorine atom or alkyl, R ² is a chlorine atom or methyl, and R ³ is trifluoroethyl.
(6) The compound of (3), wherein R ¹ is a fluorine atom, a chlorine atom or alkyl, R ² is a chlorine atom or methyl, and R ³ is trifluoroethyl.
(7) A method for controlling pests by applying an effective amount of the compound or a salt thereof, which comprises a compound of the formula (I) or a salt thereof as an active ingredient.

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

  Examples of the halogen atom in the formulas (I) and (V) or the halogen atom as a substituent include fluorine, chlorine, bromine or iodine atoms. 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.

The alkyl or alkyl moiety in the formulas (I) and (V) may be linear or branched, and specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec Examples thereof include C _1-6 such as -butyl, tert-butyl, pentyl and hexyl.

When the pyridyl in the formula (I) is substituted with R ⁴ , the number of substitutions is 1 to 4. Further, when substituted with a plurality of R ⁴ , R ⁴ may be the same or different. Examples of the pyridyl that may be substituted with R ⁴ include 2-pyridyl, 3-pyridyl, and 4-pyridyl.
When phenyl in the formula (I) is substituted with R ⁴ , the number of substitution is 1 to 5. Further, when substituted with a plurality of R ⁴ , R ⁴ may be the same or different.
When 2-pyrimidinyl or 4-pyrimidinyl in the formula (I) is substituted with R ⁴ , the number of substitutions is 1 to 3. Further, when substituted with a plurality of R ⁴ , R ⁴ may be the same or different.

Examples of the salt of the compound of 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; Inorganic acid salts such as acid salts, sulfates and nitrates; organic acid salts such as acetates and methanesulfonates.
The salt of the compound of the formula (V) includes any salt that is acceptable in the technical field. For example, alkali metal salts such as sodium salt and potassium salt; calcium salt and magnesium salt Alkaline earth metal salts such as triethylamine, N, N-dimethylaniline, pyridine, salts with organic bases such as 4-N, N-dimethylaminopyridine, and the like.

  The compound of the 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) and its starting compound are prepared by the following production methods [1], [2], [3], [Intermediate production method 1] and [Intermediate product]. Although it can manufacture according to the manufacturing method 2] and the manufacturing method of a normal salt, it is not limited to these methods.
Manufacturing method [1]

In the production method [1], Q, R ¹ , R ² and R ³ are as described above. L ¹ represents a halogen atom, a mesyl group or a tosyl group.
This reaction can be carried out by reacting the compound of formula (II) or formula (III) with a compound of formula (IV) in the presence of a base in a solvent.
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 10 times mol, preferably 1 to 5 times mol, of the compound of formula (II).
This reaction can be performed in the presence of a radical initiator, if necessary. The radical initiator can be appropriately selected from, for example, a sulfite adduct such as sulfite, sulfite, Rongalite (trade name of sodium, formaldehyde, sulfoxylate). The radical initiator can be used in an amount of 0 to 5 moles, preferably 0.1 to 2 moles, relative to 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 Esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; protic solvents such as water, methanol and ethanol; You can choose.
The reaction temperature is usually −50 to 200 ° C., preferably 0 to 150 ° C.
The reaction time is usually about 0.5 to 72 hours, preferably 1 to 48 hours.
Manufacturing method [2]

In the production method [2], Q, R ¹ , R ² and R ³ are as described above.
This reaction can be carried out by reacting the compound of formula (Ia) in a solvent in the presence of an oxidizing agent.
Examples of the oxidizing agent include hydrogen peroxide, m-chloroperbenzoic acid, perbenzoic acid, sodium periodate, oxone (OXONE, trade name of EI DuPont, potassium peroxosulfate), N- It can be appropriately selected from chlorosuccinimide, N-bromosuccinimide, tert-butyl hypochlorite, sodium hypochlorite and the like. The oxidizing agent can be used in an amount of 1 to 5 times mol, preferably 1 to 2 times mol for the compound of formula (Ia).
This reaction can be performed in the presence of a catalyst, if necessary. The catalyst can be selected from, for example, sodium tungstate and flavin. The catalyst can be used in an amount of 0.0001 to 1 mol, preferably 0.001 to 0.05 mol based on the compound of the formula (Ia).
As the solvent, any solvent may be used as long as it is inert to the reaction. For example, halogenated alkanes such as chloroform, dichloromethane and dichloroethane; aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; ethyl acetate and ethyl propionate. 1 type (s) or 2 or more types can be selected as appropriate from esters such as: acetic acid;
The reaction temperature is usually −50 to 150 ° C., preferably −10 to 50 ° C.
The reaction time is usually 0.5 to 48 hours, preferably 1 to 30 hours.
Manufacturing method [3]

In the production method [3], Q, R ¹ , R ² and R ³ are as described above. L ² represents a halogen atom or a boronyl group.
This reaction can be carried out by reacting the compound of formula (V) with a compound of formula (VI) in the presence of a base in a solvent.
Examples of the base include those similar to the above production method [1]. A base is 1-10 times mole with respect to the compound of Formula (V), 1-5 times mole can be used desirably.
This reaction can be performed in the presence of a catalyst, if necessary. The catalyst can be appropriately selected from, for example, copper (II) acetate and palladium acetate. The catalyst can be used in an amount of 0.001 to 2 moles, preferably 0.01 to 1 moles, relative to the compound of formula (V).
Examples of the solvent include those similar to the above production method [1].
The reaction temperature is usually −50 to 200 ° C., preferably 0 to 150 ° C.
The reaction time is usually about 0.5 to 72 hours, preferably 1 to 48 hours.

[Intermediate production method 1]
The compound of the formula (II) or the formula (III) which is the starting material of the production method [1] can be produced, for example, by a reaction consisting of the following (1) to (4).
(1) a first step in which a compound of formula (VII) and a compound of formula (VI) are coupled to obtain a compound of formula (VIII);
(2) a second step of halosulfonylating the compound of formula (VIII) to give a compound of formula (IX);
(3) a third stage in which the compound of formula (IX) is reduced to obtain a compound of formula (X);
(4) The fourth steps (1) to (4) in which the compound of formula (X) is hydrolyzed to obtain the compound of formula (II) or formula (III) will be described in detail below. In the following formula, Q, R ¹ , R ² and L ² are as described above, and X represents a halogen atom.

(1) The first step can be carried out according to the method [3].

(2) The second step can be performed in the presence of a halosulfonylating agent. The halosulfonylating agent can be appropriately selected from halosulfonic acid compounds such as chlorosulfonic acid and bromosulfonic acid. The halosulfonylating agent can be used in an amount of 1 to 100 times mol, desirably 1 to 10 times mol, of the compound of formula (VIII).
This reaction can be carried out in the presence of a solvent, if desired. 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; halogens such as chloroform, dichloromethane, dichloroethane, etc. Alkanes; aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; organic acids such as acetic acid and propionic acid; Can be appropriately selected.
The reaction temperature is usually −10 ° C. to 200 ° C., desirably 10 ° C. to 150 ° C.
The reaction time is usually about 0.5 to 48 hours, preferably 1 to 24 hours.

(3) The third step can be performed by reacting in acetic acid in the presence of a reducing agent. As a reducing agent, 1 type (s) or 2 or more types can be suitably selected from phosphorus compounds, such as red phosphorus and a triphenylphosphine; Halogen compounds, such as potassium iodide and an iodine, etc., for example. A reducing agent is 1-100 times mole with respect to the compound of Formula (IX), Preferably 1-10 times mole can be used.
The reaction temperature is usually 0 ° C to 200 ° C, preferably 0 ° C to 150 ° C.
The reaction time is usually about 1 to 48 hours, preferably 1 to 24 hours.

(4) The fourth step can be performed by reacting in a solvent in the presence of water and a base.
Examples of the base include those similar to the above production method [1]. A base is 1-10 times mole with respect to the compound of Formula (X), Preferably 1-5 times mole can be used.
Examples of the solvent include those similar to the above production method [1].
The reaction temperature is usually −20 ° C. to 150 ° C., desirably 0 ° C. to 100 ° C.
The reaction time is usually about 1 to 48 hours, preferably 1 to 24 hours.
[Intermediate production method 2]
The compound of the formula (V) which is the starting material of the production method [3] can be produced, for example, by a reaction consisting of the following (1) to (5).
(1) A first step of acetylating a compound of formula (VII) to obtain a compound of formula (XI);
(2) a second step of halosulfonylating the compound of formula (XI) to give a compound of formula (XII);
(3) a third stage in which the compound of formula (XII) is reduced to obtain a compound of formula (XIII);
(4) a fourth stage in which the compound of formula (XIII) is hydrolyzed to obtain the compound of formula (XIV);
(5) Fifth step of reacting a compound of formula (XIV) with a compound of formula (IV) to obtain a compound of formula (V) Here, the compound of formula (XIV) may exist as a disulfide form. is there.
(1) to (5) will be described in detail below. In the following formula, R ¹ , R ² , L ¹ and X are as described above.

(1) The first step can be carried out by reacting the compound of formula (VII) usually in a solvent in the presence of acetic anhydride and a base.
Examples of the base include those similar to the above production method [1]. A base is 1-10 times mole with respect to the compound of Formula (VII), 1-5 times mole can be used desirably.
Examples of the solvent include those similar to the above production method [1].
The reaction temperature is usually −20 ° C. to 150 ° C., desirably 0 ° C. to 100 ° C.
The reaction time is usually about 1 to 48 hours, preferably 1 to 24 hours.

(2) to (4) The second step, the third step, and the fourth step can be performed according to the method of [Intermediate Production Method 1].

(5) The fifth step can be performed according to the method of the above production method [1].

  The desirable aspect of the pest control agent containing this invention compound is described below. The pest control agent containing the compound of the present invention is, for example, a pest, mite, nematode or soil pest that is a problem in the field of agriculture and horticulture, that is, an agricultural and horticultural insecticide, acaricide, nematicide or insecticide. Useful as a soil pesticide.

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 agricultural and horticultural insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. is there. 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. In addition, agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides containing the compounds of the present invention are various resistances against drugs such as organophosphorus agents, carbamate agents, synthetic pyrethroid agents, neonicotinoid agents, etc. It is also effective for controlling pests. Furthermore, since the compound of the present invention has an excellent osmotic transfer property, the agricultural or horticultural insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention is treated on the soil. By this, it is possible to control pests in the foliage at the same time as the control of soil harmful insects, mites, nematodes, gastropods, and isopods.

  As another desirable embodiment of the insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention, the above plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods And agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides that comprehensively control soil pests and the like.

  Agricultural and horticultural insecticides, acaricides, nematicides or soil pesticides containing the compounds of the present invention are usually prepared by mixing the compound with various agricultural adjuvants, powders, granules, granulated water Although it is formulated and used in various forms such as a powder, a wettable powder, an aqueous suspension, an oily suspension, a granular aqueous solvent, an aqueous solvent, an emulsion, a liquid, a paste, an aerosol, As long as it meets the object of the present invention, it can be made into any pharmaceutical form usually 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.

  Application of agricultural and horticultural insecticides, acaricides, nematicides or soil pesticides containing the compound of the present invention is different in weather conditions, formulation form, application time, application location, types of pests and occurrences, etc. However, it is generally carried out at an active ingredient concentration of 0.05 to 800,000 ppm, preferably 0.5 to 500,000 ppm, and the application amount per unit area is 0.05 to 50,000 g of the present compound per hectare, preferably 1 ~ 30,000g. 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 agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides containing the compounds of the present invention, or dilutions thereof, is generally 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.

  In addition, agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides containing the compounds of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners, etc. In some cases, even better effects and functions 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 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, 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;
Strobilurin-based compounds such as fluacrypyrin;
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, cyanolaniliprole, cyenopyrafen, cyenopyrafen, pyriflutinazone , Amidoflumet, sulfluramid, hydramethylnon, metaldehyde, HGW-86, ryanodine, verbutin, AKD-1022, chlorobenzoate, thia Thiazolylcinnanonitrile, sulfoxaflor, fluensulfone, 3-bromo-N- (2-bromo-4-chloro-6- (1-cyclopropylethylcarbamoyl) Enyl) -1- (3-chloropyridin-2-yl) -1H-pyrazole-5-carboxamide, 3-bromo-N- (4-chloro-2- (1-cyclopropylethylcarbamoyl) -6-methylphenyl ) -1- (3-Chloropyridin-2-yl) -1H-pyrazole-5-carboxamide, 3-bromo-N- (2-bromo-4-chloro-6- (cyclopropylmethylcarbamoyl) phenyl) -1 -(3-Chloropyridin-2-yl) -1H-pyrazole-5-carboxamide, 3-bromo-N- (4-chloro-2-methyl-6- (methylcarbamoyl) phenyl) -1- (3-chloro Pyridin-2-yl) -1H-pyrazole-5-carboxamide, 3-bromo-1- (3-chloropyridin-2-yl) -N- (4-cyano-2-methyl- And a compound such as 6- (methylcarbamoyl) phenyl) -1H-pyrazole-5-carboxamide; Further, Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis, 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, combined use Rukoto can also.

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 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, and sodium metam Metam-sodium, nicobifen, metrafenone, UBF-307, diclocymet, proquinazid, amisulbrom (aka amibromdole), 3- (2,3,4 -Trimethoxy-6-methylbenzoyl) -5-chloro-2-methoxy-4-methylpyridine, 4- (2,3,4-trimethoxy-6-methylbenzoyl) -2,5-dichloro-3-trifluoromethyl Pyridine, pyriofenone, mandipropamid, fluopico Fluopicolide, carpropamid, meptyldinocap, N-[(3 ', 4'-dichloro-1,1-dimethyl) phenacyl] -3-trifluoromethyl-2-pyridinecarboxamide, N-[(3 ', 4'-dichloro-1,1-dimethyl) phenacyl] -3-methyl-2-thiophenecarboxamide, N-[(3', 4'-dichloro-1,1-dimethyl) phenacyl] -1-methyl-3-trifluoromethyl-4-pyrazolecarboxamide, N-[[2'-methyl-4 '-(2-propyloxy) -1,1-dimethyl] phenacyl] -3-trifluoromethyl- 2-pyridinecarboxamide, N-[[2'-methyl-4 '-(2-propyloxy) -1,1-dimethyl] phenacyl] -3-methyl-2-thiophenecarboxamide, N-[[2'-methyl -4 '-(2-propyloxy) -1,1-dimethyl] phenacyl] -1-methyl-3-trifluoromethyl-4-pyrazolecarboxamide, N-[[4'-(2-propyloxy) -1 , 1-dimethyl] fe Nacyl] -3-trifluoromethyl-2-pyridinecarboxamide, N-[[4 '-(2-propyloxy) -1,1-dimethyl] phenacyl] -3-methyl-2-thiophenecarboxamide, N-[[ 4 '-(2-propyloxy) -1,1-dimethyl] phenacyl] -1-methyl-3-trifluoromethyl-4-pyrazolecarboxamide, N-[[2'-methyl-4'-(2-pentyl) Oxy) -1,1-dimethyl] phenacyl] -3-trifluoromethyl-2-pyridinecarboxamide, N-[[4 '-(2-pentyloxy) -1,1-dimethyl] phenacyl] -3-trifluoro Examples thereof include methyl-2-pyridinecarboxamide, spiroxamine, S-2188 (fenpyrazamine), S-2200, ZF-9646, BCF-051, BCM-061, and BCM-062.

  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, 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
3-chloro-2- (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) thio) phenoxy) -5- (trifluoromethyl) pyridine (Compound No. 1-311) (1) A mixture of 2.50 g of 2-fluoro-4-methylphenol, 4.50 g of 2,3-dichloro-5- (trifluoromethyl) pyridine, 5.46 g of potassium carbonate, and 8 mL of N, N-dimethylformamide Was heated at 80 ° C. for 30 minutes. 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 6.44 g of oily 3-chloro-2- (2-fluoro-4-methylphenoxy) -5- (trifluoromethyl) pyridine.
(2) 10.6 mL of chlorosulfonic acid was added dropwise to 6.44 g of 3-chloro-2- (2-fluoro-4-methylphenoxy) -5- (trifluoromethyl) pyridine obtained in (1) above. The reaction was carried out at 1 ° C. for 1 hour. After allowing to cool, the mixture was poured into ice water and 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 give 5-((3-chloro-5- (trifluoromethyl) pyridin-2-yl) oxy) -4-fluoro-2-methylbenzene-1-sulfonyl chloride. .
(3) To the total amount of 5-((3-chloro-5- (trifluoromethyl) pyridin-2-yl) oxy) -4-fluoro-2-methylbenzene-1-sulfonyl chloride obtained in (2) above, Acetic acid 25mL, red phosphorus 1.5g and iodine 0.5g were added, and it heated and refluxed for 1 hour. After cooling to room temperature, the solid was filtered off and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and brine, and dried over anhydrous sodium sulfate. 5. Evaporate the solvent under reduced pressure to give oily S- (5-((3-chloro-5- (trifluoromethyl) pyridin-2-yl) oxy) -4-fluoro-2-methylphenyl) ethanethioate. 69 g was obtained.
(4) S- (5-((3-chloro-5- (trifluoromethyl) pyridin-2-yl) oxy) -4-fluoro-2-methylphenyl) ethanethioate obtained in (3) 6.69 g And 20 mL of tetrahydrofuran were added to 100 mL of 1N aqueous sodium hydroxide solution. After reacting for 14 hours at room temperature, the mixture was acidified with concentrated hydrochloric acid little by little, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 5.53 g of oily 5-((3-chloro-5- (trifluoromethyl) pyridin-2-yl) oxy) -4-fluoro-2-methylbenzenethiol. .
(5) 5-((3-chloro-5- (trifluoromethyl) pyridin-2-yl) oxy) -4-fluoro-2-methylbenzenethiol 1.98 g, potassium carbonate 1.62 g and Rongalite 0.91 g A solution of 1.86 g of 1,1,1-trifluoro-2-iodoethane in 1 mL of N, N-dimethylformamide was added dropwise to a mixture of 19 mL of N, N-dimethylformamide and allowed to react at room temperature for 3 hours. After adding water to the reaction solution and extracting with heptane, the organic layer was washed with water and brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 2.25 g of oily target product.

Synthesis example 2
3-chloro-2- (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) sulfinyl) phenoxy) -5- (trifluoromethyl) pyridine (Compound No. 1-312) Synthesis of 3-chloro-2- (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) thio) phenoxy) -5- (trifluoromethyl) pyridine and 20 mL of chloroform The mixed solution was cooled with ice water. To this solution, 1.17 g of m-chloroperbenzoic acid was added little by little and allowed to react for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with 1N aqueous sodium hydroxide solution, 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 = 80/20 / volume ratio) to obtain 1.94 g of the desired product (melting point: 90-91 ° C.). Got.

Synthesis example 3
Synthesis of 2- (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) thio) phenoxy) -5-nitropyridine (Compound No. 1-77) (1) 2-Fluoro To a mixed solution of 1.70 g of -4-methylphenol and 3.3 mL of pyridine, 1.4 mL of acetic anhydride was added and reacted at 75 ° C. for 2.5 hours. After the reaction, the solvent was distilled off under reduced pressure and added to water. After extraction with ethyl acetate, the organic layer was washed with 2N hydrochloric acid, water and brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 2.36 g of oily 2-fluoro-4-methylphenyl acetate.
(2) 4.5 mL of chlorosulfonic acid was added dropwise to 2.30 g of 2-fluoro-4-methylphenylacetate and reacted at 75 ° C. for 1.5 hours. After allowing to cool, the mixture was poured into ice water and 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 5- (chlorosulfonyl) -2-fluoro-4-methylphenyl acetate.
(3) To the total amount of 5- (chlorosulfonyl) -2-fluoro-4-methylphenylacetate obtained in (2) above, 14 mL of acetic acid, 0.47 g of red phosphorus and 0.05 g of iodine were added and heated under reflux for 3 hours. did. After cooling to room temperature, the solid was filtered off and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 1.60 g of oily 5- (acetylthio) -2-fluoro-4-methylphenyl acetate.
(4) Mix 1.60 g of 5- (acetylthio) -2-fluoro-4-methylphenylacetate obtained in (3) above and 10 mL of water, add 3.5 g of potassium hydroxide and react at 80 ° C. for 8 hours. I let you. The mixture was neutralized with 2N hydrochloric acid and 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 0.79 g of oily 2-fluoro-5-mercapto-4-methylphenol.
(5) To the mixture of 0.79 g of 2-fluoro-5-mercapto-4-methylphenol obtained in (4), 2.06 g of potassium carbonate, 0.54 g of Rongalite, and 25 mL of N, N-dimethylformamide, , 1-trifluoro-2-iodoethane (1.73 g) was added dropwise 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, and the residue was purified by silica gel column chromatography (eluent: n-heptane / ethyl acetate = 90/10, volume ratio) to give oily 2-fluoro-4-methyl-5- 0.7 g of ((2,2,2-trifluoroethyl) thio) phenol was obtained.
(6) 2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) thio) phenol 0.24 g, potassium carbonate 0.28 g and 2-chloro-5-nitropyridine 0.17 g A mixture of 3 mL of N, N-dimethylformamide was reacted at 80 ° C. for 1.5 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 = 80/20 / volume ratio) to obtain 0.13 g of the desired product (melting point: 47-49 ° C.). Got.

Synthesis example 4
Synthesis of (4-fluoro-2-methyl-5- (4-nitrophenoxy) phenyl) (2,2,2-trifluoroethyl) sulfane (Compound No. 4-61) 2-Fluoro-4-methyl-5 A mixture of 0.40 g of ((2,2,2-trifluoroethyl) thio) phenol, 0.46 g of potassium carbonate, 0.12 g of 1-fluoro-4-nitrobenzene and 3 mL of N, N-dimethylformamide at 60 ° C. The reaction was allowed for 1.5 hours. After allowing to cool to room temperature, 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 = 90/10 · volume ratio) to obtain 0.10 g of an oily target product.

Synthesis example 5
Synthesis of 1-fluoro-5-methyl-2- (4-nitrophenoxy) -4-((2,2,2-trifluoroethyl) sulfinyl) benzene (Compound No. 4-62) (4-fluoro-2 To a mixed solution of 0.052 g of -methyl-5- (4-nitrophenoxy) phenyl) (2,2,2-trifluoroethyl) sulfane and 4 mL of ethyl acetate, 0.036 g of m-chloroperbenzoic acid was added, and 1 Reacted for hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, water and brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.046 g of the desired product (melting point: 80-85 ° C.).

Synthesis Example 6
Synthesis of 5-bromo-2- (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) thio) phenoxy) pyrimidine (Compound No. 5-13) 2-Fluoro-4- 0.17 g of potassium carbonate was added to a mixed solution of 0.14 g of methyl-5-((2,2,2-trifluoroethyl) thio) phenol and 1 mL of N, N-dimethylformamide, and the mixture was stirred for 30 minutes. Thereafter, 5-bromo-2-chloropyrimidine was added and allowed to react for 21 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 = 10/1, volume ratio) to obtain 0.22 g of the desired product (melting point: 47-49 ° C.). Got.

Synthesis example 7
Synthesis of 5-bromo-2- (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) sulfinyl) phenoxy) pyrimidine (Compound No. 5-14) Add 0.035 g of m-chloroperbenzoic acid to a mixed solution of 0.056 g of (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) thio) phenoxy) pyrimidine and 2 mL of ethyl acetate. The reaction was continued for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, water and brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.078 g of the desired product (melting point 94-97 ° C.).

Representative examples of the compound of the formula (I) are shown in Tables 1 to 6, and typical examples of the compound of the formula (V) are shown in Table 7. These compounds can be produced based on the above-mentioned synthesis examples or various methods for producing the above-described compounds of the present invention. In Tables 1-7, no. Compound No. Where Me is methyl, Et is ethyl, n-Pr is normal propyl, i-Pr is isopropyl, n-Bu is normal butyl, i-Bu is isobutyl, s-Bu is secondary butyl, t-Bu represents tertiary butyl, and a compound represented by “-” in the R ⁴ column represents that R ⁴ is not substituted. For example, a compound described as “4-F” This means that only the substitution position given to the chemical structural formula in the table is substituted with R ⁴ , that is, only the 4-position is substituted with a fluorine atom. Numerical values shown as physical properties are melting points (° C.). Further, for some of the compounds of the formula (I) and the formula (V), ¹ H-NMR data [measured by ¹ H-nuclear magnetic resonance spectroscopy. δ is a chemical shift value] is shown in Table 8.

Next, test examples are described.
Test Example 1 Spider mite killing insect test A chemical solution was prepared so that the concentration of the compound of the present invention was 50 ppm. Only one kidney bean primary leaf was left and transplanted to a pot (diameter 8 cm, height 7 cm), to which about 20 adult spider mite were released. This was soaked in green beans with green beans for about 5 seconds, air-dried, and left in a constant temperature room at 25 ° C. with illumination. Life or death was determined after 2 or 3 days of treatment, and the killing rate was determined by the following formula. The detached adults and abnormal insects were regarded as dead.
Compound No. 1 1-1, 1-2, 1-13, 1-14, 1-17, 1-18, 1-21, 1-22, 1-43, 1-45, 1-46, 1-47, 1- 48, 1-49, 1-69, 1-70, 1-73, 1-77, 1-78, 1-81, 1-82, 1-255, 1-256, 1-261, 1-262, 1-303, 1-304, 1-311, 1-312, 1-313, 1-314, 1-318, 1-357, 1-358, 1-369, 1-371, 1-383, 1- 384, 1-385, 1-386, 1-399, 1-400, 1-401, 1-402, 1-433, 1-443, 1-443, 1-444, 1-449, 1-450, 1-454, 1-455, 1-456, 1-457, 1-459, 1-460, 1-465, 1-466, 1-479, 2- 7, 2-28, 3-1, 3-2, 4-35, 4-36, 4-37, 4-38, 4-55, 4-56, 4-57, 4-61, 4-62, 4-149, 4-150, 4-151, 4-161, 4-162, 4-163, 4-175, 4-185, 4-186, 4-187, 4-207, 4-208, 4- 259, 4-260, 4-283, 4-284, 4-291, 4-373, 4-374, 5-1, 5-2, 5-9, 5-10, 5-13, 5-14, When 5-23, 5-24, 5-143, 6-9, and 6-10 were tested, all of these compounds exhibited an insecticidal rate of 90% or more.
Morbidity rate (%) = (number of dead ticks / number of treated ticks) × 100

Test Example 2 Effect test on green planthopper Rice seedlings were immersed for about 10 seconds in a chemical solution adjusted so that the concentration of the compound of the present invention was 200 ppm. After the chemical solution was air-dried, the root was wrapped with wet absorbent cotton and placed in a test tube. To this, about 20 larvae of 2-3 years old were released, and the tube mouth was covered with gauze and left in a constant temperature room at 25 ° C. Five days after the insect release, the dead planthopper was judged to be alive or dead, and the mortality rate was determined by the following formula. Compound No. 1 1-1, 1-2, 1-13, 1-17, 1-21, 1-45, 1-46, 1-47, 1-48, 1-69, 1-70, 1-77, 1- 255, 1-304, 1-311, 1-312, 1-313, 1-314, 1-371, 1-383, 1-384, 1-385, 1-343, 1-434, 1-443, 1-447, 1-449, 1-455, 1-457, 1-459, 1-465, 1-479, 3-1, 3-2, 4-36, 4-37, 4-55, 4- When 149, 4-291, 5-9, 5-13, and 5-23 were tested, all of these compounds showed a death rate of 90% or more.
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 are 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 (9)

Formula (I):

[In the formula (I), R ¹ and R ² are each a hydrogen atom, a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy or cyano; R ³ is alkyl or haloalkyl; n is an integer of 0 or 1 in it; Q is at has been or 4-pyrimidinyl substituted with may also be 2-pyrimidinyl, or R ⁴ that is substituted with a phenyl, R ⁴ may be substituted by pyridyl, R ⁴ be substituted with R ⁴ R ⁴ is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano, nitro, COR ⁵ , CO ₂ R ⁵ , N (R ⁶ ) COR ⁵ , N (R ⁶ ) CO ₂ R ⁵ , NR ⁷ R ^8; , CONR ⁷ R ^8, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, or haloalkylsulfenyl Is nil, when R ⁴ have two or more, they may be different even in the ^{same; R 5, R 6, R} 7 and R ⁸ each is a hydrogen atom, alkyl or haloalkyl When R ⁷ and R ⁸ are alkyl or haloalkyl, they may form a 5- to 6-membered ring with adjacent nitrogen atoms; provided that Q is phenyl optionally substituted with R ⁴ and R ³ is when it is alkyl, R ¹ is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy or cyano; provided, Q may be substituted with may be 2-pyrimidinyl, or R ⁴ that is substituted with R ⁴ 4- In the case of pyrimidinyl, a compound represented by the above or a salt thereof, except that R ¹ is a hydrogen atom, R ² is a hydrogen atom or alkyl, and R ³ is alkyl. Formula (V):

[In the formula (V), R ¹ is a halogen atom or alkyl; R ² is a halogen atom or alkyl; R ³ is trifluoroethyl] or a salt thereof. The compound or a salt thereof according to claim 2, wherein R ¹ is a fluorine atom, a chlorine atom or an alkyl, R ² is a chlorine atom or methyl, and R ³ is trifluoroethyl.   A pest control agent comprising the compound of claim 1 or a salt thereof as an active ingredient.   An insecticide, acaricide, nematicide or soil insecticide containing the compound of claim 1 or a salt thereof as an active ingredient.   An insecticide or acaricide containing the compound of claim 1 or a salt thereof as an active ingredient.   A method for controlling pests by applying an effective amount of the compound of claim 1 or a salt thereof.   A method for controlling pests, mites, nematodes or soil pests by applying an effective amount of the compound of claim 1 or a salt thereof.   A method for controlling pests or ticks by applying an effective amount of the compound of claim 1 or a salt thereof.