TW201311149A - Pesticide - Google Patents

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Publication number
TW201311149A
TW201311149A TW101120496A TW101120496A TW201311149A TW 201311149 A TW201311149 A TW 201311149A TW 101120496 A TW101120496 A TW 101120496A TW 101120496 A TW101120496 A TW 101120496A TW 201311149 A TW201311149 A TW 201311149A
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Taiwan
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compound
atom
group
salt
alkyl
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TW101120496A
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Chinese (zh)
Inventor
Kenichi Nakamoto
Masakazu Serizawa
Yuko Nishihama
Tatsuya Kani
Tatsuya Shimada
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Ishihara Sangyo Kaisha
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Priority to JP2011140463 priority Critical
Application filed by Ishihara Sangyo Kaisha filed Critical Ishihara Sangyo Kaisha
Publication of TW201311149A publication Critical patent/TW201311149A/en

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    • C07ORGANIC CHEMISTRY
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    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/01Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
    • C07C323/09Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
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Abstract

The subject of the present invention is to provide novel pest control agents. The solution of the present invention is to provide the formula (I): □ [wherein R1 and R2 are each a hydrogen atom, a halogen atom, an alkyl group, an alkyl halide, an alkoxy group, a halogenated alkoxy group or a cyano group, and the R3 system An alkyl group or a halogenated alkyl group; n is an integer of 0 or 1; Q is a compound represented by the general formula [Q-1] to [Q-6] (refer to the specification) or a salt thereof, which contains these as an active ingredient. Pest control agent.

Description

Pest control agent

The present invention relates to a novel compound of the formula (I) or a salt thereof, that is, a pest control agent containing 3-arylphenyl sulfide as an active ingredient, which will be described later.

Patent Document 1 describes a 3-arylphenyl sulfide derivative which is suitable for use as an insecticidal or acaricidal agent, but does not describe a compound of the formula (I) or a salt thereof.

Further, Patent Document 2 describes a (3-sulfo-substituted phenyl) hexaaryl derivative which is preferably used as an insecticide or an acaricide, but does not describe a compound of the formula (I) or a salt thereof.

Prior technical literature Patent literature

[Patent Document 1] International Publication WO 99/55668

[Patent Document 2] JP-A-2008-308448

Although many pest control agents have been used for many years, the effectiveness is not sufficient, pests and the like are resistant, and various problems such as restrictions on use thereof are numerous. Therefore, it is desirable to develop novel pest control agents with few disadvantages.

The present inventors conducted various reviews on 3-arylphenyl sulfide derivatives in order to find a better pest control agent. As a result, it has been found that the novel compound of the formula (I) or a salt thereof described later has an extremely high control effect against harmful organisms in a low dose, and also has safety against crops or mammals, and the present invention has been completed.

That is, the present invention is the following formulas (1) to (16).

(1) with formula (I): Wherein R 1 and R 2 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkyl halide, an alkoxy group, a halogenated alkoxy group or a cyano group; an R 3 -based alkyl group or a halogenated alkyl group; Or an integer of 1; Q is the following general formula [Q-1]~[Q-6]: Any one of them; A 1 ~ A 8 series can be the same or different, CH or nitrogen atom, when A 1 ~ A 8 is CH, A 1 ~ A 8 can be replaced by R 4 , A 1 ~ A 8 The number of nitrogen atoms may be 0 to 3; the B 1 to B 4 systems may be the same or different, and the CH or nitrogen atom, when B 1 to B 4 are CH, the B 1 to B 4 systems may be replaced by R 4 respectively. , B 1 ~ B 4 may be 0 to 1 nitrogen atoms; B 5 ~ B 7 systems may be the same or different, C (R 5 ) (R 6 ), oxygen atom, sulfur atom, SO or SO 2 ; E 1 ~ E 4 are CH or nitrogen atoms, and when E 1 ~ E 4 are CH, E 1 ~ E 4 can be substituted by R 4 respectively, and E 1 ~ E 4 can be 0 ~1; E 5 ~E 8 series may be the same or different, C(R 5 )(R 6 ), oxygen atom, sulfur atom, SO or SO 2 ; G 1 ~G 5 and G 7 systems may be respectively the same Or different, CH or nitrogen atom, G 1 ~ G 5 and G 7 are CH, G 1 ~ G 5 and G 7 can be substituted by R 4 respectively, G 1 ~ G 5 and G 7 can be nitrogen atoms The number is 0~3; G 6 is an oxygen atom or a sulfur atom; J 1 ~ J 6 series can be the same or different, CH or nitrogen atom, when J 1 ~ J 6 is CH, J 1 ~ J 6 can be Respectively substituted with R 4 , J 1 ~ J 6 can be 0 to 2 nitrogen atoms; L 1 ~ L 5 series can be the same or different, CH or nitrogen atom, L 1 ~ L 5 is CH, L 1 ~ L 5 can be substituted by R 4 respectively, L 1 ~ L 5 can be the number of nitrogen atoms 0 to 2; L 6 is an oxygen atom or a sulfur atom; R 4 is a halogen atom, an alkyl group, an alkyl halide, an alkoxy group, a halogenated alkoxy group, a cyano group, a nitro group, a COR 7 , a CO 2 R 7 , N(R 8 )COR 7 , N(R 8 )CO 2 R 7 , NR 9 R 10 , CONR 9 R 10 , alkylthio, halogenated alkylthio, alkylsulfinyl, halogenated alkylsulfin when acyl, alkylsulfonyl group, a halogenated alkylsulfonyl group, may also be substituted with the R 11 substituted phenyl or pyridyl group of R 11, R 4 is the number of two or more, R 4 may be the same or different; R line. 5 and R 6 are each a hydrogen atom, a halogen atom, an alkyl group or a halogenated alkyl group, R 5 and R 6 in any one or both of when two or more, R 5 and R 6 may be the same Or different; R 7 , R 8 , R 9 and R 10 are each a hydrogen atom or an alkyl group; when R 9 and R 10 are alkyl groups, R 9 and R 10 and the bonded nitrogen atom may form 5 together. a compound represented by a ~6 member ring; R 11 is a halogen atom, an alkyl group, an alkyl halide group, an alkoxy group or a halogenated alkoxy group; or a salt thereof.

(2) The compound according to the above (1) or a salt thereof, wherein Q is any one of the above general formulas [Q-1] to [Q-5].

(3) The compound according to the above (1) or a salt thereof, wherein Q is the above general formula [Q-1], [Q-2] or [Q-4].

(4) The compound according to the above (1), wherein R 1 is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; R 2 is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; and R 3 is a salt; An alkyl group or a halogenated alkyl group; Q is a general formula [Q-1], [Q-2] or [Q-4].

(5) The compound according to the above (1) or a salt thereof, wherein Q is the above general formula [Q-1] or [Q-2].

(6) The compound according to the above (1), wherein R 1 is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; R 2 is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; and R 3 is a salt; An alkyl group or a halogenated alkyl group; Q is a general formula [Q-1] or [Q-2].

(7) Formula (II): [wherein, X is a bromine atom, -B(OH) 2 or a pentacolato boranyl; n is an integer of 0 or 1; and R 1 and R 2 are a hydrogen atom, a halogen atom, an alkyl group, an alkyl halide; Alkyl, alkoxy, halogenated alkoxy or cyano; R 3 alkyl or halogenated alkyl, however, R 1 is a hydrogen atom or a fluorine atom; R 2 is a methyl group; R 3 is a trifluoroethyl group; The compound represented.

(8) A compound according to the above (7), wherein R 1 is a fluorine atom, a chlorine atom or a methyl group; and R 2 is a chlorine atom or a methyl group.

(9) A compound according to the above (7), wherein R 1 is a chlorine atom; and R 2 is a chlorine atom or a methyl group.

(10) A compound according to the above (7), (8) or (9), wherein n is 0; R 3 is a trifluoroethyl group, a trifluoropropyl group, a difluoroethyl group or a n-propyl group.

(11) A pest control agent containing the compound of the above (1) or a salt thereof as an active ingredient.

(12) An insecticide, an acaricide, a nematicide or a soil-killing insecticide containing the compound of the above (1) or a salt thereof as an active ingredient.

(13) An insecticide or acaricide containing the compound of the above (1) or a salt thereof as an active ingredient.

(14) A method of controlling an effective organism by administering an effective amount of the compound of the above (1) or a salt thereof.

(15) A method of controlling pests, dust mites, nematodes or soil pests by administering an effective amount of the compound of the above (1) or a salt thereof.

(16) administering an effective amount of the compound of the above (1) or A method of controlling pests or dust mites.

The pest control agent having the compound of the above formula (I) or a salt thereof as an active ingredient has both a high drug control effect on pests and a safety against crops or mammals.

The best form for implementing the invention

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

The alkyl group or the alkyl moiety in the formula (I) may be either a straight chain or a branched chain, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group. Isobutyl, sec-butyl, tert-butyl, pentyl, hexyl C 1-6 and the like.

The pyridyl group which may be substituted with R 11 in the formula (I) may, for example, be a 2-pyridyl group, a 3-pyridyl group or a 4-pyridyl group. When the pyridyl group is substituted by R 11 , the number of substitutions is from 1 to 4. Further, when substituted for most of R 11 , R 11 may be the same or different.

When the phenyl group in the formula (I) is substituted by R 11 , the number of substitutions is from 1 to 5. Further, when substituted for most of R 11 , R 11 may be the same or different.

The salt of the compound of the above formula (I) is as long as it is permissible in the technical field, and includes, for example, a dimethylammonium salt or a triethylammonium salt. An ammonium salt of a salt; an inorganic acid salt such as a hydrochloride, a perchlorate, a sulfate or a nitrate; an organic salt such as an acetate or a methanesulfonate.

When the compound of the above formula (I) is present as an isomer of an optical isomer, in the present invention, both the isomer and the mixture of the isomers are contained. In the specification of the present application, the isomers are described in terms of a mixture unless otherwise specified. Further, the present invention is within the technical knowledge of the technical field and includes various isomers other than the above. Further, depending on the type of the isomer, there may be a chemical structure different from the above formula (I), but as long as it is the manufacturer, it is possible to fully recognize the relationship of these isomers, so it is clearly within the scope of the present invention. Inside.

The compound of the above formula (I) or a salt thereof (hereinafter referred to as the compound of the present invention) and the raw material compound thereof can be produced according to the following production methods [1] to [2] and the usual salt production method, but are not limited to these methods. By. Further, the above formula (II) of the production intermediate of the compound of the formula (I) or a salt thereof is constituted by the formula (II-a) or the formula (II-b).

System of law [1]

In the method [1], Q, R 1 , R 2 , R 3 and n are as described above. X' is -B(OH) 2 or pinacolato boranyl, and X" means a bromine atom.

The route A of the process [1] can be carried out by reacting a compound of the formula (III) with a compound of the formula (II-a) in the presence of a base and a transition metal catalyst in a solvent.

The route B of the process [1] can be carried out by reacting a compound of the formula (IV) with a compound of the formula (II-b) in the presence of a base and a transition metal catalyst in a solvent.

The compounds of the formula (II-a) and the formula (II-b) contain novel compounds which can be produced by the method described in WO2007/034755.

The compound of the formula (IV) can be produced by reacting a corresponding magnesium reagent or lithium reagent with trimethyl borate.

The transition metal catalyst can be suitably selected, for example, from palladium-activated carbon, palladium acetate, dichlorobis(triphenylphosphinepalladium), tetrakis(triphenylphosphine)palladium, tris(diphenylmethyleneacetone)palladium or the like. Palladium compounds; bis(triphenylphosphine) A nickel compound such as nickel chloride or tetrakis(triphenylphosphine)nickel. The transition metal catalyst is preferably used in an amount of from 0.001 to 1 mol, and preferably from 0.01 to 0.1 mol, based on the compound of the formula (III) or the formula (II-b).

The base may be, for example, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; an alkaline earth metal hydroxide such as calcium hydroxide or magnesium hydroxide; or an alkali metal carbonate such as sodium carbonate or potassium carbonate. Alkali metal bicarbonate such as sodium hydrogencarbonate or potassium hydrogencarbonate; alkali metal acetates such as sodium acetate or potassium acetate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxide and sodium ethoxide; Alcohol metal salts such as potassium t-butoxide; triethylamine, N,N-dimethylaniline, pyridine, 4-N,N-dimethylaminopyridine, 1,8-diazobispiro An organic base such as a ring [5.4.0]-7-undecene; or the like, one or two kinds are appropriately selected. The base system is preferably used in an amount of from 1 to 5 moles per mole of the compound of the formula (III) or the formula (II-b), and is preferably from 1.5 to 3 moles.

The solvent is any solvent which is inert to the reaction, and may be, for example, an ether such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1,4-dioxane or dimethoxyethane; benzene or toluene; Aromatic hydrocarbons such as xylene, chlorobenzene, etc.; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylhydrazine, ring Aprotic polar solvents such as butyl phthalocyanine; nitriles such as acetonitrile and propionitrile; esters of ethyl acetate and ethyl propionate; fats such as pentane, hexane, heptane, octane and cyclohexane a hydrocarbon; a protic solvent such as water, methanol or ethanol; and the like, one or two kinds are appropriately selected.

The reaction temperature is usually -50 to 200 ° C, preferably 20 to 150 ° C.

The reaction time is usually from 0.5 to 48 hours, preferably from 1 to 24 hours.

System of law [2]

In the method [2], Q, R 1 , R 2 and R 3 are as described above.

This reaction can be carried out by reacting a compound of the formula (I-a) in the presence of an oxidizing agent in a solvent.

The oxidizing agent may be appropriately selected, for example, from hydrogen peroxide water, m-chloroperbenzoic acid, perbenzoic acid, sodium periodate, OXONE (trade name of EI du Pont; potassium hydrogen persulfate), N-chlorobutane Yttrium imine, N-bromosuccinimide, t-butyl hypochlorite, sodium hypochlorite, and the like. The oxidizing agent may be used in an amount of from 1 to 5 times the molar amount of the compound of the formula (I-a), and is preferably from 1 to 2 times the molar amount.

This reaction can be carried out in the presence of a catalyst as needed. As the catalyst, for example, sodium tungstate, flavin, or the like can be selected. The catalyst system may be used in an amount of 0.0001 to 1 mol, and preferably 0.001 to 0.05 mol, based on the compound of the formula (I-a).

The solvent may be any solvent which is inert to the reaction, and may be, for example, a halogenated alkane such as chloroform, dichloromethane or dichloroethane; or an aromatic hydrocarbon such as chlorobenzene or dichlorobenzene; An ester such as ethyl ester or ethyl propionate; or acetic acid or the like, one or two kinds are appropriately selected.

The reaction temperature is usually -50 to 150 ° C, preferably 0 to 50 ° C.

The reaction time is usually from 0.5 to 48 hours, preferably from 1 to 30 hours.

[Intermediate Manufacturing 1]

In the compound of the formula (II-b) of the starting material of the method [1], the compound of the formula (II-b-1) can be reacted by, for example, the following (1) to (4). And manufacturing.

(1) Halogenating a compound of the formula (V) to obtain the first stage of the compound of the formula (VI)

(2) Reduction of a compound of formula (VI) to give a second stage of the compound of formula (VII)

(3) Hydrolyzing a compound of the formula (VII) to obtain a third stage of the compound of the formula (VIII) or (IX)

(4) reacting a compound of the formula (VIII) or (IX) with a compound of the formula (X) to give a fourth stage of the compound of the formula (II-b)

The details of (1) to (4) are as follows. In the following formulas, X ", R 1, R 2 and R 3 are as previously described system, W represents a halogen atom based, L represents a halogen atom based, methanesulfonic or toluenesulfonic acyl acyl.

(1) The first stage can be carried out in the presence of a halosulfonating agent. As the halosulfonating agent, a halosulfonic acid compound which is suitably selected from chlorosulfonic acid, bromosulfonic acid or the like Wait. The halosulfonating agent can be used in an amount of from 1 to 100 moles, preferably from 1 to 10 moles, per mole of the compound of the formula (V).

This reaction can be carried out in the presence of a solvent as required. The solvent may be any solvent which is inert to the reaction, and may be, for example, an ether such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1,4-dioxane or dimethoxyethane; chloroform; Halogenated alkanes such as methyl chloride and dichloroethane; aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; An organic acid such as propionic acid; or the like, one or two kinds are appropriately selected.

The reaction temperature is usually -10 ° C to 200 ° C, preferably 10 ° C to 150 ° C.

The reaction time is usually from 0.2 to 48 hours, preferably from 0.5 to 24 hours.

(2) The second stage can be carried out by reacting in acetic acid in the presence of a reducing agent. The reducing agent may be one or two selected from the group consisting of a phosphorus compound such as red phosphorus or triphenylphosphine; a halogen compound such as potassium iodide or iodine; and the like. The reducing agent may be used in an amount of from 1 to 100 moles per mole of the compound of the formula (VI), preferably from 1 to 10 moles.

The reaction temperature is usually from 0 ° C to 200 ° C, preferably from 0 ° C to 150 ° C.

The reaction time is usually from 1 to 48 hours, preferably from 1 to 24 hours.

(3) The third stage can be carried out by reacting in a solvent in the presence of water and a base.

The base may, for example, be the same as the above-mentioned production method [1]. The base system can be used in an amount of from 1 to 10 moles per mole of the compound of the formula (VII), preferably from 1 to 5 moles.

The solvent is, for example, the same as the above-mentioned production method [1].

The reaction temperature is usually -20 ° C ~ 150 ° C, preferably 0 ° C ~ 100 ° C.

The reaction time is usually from 1 to 48 hours, preferably from 1 to 24 hours.

(4) The fourth stage can be carried out by reacting a compound of the formula (VIII) or the formula (IX), usually in the presence of a compound of the formula (X) with a base, in a solvent.

The base may, for example, be the same as the above-mentioned production method [1]. The base system can be used in an amount of from 1 to 10 moles per mole of the compound of the formula (VII), preferably from 1 to 5 moles.

This reaction can be carried out in the presence of a radical initiator, as needed. The radical initiator is appropriately selected from, for example, sulfurous acid, sulfite, sulfite adduct such as Rongalite (trade name of Kanto Chemical Co., sodium formaldehyde sulfoxylate). The radical initiator is preferably used in an amount of from 0 to 5 moles, more preferably from 0.1 to 2 moles, relative to the compound of the formula (VIII).

The solvent is, for example, the same as the above-mentioned production method [1].

The reaction temperature is usually -50 to 200 ° C, preferably 0 to 150 ° C.

The reaction time is usually from 0.5 to 72 hours, preferably from 1 to 48 hours.

[Intermediate Production Method 2]

Among the compounds contained in the formula (II-b) of the starting material of the method [1], the compound of the formula (II-b-2) can be produced, for example, by a reaction described later. In the following formula, X", R 1 , R 2 and R 3 are as defined above.

This reaction can be carried out by reacting a compound of the formula (II-b-1) in the presence of an oxidizing agent in a solvent.

The oxidizing agent may, for example, be the same as the above-mentioned production method [2]. The oxidizing agent may be used in an amount of from 1 to 5 times the molar amount of the compound of the formula (II-b-1), and is preferably from 1 to 2 times the molar amount.

This reaction can be carried out in the presence of a catalyst as needed. As the catalyst, for example, sodium tungstate, flavin, or the like can be selected. The catalyst system may be used in an amount of 0.0001 to 1 mol, and preferably 0.001 to 0.05 mol, relative to the compound of the formula (II-b-1).

The solvent may be any one which is inert to the reaction, and may be a halogenated alkane such as chloroform, dichloromethane or dichloroethane; or an aromatic hydrocarbon such as chlorobenzene or dichlorobenzene; An ester such as ethyl acetate or ethyl propionate; or acetic acid or the like, one or two kinds are appropriately selected.

The reaction temperature is usually -50 to 150 ° C, preferably 0 to 50 ° C.

The reaction time is usually 0.5 to 48 hours, preferably 1 to 30 hours.

[Intermediate Production Method 3]

Among the compounds contained in the formula (II-a) of the starting material of the method [1], the compound of the formula (II-a-1) can be produced, for example, by a reaction described later. In the following formula, X", R 1 , R 2 , R 3 and n are as described above.

The reaction of the compound of the formula (II-b) with a metal reagent can be carried out by reacting with a trialkylborane and finally hydrolyzing it in an acid.

The metal reagent may be one or more selected from the group consisting of magnesium compounds such as magnesium and isopropylmagnesium chloride; and lithium compounds such as lithium chloride and n-butyllithium. The metal reagent is preferably used in an amount of 0.3 to 5 times the molar amount of the compound of the formula (II-b), and is preferably 0.5 to 3 times the molar amount.

As the trialkylborane, one type or two or more types may be appropriately selected from trimethylborane, triethylborane, and triisopropylborane. The trialkylborane is preferably used in an amount of from 0.3 to 5 moles per mole of the compound of the formula (II-b), and is preferably from 0.5 to 2 moles.

As the acid, one type or two or more types may be appropriately selected from acetic acid, hydrochloric acid, sulfuric acid, and the like. The acid system is preferably used in an amount of 0.3 to 5 times the molar amount of the compound of the formula (II-b), and preferably 0.5 to 3 times the molar amount.

The solvent may be, for example, an ether such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1,4-dioxane or dimethoxyethane; or an aromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene; One or two kinds of aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane are appropriately selected.

The reaction is usually carried out under an inert gas atmosphere such as nitrogen or argon.

The reaction temperature is usually -150 ° C to 150 ° C, preferably -100 ° C to 100 ° C.

The reaction time is usually from 0.5 to 48 hours, from 1 to 24 hours. should.

[Intermediate Production Method 4]

Among the compounds contained in the formula (II-a) of the starting material of the method [1], the compound of the formula (II-a-2) can be produced, for example, by a reaction described later. In the following formula, X", R 1 , R 2 , R 3 and n are as described above.

This can be carried out by reacting a compound of the formula (II-b) with a compound of the formula (XI) in the presence of a base and a transition metal catalyst in a solvent.

The transition metal catalyst may, for example, be the same as the above-mentioned production method [1]. The transition metal catalyst is preferably used in an amount of from 0.001 to 1 mol per mol of the compound of the formula (II-b), and preferably from 0.01 to 0.1 mol.

The base may, for example, be the same as the above-mentioned production method [1].

The solvent is, for example, the same as the above-mentioned production method [1].

The reaction is usually carried out under an inert gas atmosphere such as nitrogen or argon.

The reaction temperature is usually -20 ° C ~ 150 ° C, preferably 0 ° C ~ 100 ° C.

The reaction time is usually from 1 to 48 hours, preferably from 1 to 24 hours.

Suitable forms of the pest control agent containing the compound of the present invention are described below. A pest control agent containing the compound of the present invention is suitable for use as a pest, dust mites, nematode or soil which is a problem in agricultural and horticultural fields, for example. A pest control agent, that is, an agricultural and horticultural fungicide, an acaricide, a nematicide or a soil-killing insecticide or an animal parasitic pest or a dust mite control agent, that is, an animal parasitic control agent.

The compound of the invention is suitable for agricultural and horticultural fungicides, acaricides, nematicides or soil-killing insecticides, and is particularly suitable for controlling aphids such as peach red aphids and cotton aphids; such as pink moths and night worms , Spodoptera litura, Codling moth, Cicada, Tobacco budworm, Gypsy moth, Rice leaf roller, Moth, Coleoptera, Colorado golden locust, Yellow squash, cotton worm, locust, leaf mites, Agricultural pests such as scale insects, mites, white mites, hummers, mites, flower flies, chafers, budworms, tussah, and ants; such as gastropods such as snails and snails; Hygienic pests such as cockroaches, cockroaches, house flies, and house mosquitoes; such as wheat moths, red bean weevils, red worms, and parasitic worms; such as clothing moths, mites, termites Pests such as clothing and house pests; such as two-spotted spider mites, red leafhoppers, sage leaves, citrus leaf mites, European leaf mites, tea mites, orange thorns, root mites, etc. Plant parasitic mites; such as rust-eats, dust mites, southern claws, etc. a nematode such as a plant parasitic nematode such as Rhizobium nematode, cyst nematode, root rot nematode, leaf bud nematode, strawberry leaf nematode, pine wood nematode, etc.; Armadillidium vulgare, Porecellio scaber, etc. Waiting for the foot; etc. Soil pests. The agricultural and horticultural fungicides, acaricides, nematicides or soil-killing insecticides containing the compounds of the present invention are particularly suitable for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. Among them, because of the control of plant parasitic mites and agricultural pests, it shows more excellent effects. Very suitable for use as an insecticide or acaricide. In addition, agricultural and horticultural fungicides, acaricides, nematicides or soil-killing insecticides containing the compounds of the invention are also suitable for use in organophosphorus, urethane, synthetic pyrethroids, new classes Prevention and treatment of various resistant pests such as nicotine. Further, since the compound of the present invention has excellent osmotic migration property, the soil is treated by the agricultural and horticultural fungicide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention, and the harmful insects and dust in the soil are controlled. Aphids, nematodes, gastropods, and other foot types can also control pests in stems and leaves.

As other suitable forms of the fungicide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention, the aforementioned comprehensive control of plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods Agricultural and horticultural fungicides, acaricides, nematicides or soil-killing pesticides for soil pests and the like.

An agricultural and horticultural fungicide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention, usually mixed with the compound and various agricultural adjuvants, formulated into a powder, a granule, a granule hydrating agent, a hydrating agent, Aqueous suspensions, oily suspensions, particulate water solvents, aqueous solvents, emulsions, liquids, pastes, aerosols, microdispersions, and the like, but may be used in the field as long as it is suitable for the purpose of the present invention. All formulation types used. Examples of the adjuvant used in the preparation include diatomaceous earth, slaked lime, calcium carbonate, talc, white smoke, clay, bentonite, kaolin, sericite, clay, sodium carbonate, sodium hydrogencarbonate, sodium sulfate, zeolite, starch, and the like. Solid support; water, toluene, xylene, mineral spirits, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl hydrazine, N, N- a solvent such as dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, or an alcohol; for example, a fatty acid salt, a benzoate, an alkyl sulfosuccinate, a dioxane Sulfosuccinate, polycarboxylate, alkyl sulfate, alkyl sulfate, alkyl aryl sulfate, alkyl diglycol ether sulfate, alcohol sulfate, alkyl sulfonate, alkane Alkyl sulfonate, aryl sulfonate, lignosulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate salt, alkyl aryl phosphate, Styryl aryl phosphate, polyoxyethylene alkyl ether sulfate salt, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate salt, polyoxyethylene alkyl ether phosphate, Anionic surfactants of polyoxyethylene alkyl aryl phosphate salts, naphthalene sulfonate formaldehyde condensates; such as sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerides, fatty acid alcohol polyglycol ethers , ethynyl glycol, ethynyl alcohol, oxyethylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene benzene Aryl ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hardened castor oil Nonionic surfactants of polyoxypropylene fatty acid esters; olive oil, Java kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil Vegetable oil or mineral oil such as rapeseed oil, linseed oil, tung oil, liquid paraffin, and the like. These auxiliary agents can be used singly or in combination of two or more kinds as long as the object of the present invention is not exceeded. Further, in addition to the above-mentioned auxiliary agents, those known in the art may be appropriately selected and used, and for example, an extender, a tackifier, a precipitating agent, an antifreezing agent, a dispersion stabilizer, and a phytotoxicity reducing agent may be used. Mildew inhibitor And other various adjuvants that are usually used. The blending 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. When these preparations are actually used, they may be used as they are, or diluted with a diluent such as water to a predetermined concentration, and if necessary, various spreading agents (surfactants, vegetable oils, mineral oils, etc.) may be added.

Application of agricultural and horticultural fungicides, acaricides, nematicides or soil-killing insecticides containing the compound of the present invention may not be based on meteorological conditions, formulation type, application period, application site, species or occurrence of diseases and pests, etc. It is generally stated that it is generally carried out at a concentration of 0.05 to 800,000 ppm, preferably 0.5 to 500,000 ppm, and the application amount per unit area is 1 to 50,000 g per 1 acre, and the compound of the present invention is 0.05 to 50,000 g, 1 to 30,000 g. It is appropriate. Further, the present invention also includes a method for controlling pests, dust mites, nematodes or soil pests by such a method of application, particularly a method for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.

The application of various preparations for agricultural and horticultural fungicides, acaricides, nematicides or soil-killing insecticides containing the compounds of the present invention, or dilutions thereof, can be carried out by the usual usual application methods, that is, dispersion (for example) Spraying, misting, atomizing, shot, surface application, etc., soil application (mixing, infusion, etc.), surface application (coating, coating, coating, etc.), impregnation of baits, and the like. In addition, mixing the above-mentioned active ingredients with the feed for livestock can also hinder the occurrence and growth of harmful insects, especially harmful insects. In addition, it can also be based on the so-called ultra low volume application method. Apply. In this method, it may contain 100% of the active ingredient.

In addition, the agricultural and horticultural fungicide, acaricide, nematicide or soil-killing insecticide containing the compound of the present invention may be mixed or used in combination with other pesticides, fertilizers, phytotoxicity reducing agents, etc., and sometimes it is more excellent. Effect, action. Examples of other pesticides include herbicides, insecticides, acaricides, nematicides, soil-killing insecticides, bactericides, antiviral agents, attractants, antibiotics, plant hormones, plant growth modulators, and the like. In particular, the insecticidal composition, the acaricidal composition, the nematicidal composition or the soil-killing pest component of the compound of the present invention and the active ingredient compound of one or more other pesticides may be used in combination or in combination. The range, the period of treatment of the drug, the activity of the control, etc., are improved in a good direction. Further, the compound of the present invention and the active ingredient compound of other pesticides may be used in the case where the respective preparations are mixed, or may be used together after preparation. The present invention also encompasses such a composition for insecticidal use, a composition for killing, a composition for nematicidal or a composition for killing soil pests.

The mixing ratio (weight ratio) of the compound of the present invention and the active ingredient compound of other pesticides may not be uniformly determined according to meteorological conditions, formulation type, application period, application site, type of pest or occurrence, etc., but generally 1:300~300:1, preferably 1:100~100:1. Further, the amount of the total active ingredient compound per suitable amount of the application is 0.1 to 50,000 g, preferably 1 to 30,000 g. The present invention also encompasses a method for controlling pests, dust mites, nematodes or soil pests by the application method of such a pesticidal composition, acaricidal composition, a nematicidal composition or a soil-killing pest composition.

As an active ingredient compound of the above-mentioned other pesticides, insecticides, nematicides, or soil-killing insecticides (general name; including part of the application, or the Japan Plant Epidemic Prevention Association test number), such as profenofos ), dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate , prothiofos, fosthiazate, cadusafos, dislufoton, isoxathion, isofenphos, ethion, benefit Etrimfos, quinalphos, dimethylvinphos, dimethoate, sulprofos, thiometon, vamidothion, Pyraclofos, pyridaphthion, pirimiphos-methyl, propaphos, phosalone, formothion, malathion, insecticide Tetrachlorvinphos), chlorfenvinphos, cyanazine ( Cyanophos), trichlorfon, methidathion, phenthoate, ESP, azinphos-methyl, fenthion, heptenophos, methoxy Methoxychlor, parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos, neonicotinoid ), methyl parathion (parathion- Methyl), terfufos, phosphamidon, phosmet, phorate, phoxim, triazophos organophosphate compounds; Carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methodyl, oxamyl, effunk (ethiofencarb), pirimicarb, fenobucarb, carbosulfan, benfuracarb, bendiocarb, furathiocab, Isoprocarb, metolcarb, xylylcarb, XMC, fenothiocarb amide compounds; such as cartap, thiocyclam ), bensultap, thiosultap-sodium, thiosultap-disodium, monosultap, bisultap, thiocyclam hydrogen oxalate Nereis toxin derivatives; such as dicofol, tetradifon, endosulfan, dienochlo r), organic chlorinated compounds of dieldrin; such as fenbutatin oxide, xyhexatin organometallic compounds; such as fenvalerate, permethrin , cypermethrin, deltamethrin, 赛洛 Cyhalothrin, tefluthrin, ethofenprox, flufenprox, cyfluthrin, fenpropathrin, flucythrinate, blessing Fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrins, esfenvalerate, tetramethrin, resmethrin ), protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypermethrin, allethrin, gamma- gamma- Cyhalothrin), theta-cypermethrin, tau-fluvalinate, trolomethrin, profluthrin, beta-cypermethrin, betacitrine (beta-cyfluthrin), metofluthrin, phenothrin, flumethrin, decamethrin pyrethroid compounds; Diflubenzuron), chlorfluazuron, teflubenzuron, fluorine Flufenoxuron, triflumuron, hexaflumuron, lufenuron, novaluron, noififlumuron, bistrifluron, pyridinium A benzoquinone-based compound of fluazuron; such as mesoprene or pyriproxyfen , juvenile hormone compounds such as fenoxycarb, diofenolan; pyridazine compounds such as pyripaben; such as fenpyroximate, fipronil, Tebufenpyrad, ethiprole, tolfenpyrad, acetoprole, pyraproprole, pyriprazole pyrazole Such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, nidinotefruan, Datnan (dinotefuran), a nicotine-based compound such as nithiazine; a hydrazine-based compound such as tebufenozide, methoxyfenozide, chromafenozide, or halofenozide; Pyridine-based compounds such as pyridalyl and flonicamid; cyclic ketoenol compounds such as spirodiclofen, spiromesifen, and spirotetramat ; methoxy acrylate (Strobilurin) such as fluacrypyrim a compound; a pyridinamine compound such as flufenerim; a dinitro compound, an organic sulfur compound, a urea compound, a triazine compound, or an anthraquinone compound, and examples of other compounds include flupy pyridine (flupyradifurone), NNI-0711 (pyflubumide), and fulramidine. Because of (flometoquin), buprofezin, hexythiazox, amitraz, chlordimeform, silafluofen, triazamate, pymetrozine Pymetrozine), pyrimidifen, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, cyromazine, 1,3-two 1,3-dichloropropene, diafenthiuron, benclothiaz, bifenazate, propargite, clofentezine, metaflumizone , flubendiamide, cyflumetofen, chlorantraniliprole, cyantraniliprole, cyenopyrafen, pyrifluquinazon, fenazaquin, sulfonamide Ester (amidoflumet), sulfluramid, amimei Hydramethylnon, metaldehyde, HGW-86, ryanodine, verbutin, AKD-1022, chlorobenzoate, thiazolylcinonitrile ), sulfoxaflor, fluensulfone, 3-bromo-N-(2-bromo-4-chloro-6-(1-cyclopropylethylaminocarbamidine)benzene 1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide, 3-bromo-N-(4-chloro-2-() 1-cyclopropylethylaminocarbamidine)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide, 3-bromo- N-(2-Bromo-4-chloro-6-(cyclopropylmethylaminocarbazinyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate Indoleamine, 3-bromo-N-(4-chloro-2-methyl-6-(methylaminomethylhydrazine)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyridyl Oxazol-5-carboxyguanamine, 3-bromo-1-(3-chloropyridin-2-yl)-N-(4-cyano-2-methyl-6-(methylaminocarbamidine)benzene a compound of -1H-pyrazole-5-carboxyguanamine; Further, it may be combined with a crystalline protein toxin, an entomopathogenic virus agent, an entomopathogenic filamentous fungus, such as Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis Bacillus thuringiensis. Microbial pesticides such as nematode pathogenic filamentous agents; such as avermectin, emamectin benzoate, milbemectin, milbemycin, spinosad, ivermectin , lepimectin, DE-175, abamectin, emamectin, spinetoram antibiotics and semi-synthetic antibiotics; such as azadirachtin, rotenone ( The natural product of rotenone; if it is mixed with the repellent of deet, etc., and used together.

Among the other pesticides mentioned above, the active ingredient compound (general name; including part of the application, or the Japanese Plant Epidemic Prevention Association test number), such as mepanipyrim, pyrimethanil, siplow ( Cyprodinil), anilin-based compound of ferimzone; Such as 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazole [1,5-a] Pyrimidine-based compounds of pyrimidine; such as pyridinamine compounds of fluazinam; such as triadimefon, bitertanol, triflumizole, etaconazole ), propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, cis Furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, oxpoconazole fumarate, sipconazole, propionate Prothioconazole, triadimenol, flurifaol, difenoconazole, fluquinconazole, fenbuconazole, bromuconazole, diniconazole ), tricyclazole, probenazole, simeconazole, pefurazoate, ipconazole, easy amine Ibenconazole); a quinoxaline-based compound such as manno, zineb, mancozeb, polyaminocarbamate; Polycarbamate, metiram, propineb, thiram dithiocarbamate-based compound; Such as fthalide, chlorothalonil, quintozene organochlorine compounds; such as benomyl, cyazofamid, methylpoly (thiophanate-methyl), carbendazim, thiabendazole, fuberiazole imidazole-based compound; such as cymoxanil cyanoacetamide-based compound; Metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, ofurace, benalaxyl, 右本达乐(benalaxyl-M (alias kiralaxyl, chiralaxyl)), furalaxyl, cyprofuram, carboxin, oxycarboxin, thifluzamide, leucoci ( Boscalid), aniline compounds of bixafen, isotianil, tiadinil, sedaxane; such as sulfonate of dichlofluanid An amine compound; a copper compound such as cupric hydroxide or oxine copper; such as hymexazole Isoxazole-based compounds; such as fosetyl-Al, tolclofos-Methyl, S-benzylmethyl O, O-diisopropyl phosphorothioate, O-ethyl S , S-diphenyl dithiophosphate, ethyl aluminum phosphinate, granules Edifenphos), an organophosphorus compound of iprobenfos; a phthalimin-based compound such as captan, captafol, and folfet; (procymidone), iprodione, vinclozolin, a dimethyl quinone imine compound; such as flutolanil, mepronil, a benzoic acid benzene compound; Penthiopyrad, 3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9RS)-1,2,3,4-tetrahydro-9-isopropyl-1 , 4-methylenenaphthalen-5-yl]pyrazole-4-carboxamide and 3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9SR)-1,2, Mixture of 3,4-tetrahydro-9-isopropyl-1,4-methylenenaphthalen-5-yl]pyrazole-4-carboxamide (Isopyrazam), Thiobacillus Amine-based compound of silthionpham, fenoxanil, furametpyr; benzoguanamine-based compound such as fluopyram or zoxamide; such as triforine a piperazine-based compound; for example, a pyridine-based compound of pyrifenox; a carbiniol-based compound such as fenpropidin; Piperidine-based compounds; as Fenpu Fu (fenpropimorph), Suntory Finland (Tridemorph) of morpholine compounds; hydroxyalkyl such as triphenyl tin (fentin hydroxide), triphenyl tin acetate (fentin Acetate organotin-based compound; urea compound such as pencycuron; cinnamic acid compound such as dimethomorph, flumorph; phenylamine such as diehofencarb a carbamate compound; a cyanopyrrole compound such as fludioxonil or fenpiclonil; such as azoxystrobin, kresoxim-methyl, phenoxystrobin ( Metominostrobin), trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin, pyraclostrobin, fluoxastrobin methoxy acrylate compound; An oxazolidinone compound of famoxadone; a thiazolecarboxamide compound such as ethaboxam; such as iprovalicarb, isopropyl-phenylthiophene Amidoxime-based compound of benthiavalicarb-isopropyl; such as methyl N-(isopropoxycarbonyl)-L-amidoxime-(3RS)-3-(4-chlorophenyl)-β- a thiol-based acid compound of the form of valiphenalate; such as fenami Imidazolinone-based compound; such as hydroxyanilide of fenhexamid a compound; a sulfonamide compound such as flusulfamide; an oxime ether compound such as cyflufenamid; an oxime compound; a crotonic acid compound; such as validamycin , antibiotics of kasugamycin, polyoxins; such as iminoctadine, dodine, lanthanide compounds; such as 6-tert-butyl-8-fluoro- a quinoline compound of 2,3-dimethyl-4-quinolinyl acetate (tebufloquin); such as (Z)-2-(2-fluoro-5-(trifluoromethyl)phenylthio)-2-(3-( 2-methoxyphenyl)-2-thiazolidinylidene) acetonitrile (flutianil) thiazolidine compound; as other compounds, pyridencarb, isoprothiolane, Baikulong (pyroquilon), diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin, dazomet, metam-sodium, nicoride Nicobifen, metrafenone, UBF-307, diclocymet, proquinazid, amisulbrom Name amibromdole)), 3- (2,3,4- trimethoxy-6-methylbenzaldehyde XI) -5-chloro-2-methoxy-4-methylpyridine, 4- ( 2,3,4-Trimethoxy-6-methylbenzoquinone)-2,5-dichloro-3-trifluoromethylpyridine, pyriofenone, mandipropamid, fluopicolide, Carpropamid, meptyldinocap, N-[(3',4'-dichloro-1,1-dimethyl)phenylhydrazinemethyl]-3-trifluoromethyl-2- Pyridinium carboxamide, N-[(3',4'-dichloro-1,1-dimethyl)phenylhydrazinemethyl]-3-methyl-2-thiophene carboxamide, N-[(3' , 4'-Dichloro-1,1-dimethyl)phenylhydrazinemethyl]-1-methyl-3-trifluoromethyl-4-pyrazolecarboxamide, N-[[2'-- -4'-(2-propoxy)-1,1-dimethyl)phenylhydrazinemethyl]-3-trifluoromethyl-2-pyridinecarboxamide, N-[[2'-- -4'-(2-propoxy)-1,1-dimethyl)phenylhydrazinemethyl]-3-methyl-2-thiophenecarboxamide, N-[[(2'-methyl-) 4'-(2-propoxy)-1,1-dimethyl)phenylhydrazinemethyl]-1-methyl-3-trifluoromethyl-4-pyrazolecarboxamide, N-[[( 4'-(2-propoxy)-1,1-dimethyl)phenylhydrazinemethyl]-3-trifluoromethyl-2-pyridinecarboxamide, N-[[(4'-(2- Propyl)-1,1-dimethyl)phenylhydrazinemethyl]-3-methyl-2-thiophenecarboxamide, N-[[(4'-(2-propoxy)-1,1 - dimethyl)phenylhydrazine methyl]-1-methyl-3-trifluoromethyl-4-pyrazole carboxamide, N-[[(2'-methyl-4'-(2 -benzyloxy)-1,1-dimethyl)phenylhydrazinemethyl]-3-trifluoromethyl-2-pyridinecarboxamide, N-[[(4'-(2-benzyloxy) )-1,1-dimethyl)phenylhydrazinemethyl]-3-trifluoromethyl-2-pyridinecarboxamide, spiroxamine, S-2188 (fenpyrazamine) ), S-2200, ZF-9646, BCF-051, BCM-061, BCM-062, etc.

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

As an animal parasite controlling agent, specifically, it is a harmful external parasite that is parasitic on the body surface of the host animal (back, underarm, lower abdomen, inner thigh, etc.) or parasitic in the host animal (stomach, intestine) The control of harmful internal parasites in lungs, heart, liver, blood vessels, subcutaneous, lymphoid tissues, etc. is effective, but among them, the control of external parasites is effective.

Examples of the external parasite include, for example, animal parasitic mites or mites. Since there are many such types, it is difficult to enumerate all of them, so an example is given.

Examples of animal parasitic mites include, for example, Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, and Haemaphysalis campanulata. ), Haemaphysalis concinna, Haemaphysalis japonica, Haemaphysalis kitaokai, Haemaphysalis ias, Ixodes ovatus, Ixodes nipponensis, full furrow (Ixodes persulcatus), Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, Dermacentor taiwanesis, such as the chicken skin hedgehog (Dermanyssus) Gallinae), Ornithonyssus sylviarum, or avian locust (Ornithonyssus bursa); such as Eutrombicula wichmanni, Leptotrombidium akamushi, Leptotrombidium Pallidum), Leptotrombidium fuji, (Leptotrombidium tosa), autumn harvest (Neotrombicula) Autumnalis), Autumbicula alfreddugesi, (Helenicula miyagawai) aphids; (Cheyletiella yasguri), rabbit skin cheet (Cheyletiella parasitivorax), Cheyletiella blakei carnivorous mites; ear Aphids (Psoroptes cuniculi), Choriopteres bovis, Otodectes cynotis, Sarcoptes scabiei, Notoedres cati; such as canine hair follicles Demodex canis), such as hair follicles. Among them, the animal parasite controlling agent containing the compound of the present invention is particularly effective for the control of sputum and the like.

Examples of the animal parasitic cockroach include an external parasitic wingless insect belonging to the order of Siphonaptera, and more specifically, a genus belonging to the genus Pulicidae or Ceratephyllus. Examples of the genus belonging to the genus Aphididae include Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga gallinacea, Xenopsylla cheopis, and scorpion (Leptopsylla segnis), European squid (Nosopsyllus fasciatus), Monosyllus anisus; Among them, the animal parasite controlling agent containing the compound of the present invention is effective for the control of the mites belonging to the genus Aphididae, especially scorpion, cat mites and the like.

As other external parasites, for example, burdock, horse owl, sheep pheasant, long-nosed burdock, cockroach cockroach; cockroach such as cockroach, cockroach, cockroach, and claw thorn Hymenoptera pests, etc. In addition, as internal parasites, for example, lung insects, whipworms, nodular insects, intragastric parasites, and aphids , nematodes of filamentous worms; mites of Mann's mites, mites, mites, locusts, aphids, and aphids; such as schistosomiasis and ticks in the liver; Such as coccidia, Plasmodium, intestinal sarcocyst, toxoplasma, protozoa of Cryptosporidium.

Examples of the host animal include various kinds of animals, livestock, poultry, and the like. More specifically, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, baboons, and birds (for example, pigeons, parrots, and caskets, Wenbird, Budgerigar, Ten Sisters, Canary, etc.), cattle, horses, pigs, sheep, ducks, chickens, etc. Among them, the animal parasite controlling agent containing the compound of the present invention is effective for controlling pests or mites which are externally parasitic to the animal or livestock. Dogs, cats, cows or horses are particularly effective in playing animals or livestock.

When the compound of the present invention is used as an animal parasite controlling agent, it can be used as it is, or can be formulated together with a suitable auxiliary agent into a powder, a granule, a lozenge, a powder, a capsule, a liquid, an emulsion, an aqueous suspension. , various types of oily suspensions, etc. are used. Further, in addition to the aforementioned formulation type, all formulation forms generally used in the field can be used as long as it is suitable for the purpose of the present invention. Examples of the auxiliary agent to be used in the preparation include an anionic surfactant or a nonionic interfacial surfactant exemplified as an adjuvant for preparation of the above-mentioned agricultural and horticultural fungicide, acaricide, nematicide or soil-killing insecticide. a cationic surfactant such as cetyltrimethylammonium bromide; such as water, acetone, acetonitrile, N-methylacetamide, N,N-dimethylacetamide, N,N-di Methylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxygen Ethylene glycol, butyl Ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol n-butyl ether Solvents; such as butylated hydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium metabisulfite, propyl gallate, sodium thiosulfate antioxidants; such as polyvinylpyrrolidone, polyvinyl alcohol, vinyl acetate And a film forming agent of a copolymer of vinylpyrrolidone; a vegetable oil or a mineral oil exemplified as an auxiliary agent for the preparation of the above-mentioned agricultural and horticultural fungicide, acaricide, nematicide or soil-killing insecticide; for example, lactose, sucrose, glucose , starch, wheat flour, corn flour, soybean oil meal, defatted rice bran, calcium carbonate, other commercially available feed ingredients carrier; Each of the components of the above-mentioned auxiliary agents may be used singly or in combination of two or more kinds as long as the object of the present invention is not exceeded. In addition, the auxiliary agent may be appropriately selected and used in the field, and may be appropriately selected from various adjuvants used in the agricultural and horticultural fields.

The blending ratio (weight ratio) of the compound of the present invention to various adjuvants is usually about 0.1:99.9 to 90:10. In actual use, when such a preparation is used, it can be used as it is, or diluted with a diluent such as water to a predetermined concentration, and if necessary, various spreading agents (surfactant, vegetable oil, mineral oil, etc.) can be added.

Administration of the compounds of the invention to a host animal is carried out by oral or parenteral administration. The oral administration method may, for example, be a method of administering a tablet, a liquid preparation, a capsule, a wafer, a soft cake, a ground meat, or other feed containing the compound of the present invention. As a method for parenteral administration, for example, a compound of the present invention is prepared into an appropriate preparation, and administered by intravenous injection, intramuscularly. Administration, intradermal administration, subcutaneous administration, etc., a method of entering the body; a method of administering to the surface of the body by spot-on treatment, pour-on treatment, spray treatment, etc.; embedding a compound containing the compound of the present invention The resin sheet is equal to the method of subcutaneous administration of a host animal or the like.

The administration amount of the compound of the present invention to a host animal varies depending on the administration method, the purpose of administration, the symptoms of the disease, and the like, but usually, the appropriate administration ratio is 0.01 mg to 100 g to 0.1 mg with respect to the body weight of 1 kg of the host animal. ~10g is appropriate.

The present invention also encompasses methods for controlling animal parasites, such as external parasites or internal parasites, by methods of administration or administration of the aforementioned methods.

Further, in the present invention, by controlling the harmful parasites as described above, it is possible to prevent or treat various diseases of host animals caused by these. Thus, the present invention also encompasses a prophylactic or therapeutic agent for an animal disease caused by a parasite comprising the compound of the present invention as an active ingredient, and a method for preventing or treating an animal disease caused by the parasite.

When the compound of the present invention is used as an animal parasite controlling agent, it may be mixed with an auxiliary agent or used in combination with various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, fungicides, and coloring agents. Agents, fragrances, preservatives, etc. In addition, other animal drugs or pesticides such as insect repellents, anticoccidial agents, insecticides, acaricides, acaricides, nematicides, fungicides, antibacterial agents, etc. may be mixed or used as needed. It also shows better results. The present invention relates to an animal parasite controlling composition which is used in combination or in combination with various components as described above, and also includes A method for controlling animal parasites thereof, particularly a method for controlling external parasites or internal parasites.

Example

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

Synthesis Example 1 2,2-difluoro-5-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)benzo[d][1,3] Synthesis of oxolene (Compound No. 37-29)

1.0 g of 5-bromo-2,2-difluorobenzo[d][1,3]dioxole, 1.4 g of (2-fluoro-4-methyl-5-(2, a mixed solution of 2,2-trifluoroethyl)thio)phenyl)phorone acid, 0.12 g of tetrakis(triphenylphosphine)palladium, 0.89 g of sodium carbonate, 5 ml of tetrahydrofuran and 5 ml of water, heated to reflux 18 hours. After adding water to the reaction mixture and extracting with ethyl acetate, the organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified to silica gel column chromatography (yield: n-heptane / ethyl acetate = 95/5 (capacity ratio)) to obtain 1.6 g of oily substance.

Synthesis Example 2 2,2-difluoro-5-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)benzo[d][1,3] Combination of oxolene (Compound No. 37-30) to make

In 1.3 g of (2,2-difluoro-5-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)benzo[d][ 1,3] a mixed solution of dioxane and 10 ml of ethyl acetate, 0.86 g of chloroperbenzoic acid was added in two portions, and allowed to react at room temperature for 2 hours. Water was added to the reaction solution to acetic acid. After extracting the ethyl ester, the organic layer was washed with sodium hydrogencarbonate water, water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was chromatographed on a silica gel column (eluent: The n-heptane / ethyl acetate = 60 / 40 (capacity ratio) was purified to obtain 1.2 g of the desired product (melting point: 80-85 ° C).

Synthesis Example 3 Synthesis of 6-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)quinazoline (Compound No. 31-1)

0.11 g of bromoquinazoline, 0.16 g of (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)phorone acid, 0.030 g of A mixed solution of tetrakis(triphenylphosphine)palladium, 0.11 g of sodium carbonate, 3 ml of tetrahydrofuran and 3 ml of water was heated under reflux for 19 hours. After adding water to the reaction mixture and extracting 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 = 50/50 (capacity ratio)) to give the object (0.11 g). -105 ° C).

Synthesis Example 4 5-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfanyl)phenyl)-2,2- Synthesis of difluoro[d][1,3]dioxole (Compound No.37-55)

0.71 g of 5-bromo-2,2-difluorobenzo[d][1,3]dioxole, 1.1 g of (2-fluoro-4-methyl-5-(2, a mixed solution of 2,2-trifluoroethyl)thio)phenyl)phorone acid, 0.17 g of tetrakis(triphenylphosphine)palladium, 1.0 g of potassium carbonate, 15 ml of tetrahydrofuran and 15 ml of water, heated to reflux 13 hours. After adding water to the reaction mixture and extracting with ethyl acetate, the organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified to silica gel column chromatography (yield: n-heptane/ethyl acetate = 98/2 (capacity ratio)) to obtain 1.0 g of an oily product.

Synthesis Example 5 5-(2-Fluoro-4-methyl-5-((2,2,2-trifluoroethyl) sulfinyl)phenyl)-2,2-difluoro[d][1,3] Synthesis of Dioxole (Compound No. 37-56)

5-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-2,2-difluoro[d][1,3 A mixed solution of dioxane and 18 ml of chloroform was added, and a mixed solution of 0.62 g of chloroperbenzoic acid and 8 ml of chloroform was added thereto, and the mixture was reacted at 0 ° C for 30 minutes, and then reacted at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and then aqueous sodium hydrogen sulfate was evaporated, and ethyl acetate was evaporated to ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-heptane / ethyl acetate = 85 / 15 (capacity ratio)) to give the object (yield 134) -135 ° C).

Synthesis Example 6 Synthesis of (5-bromo-4-chloro-2-methylphenyl)-2,2,2-trifluoroethyl sulfide (intermediate compound No. 55-33)

(1) To 16 ml of chlorosulfonic acid, 8.0 g of 1-bromo-2-chloro-4-methylbenzene was added dropwise at 0 ° C, and allowed to react at room temperature for 30 minutes and at 60 ° C for 1 hour. After cooling to room temperature, ice water was added, and the precipitated crystals were filtered and washed with water to obtain 12 g of 5-bromo-4-chloro-2-methylbenzene-1-sulfonium chloride (melting point 90-91). °C).

(2) In 12 g of the 5-bromo-4-chloro-2-methylbenzene-1-sulfonium chloride obtained in the above (1), 22 ml of acetic acid, 2.5 g of red phosphorus and 0.15 g of iodine are added, and heated to reflux. 4.5 hours. After cooling to room temperature, the solid was filtered, and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, sodium hydrogencarbonate water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 10 g of s-(5-bromo-4-chloro-2-methylphenyl) thioacetate (melting point 42-43 ° C).

(3) 9.8 g of the S-(5-bromo-4-chloro-2-methylphenyl)thioacetate obtained in the above (2), 25 ml of ethanol and 25 ml of water were mixed, and 3.5 g of the solution was added. Sodium hydroxide was allowed to react at room temperature for 15 hours. Ethanol was distilled off under reduced pressure, and the mixture was neutralized with concentrated hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give EtOAc (yield::::::::::

(4) 5.0 g of 5-bromo-4-chloro-2-methyl-thiophenol obtained in the above (3), 4.7 g of potassium carbonate, 2.6 g of sodium formaldehyde sulfoxylate and 20 ml of A mixed solution of N,N-dimethylformamide was added dropwise 5.3 g of 1,1,1-trifluoro-2-iodoethane. After the completion of the dropwise addition, the reaction was allowed to proceed at room temperature for 20 hours. Water was added to the reaction mixture, and the mixture was extracted with a mixed solvent of n-heptane / tert-butyl methyl ether = 75 / 25 (volume ratio), and the organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 5.3 g of m.

Synthesis Example 7 Synthesis of (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfanyl)phenyl)phorone (Intermediate Compound No. 55-42)

A mixed solution of 10 g of (5-bromo-4-chloro-2-methylphenyl)-2,2,2-trifluoroethyl sulfide and 80 ml of diethyl ether was cooled to -70 under a nitrogen atmosphere. °C. To this solution, 21 ml of n-butyllithium (n-hexane solution, 1.59 mol/L) was added dropwise over 10 minutes. After 10 minutes, a mixed solution of a mixed solution of 3.4 g of trimethoxyborane and 25 ml of diethyl ether at -60 ° C to -55 ° C was added dropwise over 15 minutes. Thereafter, the temperature was raised to -20 ° C, 60 g of 20% sulfuric acid was added dropwise, and the reaction was further carried out at room temperature for 2 hours. The organic layer was separated from the reaction mixture, washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated. The obtained solid was washed with n-heptane to give 5.5 g of the object (melting point: 154 to 156 ° C).

Representative examples of the compounds of the above formula (1) are shown in Tables 1 to 54, and representative examples of the intermediate compounds are shown in Table 55. These compounds can be produced by various production methods of the above-mentioned synthesis examples or the compounds of the above formula (1) and intermediate compounds. In Tables 1 to 55, respectively, a Me-based methyl group, an Et-ethyl group, an n-Pr-based n-propyl group, an i-Pr-based isopropyl group, an n-Bu-based n-butyl group, and an i-Bu-based isobutyl group are respectively shown. , s-Bu sec-butyl, t-Bu t-butyl, n-Pentyl n-pentyl, Ph phenyl, Py pyridyl, 2-F-Ph means F substituted phenyl at position 2 3-CF 3 -2-Py means that CF 3 is substituted for the 2-pyridyl group at the third position. Further, the compound indicating "-" in the column of R 4 indicates that R 4 is unsubstituted. For example, the compound described as "4-F" represents the substitution position indicated by the chemical structural formula in the table, and R 4 is substituted, that is, The fourth position is replaced by a fluorine atom. The value indicating the physical property is the melting point (°C). Further, several compounds of the above formula (I) and intermediate compounds are shown in Tables 56 and 57 for 1 H-NMR data [ 1 H-NMR spectrometry. Delta chemical shift value]. In the tables 1 to 57, No. indicates the compound No..

Next, a test example is described.

Test Example 1 Test of killing adult mites

A chemical solution having a concentration of the compound of the present invention of 50 ppm is prepared. Only the first leaves of the peas were transplanted with leaves (8 cm in diameter and 7 cm in height), and about 20 of them were placed in the larvae. This product was immersed in the above-mentioned chemical solution together with the pea leaf for about 5 seconds, air-dried, and placed in a lighting constant temperature room at 25 °C. After 2 or 3 days of treatment, the life and death were determined, and the adultery rate was determined according to the following formula. In addition, adult or abnormal worms that are detached are considered dead. The aforementioned compounds No. 1-1, 1-24, 1-25, 3-1, 4-1, 4-2, 4-5, 4-6, 4-7, 4-8, 4-11, 4 were tested. -13, 4-14, 4-15, 4-17, 4-18, 4-19, 4-20, 4-23, 4-29, 4-75, 4-77, 4-79, 4-80 , 4-81, 4-85, 4-86, 4-87, 4-89, 4-93, 4-94, 4-95, 4-96, 5-1, 5-2, 5-5, 5 -6, 5-9, 5-10, 5-111, 5-15, 5-17, 5-25, 5-75, 5-86, 5-87, 5-88, 5-89, 5-91 , 5-93, 5-95, 5-99, 5-105, 5-106, 5-107, 5-108, 5-109, 5-112, 6-1, 6-11, 6-28, 6 -30, 6-31, 6-34, 7-1, 9-1, 9-55, 10-1, 10-15, 12-1, 12-2, 12-75, 13-1, 13-2 , 13-5, 13-11, 13-15, 13-18, 13-19, 13-20, 13-75, 13-76, 13-85, 13-86, 14-1, 15-1, 16 -27, 17-1, 18-1, 18-15, 18-29, 18-30, 20-1, 20-2, 22-1, 22-2, 24-1, 24-2, 24-27 , 25-1, 25-3, 25-4, 25-9, 25-10, 25-27, 25-29, 25-31, 27-1, 27-29, 27-30, 28-1, 31 -1, 31-2, 31-27, 31-29, 31-30, 31-31, 31-32, 31-45, 31-49, 31-50, 31-55, 31- 56, 31-57, 31-58, 31-59, 31-60, 31-65, 31-67, 31-68, 31-69, 31-70, 32-1, 32-2, 32-3, 32-4, 32-9, 32-27, 32-29, 32-30, 33-1, 34-1, 35-1, 36-25, 36-26, 36-29, 36-30, 37- 25, 37-26, 37-29, 37-30, 37-35, 37-36, 37-51, 37-52, 37-53, 37-54, 37-55, 37-56, 37-57, 37-58, 37-59, 37-60, 37-65, 37-66, 37-67, 37-68, 37-75, 37-76, 37-85, 37-86, 37-87, 37- 88, 37-89, 37-90, 37-99, 37-100, 37-101, 37-102, 37-103, 37-104, 37-110, 37-117, 37-141, 37-143, 37-144, 37-145, 37-146, 37-147, 37-148, 37-149, 37-150, 37-151, 37-152, 37-157, 37-159, 37-160, 37- 162, 37-163, 37-164, 37-167, 37-168, 37-169, 37-170, 37-171, 37-172, 37-177, 37-178, 37-189, 37-190, 37-191, 37-192, 37-193, 37-194, 37-205, 37-206, 37-207, 37-208, 37-215, 37-216, 37-223, 37-224, 38- 3, 38-4, 39-13, 41-9, 41-21, 41-22, 41-29, 41-31, 41-32, 41-33, 41-35, 41-37, 42-9, 42-10, 42-13, 42-14, 42-15, 42-16, 42-17, 42-18, 42-19, 4 2-20, 42-21, 42-22, 42-29, 42-31, 42-32, 42-33, 42-34, 42-35, 42-36, 42-37, 42-38, 42- 39, 43-9, 43-10, 43-21, 43-22, 44-15, 44-25, 46-15, 48-1, 50-1, all of these compounds showed more than 90% killing Adult rate.

Rate of killing adults (%) = (number of leaves of death two leaves / number of treated leaves) × 100

Test Example 2 Effect test on brown planthopper

The rice seedlings were immersed for about 10 seconds by adjusting the concentration of the compound of the present invention to 200 ppm. After the liquid is air-dried, wrap the roots with wet cotton wool and place in a test tube. About 20 of the 2 to 3 years old brown locusts were placed, and the nozzles were covered with gauze and placed in a temperature-controlled room with illumination at 25 °C. Five days after the larvae, the brown planthopper was judged to be dead and alive, and the mortality rate was determined by the following calculation formula. Test the aforementioned compounds N0.3-1, 4-17, 4-85, 6-1, 6-11, 6-28, 6-34, 7-1, 20-1, 24-1, 24-27, 25 -3, 25-27, 36-25, 36-26, 37-25, 37-29, 37-30, 37-51, 37-52, 37-65, 37-76, 37-85, 37-87 , 37-88, 37-89, 37-90, 37-143, 37-144, 37-145, 37-146, 37-147, 37-152, 37-159, 37-160, 37-162, 37 -163, 37-164, 37-167, 37-193, 37-194, 37-205, 38-3, 38-4, 41-9, 41-10, 41-21, 41-31, 42-9 , 42-10, 42-13, 42-15, 42-17, 42-29, 42-31, 42-32, 42-33, 42-34, 42-35, 43-9, 43-10, 46 At -15, 48-1, and 50-1, all of these compounds showed a mortality rate of more than 90%.

Dead insect rate (%) = (number of dead insects / number of insects) × 100

Next, a formulation example will be described.

Formulation Example 1

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

(2) clay 70 parts by weight

(3) White smoke 5 parts by weight

(4) sodium polycarboxylate 3 parts by weight

(5) sodium alkylnaphthalenesulfonate 2 parts by weight

The above materials were uniformly mixed to form a water and an agent.

Formulation Example 2

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

(2) talc 60 parts by weight

(3) calcium carbonate 34.5 parts by weight

(4) Flowing paraffin 0.5 parts by weight

The above materials were uniformly mixed and mixed into a powder.

Formulation Example 3

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

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

(3) polyoxyethylene tristyrylphenyl ether 10 parts by weight

(4) calcium dodecylbenzenesulfonate 2 parts by weight

(5) xylene 48 parts by weight

The above materials were uniformly mixed and dissolved to form an emulsion.

Formulation Example 4

(1) clay 68 parts by weight

(2) sodium lignosulfonate 2 parts by weight

(3) polyoxyethylene alkyl aryl sulfate 5 parts by weight

(4) White smoke 25 parts by weight

Mixing the above ingredients with the compound of the invention in a weight of 4:1 The ratios are mixed to form a water and a dose.

Formulation Example 5

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

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

(3) eucalyptus oil 0.2 parts by weight

(4) water 47.8 parts by weight

The above materials are uniformly mixed and pulverized in the stock solution, and then added

(5) sodium polycarboxylate 5 parts by weight

(6) anhydrous sodium sulfate 42.8 parts by weight

It is uniformly mixed, granulated, and dried to become a particulate hydrating agent.

Formulation Example 6

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

(2) polyoxyethylene octyl phenyl ether 1 part by weight

(3) Polyoxyethylene alkyl ether phosphate 0.1 parts by weight

(4) Granular calcium carbonate 93.9 parts by weight

(1) to (3) are uniformly mixed in advance, diluted with an appropriate amount of acetone, and then blown to (4) to remove acetone to become a granule.

Formulation Example 7

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

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

(3) Soybean oil 95.0 parts by weight

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

Formulation Example 8

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

(2) Diethylene glycol monoethyl ether 80 parts by weight

(3) polyoxyethylene alkyl ether 10 parts by weight

The above materials were uniformly mixed to form a liquid.

Claims (15)

  1. A compound or a salt thereof, which is characterized by the formula (I). Wherein R 1 and R 2 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkyl halide, an alkoxy group, a halogenated alkoxy group or a cyano group; an R 3 -based alkyl group or a halogenated alkyl group; Or an integer of 1; Q is the following general formula [Q-1]~[Q-6]: Any one of them; A 1 ~ A 8 series can be the same or different, CH or nitrogen atom, when A 1 ~ A 8 is CH, A 1 ~ A 8 can be replaced by R 4 , A 1 ~ A 8 The number of nitrogen atoms may be 0 to 3; the B 1 to B 4 systems may be the same or different, and the CH or nitrogen atom, when B 1 to B 4 are CH, the B 1 to B 4 systems may be replaced by R 4 respectively. , B 1 ~ B 4 may be 0 to 1 nitrogen atoms; B 5 ~ B 7 systems may be the same or different, C (R 5 ) (R 6 ), oxygen atom, sulfur atom, SO or SO 2 ; E 1 ~ E 4 are CH or nitrogen atoms, and when E 1 ~ E 4 are CH, E 1 ~ E 4 can be substituted by R 4 respectively, and E 1 ~ E 4 can be 0 ~1; E 5 ~E 8 series may be the same or different, C(R 5 )(R 6 ), oxygen atom, sulfur atom, SO or SO 2 ; G 1 ~G 5 and G 7 systems may be respectively the same Or different, CH or nitrogen atom, G 1 ~ G 5 and G 7 are CH, G 1 ~ G 5 and G 7 can be substituted by R 4 respectively, G 1 ~ G 5 and G 7 can be nitrogen atoms The number is 0~3; G 6 is an oxygen atom or a sulfur atom; J 1 ~ J 6 series can be the same or different, CH or nitrogen atom, when J 1 ~ J 6 is CH, J 1 ~ J 6 can be Respectively substituted with R 4 , J 1 ~ J 6 can be 0 to 2 nitrogen atoms; L 1 ~ L 5 series can be the same or different, CH or nitrogen atom, L 1 ~ L 5 is CH, L 1 ~ L 5 can be substituted by R 4 respectively, L 1 ~ L 5 can be the number of nitrogen atoms 0 to 2; L 6 is an oxygen atom or a sulfur atom; R 4 is a halogen atom, an alkyl group, an alkyl halide, an alkoxy group, a halogenated alkoxy group, a cyano group, a nitro group, a COR 7 , a CO 2 R 7 , N(R 8 )COR 7 , N(R 8 )CO 2 R 7 , NR 9 R 10 , CONR 9 R 10 , alkylthio, halogenated alkylthio, alkylsulfinyl, halogenated alkylsulfin when acyl, alkylsulfonyl group, a halogenated alkylsulfonyl group, may also be substituted with the R 11 substituted phenyl or pyridyl group of R 11, R 4 is the number of two or more, R 4 may be the same or different; R line. 5 and R 6 are each a hydrogen atom, a halogen atom, an alkyl group or a halogenated alkyl group, R 5 and R 6 in any one or both of when two or more, R 5 and R 6 may be the same Or different; R 7 , R 8 , R 9 and R 10 are each a hydrogen atom or an alkyl group; when R 9 and R 10 are alkyl groups, R 9 and R 10 and the bonded nitrogen atom may form 5 together. ~6 member ring; R 11 is a halogen atom, an alkyl group, an alkyl halide group, an alkoxy group or a halogenated alkoxy group].
  2. The compound of claim 1 or a salt thereof, wherein Q is any one of the above general formulas [Q-1] to [Q-5].
  3. The compound of claim 1 or a salt thereof, wherein Q is a general formula [Q-1], [Q-2] or [Q-4].
  4. The compound of claim 1 or a salt thereof, wherein R 1 is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; R 2 is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; and an R 3 -based alkane Or a halogenated alkyl group; Q is a general formula [Q-1], [Q-2] or [Q-4].
  5. The compound of claim 1 or a salt thereof, wherein Q is a general formula [Q-1] or [Q-2].
  6. The compound of claim 1 or a salt thereof, wherein R 1 is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; R 2 is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; and an R 3 -based alkane Or a halogenated alkyl group; Q is a general formula [Q-1] or [Q-2].
  7. A compound characterized by the formula (II). [wherein, X is a bromine atom, -B(OH) 2 or a pentacolato boranyl; n is an integer of 0 or 1; and R 1 and R 2 are a hydrogen atom, a halogen atom, an alkyl group, an alkyl halide; Alkyl, alkoxy, halogenated alkoxy or cyano; R 3 alkyl or halogenated alkyl, however, R 1 is a hydrogen atom or a fluorine atom; R 2 is a methyl group; R 3 is a trifluoroethyl group; .
  8. A compound according to claim 7 wherein R 1 is a fluorine atom, a chlorine atom or a methyl group; and R 2 is a chlorine atom or a methyl group.
  9. A compound according to claim 7 or 8, wherein n is 0; R 3 is trifluoroethyl, trifluoropropyl, difluoroethyl or n-propyl.
  10. A pest control agent characterized by containing a compound of the first aspect of the patent application or a salt thereof as an active ingredient.
  11. An insecticide, acaricide, nematicide or soil-killing insecticide characterized by containing a compound of the first aspect of the patent application or a salt thereof as an active ingredient.
  12. An insecticide or acaricide characterized by containing a compound of the first aspect of the patent application or a salt thereof as an active ingredient.
  13. A method for controlling pests, characterized by administering an effective amount of a compound or a salt thereof as in claim 1 of the patent application.
  14. A method for controlling pests, dust mites, nematodes or soil pests, characterized in that an effective amount of a compound of the first aspect of the patent application or a salt thereof is applied.
  15. A method of controlling pests or dust mites, characterized by administering an effective amount of a compound or a salt thereof as in claim 1 of the patent application.
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Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AP3772A (en) 2012-04-20 2016-08-31 Kumiai Chemical Industry Co Alkylphenylsulphide derivative and pest control agent
BR112015030074A2 (en) * 2013-06-04 2017-07-25 Bayer Cropscience Ag bicyclic aryl sulfide and aryl sulfoxide derivatives as pest control agents
JP2016526538A (en) 2013-06-20 2016-09-05 バイエル・クロップサイエンス・アクチェンゲゼルシャフト Aryl sulfide and aryl sulfoxide derivatives as acaricides and insecticides
JP2016526539A (en) 2013-06-20 2016-09-05 バイエル・クロップサイエンス・アクチェンゲゼルシャフト Aryl sulfide and aryl sulfoxide derivatives as acaricides and insecticides
EP3019481B1 (en) 2013-07-08 2019-03-06 Bayer CropScience Aktiengesellschaft Six-membered c-n linked arylsulfide and arylsulfoxide derivatives as pesticides
PE20160608A1 (en) * 2013-10-14 2016-07-08 Eisai Randd Man Co Ltd Quinoline compounds selectively substituted
WO2015084842A1 (en) 2013-12-02 2015-06-11 Chemocentryx, Inc. Ccr6 compounds
CA2939082A1 (en) 2014-02-13 2015-08-20 Incyte Corporation Cyclopropylamines as lsd1 inhibitors
EP3105219B9 (en) 2014-02-13 2018-10-03 Incyte Corporation Cyclopropylamines as lsd1 inhibitors
WO2015123437A1 (en) 2014-02-13 2015-08-20 Incyte Corporation Cyclopropylamines as lsd1 inhibitors
SG10201806846RA (en) 2014-02-13 2018-09-27 Incyte Corp Cyclopropylamines as lsd1 inhibitors
SG11201607973XA (en) * 2014-03-24 2016-11-29 Guangdong Zhongsheng Pharmaceutical Co Ltd Quinoline derivatives as smo inhibitors
US9695168B2 (en) 2014-07-10 2017-07-04 Incyte Corporation Substituted imidazo[1,5-α]pyridines and imidazo[1,5-α]pyrazines as LSD1 inhibitors
TW201613925A (en) 2014-07-10 2016-04-16 Incyte Corp Imidazopyrazines as LSD1 inhibitors
US9758523B2 (en) 2014-07-10 2017-09-12 Incyte Corporation Triazolopyridines and triazolopyrazines as LSD1 inhibitors
US9695167B2 (en) 2014-07-10 2017-07-04 Incyte Corporation Substituted triazolo[1,5-a]pyridines and triazolo[1,5-a]pyrazines as LSD1 inhibitors
AR102942A1 (en) 2014-12-11 2017-04-05 Bayer Cropscience Ag Arylsulfide derivatives and arylsulfoxide five cn-connected members, such as pesticides
BR112017017032A2 (en) 2015-02-11 2018-04-10 Basilea Pharmaceutica Int Ag substituted mono and polyiazanaphthalene derivatives and their use
WO2016143823A1 (en) * 2015-03-10 2016-09-15 国立大学法人大阪大学 Compound, and organic semiconductor material containing same
EP3277689B1 (en) 2015-04-03 2019-09-04 Incyte Corporation Heterocyclic compounds as lsd1 inhibitors
CN107635986A (en) * 2015-05-13 2018-01-26 赛尔维他股份公司 Substituted quinoxaline derivant
CA2995361A1 (en) 2015-08-12 2017-02-16 Incyte Corporation Salts of an lsd1 inhibitor
CN109414410A (en) 2016-04-22 2019-03-01 因赛特公司 The preparation of LSD1 inhibitor
WO2018015797A1 (en) 2016-07-18 2018-01-25 Insecticides (India) Limited Novel benzylamide compound, method for producing the same, and miticide
KR20190039694A (en) 2016-07-18 2019-04-15 인섹티사이즈 (인디아) 리미티드 A novel benzylamide compound, a method for producing the same,
WO2018051252A2 (en) 2016-09-15 2018-03-22 Insecticides (India) Limited Novel amide compound, method for producing the same, and miticide

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3000886A (en) * 1958-10-06 1961-09-19 Smith Kline French Lab Substituted aroylalkyl phenothiazinylalkyl piperazines
US5013744B1 (en) * 1989-12-29 1994-09-20 Allegran Inc Acetylenes disubstituted with a pyridinyl group and a substituted phenyl group having retinoid like activity
IL108630D0 (en) * 1993-02-18 1994-05-30 Fmc Corp Insecticidal substituted 2,4-diaminoquinazolines
US5994379A (en) * 1998-02-13 1999-11-30 Merck Frosst Canada, Inc. Bisaryl COX-2 inhibiting compounds, compositions and methods of use
EP1076053B1 (en) * 1998-04-27 2006-11-29 Kumiai Chemical Industry Co., Ltd. 3-arylphenyl sulfide derivatives and insecticides and miticides
AR037517A1 (en) * 2001-11-05 2004-11-17 Novartis Ag Naphthyridines derivatives, a process for their preparation, pharmaceutical composition and use thereof for the preparation of a medicament for the treatment of an inflammatory disease
GB0229281D0 (en) * 2002-12-16 2003-01-22 Novartis Ag Organic compounds
KR100915481B1 (en) * 2004-11-09 2009-09-03 에프. 호프만-라 로슈 아게 Aminoquinazolines compounds
JP4950894B2 (en) 2005-09-21 2012-06-13 イハラケミカル工業株式会社 Biphenyl sulfide compounds and insecticide / acaricide
JP2008308448A (en) 2007-06-15 2008-12-25 Sankyo Agro Kk (3-sulfur atom-substituted phenyl)heteroaryl derivative
DE102007032739A1 (en) * 2007-07-13 2009-01-15 Merck Patent Gmbh Chinazolinamidderivate
EP2344451A4 (en) * 2008-09-05 2014-08-13 Acucela Inc Sulfur-linked compounds for treating opthalmic diseases and disorders
MX2011013667A (en) * 2009-06-25 2012-03-06 Amgen Inc Heterocyclic compounds and their uses as inhibitors of pi3 k activity.
US8796180B2 (en) * 2009-09-24 2014-08-05 Basf Se Aminoquinazoline compounds for combating invertebrate pests
WO2011123937A1 (en) * 2010-04-06 2011-10-13 University Health Network Kinase inhibitors and method of treating cancer with same
CA2796967C (en) * 2010-05-04 2015-12-01 Pfizer Inc. Heterocyclic derivatives as alk inhibitors
WO2012066122A1 (en) * 2010-11-18 2012-05-24 Syngenta Participations Ag 2 - (pyridin- 2 -yl) -quinazoline derivatives and their use as microbicides

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