WO2013111864A1 - Agent de lutte contre les parasites - Google Patents

Agent de lutte contre les parasites Download PDF

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WO2013111864A1
WO2013111864A1 PCT/JP2013/051611 JP2013051611W WO2013111864A1 WO 2013111864 A1 WO2013111864 A1 WO 2013111864A1 JP 2013051611 W JP2013051611 W JP 2013051611W WO 2013111864 A1 WO2013111864 A1 WO 2013111864A1
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PCT/JP2013/051611
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中元　健一
悠子 西濱
達也 可児
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石原産業株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom not containing sulfur-to-oxygen bonds, e.g. polysulfides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
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    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • C07C323/10—Thiols, 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 singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, 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 singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, 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 singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
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    • C07D213/65—One oxygen atom attached in position 3 or 5
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
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Definitions

  • the present invention relates to a pest control agent containing a novel compound represented by the 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.
  • Patent Document 2 describes phenoxypyrimidine derivatives useful as acaricides and herbicides.
  • 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).
  • An object of the present invention is to provide a compound having high activity against pests, to provide a pest control agent containing 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 the novel compound represented by the formula (I) or a salt thereof has a low dose and extremely high control effect against pests, and also has safety against crops. Was completed.
  • the gist of the present invention is the following (1) to (9).
  • R 1 and R 2 are each independently a hydrogen atom, a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy or cyano; R 3 is alkyl or haloalkyl; n is 0 or It is an integer of 1.
  • Q is a pyridyl which may be substituted by R 4, there by R 4 phenyl which may be substituted, and which may be also 4-pyrimidinyl substituted with or pyrimidinyl, or R 4 that may be substituted by R 4;
  • R 4 I 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 haloalkylsulfonyl, when two or more R 4 are present, they may be the same or different.
  • R 5 , R 6 , R 7 and R 8 are each independently a hydrogen atom, alkyl or haloalkyl; when R 7 and R 8 are alkyl or haloalkyl, a 5- to 6-membered ring with an adjacent nitrogen atom is attached. It may be formed. However, when Q is phenyl which may be substituted with R 4 and R 3 is alkyl, R 1 is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy or cyano.
  • R 1 is a hydrogen atom
  • R 2 is a hydrogen atom or alkyl
  • R 4 is substituted with R 4
  • R 1 is a hydrogen atom
  • 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
  • R 1 is a halogen atom or alkyl
  • R 2 is a halogen atom or alkyl
  • R 3 is trifluoroethyl.
  • a salt thereof (4) The compound according to (3), which is represented by formula (V).
  • R 1 is a fluorine atom, a chlorine atom or alkyl
  • R 2 is a chlorine atom or methyl
  • R 3 is trifluoroethyl.
  • R 1 is a fluorine atom, a chlorine atom or alkyl
  • R 2 is a chlorine atom or methyl
  • R 3 is trifluoroethyl.
  • 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.
  • the active ingredient contained in the pest control agent of the present invention is a novel compound represented by the formula (I) or a salt thereof.
  • the compound represented by the formula (V) or a salt thereof is a raw material compound of the formula (I).
  • halogen atom in the above formulas (I) and (V) or the halogen atom as a substituent examples 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 moiety in the alkyl or haloalkyl, alkoxy, haloalkoxy and the like in the formula (I) and the formula (V) may be either linear or branched, and specific examples thereof include methyl, ethyl, propyl, Examples thereof include those of C 1-6 such as isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl. Of these, methyl and ethyl are preferable.
  • the number of substitution is 1 to 4, preferably 1 to 2. Also, when substituted by a plurality of R 4, R 4 may be the same or different. Examples of 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, preferably 1 to 3. It is. Also, when substituted by a plurality of R 4, R 4 may be the same or different.
  • R 4 When 2-pyrimidinyl or 4-pyrimidinyl in formula (I) is substituted with R 4 , the number of substitutions is 1 to 3, preferably 1 to 2. It is. Also, when substituted by a plurality of R 4, R 4 may be the same or different.
  • the salt of the compound of formula (I) includes any salt that is acceptable in the art, but examples include ammonium salts such as dimethylammonium salt and triethylammonium salt; hydrochloride salt, perchlorine Inorganic acid salts such as acid salts, sulfates and nitrates; organic acid salts such as acetates and methanesulfonates. Further, the salt of the compound of the formula (V) includes any salt as long as it is acceptable in the technical field.
  • alkali metal salts such as sodium salt and potassium 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 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.
  • 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 formula (I). However, since those skilled in the art can sufficiently recognize that they are related to isomers, the scope of the present invention It is clear that it is within.
  • the compound of 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 production method]. 2], and can be produced according to ordinary salt production methods, but is not limited to these methods.
  • 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.
  • the base examples 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.
  • 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
  • the base can be used in an amount of 1 to 10 moles, preferably 1 to 5 moles compared to the compound of the 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, sulfites, sulfites, sulfite adducts such as Rongalite (manufactured by Kanto Chemical Co., Ltd., trade name: 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 the formula (II). Any solvent may be used as long as it is inert to the reaction.
  • ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1,4-dioxane, dimethoxyethane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide and sulfolane; Nitriles such as acetonitrile and propionitrile; Esters such as ethyl acetate and ethyl propionate; Pentane, hexane, heptane and octane 1 type, or 2 or more types can be appropriately selected from aliphatic hydrocarbons such as cyclohexane, protic solvents such as water, methanol, and ethanol.
  • the reaction temperature is usually ⁇ 50 to 200 ° C
  • This reaction can be carried out by reacting the compound of formula (Ia) in a solvent in the presence of an oxidizing agent.
  • the oxidizing agent include aqueous hydrogen peroxide, m-chloroperbenzoic acid, perbenzoic acid, sodium periodate, oxone (OXONE, manufactured by EI Dupont, trade name: containing potassium peroxosulfate), It can be appropriately selected from N-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 times mol, preferably 0.001 to 0.05 times mol, of the compound of formula (Ia). Any solvent may be used as long as it is inert to the reaction.
  • halogenated alkanes such as chloroform, dichloromethane and dichloroethane
  • aromatic hydrocarbons such as chlorobenzene and dichlorobenzene
  • esters such as ethyl acetate and ethyl propionate
  • acetic acid be able to.
  • the reaction temperature is usually ⁇ 50 to 150 ° C., desirably ⁇ 10 to 50 ° C.
  • the reaction time is usually 0.5 to 48 hours, preferably 1 to 30 hours.
  • 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.
  • the base include those similar to the above production method [1].
  • the base can be used in an amount of 1 to 10 moles, preferably 1 to 5 moles compared to the compound of the formula (V).
  • 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 per mole of 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.
  • the compound of formula (II) or formula (III) which is the starting material of the production method [1] can be produced, for example, by a reaction comprising the following (1) to (4).
  • the fourth steps (1) to (4) for hydrolyzing the compound of the formula (X) to obtain the compound of the formula (II) or the formula (III) will be described in detail below.
  • Q, R 1 , R 2 and L 2 are as described above, and X represents a halogen atom.
  • the first step can be performed according to the method of the above production method [3].
  • the second stage 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, preferably 1 to 10 times mol, of the compound of the formula (VIII).
  • This reaction can be carried out in the presence of a solvent, if desired. Any solvent may be used as long as it is inert to the reaction.
  • ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1,4-dioxane and dimethoxyethane; halogenated alkanes such as chloroform, dichloromethane and dichloroethane; aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; pentane and hexane , Heptane, octane, cyclohexane, and other aliphatic hydrocarbons; acetic acid, propionic acid, and other organic acids; and the like.
  • the reaction temperature is usually ⁇ 10 to 200 ° C., preferably 10 to 150 ° C.
  • the reaction time is usually about 0.5 to 48 hours, preferably 1 to 24 hours.
  • the third stage can be performed by reacting in acetic acid in the presence of a reducing agent.
  • 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.
  • the reducing agent can be used in an amount of 1 to 100 times mol, preferably 1 to 10 times mol for the compound of formula (IX).
  • the reaction temperature is usually 0 to 200 ° C., preferably 0 to 150 ° C.
  • the reaction time is usually about 1 to 48 hours, preferably 1 to 24 hours.
  • the fourth step can be performed by reacting in a solvent in the presence of water and a base.
  • the base include those similar to the above production method [1].
  • the base can be used in an amount of 1 to 10 moles, preferably 1 to 5 moles based on the compound of the formula (X).
  • Examples of the solvent include those similar to the above production method [1].
  • the reaction temperature is usually ⁇ 20 to 150 ° C., desirably 0 to 100 ° C.
  • the reaction time is usually about 1 to 48 hours, preferably 1 to 24 hours.
  • 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).
  • the compound of the formula (XIV) may exist as a disulfide.
  • the first stage can be carried out by reacting the compound of formula (VII) usually in the presence of acetic anhydride and a base in a solvent.
  • the base include those similar to the above production method [1].
  • the base can be used in an amount of 1 to 10 times mol, preferably 1 to 5 times mol for the compound of formula (VII).
  • the solvent include those similar to the above production method [1].
  • the reaction temperature is usually ⁇ 20 to 150 ° C., desirably 0 to 100 ° C.
  • the reaction time is usually about 1 to 48 hours, preferably 1 to 24 hours.
  • the second stage, the third stage, and the fourth stage can be performed according to the method of [Intermediate Production Method 1].
  • the fifth step can be performed according to the method of the above production method [1].
  • the desirable mode of the pest control agent containing the compound of the present invention 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 has 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.
  • aphids such as peach aphid, cotton aphid, etc .; longhorn beetle, weevil, lotus moth, codling moth, ball worm, tobacco bad worm, maiigaiga, kobinomeiga, chanocokakumonhamaki, colorado beetle, cucumber potato beetle, ball weevil Pests such as slugs, maimai, etc .; planthoppers, leafhoppers, scale insects, stink bugs, whiteflies, thrips, grasshoppers, fly flies, scarabs, snails, cabbage moths, ants, etc .; Sanitary pests such as house dust mites, cockroaches, house flies, mosquitoes, etc .; Pests stored in storage such as bark moths, azuki beetles, bark beetles, bark beetles, etc .; clothing, house pests such as moths, swordflies, termites, etc.
  • Plant parasitic mites such as nymph mite, black spider mite, citrus spider mite, apple spider mite, apple spider mite, citrus mite, mite, etc .; Plant parasitic nematodes such as cyst nematodes, nematode nematodes, rice scented nematodes, strawberry nematodes, pine wood nematodes, etc .; Effective for pest control.
  • 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.
  • 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.
  • the compound of the present invention 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.
  • 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.
  • 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,
  • 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
  • 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.
  • it can be used by appropriately selecting from those known in the art.
  • a bulking agent for example, a bulking agent, a thickening agent, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a phytotoxicity reduction.
  • Various commonly used adjuvants such as agents, antifungal agents and the like can also be used.
  • the compounding ratio (weight ratio) of the compound of the present invention and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10. In actual use of these preparations, use them as they are or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.
  • the 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.
  • 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. .
  • 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.
  • this invention compound and the active ingredient compound of other agricultural chemicals may be used by mixing each separately formulated at the time of spraying, or by combining both 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.
  • the appropriate amount to be applied is 0.1 to 50,000 g, preferably 1 to 30,000 g as the total amount of active ingredient compounds 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.
  • 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.
  • an active ingredient compound 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,
  • 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, it was poured into ice water and extracted with ethyl acetate. Thereafter, 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- (chlorosulfonyl) -2-fluoro-4-methylphenyl acetate.
  • 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 was added at 60 ° C. 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.
  • Synthesis example 5 Synthesis of 1-fluoro-5-methyl-2- (4-nitrophenoxy) -4-((2,2,2-trifluoroethyl) sulfinyl) benzene (Compound No. 4-62) 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 was added 0.036 g of m-chloroperbenzoic acid and left as it was. The reaction was carried out for 1 hour. Next, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate.
  • a compound represented by “4-F” is given to the chemical structural formula in the table. Only the substituted position 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, some of the compounds of formula (I) and formula (V) were measured by 1 H-NMR data [ 1 H-nuclear magnetic resonance spectroscopy (JEOL, JNM-ECX500). ⁇ is a chemical shift value using tetramethylsilane as an internal standard. Are shown in Table 8.
  • 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.
  • 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. 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.
  • Formulation Example 1 (1) Compound of the present invention 20 parts by weight (2) Clay 70 parts by weight (3) White carbon 5 parts by weight (4) Sodium polycarboxylate 3 parts by weight (5) Sodium alkylnaphthalene sulfonate 2 parts by weight or more To make a wettable powder.
  • Formulation Example 2 (1) Compound of the present invention 5 parts by weight (2) Talc 60 parts by weight (3) Calcium carbonate 34.5 parts by weight (4) Liquid paraffin 0.5 parts by weight or more are uniformly mixed to obtain a powder.
  • Formulation Example 3 (1) Compound of the present invention 20 parts by weight (2) N, N-dimethylacetamide 20 parts by weight (3) Polyoxyethylene tristyryl phenyl ether 10 parts by weight (4) Calcium dodecylbenzenesulfonate 2 parts by weight (5) Xylene 48 A mixture of more than parts by weight is uniformly mixed and dissolved to obtain an emulsion.
  • Formulation Example 4 (1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) White carbon 25 parts by weight A mixture of each component and the present compound Mix at a weight ratio of 4: 1 to make a wettable powder.
  • Formulation Example 5 (1) Compound of the present invention 50 parts by weight (2) Sodium alkylnaphthalene sulfonate formaldehyde condensate 2 parts by weight (3) Silicone oil 0.2 parts by weight (4) Water 47.8 parts by weight or more uniformly mixed In addition to the crushed stock solution (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are added, 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 mixed uniformly 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, dissolved and applied in a trace amount (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.
  • the pest control agent containing the compound of the present invention has an extremely high pest control effect against pests with a low dosage, and also has safety against crops. It is useful as an agent, nematicide or soil pesticide.
  • Japanese Patent Application No. 2012-013051 filed on January 25, 2012
  • Japanese Patent Application No. 2012-057618 filed on March 14, 2012
  • the entire contents of the specification, claims, and abstract of patent application 2012-120245 are hereby incorporated herein by reference as the disclosure of the specification of the present invention.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un nouvel agent de lutte contre les parasites. L'invention concerne ainsi un composé représenté par la formule (I) ou un sel associé et un agent de lutte contre les parasites le comprenant comme principe actif. Dans la formule (I) : R1 et R2 représentent indépendamment un atome d'hydrogène, un atome d'halogène, un alkyle, un halogénoalkyle, un alcoxy, un halogénoalcoxy ou un cyano ; R3 représente un alkyle ou un halogénoalkyle ; n représente un nombre entier égal à 0 ou 1 ; et Q représente un pyridyle éventuellement substitué, un phényle éventuellement substitué, un 2-pyrimidinyle éventuellement substitué ou un 4-pyrimidinyle éventuellement substitué.
PCT/JP2013/051611 2012-01-25 2013-01-25 Agent de lutte contre les parasites WO2013111864A1 (fr)

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JP2012013051 2012-01-25
JP2012-013051 2012-01-25
JP2012057618 2012-03-14
JP2012-057618 2012-03-14
JP2012120245 2012-05-25
JP2012-120245 2012-05-25

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Cited By (2)

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CN108137502A (zh) * 2015-10-21 2018-06-08 住友化学株式会社 吡啶化合物
WO2019167814A1 (fr) 2018-02-27 2019-09-06 クミアイ化学工業株式会社 Procédé de production d'un composé mercapto-phénol et d'un intermédiaire dudit composé

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BR112014025190B1 (pt) * 2012-04-20 2020-12-08 Kumiai Chemical Industry Co. Ltd derivado de sulfeto de alquil fenila e agente de controle de peste
JP2022116370A (ja) * 2019-06-13 2022-08-10 アグロカネショウ株式会社 新規な１－ベンジルアミン誘導体及びこれを有効成分とする農園芸用薬剤

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JPS5147695B1 (fr) * 1970-12-29 1976-12-16
JPS5492978A (en) * 1977-12-28 1979-07-23 Sankyo Co Ltd Phenoxypyrimidine derivative
WO1997024330A1 (fr) * 1995-12-28 1997-07-10 Kureha Kagaku Kogyo Kabushiki Kaisha Nouveaux n-(non substitue ou substitue)-4-substitue-6-(non substitue ou substitue) phenoxy-2-pyridinecarboxamides ou thiocarboxamides, leurs procedes de production, et herbicides
WO1999000370A1 (fr) * 1997-06-27 1999-01-07 Kureha Kagaku Kogyo Kabushiki Kaisha Acide 6-phenoxypicolinique, derives d'alkylidenehydrazide, leur procede de production, et herbicide
JP2005504728A (ja) * 2001-04-11 2005-02-17 ファイザー・インク セロトニン再吸収阻害剤としてのフェニル複素環式エーテル誘導体
JP2006528660A (ja) * 2003-07-25 2006-12-21 ファイザー・インク Ｐｄｅ４阻害薬として有用なニコチンアミド誘導体

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JPS5147695B1 (fr) * 1970-12-29 1976-12-16
JPS5179723A (en) * 1974-12-27 1976-07-12 Nippon Kayaku Kk Satsudanizai
JPS5492978A (en) * 1977-12-28 1979-07-23 Sankyo Co Ltd Phenoxypyrimidine derivative
WO1997024330A1 (fr) * 1995-12-28 1997-07-10 Kureha Kagaku Kogyo Kabushiki Kaisha Nouveaux n-(non substitue ou substitue)-4-substitue-6-(non substitue ou substitue) phenoxy-2-pyridinecarboxamides ou thiocarboxamides, leurs procedes de production, et herbicides
WO1999000370A1 (fr) * 1997-06-27 1999-01-07 Kureha Kagaku Kogyo Kabushiki Kaisha Acide 6-phenoxypicolinique, derives d'alkylidenehydrazide, leur procede de production, et herbicide
JP2005504728A (ja) * 2001-04-11 2005-02-17 ファイザー・インク セロトニン再吸収阻害剤としてのフェニル複素環式エーテル誘導体
JP2006528660A (ja) * 2003-07-25 2006-12-21 ファイザー・インク Ｐｄｅ４阻害薬として有用なニコチンアミド誘導体

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Publication number Priority date Publication date Assignee Title
CN108137502A (zh) * 2015-10-21 2018-06-08 住友化学株式会社 吡啶化合物
CN108137502B (zh) * 2015-10-21 2021-03-16 住友化学株式会社 吡啶化合物
WO2019167814A1 (fr) 2018-02-27 2019-09-06 クミアイ化学工業株式会社 Procédé de production d'un composé mercapto-phénol et d'un intermédiaire dudit composé
CN114478336A (zh) * 2018-02-27 2022-05-13 组合化学工业株式会社 巯基酚化合物的制造方法及其中间体
CN114478336B (zh) * 2018-02-27 2024-05-14 组合化学工业株式会社 巯基酚化合物的制造方法及其中间体

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