WO2018052136A1 - Composition d'agent de lutte contre des nuisibles et procédé de lutte contre des nuisibles - Google Patents

Composition d'agent de lutte contre des nuisibles et procédé de lutte contre des nuisibles Download PDF

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WO2018052136A1
WO2018052136A1 PCT/JP2017/033541 JP2017033541W WO2018052136A1 WO 2018052136 A1 WO2018052136 A1 WO 2018052136A1 JP 2017033541 W JP2017033541 W JP 2017033541W WO 2018052136 A1 WO2018052136 A1 WO 2018052136A1
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compound
active ingredient
active compound
rot
ingredient group
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PCT/JP2017/033541
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Japanese (ja)
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泰徳 溝山
洋人 松井
誠 稲田
佑介 南條
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日産化学工業株式会社
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Priority claimed from JP2017137176A external-priority patent/JP2019196310A/ja
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Publication of WO2018052136A1 publication Critical patent/WO2018052136A1/fr

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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
    • A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
    • A01N63/20—Bacteria; Substances produced thereby or obtained therefrom
    • A01N63/22—Bacillus
    • 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
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/22—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom rings with more than six members
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • 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
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • 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
    • 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
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • 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
    • A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
    • A01N63/20—Bacteria; Substances produced thereby or obtained therefrom
    • A01N63/22—Bacillus
    • A01N63/23—B. thuringiensis

Definitions

  • the present invention includes a pesticide composition characterized by comprising a condensed heterocyclic compound represented by the specific formula (1) and an active ingredient compound of a known pest control agent, and these two components. It relates to the pest control method used.
  • the condensed heterocyclic compound represented by the formula (1) (hereinafter abbreviated as “compound (1)”), which is the first active ingredient compound in the composition of the present invention, is a known compound and its pest control.
  • the activity is known as an agent (for example, refer to Patent Document 1).
  • compounds having pest control activity such as insecticidal activity, acaricidal activity, nematicidal activity, molluscicidal activity, bactericidal activity, and bactericidal activity, which are the second active ingredient compounds in the composition of the present invention. (For example, see Non-Patent Document 1).
  • the present inventors have eagerly developed a pest control agent that exhibits excellent pest control activity and has less adverse effects on non-target organisms such as mammals, fish, natural enemies and beneficial insects.
  • the composition containing the compound (1) and a compound having a specific pest control activity has an excellent synergistic pest control effect that cannot be predicted from use alone.
  • the present invention has been completed. That is, the present invention relates to the following compositions [1] to [6] (hereinafter referred to as the present composition) and the control methods [7] to [19] (hereinafter referred to as the present method). Is.
  • a pest control composition comprising a synergistically effective amount of at least two active compounds of a first active ingredient and a second active ingredient,
  • the first active ingredient comprises at least one active compound I selected from a condensed heterocyclic compound represented by the following formula (1) or an N-oxide thereof or a salt thereof
  • the second active ingredient consists of at least one active compound II selected from the following active ingredient groups BI to B-XXVI: Said composition.
  • Q represents a ring represented by either Q1 or Q3;
  • a 1a represents C 1 -C 6 alkyl
  • a 4 represents a nitrogen atom or CH
  • a 5 represents a nitrogen atom or CH
  • R 1 represents C 1 -C 6 alkyl
  • R 3 represents halo (C 1 -C 6 ) alkyl, halo (C 1 -C 6 ) alkylthio, halo (C 1 -C 6 ) alkylsulfinyl or halo (C 1 -C 6 ) alkylsulfonyl
  • Y2, Y3 and Y4 each independently represent a hydrogen atom, a halogen atom, halo (C 1 -C 6 ) alkyl or cyano
  • n represents an integer of 0, 1 or 2.
  • Active ingredient group BI metalaxyl-M and hymexazole.
  • Active ingredient group B-II Benomyl, thiophanate-methyl, dietofencarb, ethaboxam, zoxamide, penciclone and fluopicolide.
  • Active ingredient group B-III benzovindiflupyr, bixafen, boscalid, fluindapir, fluopyram, flutolanil, fluxapyroxad, furametopil, isoflucipram, impylfluxam, isofetamide, isopyrazam, mepronil, penflufen, pentiopyrad, sedaxane, Tifluzamide, azoxystrobin, cumoxystrobin, dimoxystrobin, enestrobine, enoxastrobin, famoxadone, phenamidon, phenaminestrobin, fluphenoxystrobin, fluoxastrobin, cresoxime-methyl, mandestrobin, metomi Nostrobin, orissastrobin, picoxystrobin, pyraclostrobin, pyramethostrobin, pyroxystrobin, pyribencarb methyl, pyrimino Thrombin, trichloride pyridinium
  • Active ingredient group B-IV mepanipyrim and kasugamycin. Active ingredient group BV: quinoxyphene and fludioxonil. Active ingredient group B-VI: iprodione and procymidone. Active ingredient group B-VII: Torquelophos-methyl and Bacillus subtilis.
  • Active ingredient group B-VIII bromconazole, cyproconazole, difenoconazole, diniconazole-M, epoxiconazole, phenarimol, fenbuconazole, fluquinconazole, hexaconazole, imazalyl, imibenconazole, ipconazole, metconazole, microbutanyl , Penconazole, prochloraz, propiconazole, prothioconazole, cimeconazole, tebuconazole, tetraconazole, triflumizole, fenpropidin, fenhexamide, fenpyrazamine, ipfentrifluconazole and mefentrifluconazole.
  • Active ingredient group B-IX Validamycin, polyoxin, polyoxin-D, benchavaricarb-isopropyl, dimethomorph, iprovaricarb and mandipropamide.
  • Active ingredient group BX fusaride, tricyclazole, carpropamide and diclocimet.
  • Active ingredient group B-XI Acibenzoral-S-methyl, probenazole, isotianil, diclobenchazox and thiazinyl.
  • Active ingredient group B-XII Bordeaux liquid, basic copper carbonate, cupric hydroxide, copper naphthenate, copper oleate, basic copper chloride, copper sulfate, basic copper sulfate, oxyquinoline copper, lime sulfur mixture, Sulfur, mancozeb, mannebu, polycarbamate, propineb, captan, phorpet, chlorothalonil, iminoctadine-albesylate and iminoctadine acetate.
  • Active ingredient group B-XIII aminopyrifen, cyflufenamide, simoxanyl, fursulfamide, fluthianyl, fosetyl-aluminum, metraphenone, oxathiapiproline, pyriophenone, picalbutradox, dipimethitrone, quinofumerin, lipopeptide, phosphorous acid, BCF- 082 (test name), NF-180 (test name), S-2399 (test name), AKD-5195 (test name) and S-2190 (test name).
  • Active ingredient group B-XIV acephate, kazusafos, chlorpyrifos, diazinon, dichlorvos, dimethoate, EPN, malathion, methamidophos, parathion-methyl, phentoate, folate, phosmet, oxime, profenofos and terbufos.
  • Active ingredient group B-XV aldicarb, benfuracarb, carbaryl, carbofuran, carbosulfan, mesomil, pirimicarb and thiodicarb.
  • Active ingredient group B-XVI Acrinatrin, bifenthrin, cyfluthrin, cypermethrin, deltamethrin, esfenvalerate, etofenprox, permethrin, teflutrin, lambda-cyhalothrin and tau-fulvalinate.
  • Active ingredient group B-XVII bensultap, cartap and thiocyclam.
  • Active ingredient group B-XVIII Acetamiprid, clothianidin, dinotefuran, flupirmine, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, sulfoxafurol, flupiradiflon, triflumezopyrim and dichloromezothiaz.
  • Active ingredient group B-XIX Spinetoram and spinosad
  • Active ingredient group B-XX Ethiprole, fipronil and brofuranilide.
  • Active ingredient group B-XXI Abamectin, emamectin benzoate, repimectin and milbemectin.
  • Active ingredient group B-XXII chlorantraniliprole, cyantraniliprole, fulvendiamide, cyclaniliprol, tetraniliprol and cyhalodiamide.
  • Active ingredient group B-XXIII diafenthiuron, fenpyroximate, pyridaben, tolfenpyrad, sienopyrafen, cyflumethofene, piflumide, hydramethylnon, acequinosyl and chlorfenapyr.
  • Active ingredient group B-XXIV benzpyrimoxane, pyriproxyfen, methoxyphenozide, diflubenzuron, flufenoxuron, lufenuron, nobarulone, teflubenzuron, buprofezin, hexathiazox and etoxazole.
  • Active ingredient group B-XXV Bacillus thuringiensis and Bacillus sphaericus.
  • Active ingredient group B-XXVI Acinonapyr, Pymetrozine, Pyrifluquinazone, Afidopyropene, Flonicamid, Spirodiclofen, Spiromesifene, Spiropidione, Spirotetramat, Indoxacarb, Metaflumizone, Siromazine, Azadilactin, Pyridalil, Bifenazate, Floxamethamide, Aldehyde, ME-5382 (test name), NA-89 (test name), NNI-1501 (test name), BAI1602 (test name), DKN-2601 (test name) and DAI-1601 (test name).
  • the condensed heterocyclic compound represented by the formula (I) is Q is a ring represented by Q1, A 4 is CH, A 5 is a nitrogen atom, R 3 is halo (C 1 -C 6 ) alkyl or halo (C 1 -C 6 ) alkylsulfinyl; Y2 and Y3 are each independently a hydrogen atom, a halogen atom or halo (C 1 -C 6 ) alkyl; Y4 is a hydrogen atom, a halogen atom or cyano, and n is 2.
  • the condensed heterocyclic compound represented by the formula (I) is Q is a ring represented by Q1, A 4 is a nitrogen atom, A 5 is CH, R 3 is halo (C 1 -C 6 ) alkyl; Y2, Y3 and Y4 are each independently a hydrogen atom or halo (C 1 -C 6 ) alkyl, and n is 2.
  • the condensed heterocyclic compound represented by the formula (I) is Q is a ring represented by Q3; R 3 is halo (C 1 -C 6 ) alkyl; Y2, Y3 and Y4 are each independently a hydrogen atom or a halogen atom, n is 2.
  • the active compound II is acetamiprid, clothianidin, imidacloprid, thiamethoxam, sulfoxafurol, spinetoram, emamectin benzoate, chlorantraniliprole, cyantraniliprole, fulvendiamide, pyridaben, cienopyrafen, chlorfenapyr, bacillus thuringiensis pyromidensis, pimetrozin
  • the composition according to any one of [1] to [4] above, which is an active compound selected from tetramat, indoxacarb, pyridalyl, bifenazate and fluxamethamide.
  • the combination ratio of active compound I and active compound II is 100: 1 to 1: 100, expressed as a weight ratio of active compound I: active compound II, according to any one of [1] to [5] above Composition.
  • the control method according to [7], wherein the active compound I according to [1] is the active compound I according to [4].
  • the combination ratio of active compound I and active compound II is 100: 1 to 1: 100, expressed as a weight ratio of active compound I: active compound II, according to any one of [7] to [11] above Control method.
  • composition of the present invention and the method of the present invention have an excellent synergistic control effect against various pests, and are also sufficiently synergistic with respect to pests that have acquired resistance to existing pest control agents. Demonstrates control effect. Therefore, the present invention provides a useful novel pest control composition and an effective pest control method using the composition and components of the composition.
  • n- means normal
  • i- means iso
  • s- means secondary
  • tert- means tertiary.
  • halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the notation “halo” also represents these halogen atoms.
  • C a -C b alkyl represents a linear or branched hydrocarbon having a carbon number of a to b, for example, methyl, ethyl, n-propyl, i Specific examples include -propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, n-hexyl, etc., each having a specified number of carbon atoms Selected.
  • halo (C a -C b ) alkyl refers to a straight chain composed of a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, or A branched hydrocarbon is represented, and when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other.
  • halo (C a -C b ) alkylthio represents the above-mentioned haloalkyl-S— consisting of a to b carbon atoms, and includes, for example, difluoromethylthio, trifluoromethylthio, Chlorodifluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, pentafluoroethyl Thio, 1,1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylthio, nonafluorobutylthio, etc. Specific examples are given, each selected
  • halo (C a -C b ) alkylsulfinyl represents the above-mentioned haloalkyl-S (O) — having from a to b carbon atoms, for example, difluoromethylsulfinyl.
  • Trifluoromethylsulfinyl Trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylsulfinyl, nonafluoro Specific examples include butylsulfinyl and the like, each selected within the range of the designated number of carbon atoms.
  • halo (C a -C b ) alkylsulfonyl represents the above-mentioned haloalkyl-SO 2 — having a carbon number of a to b, such as difluoromethylsulfonyl, tri Fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2-chloro-1,1,2-trifluoro Specific examples include ethylsulfonyl and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylcarbonyl represents alkyl-C (O) — having the above-mentioned meanings consisting of a to b carbon atoms, such as acetyl, propionyl, pivaloyl, etc. Are given as specific examples and are selected within the range of each designated number of carbon atoms.
  • the condensed heterocyclic compound represented by the formula (1) is also referred to as “compound (1)”, and “the compound represented by the formula (1-Q1)” is “compound (1)”. -Q1) ".
  • the other compounds are similarly described.
  • Compound (1) contained in the active compound I which is the first active ingredient of the composition of the present invention will be described in detail below.
  • Compound (1) includes an optically active substance resulting from the presence of one or more asymmetric carbon atoms or an asymmetric sulfur atom, but the present invention includes all optically active substances or racemates. .
  • those which can be converted into acid addition salts according to a conventional method are, for example, hydrohalic acid salts such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, nitric acid , Inorganic acid salts such as sulfuric acid, phosphoric acid, chloric acid, perchloric acid, sulfonic acid salts such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, formic acid, Acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid and other salts of carboxylic acids or glutamic acid, It can be a salt
  • N-oxide is a compound in which a nitrogen atom constituting a ring on a heterocyclic ring is oxidized.
  • heterocyclic ring that can form an N-oxide include condensed rings including a pyridine ring.
  • the compound (1) contained in the active compound I which is the first active ingredient of the composition of the present invention can be produced, for example, by the following production methods 1 to 8.
  • a compound (1-Q1-b) in which Q is Q1 and n is an integer of 0 and a compound (1-Q1-b1) in which Q is Q1 and n is an integer of 1 or 2 a) can be produced, for example, by the following production method. (Wherein R 1 , R 3 , A 4 , A 5 , A 1a , Y 2, Y 3 and Y 4 represent the same meaning as described above, and m represents 1 or 2).
  • Step 1 Compound (2-Q1-b) is obtained by dehydrating and condensing compound (30) and compound (31-1-b) in the presence of a base (eg, pyridine, triethylamine, potassium carbonate, cesium carbonate, etc.).
  • a base eg, pyridine, triethylamine, potassium carbonate, cesium carbonate, etc.
  • 1H-benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate, N, N′-dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, etc.] Can be produced by reacting with each other.
  • Step 2 Compound (1-Q1-b) is prepared in the presence of an acid (eg, paratoluenesulfonic acid, polyphosphoric acid, acetic acid, propionic acid, etc.) or a dehydrating agent (eg, phosphorus oxychloride, acetic anhydride, etc.) It can be produced by subjecting 2-Q1-b) to a dehydration cyclization reaction.
  • an acid eg, paratoluenesulfonic acid, polyphosphoric acid, acetic acid, propionic acid, etc.
  • a dehydrating agent eg, phosphorus oxychloride, acetic anhydride, etc.
  • Step 3 Compound (1-Q1-a) is an oxidizing agent [for example, peracid such as metachloroperbenzoic acid, peracetic acid, hydrogen peroxide, OXONE, trade name of EI Dupont; potassium peroxosulfate
  • peracid such as metachloroperbenzoic acid, peracetic acid, hydrogen peroxide, OXONE, trade name of EI Dupont
  • potassium peroxosulfate The compound (1-Q1-b) can be produced by oxidation using the In some cases, a catalyst (such as sodium tungstate) can be used.
  • the compound (1-Q1) in which Q is Q1 can be produced by the following production method.
  • R 1 , R 3 , A 4 , A 5 , A 1a , Y 2, Y 3, Y 4 and n represent the same meaning as described above, and J represents a leaving group such as a halogen atom.
  • Step 1 Compound (2-Q1) is produced by reacting Compound (30) with Compound (31) in the presence of a base (for example, pyridine, triethylamine, sodium hydrogen carbonate, potassium carbonate, cesium carbonate, etc.). be able to.
  • a base for example, pyridine, triethylamine, sodium hydrogen carbonate, potassium carbonate, cesium carbonate, etc.
  • Some of the compounds (30) are known compounds, and some of them are available as commercial products.
  • Step 2 Compound (1-Q1) can be produced by a method analogous to production method 1, step 2.
  • compound (1-Q1-a) and compound (1-Q1-b) can be produced by the following production method.
  • R 1 , R 3 , A 4 , A 5 , A 1a , Y 2, Y 3, Y 4 and m represent the same meaning as described above, and X 1 represents a halogen atom.
  • Step 1 Compound (4) can be produced by reacting Compound (9) with Compound (34) under heating conditions according to the method described in International Publication No. 2007/148755.
  • a base for example, pyridine, triethylamine, potassium carbonate, cesium carbonate, etc.
  • Some of the compounds (34) are known compounds, and some of them can be obtained as commercial products.
  • Step 2 Of compound (1), compound (1-Q1-b) is a halogenating agent (for example, chlorine, bromine, iodine, iodine monochloride, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, Compound (4) and compound in the presence of 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, etc. (50) or by reacting with compound (59). Some of compound (50) and compound (59) are known compounds, and some of them are commercially available.
  • Step 3 Compound (1-Q1-a) can be produced by a method analogous to step 3 of Production Method 1.
  • compound (1-Q1-a) and compound (1-Q1-b) can be produced by the following production method. (In the formula, R 1 , R 3 , A 4 , A 5 , A 1a , Y 2, Y 3, Y 4, m, and X 1 represent the same meaning as described above.)
  • Step 1 Compound (1-Q1-b) can be produced by reacting compound (5) with compound (34) by a method analogous to production method 3, step 1. Some of the compounds (34) are known compounds, and some of them can be obtained as commercial products.
  • Step 2 Compound (1-Q1-a) can be produced by a method analogous to Production Method 1, Step 3.
  • Step 1 Compound (6-2) can be obtained according to Organic Letters 2007, 9, 3687, Tetrahedron 1998, 44, 1187, International Publication No. 2011/159839, etc.
  • the compound (6-1) produced according to the method described in Production Method 2 and a thiolating agent (for example, 2-ethylhexyl 3-mercaptopropionate, sodium hydrogen sulfide, sodium sulfide, etc.) Can be made to react.
  • Step 2 Compound (1-Q1-d) is prepared according to the method described in International Publication No. 2013/043962, International Publication No. 2013/040863, International Publication No. 2012/082566, etc.
  • Step 3 Compound (1-Q1-c) can be produced by a method according to Step 3 of Production Method 1.
  • compound (1-Q1) can be produced, for example, by reacting compound (8-1) with compound (35).
  • R 1 , R 3 , A 4 , A 5 , A 1a , Y 2, Y 3 and Y 4 represent the same meaning as described above, and R 10 represents C 1 -C 6 alkylcarbonyl.
  • Compound (1-Q1) is prepared according to the method described in Organic Letters 2013, Vol. 15, page 6254, oxygen and a copper catalyst [for example, copper chloride (I), copper bromide (I), By reacting compound (8-1) with compound (35) in the presence of copper (I) iodide, copper (I) oxide, copper (II) chloride, copper (II) trifluoromethanesulfonate, etc.] Can be manufactured. In some cases, an acylating agent (for example, acetic anhydride, propionic anhydride, isobutyric anhydride, pivalic anhydride, etc.) may be used.
  • the compound (8-1) includes E-form, Z-form or a mixture containing E-form and Z-form in an arbitrary ratio. Some of the compounds (35) are known compounds, and some of them can be obtained as commercial products.
  • the compound (1-Q1-e) can be produced, for example, by the following production method. (Wherein R 1 , R 3 , A 4 , A 5 , A 1a , Y 2, n and X 2 represent the same meaning as described above, and R 10 and R 11 are each independently C 1 -C 6 alkyl. Represents carbonyl.)
  • Step 1 Compound (7-1) is prepared by reacting oxygen, a copper catalyst [for example, copper chloride (I), copper bromide (I), copper iodide (I), copper oxide (I), copper chloride (II), trifluoro
  • a copper catalyst for example, copper chloride (I), copper bromide (I), copper iodide (I), copper oxide (I), copper chloride (II), trifluoro
  • an acylating agent for example, acetic anhydride, propionic anhydride, isobutyric anhydride, pivalic anhydride, etc.
  • compound (8-1) and compound (35- It can be produced by reacting with 2).
  • the compound (8-1) includes E-form, Z-form or a mixture containing E-form and Z-form in an arbitrary ratio.
  • Step 2 Compound (7-2) can be produced by hydrolyzing Compound (7-1) in the presence of an acid (eg, acetic acid, hydrochloric acid, sulfuric acid, etc.). In some cases, the acid may be used as a solvent.
  • an acid eg, acetic acid, hydrochloric acid, sulfuric acid, etc.
  • the acid may be used as a solvent.
  • Step 3 A halogenating agent (for example, chlorine, bromine, iodine, iodine monochloride) according to the method described in The Journal of Organic Chemistry, 1965, 30, 1101, etc.
  • Compound (7-3) can be produced by reacting compound (7-2) with 5-dimethylhydantoin or the like.
  • Step 4 Compound (1-Q1-e) is an acid (for example, acetic acid, hydrochloric acid, sulfuric acid, etc.) according to the method described in Russian Chemical Bulletin 2004, 53, 471. It can be produced by reacting nitrite (for example, sodium nitrite) with compound (7-3) in the presence.
  • nitrite for example, sodium nitrite
  • copper catalyst eg, copper (I) chloride, copper bromide (I), copper iodide (I), copper oxide (I), copper chloride (II), copper trifluoromethanesulfonate (II), etc.
  • a compound (1-Q2-a) in which Q is Q2 and n is an integer of 1 or 2 and a compound (1-Q2- in which Q is Q2 and n is 0) b) can be produced, for example, by the following production method. (Wherein R 1 , R 3 , Y 2, Y 3 , Y 4, n and X 1 represent the same meaning as described above.)
  • Step 1 Compound (33-2) can be produced by reacting compound (33-1) with sodium azide according to a known method.
  • Step 2 Compound (3) is prepared from a base (for example, pyridine, triethylamine, sodium hydrogen carbonate, potassium carbonate, cesium carbonate, etc.) and a Lewis acid (for example, titanium tetrachloride) according to the method described in International Publication No. 2012/066061. Etc.) in the presence of the compound (33-2) and the compound (32).
  • Compound (3) includes E-form, Z-form, or a mixture containing E-form and Z-form in an arbitrary ratio.
  • Step 3 Compound (1-Q2-b) can be produced by cyclizing compound (3) according to the method described in International Publication No. 2012/066061.
  • Step 4 Compound (1-Q2-a) can be produced by a method analogous to production method 1, step 3.
  • Compound (31-1-b) used in Production Method 1 can be produced, for example, according to the following production method.
  • [Reaction Formula 1] (In the formula, R 1 , Y 2, Y 3, Y 4 and X 1 represent the same meaning as described above, R a represents C 1 -C 6 alkyl, and L 1 represents a halogen atom.)
  • Step 1 Compound (42) is obtained by reacting Compound (34) with Compound (57) under heating conditions according to the methods described in International Publication No. 2013/087772, International Publication No. 2012/096929, etc. Can be manufactured. Some of the compound (34) and the compound (57) are known compounds, and some of them are commercially available.
  • Step 2 Compound (42) and a halogenating agent (for example, chlorine, bromine, iodine) according to the method described in International Publication No. 2010/033978, International Publication No. 2011/075643, International Publication No. 2007/0875548, etc.
  • a halogenating agent for example, chlorine, bromine, iodine
  • N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5, Compound (43) can be produced by reacting with 5-dimethylhydantoin or the like.
  • Step 3 In accordance with the method described in Organic Letters 2007, Vol. 9, p. 3687, etc., a palladium catalyst [for example, palladium-carbon, palladium (II) chloride, palladium (II) acetate, bis (tri Phenylphosphine) palladium (II) dichloride, tetrakis (triphenylphosphine) palladium (0), bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0) etc.] and a base (eg pyridine, Compound (31-2-b) can be produced by reacting compound (43) with compound (50) in the presence of triethylamine, sodium hydrogen carbonate, potassium carbonate, cesium carbonate or the like.
  • a palladium catalyst for example, palladium-carbon, palladium (II) chloride, palladium (II) acetate, bis (tri Phenylpho
  • Step 4 Compound (31-1-b) can be produced by hydrolyzing compound (31-2-b) according to a known method.
  • the above compound (31-2-b) can also be produced, for example, by the following method.
  • [Reaction Formula 2] (In the formula, R 1 , Y 2, Y 3, Y 4 and R a represent the same meaning as described above.)
  • Compound (31-2-b) can be produced by reacting compound (42) with compound (50) or compound (59) according to the method described in Step 2 of Production Method 3.
  • compound (31-a) wherein n is 1 or 2 can be produced, for example, according to the following production method.
  • reaction Formula 3 (Wherein R 1 , Y 2, Y 3, Y 4, m, R a and J represent the same meaning as described above).
  • Step 1 Compound (31-2-a) can be produced by oxidizing compound (31-2-b) according to the method described in Production Method 1.
  • Step 2 Compound (31-1-a) can be produced by hydrolyzing compound (31-2-a) according to a known method.
  • Step 3 According to a known method, compound (31-1-a) and a halogenating agent (for example, hydrogen fluoride, potassium fluorinated, oxalyl dichloride, thionyl chloride, phosphorus oxychloride, phosphorus oxybromide, bromide)
  • a halogenating agent for example, hydrogen fluoride, potassium fluorinated, oxalyl dichloride, thionyl chloride, phosphorus oxychloride, phosphorus oxybromide, bromide
  • Compound (31-a) can be produced by reacting with acetyl and the like.
  • compound (31-b) in which n is 0 can be produced, for example, according to the following production method.
  • Reaction Formula 4 (In the formula, R 1 , Y 2, Y 3, Y 4 and J represent the same meaning as described above.)
  • Compound (31-b) can be produced by reacting compound (31-1-b) according to the method described in the step of Reaction Scheme 3.
  • Compound (9) used in production method 3 can be produced, for example, according to the production route represented by the following reaction formula.
  • reaction Formula 5 In the formula, R 3 , A 4 , A 5 , A 1a , X 1 and J represent the same meaning as described above.
  • Step 1 Compound (30) and Compound (52) are condensed according to a known method, then Synthesis 1991, page 465, Bioorganic & Medicinal Chemistry Letters ) Deacetylation reaction according to the method described in 2011, Vol. 21, p. 4602, etc., followed by dehydration cyclization reaction according to the method described in Step 2 of the above production method 1, thereby yielding a compound ( 38) can be produced.
  • Some of the compounds (52) are known compounds, and some of them can be obtained as commercial products.
  • Step 2 Compound (39) is produced by oxidizing compound (38) according to the method described in Journal of Medicinal Chemistry 1982, Vol. 25, page 1342, etc. Can do.
  • Step 3 Compound (9) comprises compound (39) and a halogenating agent (for example, chlorine, bromine, iodine, iodine monochloride, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro- 5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, trimethylphenylammonium tribromide, hydrobromic acid, acetic acid solution of hydrogen bromide Etc.) can be reacted.
  • a halogenating agent for example, chlorine, bromine, iodine, iodine monochloride, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro- 5,5-di
  • additives such as hydrobromic acid and acetic acid solution of hydrogen bromide may be used.
  • This step is produced by reacting compound (39) in the presence of a silylating agent (for example, trimethylsilyl trifluoromethanesulfonate) and a base (for example, pyridine, triethylamine, sodium bicarbonate, potassium carbonate, cesium carbonate, etc.).
  • a silylating agent for example, trimethylsilyl trifluoromethanesulfonate
  • a base for example, pyridine, triethylamine, sodium bicarbonate, potassium carbonate, cesium carbonate, etc.
  • the silylated compound (39) may be directly reacted with a halogenating agent without isolation / purification.
  • the compound (52) and the compound (38) have optically active substances resulting from the presence of one asymmetric carbon, they include all optically active substances and racemates.
  • Compound (5) used in production method 4 can be produced, for example, according to the production route represented by the following reaction formula.
  • reaction Scheme 6 (Wherein R 1 , R 3 , A 4 , A 5 , A 1a and X 1 represent the same meaning as described above, X 3 represents a halogen atom, and W 1 represents a hydrogen atom, a sodium atom or a potassium atom. .)
  • Step 1 Compound (10) can be produced by reacting compound (9) with compound (51) according to a known method.
  • a base for example, pyridine, triethylamine, sodium hydrogen carbonate, potassium carbonate, cesium carbonate, etc.
  • Some of the compounds (51) are known compounds, and some of them are available as commercial products.
  • Step 2 Compound (5) can be produced by reacting Compound (10) according to the method described in Step 3 of Reaction Scheme 5.
  • reaction Scheme 7 (Wherein R 1 , R 3 , A 4 , A 5 , A 1a , m, R 10 and X 1 represent the same meaning as described above.)
  • Step 1 Compound (54) is prepared by reacting Compound (55) and Compound (56) in the presence of a base (for example, pyridine, triethylamine, sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium hydroxide, cesium carbonate, etc.). It can be produced by reacting. Some of the compound (55) and the compound (56) are known compounds, and some of them are commercially available.
  • Step 2 Compound (40-1) can be produced by performing a dehydration condensation reaction between Compound (30) and Compound (54) in the presence of an acid (for example, acetic acid, hydrochloric acid, sulfuric acid, etc.).
  • an acid for example, acetic acid, hydrochloric acid, sulfuric acid, etc.
  • a dehydrating agent for example, anhydrous magnesium sulfate, anhydrous sodium sulfate, molecular sieve, silica gel, etc.
  • the amount of the dehydrating agent used can be 0.1 to 100 parts by weight, preferably 0.1 to 20 parts by weight, based on the compound (30).
  • Step 3 Compound (41-1) can be produced by reacting compound (40-1) according to the method described in Step 2 of Production Method 1.
  • Step 4 Compound (8-2-a) can be produced by oxidizing compound (41-1) according to the method described in Step 3 of Production Method 1.
  • Step 5 Compound (8-1-a) is prepared in the presence of a base (eg, pyridine, triethylamine, sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium hydroxide, cesium carbonate, etc.) ) And an acylating agent (for example, acetyl chloride, propionyl chloride, isobutyryl chloride, pivaloyl chloride, acetic anhydride, propionic anhydride, isobutyric anhydride, pivalic anhydride, etc.) be able to.
  • Compound (55), Compound (54), Compound (40-1) and Compound (41-1) have optically active substances resulting from the presence of one asymmetric carbon. Body and racemate.
  • the compound (8-2-a) and the compound (8-1-a) include E-form, Z-form, or a mixture containing E-form and Z-form in an arbitrary ratio.
  • Step 1 Compound (8-2-b) is prepared from a base (for example, pyridine, triethylamine, sodium bicarbonate, sodium hydroxide) according to the method described in International Publication No. 2001/83479, Japanese Patent No. 4237497, etc. In the presence of potassium carbonate, potassium hydroxide, cesium carbonate, etc.), hydroxylamine or a salt thereof (for example, hydrochloride, sulfate) and compound (10) produced by the method described in Reaction Scheme 6, Step 1 It can be produced by reacting.
  • Step 2 Compound (8-2-a) can be produced by oxidizing compound (8-2-b) according to the method described in Step 3 of Production Method 1.
  • Step 3 Compound (8-1-a) can be synthesized by acylating compound (8-2-a) according to the method described in Step 5 of Reaction Scheme 7.
  • the compound (8-2-b), the compound (8-2-a) and the compound (8-1-a) include E-form, Z-form or a mixture containing E-form and Z-form in an arbitrary ratio. .
  • Reaction Scheme 9 (In the formula, R 1 , R 3 , A 4 , A 5 , A 1a , R 11 and J have the same meaning as described above.)
  • Step 1 A compound produced by the method according to Step 1 of Reaction Scheme 7 in the presence of a base (for example, pyridine, triethylamine, sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium hydroxide, cesium carbonate, etc.) ( 54) and an acylating agent (for example, acetyl chloride, propionyl chloride, isobutyryl chloride, pivaloyl chloride, acetic anhydride, propionic anhydride, isobutyric anhydride, pivalic anhydride, etc.) in a known manner.
  • the compound (60) can be produced by reacting accordingly.
  • Step 2 Compound (40-2) can be produced by subjecting Compound (30) and Compound (60) to a condensation reaction according to the method described in Step 2 of Reaction Scheme 7.
  • Step 3 Compound (41-2) can be produced by subjecting compound (40-2) to a dehydration cyclization reaction according to the method described in Step 2 of Production Method 1.
  • Step 4 Compound (41-1) can be produced by subjecting compound (41-2) to a deacylation reaction according to the method described in Step 2 of Production Method 7.
  • Compound (54), Compound (60), Compound (40-2), Compound (41-2) and Compound (41-1) above have optically active substances resulting from the presence of one asymmetric carbon. However, all optically active forms and racemates are included.
  • Compound (32) used in production method 8 can be produced, for example, according to the production route represented by the following reaction formula.
  • reaction Formula 10 (Wherein R 1 , Y2, Y3 and Y4 represent the same meaning as described above, and R b represents C 1 -C 6 alkyl)
  • Step 1 Compound (44) is compound (31-1-b), which can be produced according to Reaction Scheme 1, in the presence of an alcohol (eg, methanol, ethanol, propanol, tertiary butanol, etc.) in the presence of diphenylphosphoryl azide ( It can be produced by reacting with (DPPA).
  • Step 2 Compound (32) is prepared from Compound (44) in the presence of an acid (for example, hydrochloric acid, sulfuric acid, etc.) according to the methods described in International Publication Nos. 2012/174312 and 2003/018021. It can be produced by hydrolysis.
  • an alcohol eg, methanol, ethanol, propanol, tertiary butanol, etc.
  • diphenylphosphoryl azide It can be produced by reacting with (DPPA).
  • Step 2 Compound (32) is prepared from Compound (44) in the presence of an acid (for example, hydrochloric acid, sulfuric acid, etc.) according to the methods described in International Public
  • reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, washed with water, poured into ice water, or concentrated after extraction with an organic solvent. To obtain the desired compound. Moreover, when the necessity for purification arises, it can be separated and purified by a purification method such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatographic fractionation or the like.
  • Step 1 2- [3- (Ethylthio) -6- (trifluoromethyl) imidazo [1,2-a] pyridine-2- Yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine Synthesis N 2 -methyl-5- (trifluoromethyl) pyridine-2,3-diamine 191 mg, 3 To a mixed solution of 291 mg of-(ethylthio) -6- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylic acid, 40 mg of 4- (dimethylamino) pyridine and 10 ml of pyridine at room temperature 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 384 mg was added.
  • Step 2 2- [3- (Ethylsulfonyl) -6- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo Synthesis of [4,5-b] pyridine (Compound No. 1-004)
  • Tokyo metachloroperbenzoic acid
  • Tokyo metachloroperbenzoic acid
  • Step 1 2- [3- (Ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2- Synthesis of Nyl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c] pyridine 303 mg of N 3 -methyl-6- (trifluoromethyl) pyridine-3,4-diamine and pyridine To 15 ml of the mixed solution at room temperature, 552 mg of 3- (ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylic acid and 1-ethyl-3- (3-dimethyla 732 mg of minopropyl) carbodiimide hydrochloride was added.
  • Step 2 2- [3- (Ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo Synthesis of [4,5-c] pyridine (Compound No. 2-001)
  • 323 mg of 65 wt% metachloroperbenzoic acid was added under ice cooling. did. After the addition was complete, the mixture was stirred at room temperature for 1 hour.
  • Step 2 3- (Ethylthio) -6-iodo-2- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] imidazo [1,2- a] Synthesis of pyridine-8-carbonitrile To a mixed solution of 337 mg of the white solid obtained in Step 1 and 5 ml of 1,2-dichloroethane, 264 mg of diethyl disulfide and 192 mg of N-chlorosuccinimide were sequentially added at room temperature. After the addition was complete, the mixture was stirred for 1.5 hours under heating to reflux.
  • the obtained organic layer was washed with 10 ml of a 1 mol / L sodium hydroxide aqueous solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • Step 3 3- (Ethylsulfonyl) -6-iodo-2- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] imidazo [1,2 -A] Synthesis of pyridine-8-carbonitrile (Compound No. 1-007) To a mixed solution of 182 mg of the white solid obtained in Step 2 and 5 ml of chloroform, 201 mg of 65 wt% metachloroperbenzoic acid was added under ice cooling. Added. After the addition was complete, the mixture was stirred at room temperature for 4 hours.
  • Step 1 2- [3- (Ethylthio) -6-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6 Synthesis of-(trifluoromethyl) -3H-imidazo [4,5-b] pyridine 2-Bromo-2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4 , 5-b] pyridin-2-yl] ethane-1-one and a mixed solution of 25 ml of acetonitrile at room temperature were added 3.17 g of 5-iodopyridin-2-amine. After the addition was complete, the mixture was stirred for 7 hours under heating to reflux.
  • Step 2 2- [3- (Ethylsulfonyl) -6-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5 -B] Synthesis of Pyridine (Compound No. 1-003) 1.29 g of 65 wt% metachloroperbenzoic acid was added to a mixed solution of 1.36 g of the light brown solid obtained in Step 1 and 10 ml of chloroform under ice cooling. Added. After the addition was complete, the mixture was stirred at room temperature for 2 hours.
  • Step 1 2- [3- (Ethylthio) -7-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6 Synthesis of-(trifluoromethyl) -3H-imidazo [4,5-b] pyridine 2-Bromo-2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4 , 5-b] pyridin-2-yl] ethane-1-one and 1.7 ml of 4-iodo-2-aminopyridine were added at room temperature to a mixed solution of 3.0 g of acetonitrile and 26 ml of acetonitrile.
  • Step 2 2- [3- (Ethylsulfonyl) -7-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5 -B] Synthesis of pyridine (Compound No. 1-006) To a mixed solution of 1.56 g of the light brown solid obtained in Step 1 and 10 ml of chloroform, 1.73 g of 65 wt% metachloroperbenzoic acid was added under ice cooling. Added. After the addition was complete, the reaction mixture was stirred at room temperature for 3 hours.
  • Step 1 2- [7-Chloro-3- (ethylthio) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6 Synthesis of-(trifluoromethyl) -3H-imidazo [4,5-b] pyridine 2-Bromo-2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4 , 5-b] pyridin-2-yl] ethane-1-one (828 mg) and acetonitrile (7 ml) were mixed with 4-chloropyridin-2-amine (334 mg) at room temperature. After the addition was complete, the mixture was stirred for 5 hours under heating to reflux.
  • Step 2 2- [7-Chloro-3- (ethylsulfonyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5 -B] Synthesis of pyridine (Compound No. 1-005) To a mixed solution of 4.18 g of the yellow solid synthesized by the method of Step 1 and 20 ml of chloroform, 6.20 g of 65 wt% metachloroperbenzoic acid was added under ice cooling. Was added. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour.
  • Step 2 2- [3- (Ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -6-iodo-3-methyl-3H-imidazo [4,5- b] Synthesis of pyridine
  • a mixed solution of 2.49 g of the gray solid obtained in Step 1 and 15 ml of acetic acid was stirred for 3.5 hours under heating to reflux. After completion of the reaction, water was added to the reaction mixture. The precipitated solid was filtered, and the obtained solid was washed with n-hexane to obtain 2.02 g of the desired product as a brown solid.
  • Step 3 2-ethylhexyl 3-[(2- [3- (ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-3H-imidazo Synthesis of [4,5-b] pyridin-6-yl) thio] propanoate
  • 387 mg of diisopropylethylamine, 4,5 -58 mg of bis (diphenylphosphino) -9,9-dimethylxanthene, 92 mg of tris (dibenzylideneacetone) dipalladium (0) and 262 mg of 2-ethylhexyl 3-mercaptopropionate were sequentially added.
  • Step 4 2- [3- (Ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6-[(trifluoromethyl) thio] -3H -Synthesis of imidazo [4,5-b] pyridine Under a nitrogen atmosphere, 159 mg of potassium tert-butoxide was added to a mixed solution of 560 mg of the yellow solid obtained in Step 3 and 5 ml of tetrahydrofuran under ice cooling. After completion of the addition, the mixture was stirred for 30 minutes under ice cooling.
  • Step 5 2- [3- (Ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6-[(trifluoromethyl) thio]- Synthesis of 3H-imidazo [4,5-b] pyridine
  • 38 mg of 65 wt% metachloroperbenzoic acid was added under ice cooling. After the addition was complete, the mixture was stirred at room temperature for 2 hours.
  • Step 6 2- [3- (Ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6-[(trifluoromethyl) sulfinyl]- Synthesis of 3H-imidazo [4,5-b] pyridine (Compound No. 1-009)
  • a white solid synthesized by the method of Step 5 and 5 ml of chloroform 65 wt% metachloroperoxide was added under ice cooling. 43 mg of benzoic acid was added. After the addition was complete, the mixture was stirred at room temperature for 24 hours.
  • the reaction mixture was filtered through celite, and the celite was washed with 100 ml of ethyl acetate.
  • the obtained filtrate and washing solution were combined and the solvent was distilled off under reduced pressure.
  • 30 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (30 ml ⁇ 3).
  • the obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • Step 1 N- [3- (Ethylsulfonyl) -2- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5 Synthesis of -b] pyridin-2-yl) imidazo [1,2-a] pyridin-8-yl] acetamide (Z) -2- (ethylsulfonyl) -1- [3-methyl-6- (trifluoromethyl ) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one O-acetyl oxime 90 mg, 3-aminopyridine 70 mg, copper trifluoromethanesulfonate (II) 30 mg and N-methylpyro In a mixed solution of Don 1 ml, at room temperature, it was added acetic anhydride 70 mg.
  • Step 2 3- (Ethylsulfonyl) -2- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] imidazo [1,2-a] pyridine Synthesis of -8-amine
  • 3.72 g of trifluoroacetic acid was added at room temperature. After the addition was complete, the mixture was stirred at room temperature for 1 hour. Thereafter, 1.49 g of trifluoroacetic acid was added to the reaction mixture, and the reaction mixture was stirred at room temperature for 1 hour.
  • Step 3 3- (Ethylsulfonyl) -7-iodo-2- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] imidazo [1,2 -A] Synthesis of Pyridin-8-amine To a mixed solution of 1.27 g of the yellow resinous substance obtained in Step 2 and 50 ml of N, N-dimethylformamide at room temperature, 1,3-diiodo-5,5- 494 mg of dimethylhydantoin was added. After the addition was complete, the mixture was stirred at room temperature for 3 hours.
  • Step 4 2- [3- (Ethylsulfonyl) -7-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5 -B] Synthesis of pyridine (Compound No. 1-006)
  • a mixed solution of 80 mg of the yellow solid obtained in Step 3 3 ml of ethanol and 0.5 ml of acetic acid, 46 mg of copper (I) oxide and sodium nitrite at room temperature. 100 mg water 0.5 ml solution was added sequentially. After the addition was complete, the mixture was stirred at room temperature for 17 hours.
  • Step 2 2- [6-Bromo-3- (ethylthio) imidazo [1,2-a] pyridin-2-yl] -6- (trifluoromethyl) -2H-pyrazolo [4,3-c] pyridine Synthesis A mixture of 400 mg of white solid obtained in Step 1, 6-bromo-3- (ethylthio) imidazo [1,2-a] pyridin-2-amine 503 mg and dichloromethane 10 ml is mixed with 562 mg of triethylamine under ice cooling. Then, 1.11 ml of a dichloromethane solution (manufactured by Tokyo Chemical Industry Co., Ltd.) of about 1 mol / L titanium chloride (IV) was sequentially added.
  • a dichloromethane solution manufactured by Tokyo Chemical Industry Co., Ltd.
  • reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was filtered through celite, and the celite was washed with 30 ml of xylene. The obtained washing liquid was stirred for 3 hours under heating to reflux. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with chloroform (30 ml ⁇ 2). The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • Step 3 2- [6-Bromo-3- (ethylsulfonyl) imidazo [1,2-a] pyridin-2-yl] -6- (trifluoromethyl) -2H-pyrazolo [4,3-c] pyridine Synthesis of (Compound No. 3-001)
  • 483 mg of 65 wt% metachloroperbenzoic acid was added under ice cooling. After the addition was complete, the mixture was stirred at room temperature overnight. After completion of the reaction, a saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml ⁇ 2).
  • the obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution.
  • the organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • Step 2 Synthesis of ethyl 3-iodo-7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylate 3.73 g of yellow solid obtained in Step 1 and 20 ml of N, N-dimethylformamide 6.5 g of N-iodosuccinimide was added to the mixed solution at room temperature. After the addition was complete, the mixture was stirred at 80 ° C. for 5 hours. After completion of the reaction, water was added to the reaction mixture, and the precipitated solid was filtered. The obtained solid was dissolved in 20 ml of chloroform, and washed with a saturated aqueous sodium thiosulfate solution and then with saturated sodium hydrogen carbonate.
  • Step 3 Synthesis of ethyl 3- (ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylate 5.73 g of light orange solid obtained in Step 2 and 1,4- To a solution of 40 ml of dioxane, 5.79 g of diisopropylethylamine, 862 mg of 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene, 682 mg of tris (dibenzylideneacetone) dipalladium (0) and ethanethiol at room temperature 1.85 g was added sequentially.
  • the inside of the reaction vessel was replaced with nitrogen gas, and then stirred for 2 hours under heating and reflux.
  • the reaction mixture was filtered through celite, and the celite was washed with 30 ml of chloroform.
  • the obtained filtrate and washing solution were combined and the solvent was distilled off under reduced pressure.
  • Step 4 Synthesis of 3- (ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylic acid 5.58 g of the brown solid obtained in Step 3, 60 ml of ethanol and 30 ml of tetrahydrofuran To the mixed solution, 10 ml of 3 mol / L aqueous sodium hydroxide solution was added at room temperature. After the addition was complete, the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure.
  • Step 2 Synthesis of 3- (ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylic acid 7.07 g of yellow solid obtained in Step 1, ethanol 40 ml and tetrahydrofuran 40 ml 10 ml of a 4 mol / L aqueous sodium hydroxide solution was added to the mixed solution at room temperature. After the addition was complete, the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. 1 mol / L hydrochloric acid was added to the obtained residue to adjust the pH of the aqueous layer to 2, followed by extraction with chloroform (20 ml ⁇ 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 6.43 g of the desired product as a white solid. Melting point: 158-160 ° C
  • Step 3 Synthesis of 3- (ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylic acid chloride Mixing 5.36 g of the white solid obtained in Step 2 and 110 ml of dichloromethane To the solution, 5.28 g of oxalyl dichloride and 30 mg of N, N-dimethylformamide were sequentially added under ice cooling. After the addition was complete, the mixture was stirred at room temperature for 3 hours. After completion of the stirring, the solvent was distilled off from the reaction mixture under reduced pressure. The precipitated solid was added with 20 ml of n-hexane and filtered to obtain 5.22 g of the desired product as a white solid. Melting point: 171-175 ° C
  • Step 2 Synthesis of 1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one Black solid 48 obtained in Step 1
  • a mixed solution of .3 g and 200 ml of acetic acid was heated to 90 ° C., and 14.8 g of chromium (VI) oxide dissolved in 50 ml of water was added. After the addition was complete, the mixture was stirred for 1.5 hours under heating to reflux. Thereafter, 5 g of chromium (VI) oxide dissolved in 10 ml of water was added to the reaction mixture at 90 ° C., and the reaction mixture was stirred for 1.5 hours under heating to reflux.
  • Step 3 Synthesis of 2-bromo-1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethan-1-one obtained in Step 2
  • 17.2 g of triethylamine and 180 ml of dichloromethane 17.2 g of trimethylsilyl trifluoromethanesulfonate was added under ice cooling. After completion of the addition, the mixture was stirred for 1 hour under ice cooling. After completion of the stirring, 28.7 g of trimethylphenylammonium tribromide was added to the reaction mixture under ice cooling.
  • Step 2 of 2-bromo-2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one Synthesis 8.8 g of trimethylsilyl trifluoromethanesulfonate was added to a mixed solution of 11.4 g of the pale yellow solid obtained in Step 1, 4.2 g of triethylamine and 100 ml of dichloromethane at ⁇ 20 ° C. After completion of the addition, the reaction mixture was stirred for 20 minutes under ice cooling. After stirring, the reaction mixture was cooled to ⁇ 20 ° C.
  • Step 2 Synthesis of (R) -2-amino-3- (ethylthio) -N- [2- (methylamino) -5- (trifluoromethyl) pyridin-3-yl] propanamide N 2 -Methyl-5
  • 50 mg of magnesium sulfate was added at room temperature. After the addition was complete, the mixture was heated to 110 ° C. and 551 mg of sulfuric acid was added. After the addition was complete, the mixture was stirred at 110 ° C.
  • Step 4 Synthesis of 2- (ethylsulfonyl) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one oxime
  • 43 mg of sodium tungstate dihydrate and 372 mg of 30 wt% hydrogen peroxide solution were sequentially added at room temperature. After the addition was complete, the reaction mixture was stirred at 50 ° C. for 3 hours.
  • the obtained target product was a mixture of two geometric isomers derived from the oxime structure, and the geometric isomer ratio was 99: 1 (geometric isomer A: geometric isomer B).
  • the geometric isomer ratio was calculated from the integrated value of the 1 H-NMR spectrum signal of the geometric isomer mixture.
  • Step 5 (Z) -2- (Ethylsulfonyl) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one Synthesis of O-acetyl oxime
  • 101 mg of triethylamine and 51 mg of acetic anhydride were sequentially added at room temperature. After the addition was complete, the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with dichloromethane (20 ml).
  • the obtained target product was a mixture of two geometric isomers derived from the oxime structure, and the geometric isomer ratio was 6: 4 (geometric isomer A: geometric isomer B).
  • the geometric isomer ratio was calculated from the integrated value of the 1 H-NMR spectrum signal of the geometric isomer mixture.
  • Step 2 Synthesis of 2- (ethylsulfonyl) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one oxime
  • a mixed solution of 1.15 g of the white solid obtained in 1 and 20 ml of dichloromethane 1.8 g of 65 wt% metachloroperbenzoic acid was added under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 4 hours. After completion of the reaction, 20 ml of a saturated aqueous sodium thiosulfate solution was added to the reaction mixture, followed by extraction with chloroform (20 ml ⁇ 2).
  • the obtained organic layer was washed with a saturated aqueous solution of sodium bicarbonate, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product of the intended product.
  • the obtained crude product of the target product was a mixture of two geometric isomers derived from the oxime structure.
  • Step 2 Synthesis of (R) -2-acetamido-3- (ethylthio) -N- [2- (methylamino) -5- (trifluoromethyl) pyridin-3-yl] propanamide N 2 -Methyl-5
  • Step 3 (R) -N- [2- (Ethylthio) -1- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl) ethyl] acetamide
  • a mixed solution of 2.0 g of the white solid obtained in Step 2 and 10 ml of acetic acid was stirred at 80 ° C. for 3 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture. 10 ml of ethyl acetate was added to the precipitated solid, followed by filtration to obtain 1.23 g of the target product (estimated configuration) as a light yellow solid.
  • Step 4 (R) -2- (Ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethan-1-amine Synthesis 5 ml of 12 mol / L hydrochloric acid was added at 80 ° C. to a mixed solution of 1.13 g of light yellow solid obtained in Step 3 and 10 ml of ethanol. After the addition was complete, the mixture was stirred at 80 ° C. for 4 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture. To the obtained residue, 10 ml of water was added and washed with ethyl acetate (10 ml).
  • a 1 mol / L aqueous sodium hydroxide solution was added to the obtained aqueous layer to adjust the pH of the aqueous layer to 10 to 11, and the mixture was extracted with ethyl acetate (5 ml ⁇ 3).
  • the obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 634 mg of the desired product (stereo configuration estimated) as a yellow solid.
  • Step 2 Synthesis of 6-bromo-3- (ethylthio) imidazo [1,2-a] pyridin-2-amine To a mixed solution of 2.05 g of the brown resinous material obtained in Step 1 and 10 ml of dichloromethane, Below, 10 ml of trifluoroacetic acid was added. After the addition was complete, the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture. To the obtained residue, 4 ml / L hydrochloric acid (10 ml) was added and washed with ethyl acetate (10 ml ⁇ 2).
  • Compound (1) is a known compound described in International Patent Application No. 2016/129684, and specific examples thereof include compounds shown in Tables 1 to 3.
  • the condensed heterocyclic compound used as the first active ingredient of the composition of the present invention is not limited to these.
  • “Et” represents ethyl and “Me” represents methyl.
  • “mp” represents a melting point (unit: ° C.).
  • the compound contained in the active compound II which is the second active ingredient of the composition of the present invention is a compound known as a compound having pest control activity, and is selected from the following active ingredient groups BI to B-XXVI It is. Specific examples thereof are shown in the following Tables 4 to 29 together with Compound Nos. These compounds tend to increase the amount of sprayed medicine and the number of spraying due to the emergence of resistant pests or resistant bacteria, and the lack of insecticidal sterilization spectrum and residual effects. There are also cases where improvements are required from the viewpoint of environmental safety, such as an increase in the risk to aquatic organisms.
  • Active ingredient group BI [Table 4] ⁇ No. Compound name (generic name) ⁇ A01 Metalaxyl-M A02 Hymexazol ⁇
  • Active ingredient group B-II [Table 5] ⁇ No. Compound name (generic name) ⁇ B01 benomyl B02 Thiophanate-methyl B03 Diethofencarb B04 ethaboxam B05 Zoxamide B06 Pencicuron B07 fluopicolide ⁇
  • Active ingredient group B-III [Table 6] ⁇ No. Compound name (generic name) ⁇ C01 Benzovindiflupyr C02 Bixafen C03 Boscalid C04 fluopyram C05 Flutolanil C06 Fluxapyroxad C07 Furametpyr C08 Isofetamid C09 Isopyrazam C10 mepronil C11 penflufen C12 penthiopyrad C13 sedaxane C14 thifluzamide C15 Azoxystrobin C16 coumoxystrobin C17 dimoxystrobin C18 enestrobin C19 enoxastrobin C20 Famoxadone C21 fenamidone C22 phenaminstrobin C23 flufenoxystrobin C24 fluoxastrobin C25 kresoxim-methyl C26 mandestrobin C27 Metominostrobin C28 orysastrobin C29 picoxystrobin C30 pyraclostrobin C31 pyrametostro
  • Active ingredient group B-IV [Table 7] ⁇ No. Compound name (generic name) ⁇ D01 Mepanipyrim D02 kasugamycin ⁇
  • Active ingredient group BV [Table 8] ⁇ No. Compound name (generic name) ⁇ E01 Quinoxyfen E02 Fludioxonil ⁇
  • Active ingredient group B-VI [Table 9] ⁇ No. Compound name (generic name) ⁇ F01 iprodione F02 Procymidone ⁇
  • Active ingredient group B-VII [Table 10] ⁇ No. Compound name (generic name) ⁇ G01 tolclofos-methyl G02 Bacillus subtilis, Strain: D747, FZB24, GBO3, HAI0404, MBI600, QST713, Y1336, etc.) ⁇
  • Active ingredient group B-VIII [Table 11] ⁇ No. Compound name (generic name) ⁇ H01 Bromuconazole H02 Cyproconazole H03 Difenoconazole H04 Diniconazole-M H05 Epoxiconazole H06 Fenarimol H07 Fenbuconazole H08 fluquinconazole H09 hexaconazole H10 Imazalil H11 imibenconazole H12 ipconazole H13 metconazole H14 myclobutanil H15 penconazole H16 prochloraz H17 propiconazole H18 prothioconazole H19 simeconazole H20 tebuconazole H21 tetraconazole H22 Triflumizole H23 Fenpropidin H24 Fenhexamid H25 Fenpyrazamine H26 ipfentrifluconazole H27 mefentrifluconazole ⁇
  • Active ingredient group B-IX [Table 12] ⁇ No. Compound name (generic name) ⁇ I01 Validamycin I02 Polyoxins I03 Polyoxin-D (polyoxorim) I04 Benthiavalicarb-isopropyl I05 Dimethomorph I06 iprovalicarb I07 mandipropamid ⁇
  • Active ingredient group BX [Table 13] ⁇ No. Compound name (generic name) ⁇ J01 phthalide J02 tricyclazole J03 Carpropamid J04 diclocymet ⁇
  • Active ingredient group B-XI [Table 14] ⁇ No. Compound name (generic name) ⁇ K01 Acibenzolar-S-methyl K02 probenazole K03 Isotianil K04 Diclobentiazox K05 Thiadinil ⁇
  • Active ingredient group B-XII [Table 15] ⁇ No. Compound name (generic name) ⁇ L01 Bordeaux mixture L02 Copper carbonate, basic L03 Copper hydroxide L04 Copper naphthenate L05 Copper oleate L06 Basic oxychloride L07 copper sulfate L08 Copper sulfate, basic L09 oxine copper L10 calcium polysulfide L11 sulfur L12 mancozeb L13 maneb L14 polycarbamate L15 propineb L16 captan L17 folpet L18 chlorothalonil L19 iminoctadine-albesilate L20 iminoctadine-triacetate ⁇
  • Active ingredient group B-XIII [Table 16] ⁇ No. Compound name (generic name) ⁇ M01 Cyflufenamid M02 Simoxanil M03 flusulfamide M04 Flutianil M05 Fosetyl-aluminium M06 metrafenone M07 Oxathiapiprolin M08 Pyriophenone M09 Picarbutrazox M10 dipymetitrone M11 quinofumelin M12 Lipopeptide M13 Phosphorous acid M14 BCF-082 (test name) M15 NF-180 (test name) M16 S-2399 (test name) M17 AKD-5195 (test name) M18 S-2190 (test name) M19 aminopyrifen ⁇
  • Active ingredient group B-XIV [Table 17] ⁇ No. Compound name (generic name) ⁇ N01 Acephate N02 Cadusafos N03 Chlorpyrifos N04 Diazinon N05 Dichlorvos N06 Dimethoate N07 EPN (EPN) N08 Malathion N09 Methamidophos N10 Parathion-methyl N12 Phenthoate N13 Phorate N14 Phosmet N15 Phoxim N16 Profenofos N17 Terbufos ⁇
  • Active ingredient group B-XV [Table 18] ⁇ No. Compound name (generic name) ⁇ O01 Aldicarb O02 Benfuracarb O03 Carbaryl O04 Carbofuran O05 Carbosulfan O06 Methomyl O07 Pirimicarb O08 Thiodicarb ⁇
  • Active ingredient group B-XVI [Table 19] ⁇ No. Compound name (generic name) ⁇ P01 Acrinathrin P02 Bifenthrin P03 Cyfluthrin P04 Cypermethrin P05 Deltamethrin P06 Esfenvalerate P07 Etofenprox P08 Permethrin P09 Tefluthrin P10 Lambda-Cyhalothrin P11 tau-Fluvalinate ⁇
  • Active ingredient group B-XVII [Table 20] ⁇ No. Compound name (generic name) ⁇ Q01 Bensultap Q02 Cartap hydrochloride Q03 Thiocyclam ⁇
  • Active ingredient group B-XVIII [Table 21] ⁇ No. Compound name (generic name) ⁇ R01 Acetamiprid R02 Clothianidin R03 Dinotefuran R04 Imidacloprid R05 Nitenpyram R06 Thiacloprid R07 Thiamethoxam R08 Sulfoxaflor R09 Flupyradifurone R10 Triflumezopyrim R11 Dicloromezotiaz R12 flupyrimin ⁇
  • Active ingredient group B-XIX [Table 22] ⁇ No. Compound name (generic name) ⁇ S01 Spinetoram S02 Spinosad ⁇
  • Active ingredient group B-XX [Table 23] ⁇ No. Compound name (generic name) ⁇ T01 Ethiprole T02 Fipronil T03 Broflanilide ⁇
  • Active ingredient group B-XXI [Table 24] ⁇ No. Compound name (generic name) ⁇ U01 Abamectin U02 Emamectin benzoate U03 Lepimectin U04 Milbemectin ⁇
  • Active ingredient group B-XXII [Table 25] ⁇ No. Compound name (generic name) ⁇ V01 Chlorantraniliprole V02 Cyantraniliprole V03 Flubendiamide V04 Cyclaniliprole V05 Tetraniliprole V06 Cyhalodiamide ⁇
  • Active ingredient group B-XXIII [Table 26] ⁇ No. Compound name (generic name) ⁇ W01 Diafenthiuron W02 Fenpyroximate W03 Pyridaben W04 Torfenpyrad W05 Cyenopyrafen W06 Cyflumetofen W07 Pyflubumide W08 Hydramethylnon W09 Acequinocyl W10 Chlorfenapyr ⁇
  • Active ingredient group B-XXIV [Table 27] ⁇ No. Compound name (generic name) ⁇ X01 Pyriproxyfen X02 Methoxyfenozide X03 Diflubenzuron X04 Flufenoxuron X05 Lufenuron X06 Novaluron X07 Teflubenzuron X08 Buprofezin X09 Hexathiazox X10 Etoxazole X11 benzpyrimoxan ⁇
  • Active ingredient group B-XXV [Table 28] ⁇ No. Compound name (generic name) ⁇ Y01 Bacillus thuringensis Y02 Bacillus sphaericus ⁇
  • Active ingredient group B-XXVI [Table 29] ⁇ No. Compound name (generic name) ⁇ Z01 Pymetrozine Z02 Pyrifluquinazon Z03 aphidopyropen Z04 Flonicamid Z05 Spirodiclofen Z06 Spiromesifen Z07 Spirotetramat Z08 Indoxacarb Z09 Metaflumizone Z10 Cyromazine Z11 Azadirachtin Z12 Pyridalyl Z13 Bifenazate Z14 Fluxametamide Z15 Metaldehyde Z16 ME-5382 (Exam name) Z17 NA-89 (Exam name) Z18 NNI-1501 (Exam name) Z19 BAI-1602 (Exam name) Z20 DKN-2601 (test name) Z21 DAI-1601 (Exam name) Z22 Asinonapyr (acynonapyr) Z23 spiropidion ⁇
  • pests to be controlled in the present invention include arthropods such as insects and mites, mollusks, nematodes, basidiomycetes, ascomycetes, fungi such as zygomycetes, eukaryotic microorganisms such as oomycete, and bacteria Prokaryotic microorganisms may be mentioned.
  • arthropods such as insects and mites, mollusks, nematodes, basidiomycetes, ascomycetes, fungi such as zygomycetes, eukaryotic microorganisms such as oomycete, and bacteria Prokaryotic microorganisms may be mentioned.
  • specific examples of these pests include so-called agricultural pests that harm agricultural and horticultural crops and trees, agricultural diseases, so-called livestock pests parasitic on livestock and poultry, so-called sanitary pests that adversely affect the human living environment such as houses, And mites, nematodes, and molluscs that
  • composition of the present invention and the method of the present invention are characterized in that, firstly, pests such as insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal, bactericidal, etc., compared to the case where each drug is applied alone.
  • the control effect is clearly enhanced and an immediate pest control effect is imparted.
  • a wide pest control spectrum and a long residual effect that are not observed in existing pest control agents are induced.
  • the active compound I as the first active ingredient and the active compound II as the second active ingredient in the present invention can be applied by various application methods as follows. 1. Simultaneous application, ie a) Mixed application (ie as a mixture, eg ready-to-use formulations or as a tank mix) b) Individual application (ie application in separate tanks), or 2. The continuous individual application, in this case the sequence, generally does not have any influence on the results of the control method. Therefore, the method for controlling pests is to apply active compound I and active compound II separately or together, or by mixed application of active compound I and active compound II, before or after sowing, or It is carried out by spraying or dusting plants or soil before or after plant emergence.
  • a suitable combination ratio (weight ratio) of the active compound I which is the first active ingredient and the active compound II which is the second active ingredient in the composition of the present invention and the method of the present invention is 100: It can be used in the range of 1 to 1: 100, preferably 20: 1 to 1:20, particularly 10: 1 to 1:10.
  • the preferred application amount of the active ingredient compound in the composition of the present invention and the method of the present invention depends on the type of the target pest to be controlled, but usually the active compound I as the first active ingredient is 0.1 to 1000 gai / ha, the active compound II as the second active ingredient is 0.1 to 1000 gai / ha, preferably the former is 1 to 300 gai / ha, and the latter is 1 to 300 gai / ha.
  • “Gai / ha” means “gram active ingredient per hectare”.
  • the active compound I which is the first active ingredient and the active compound II which is the second active ingredient in the present invention can be treated on the seeds before sowing.
  • the method for treating the seed include a coating granulation method, a gel coating method (see JP-A-2002-0010011), a dressing treatment, and the like.
  • the method is not particularly limited as long as it can be attached to the seed.
  • the coating granulation method is a method in which a coating material made of an active compound, a binder, or the like is used to fix the seed surface and then blown or forcedly dried.
  • granulating apparatuses such as a seed dresser, a fluidized bed granulator, a rolling granulator, and a bread granulator can be used.
  • agrochemical active compounds and binders extenders, surfactants, plasticizers, colorants, preservatives, water repellents, anti-caking agents, decomposition inhibitors and the like can also be added to the coating material.
  • the gel coating method requires plant seeds to be enclosed in an aqueous gel capsule.
  • An aqueous gel capsule containing seeds is formed, for example, by forming a droplet of an aqueous solution having an aqueous gel-forming polymer at the tip of a thin tube, and adding one or more seeds to the liquid droplet using the thin tube, It can be produced by dripping into a coagulating liquid having a function of coagulating the droplets. At this time, a gas such as air or oxygen can be sealed as required.
  • Powder coating treatment is a method in which a powder or wettable powder containing an agrochemical active compound is sprinkled directly on plant seeds. In principle, seeds or seeds moistened with water and solid or liquid pesticide preparations are put in a container.
  • the powder coating process in the present invention includes a powder coating method, a smearing method (slurry method), and a liquid immersion method.
  • the treatment agent for dressing plant seeds may be prepared by diluting with an agrochemical formulation itself or with water. Examples of a method for dressing seeds with a liquid preparation or a liquid preparation obtained by diluting a solid preparation in water include a smearing method and a liquid immersion method.
  • the smearing method is an improvement of the powder coating method, in which a solid preparation is immersed in a small amount of water (slurry or liquid) and stirred together with seeds in a container to adhere the agrochemical active compound.
  • a solid preparation is immersed in a small amount of water (slurry or liquid) and stirred together with seeds in a container to adhere the agrochemical active compound.
  • the preparation itself or a solution diluted with water is placed in a container, the plant seeds are immersed, and the drug penetrates into the seeds. After the chemical solution is immersed, it may be air-dried.
  • the immersion time is not particularly limited.
  • a surfactant or the like can be added at the time of dilution.
  • the powder coating treatment can be carried out using a seed treatment mixer, a fertilizer blender, a plastic bag, or a vinyl sheet, but the type of container is not particularly limited.
  • the seeds that have been powdered can be dried and stored, but may be sown without drying.
  • the above agrochemical formulation When the above agrochemical formulation is treated on plant seeds by a smearing method or a liquid soaking method, it can be applied usually diluted 1 to 20000 times with water.
  • the amount of the active ingredient to be adhered by the coating granulation method, the gel-like coating method and the dressing treatment is preferably 1 to 10000 g per 100 kg of seeds.
  • the composition of the present invention and the method of the present invention are a so-called agricultural pest that harms agricultural and horticultural crops, trees, etc., an agricultural disease, a so-called livestock pest parasitic on livestock and poultry, and a so-called sanitary pest that adversely affects the human living environment such as a house. It can be applied to mites, nematodes and molluscs that occur and harm in similar situations. Specific examples of pests, mites, nematodes, molluscs, and diseases caused by the pests that can be controlled using the composition of the present invention and the method of the present invention include the following, but are not limited thereto. It is not something.
  • insect pests include the following insects.
  • Hymenoptera insect Chestnut gall wasp (Dryocosmus kuriphilus), Argentine ant Argentine ant (Linepithema humile), Gunmy ant Army ant (Eciton burchelli, E.
  • Lepidoptera insects Pear leaf miner (Bucculatrix pyrivorella), Chanohosoga Tea leafroller (Caloptilia theivora), kingfisher Apple leafminer (Phyllonorycter ringoniter), Citrusella leaflet Pink bollworm (Pectinophora gossypiella), Persimmon fruit moth (Stathmopoda niessa), Peach fruit moth (Carposina sasakii), Allium leafminer (Acrolepiopsis sapporensis), ⁇ epiella moss Ginmon-spotted moth (Lyonetia prunifoliella malinella), diamondback moth (Plutella xylostella), green moth Rice stem borer (Chilo suppressalis), Shibatatsuga Blue grass webworm (Parapediasia teterrella), red eel moth Cabbage webworm (Hellula undalis), white moth Rice leaf
  • Diptera insects the fruit fly Melon fly (Bactrocera cucurbitae), the fruit fly Oriental fruit fly (Bactrocera dorsalis), the Queensland fruit fly Queensland fruit fly (Bactrocera tryoni), the fruit fly Japanese ⁇ orange fly Ceratitis capitata), Mexican fruit fly Mexican fruit fly (Anastrepha ludens), Ring fly, Apple ⁇ ⁇ maggot (Rhagoletis pomonella), Rice leaf fly, Rice leaf miner (Agromyza oryzae), Salamander, Pealeaf Eggplant leaf fly Tomato leaf miner (Liriomyza bryoniae), green leaffly Stone leek leafminer (Liriomyza chinensis), sand leaflet Pea leafminer (Liriomyza huidobrensis), tomato leaffly Tomato leafminer (Liriom yza sativae), beetle leaflet Serpentine leafminer (Liriomyza tri
  • Coleoptera insects Tobacco beetle (Lasioderma serricorne), common bean weevil Common bean weevil (Acanthoscelides obtectus), adzuki bean weevil Adzuki bean beetle (Callosobruchus chinensis), Grape -horn beetle (Anoplophora glabripennis), White-spotted longicorn beetle (Anoplophora malasiaca), Japanese pine ⁇ sawyer (Monochamus alternatus) ), Mustard leaf beetle Mustard leaf beetle (Phaedon cochleariae), rice beetle Rice leaf beetle (Oulema oryzae), spotted beetle Reaf beetle (Demotina fasciculata), cucumber ham Cucurbit leaf beetle (Aulacophora femoralis), Beet flea beetle (Chaetocnema concinna), Northern corn root
  • Hemiptera insects citrus white owl Asian citrus ll Silverleaf whitefly (Bemisia argentifolii), tobacco whitefly Sweetpotato whitefly (Bemisia tabaci), citrus whitefly Citrus whitefly (Dialeurodes ⁇ citri), green ⁇ white fly (Trialeurodes vaporcrum pea phipi ), Bean aphid Black bean aphid (Aphis fabae), soybean aphid Soybean aphid (Aphis glycines), cotton aphid Cotton aphid (Aphis gossypii), apple aphid Green apple ap hid (Aphis pomi), snowy spider eagle beetle Spiraea aphid (Aphis spiraecola), potato beetle aphid Foxglove aphid (Aulacorthum solani), wheat mullet aphid aphid (Chrom
  • Thysanoptera insects Thysanoptera Flower thrips (Frankliniella intonsa), Western flower thrips (Frankliniella occidentalis), Croton thrips Greenhouse thrips (Heliothrips haemorrhoidalis), Tea rips Melon thrips (Thrips palmi), Japanese thrips, Onion thrips (Thrips tabaci), Japanese gall-forming thrips (Ponticulothrips diospyrosi), etc.
  • Orthoptera insects desert locust (Schistocerca gregaria), Australian locust Australian plague locust (Chortoicetes terminifera), locust migratory locust (Locusta migratoria), red sea grasshopper Lesser paddy grasshopper (Oxya janena) Oxya yezoensis), Emma field cricket (Teleogryllus emma), Kera Oriental mole cricket (Gryllotalpa orientalis), etc.
  • Dictyoptera insects German cockroach (Blattella germanica), American cockroach (Periplaneta americana), Black cockroach Smoky-brown cockroach (Periplaneta fuliginosa), Japanese cockroach (Periplaneta japonica) -Daiko termite (Cryptotermes domesticus), American white-tailed termite Western dry-wood termite (Incisitermes minor), Japanese termite Forosan subterranean termite (Coptotermes formosanus), Japanese termite termite Japanese subterranean termite (Reticulitermes speratus), Thai-white termite Black-es .
  • Collembola hexapod Rootfeeding springtail (Onychiurus folsomi), Siberian whitefly, Onychiurus sibiricus, Garden springtail (Bourletiella hortensis), etc.
  • Examples of harmful arthropods other than insects include the following arthropods.
  • Isopoda crustaceans Pill bug (Armadillidium vulgare), common rough woodlouse (Porcellio scaber), etc.
  • Scolopendromorpha polypods Tobism cadets, Chinese red-headed centipede (Scolopendra subspinipes mutilans), Scolopendra japonica, Scolopendra multidens, etc.
  • Lithobiomorpha polypods Bothropolys asperatus and the like.
  • Scutigeromorpha polypod Gedi House centipede (Thereuonema tuberculata) etc.
  • Astigmata mites Brown-legged grain mite (Aleuroglyphus ovatus), spinach mite (Tyrophagus similis), Robin mite Bulb mite (Rhizoglyphus robini) and the like.
  • Prostigmata ticks Tulip rust mite Waccurl mite (Aceria tulipae), Pear rust mite (Eriophyes chibaensis), Peach bud mite (Eriophyes insidiosus), Pearleaf blister mate Pearleaf blister mite (Eriophyes) pyri), Chinese rust mite Tea rust mite (Acaphylla theavagrans), tomato rust mite Tomato russet mite (Aculops lycopersici), citrus red mite Pink citrus rust mite (Aculops pelekassi), apple rust mite Apple rust mite (Aculus pointedend rust rustle mite (Phyllocoptruta oleivora), mite dust mit
  • Examples of harmful molluscs include the following gastropods: Architaenioglossa gastropod: Apple snail (Pomacea canaliculata) etc.
  • Stylommatophora gastropods Giant African snail (Achatina fulica), terrestrial slug (Limax marginatus), slug (Meghimatium bilineatum), round round snail (Acusta and snail mys) (Euhadra peliomphala) etc.
  • Examples of harmful nematodes include the following nematodes.
  • Aphelenchida nematode Rice white nematode (Aphelenchoides besseyi), Pine wood nematode (Bursaphelenchus xylophilus), etc.
  • Tylenchida nematode Potato cyst nematode (Globodera rostochiensis), wheat cyst nematode, Cereal cyst nematode (Heterodera avenae), soybean cyst nematode, Soybean cyst nematode (Heterodera glycines), Arenaria nematode (Meloidogyne arenaria), Northern root-knot nematode (Meloidogyne hapla), Southern root-knot nematode (Meloidogyne incognita), Java root-knot nematode (Meloidogyne javanea dene-lesion) (Pratylenchus coffeae), tea root-lesion nematode (Pratylenchus loosi), red-breasted nematode Cobb's root-lesion nematode (Pratylenchus penetrans), Walnut root-
  • specific plant diseases that can be controlled by using the composition of the present invention and the method of the present invention include, but are not limited to, the following plant diseases.
  • Diseases of konjac dry rot Dry rot (Fusarium oxysporum, F. solani f. Sp. Radicicola), white silkworm Stem rot (Athelia rolfsii), root rot Root rot (Pythium aristosporum), leaf blight Bacterial leaf blight ( Acidovorax konjaci), rot soft rot (Erwinia carotovora subsp. Carotovora).
  • Leaf mold (Cladosporium colocasiae), dry rot Dry rot (Fusarium oxysporum f. Sp. Colocasiae), black rot Black rot (Ceratocystis sp.), Plague Phytophthora blight (Phytophthora colocasiae), root rot Disease (Pythium aristosporum, P. myriotylum), soft rot Bacterial soft rot (Pectobacterium carotovorum).
  • Yellow spot Leaf spot (Heterosporium allii), Black spot disease Alternaria leaf spot (Alternaria porri), Leaf blight Leaf spot (Pleospora herbarum, Stemphylium botryosum, S. vesicarium), Pink root rot (Pyrenochaeta terrestris, Pyrenochaeta sp.), Leaf blight leaf blight (Botrytis cinerea, B. byssoidea, B.
  • Stem rot Helminthosporium sigmoideum var. Irregulare
  • Brown spot Cochliobolus miyabeanus
  • Seedling blight Phoma sp., Trichoderma viride, Fusarium solani, Gibberella avenacea, Mucor
  • Rhizopus arrhizus R. chinensis
  • R. oryzae Pythium arrhenomanes
  • P. graminicola P. irregulare
  • P. spinosum P.
  • Eye spot disease Eyespot (Tapesia acuformis, T. yallundae), snow rot large-sized mycobacterial disease Sclerotinia snow blight (Sclerotinia borealis), ergot disease Ergot (Claviceps purpurea), Fusarium blight (Fusarium crookwellense, F. culmorum, Gibberella avenacea, G.
  • zeae blight Take-all (Gaeumannomyces graminis), red snow rot Snow mold (Monographella nivalis), streak disease Cephalosporium stripe (Cephalospori) um gramineum), cloudy disease Scald (Rhynchosporium secalis), black rust Stem rust (Puccinia graminis), barley leaf rust (Puccinia hordei), red rust Brown rust (Puccinia recondita), yellow rust Stripe rust (Puccinia) striiformis var.
  • Sugarcane diseases Leaf scorch leaf scorch (Stagonospora sacchari), top rot (Fusarium moniliforme var. Majus, Gibberella fujikuroi, G. fujikuroi var. Subglutinans), yellow rust Orange rust (Puccinia kuehnii) Brown rust (Puccinia melanocephala), smut Sugarcane smut (Sporisorium scitamineum).
  • Maize diseases sesame leaf blight, Southern leaf blight (Cochliobolus heterostrophus), soot scab, Northern leaf blight (Setosphaeria turcica), seedling blight Seedling blight (Gibberella avenacea, Penicillium sp.), Southern rust (Puccinia polysora) ), Smut, Corn smut (Ustilago maydis), coat blight, Sheath blight (Thanatephorus cucumeris), root rot, Browning root rot (Pythium arrhenomanes, P. graminicola).
  • Banana disease Sigatoka disease Black sigatoka (Mycosphaerella fijiensis), yellow leaf sigatoka leaf spot (Mycosphaerella musicola), Panama disease (Fusarium oxysporum f. Sp. Cubense).
  • Diseases of ginger crops Leaf spot (Mycosphaerella zingiberis), Ginger white spot disease (Phyllosticta zingiberis), Blast (Pyricularia zingiberis), Blight (Rhizoctonia solani), Root rot (Pythiumul) , P. zingiberis).
  • Sugar beet diseases brown spot disease Cercospora leaf spot (Cercospora beticola), spot disease Ramularia leaf spot (Ramularia beticola), snake eye disease Leaf spot (Pleospora betae), powdery mildew Powdery mildew (Erysiphe betae), leaf rot leaf blight Root rot Root rot (Thanatephorus cucumeris), black root disease Aphanomyces root rot (Aphanomyces cochlioides), seedling blight Damping-off (Pleospora betae, Fusarium sp., Colletotrichum dematium, Rhizoctonia solani, Aphanomyces cochliobaryanum, Pythium) Diseases of spinach: Brown spot disease Leaf spot (Cercospora beticola), Spot disease Leaf mold (Cladosporium variabile), wilt disease Fusarium wilt (Fusarium oxysporum f.
  • Sp. Spinaciae anthracnose disease Anthracnose (Colletotrichum dematium f. Spinacia) Diseases Foot rot (Rhizoctonia solani), root rot Root rot (Aphanomyces cochlioides), downy mildew (Peronospora farinosa f. Sp. Spinaciae), withering disease Damping-off (Pythium aphanidermatum, P. myriotylum, P. paroecandrum) , P. ultimum var. Ultimum), Bacterial leaf spot (Pseudomonas syringae pv. Spinaciae).
  • Brown Spot Disease Isariopsis leaf spot (Pseudocercospora vitis), Black Mold Anthracnose (Elsinoe ampelina), Powdery Mildew Powdery mildew (Uncinula necator), Gray Mold (Botrytis cinerea), Swelling Arm (Diaporthe) kyushuensis), bud blight Bud blight (Diaporthe rudis), vine split disease Dead arm (Phomopsis viticola), late rot Ripe rot (Colletotrichum acutatum, Glomerella cingulata), rust disease Rust (Physopella ampelopsidis), downy mildew (downy mildew) Plasmopara viticola).
  • kidney bean anthracnose Anthracnose (Colletotrichum lindemuthianum), azuki bean anthracnose (Colletotrichum phaseolorum. ), Deciduous leaf disease Brown stem rot (Phialophora gregata), soybean rust, soybean rust (Phakopsora pachyrhizi), azuki rust Rust (Uromyces phaseoli var. Azukicola), kidney bean rust Rust (Uromyces phaseoli var. Phaseust), Uromyces viciae-fabae var.
  • Viciae-fabae white silkworm Southern blight (Athelia rolfsii), downy mildew Downy mildew (Peronospora manshuric) a), soybean stem blight Phytophthorathroot and stem rot (Phytophthora sojae), azuki bean plague (Phytophthora vignae f. sp. adzukicola), soybean leaf burning Bacterial pustule (Xanthomonas campestris pv. Pseudomonas savastanoi pv. Glycinea), common bean pod blight, Halo ⁇ blight (Pseudomonas savastanoi pv. Phaseolicola), azuki bean bacterial disease (Pseudomonas syringae pv. Syringae).
  • Hop diseases powdery mildew (Oidium sp., Sphaerotheca intermedia), gray mold (Botrytis cinerea), wilt disease, Hop wilt (Verticillium albo-atrum), downy mildew (Pseudoperonospora humuli).
  • Fig disease yeast rot Souring (Candida sorbosa, Candida sp., Pichia kluyveri), common scab Fig scab (Sphaceloma caricae), gray mold (Botrytis cinerea), bacterial wilt Ceratocystis canker (Ceratocystis fimbriata), White root rot (Rosellinia necatrix), anthracnose Anthracnose (Glomerella cingulata), rust Rust (Phakopsora nishidana), black mold Rhizopus rot (Rhizopus stolonifer var. Stolonifer), plague White powdery rot (Phytophthora palmiv).
  • Rose diseases Stem blight Stem canker (Leptosphaeria coniothyrium), powdery mildew Powdery mildew (Podosphaera pannosa, Uncinuliella simulans), black spot disease Black spot (Diplocarpon rosae), gray mold disease Botrytis blight (Botrytis cinerea), rust disease Rust ( Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae), downy mildew (Peronospora sparsa), root gall disease Crown gall (Agrobacterium tumefaciens).
  • Strawberry Diseases Janame Disease Leaf spot (Mycosphaerella fragariae), Powdery Mildew Powdery mildew (Sphaerotheca aphanis var. Aphanis), Gray Mold (Botrytis cinerea), Dwarf Fusarium wilt (Fusarium oxysporum f. Sp. Fragariae) ), Leaf spot leaf blight (Phomopsis obscurans), anthrax Crown rot (Colletotrichum acutatum, C. fragariae, Glomerella cingulata), plague Phytophthora rot (Phytophthora cactorum, P.
  • Piricola soot spot Fly speck (Schizothyrium pomi), powdery mildew (Podosphaera leucotricha), brown spot Blotch (Diplocarpon mali), moniliosis Blossom blight (Monilinia mali), rot Valsa canker (Valsa ceratosperma), white root rot (Rosellinia necatrix), anthrax Bitter rot (Colletotrichum acutatum, Glomerella cingulata), soot spot Sooty blotch (Phyllachora pomigena), purple leaf rot Violet root rot (Helicobasidium longisporum), red rot Rust (Gymnosporangium yamadae) blight (Erwinia amylovora).
  • Black spot disease Black spot (Alternaria kikuchiana), Brown spot disease Brown spot (Stemphylium sp.), Black star disease Scab (Venturia nashicola), Ring rot Ring rot (Botryosphaeria berengeriana f. Sp.
  • Piricola Diseases Shoot blight (Botryosphaeria dothidea), powdery mildew Powdery mildew (Phyllactinia mali), blight disease Phomopsis canker (Phomopsis fukushii), keratocarcinoma Coral spot (Nectria cinnabarina), white root rot (Rosellinia) necatrix), Anthracnose (Colletotrichum acutatum, Glomerella cingulata), Rust (Gymnosporangium asiaticum), Plague Phytophthora fruit rot (Phytophthora cactorum, P. syringae), Bacterial black spot (syringae p. syringae. Fire blight (Erwinia amylovora).
  • Plum disease Scab (Venturia carpophila), Gray mold (Botrytis cinerea), Zonate leaf spot (Grovesinia pruni), Brown rot (Monilia mumecola, Monilinia fructicola, M. laxa) ), Anthracnose (Colletotrichum acutatum, Glomerella cingulata), Sooty blotch (Peltaster sp.), Chloranthy (Blastospora smilacis), Bacterial canker (Pseudomonas syringae pv.
  • tridactyla var tridactyla
  • ash blight Brown rot Monilinia fructicola, M. fructigena
  • homoposis rot Phomopsis rot Phomopsis sp.
  • blight Cytospora canker Leucostoma persoonii
  • anthracnose Anthracnose Coldletotrichum acutatum, Glomerella cing
  • Fruit red spot Ellisembia sp.
  • Brown rust Tranzschelia discolor
  • Bacterial shot hole Xanthomonas arboricola pv. Pruni, Pseudomonas syringae pv. Syringae, Brenneria nigrifluens).
  • Brown perforated disease Cylindrosporium leaf spot (Mycosphaerella cerasella, Blumeriella jaapii), brown rot (Monilinia fructicola, M. fructigena, M. laxa), juvenile sclerotia young-fruit rot (Monilinia kusanoi), White root rot (Rosellinia necatrix), anthracnose Anthracnose (Colletotrichum acutatum, Glomerella cingulata), black mold Rhizopus rot (Rhizopus stolonifer var. Stolonifer), resinous bacterial disease Bacterial canker (Pseudomonas syringae, P. s. P. S. syringae, P. viridiflava).
  • ishikarien ishikariensis mycorrhizal disease Sclerotinia rot (Sclerotinia sclerotiorum), yellowish disease Yellows (Fusarium oxysporum f. sp. conglutinans), Japanese radish yellowish disease Yellows (Fusarium oxysporum f. sp. raphani), blackberry Verticillium black spot Verticillium albo-atrum, V. dahliae), Chinese cabbage yellow disease Yellows (Verticillium dahliae), cabbage verticillium wilt llium longisporum), anthracnose Anthracnose (Colletotrichum dematium, C. destructivum, C.
  • Papaya disease soft rot Phytophthora blight (Phytophthora nicotianae).
  • Diseases of okra Leaf leaf mold (Pseudocercospora abelmoschi), fruit black spot disease Alternaria rot (Alternaria alternata), ring rot pod spot (Phoma exigua var. Exigua), powdery mildew Powdery mildew (Leveillula taurica), gray Mold mold Gray mold (Botrytis cinerea), black root disease Black root rot (Thielaviopsis basicola), seedling blight Damping-off (Rhizoctonia solani, Pythium ultimum var.
  • Citrus canker Xanthomonas citri subsp. Citri.
  • Diseases of kiwifruit Sooty spot disease (Pseudocercospora actinidiae), soft rot of fruit soft rot (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.), Gray mold (Botrytis cinerea), white root rot (white root rot) Rosellinia necatrix), Anthracnose (Colletotrichum acutatum, Glomerella cingulata), Bacterial bacterial disease Bacterial blossom blight (Pseudomonas marginalis pv. Marginalis, P. syringae pv. Syringae, P. viridiflava) actinidiae).
  • Oyster diseases angular leaf spot (Cercospora kaki), circular leaf spot (Mycosphaerella nawae), black spot (Fusicladium levieri), soot spot Fly speck (Schizothyrium pomi), powdery mildew Powdery mildew (Phyllactinia kakicola), gray mold (Botrytis cinerea), black leaf spot (Discostroma sp.), Anthracnose Anthracnose (Glomerella cingulata). Blueberry diseases: Gray mold (Botrytis cinerea), Valdensia leaf blight (Valdensia heterodoxa).
  • Tea diseases Brown round spot (Cercospora chaae, Pseudocercospora ocellata), Anthracnose (Discula theae-sinensis), Ring blight Gray blight (Pestalotiopsis longiseta, P.
  • Sesame Diseases White Silk Disease Stem rot (Athelia rolfsii), Bacterial wilt (Ralstonia solanacearum), Bacterial leaf spot (Pseudomonas syringae pv. Sesami).
  • stem rot (Fusarium oxysporum f. Sp. Batatas, F. solani), black spot black rot (Ceratocystis fimbriata), purple leaf rot Violet root rot (Helicobasidium longisporum), soft rot Soft rot ( Rhizopus stolonifer var. Stolonifer, R. tritici), withering disease Soil rot (Streptomyces ipomoeae).
  • Tomato diseases Leaf mold (Mycovellosiella fulva), mold mold Cercospora leaf mold (Pseudocercospora fuligena), brown ring disease Corynespora target spot (Corynespora cassiicola), ring blight disease Early blight (Alternaria solani), leaf spot disease spot (Stemphylium lycopersici, S.
  • Radicis-lycopersici Verticillium wilt Verticillium dahliae), white silk disease Southern blight (Athelia rolfsii), seedling blight Damping-off (Rhizoctonia solani, Pythium vexans), plague Late blight (Phytophthora infestans), scab disease Bacterial canker (Clavibacter michig) anensis subsp. michiganensis), bacterial wilt (Ralstonia solanacearum), bacterial spot Bacterial spot (Xanthomonas campestris pv. vesicatoria), soft rot Bacterial soft rot (Pectobacterium carotovorum).
  • Potato Diseases Summer blight Early blight (Alternaria solani), Dry rot Dry rot (Fusarium oxysporum, Fusarium solani f. Sp. Eumartii, f. Sp. Radicicola), Anthracnose (Colletotrichum coccodes), Black scurf (Thanatephorus cucumeris), powdery scab, Powdery Scab (Spongospora subterranea f. Sp. Subterranea), plague Late blight (Phytophthora infestans), ring rot Ring rot (Clavibacter michiganensis subsp.
  • Sepedonicus Sepedonicus
  • scab Scab Streptomyces sp
  • Bacterial wilt Ralstonia solanacearum
  • black leg Dickeya dianthicola, Pectobacterium atrosepticum, P. carotovorum
  • soft rot Bacterial soft rot Pectobacterium carotovorum.
  • Tobacco disease Red spot disease Brown spot (Alternaria alternata), back fracture Sore shin (Rhizoctonia solani), plague Black shank (Phytophthora nicotianae), blight Bacterial wilt (Ralstonia solanacearum).
  • Black spot disease spot spot (Alternaria panax, Alternaria sp.), Sclerotia disease Sclerotinia rot (Sclerotinia sclerotiorum), wilt disease Verticillium wilt (Verticillium dahliae, V. nigrescens), white silk disease Southern blight (Athelia rolfsii) The plague Phytophthora rot (Phytophthora cactorum).
  • Lettuce diseases Gray mold (Botrytis cinerea), sclerotia Stem rot (Sclerotinia sclerotiorum), root rot Root rot (Fusarium oxysporum f. Sp. Lactucae), bottom rot Bottom rot (Rhizoctonia solani) Downy mildew (Bremia lactucae), Bacterial spot (Xanthomonas axonopodis pv. Vitians), rot Bacterial rot (Pseudomonas cichorii, P. marginalis pv. Marginalis, P. viridiflava), soft rot Bacterial soft carrot (Pectobacterium) ).
  • Cichoracearum gray mold disease Botrytis blight (Botrytis cinerea), sclerotia Stem rot (Sclerotinia sclerotiorum), half body wilt Wilt (Verticillium dahliae), brown rust Rust (Phakopsora artemisiae), white rust Rust (Puccinia horiana), black rust Rust (Puccinia) tanaceti var.
  • Leaf blight Leaf blight (Cercospora chrysanthemi), anthracnose Anthracnose (Colletotrichum acutatum), downy mildew (Peronospora chrysanthemi-coronarii).
  • Diseases of sunflower Brown spot disease (Septoria helianthi), black spot disease spot spot (Alternaria helianthi), powdery mildew Powdery mildew (Erysiphe cichoracearum, Golovinomyces cichoracearum var.
  • Buffalo disease Verticillium wilt (Verticillium dahliae), white silkworm Southern blight (Athelia rolfsii). Burdock Diseases: Black Spot Disease Spot (Phoma exigua var. Exigua), Powdery Mildew Powdery mildew (Podosphaera fusca), Black Stripe Black streak (Itersonilia perplexans), Black Pill Black scurf (Rhizoctonia solani), Root Rot (Pythium irregulare), Bacterial spot (Xanthomonas campestris pv. Nigromaculans).
  • composition of the present invention and the method of the present invention are also extremely effective against pests that have developed resistance to existing insecticides such as organophosphorus compounds, carbamate compounds, or pyrethroid compounds, and Coleoptera ( (Coleoptera), Hymenoptera (Hymenoptera), Lepidoptera (Lepidoptera), Diptera (Flyes), Hemiptera (Thysanoptera), Hemiptera (Hymenoptera and Hemiptera), Straight ( Grasshoppers), reticulates (roaches), isopods (termites), insects such as slime (Coleoptera), crustaceans such as isopoda (aphididae), centipedes, scorpiones, Reduces pests belonging to gastropods and other ticks, gastroids (Acaridaceae), mites (Apisidae, Dustidae, Acaridaceae, Midarididae, Azalea) and gastropod
  • composition of the present invention and the method of the present invention have extremely adverse effects on mammals, fish, crustaceans and beneficial insects (useful insects such as honeybees, bumblebees, natural enemies such as honeybees, wasps, mistletoe, and stink bugs). Has few useful features.
  • Plant in this specification refers to cereals and fruit trees / vegetables cultivated as human food, feed crops such as livestock and poultry, appreciation plants that love their form and shape, or planting in parks, streets, etc. It means vascular plant (Tracheophyta). Specific examples include the following plants, but are not limited thereto.
  • Pinaceae plants belonging to Pinaceae such as Japanese red pine (Pinus densiflora), European red pine Scots Pine (Pinus sylvestris), Japanese black pine (Pinus thunbergii).
  • Pepper (Piper nigrum) such as Pepperaceae (Piperaceae), Avocado Avocado (Persea americana) and other magnoliaceae (Lauraceae) etc., magnoliids, Konjac (Amorphophallus konjac), taro edode (Colocasia esculenta) and other taro (Araceae), Chinese yam (Dioscorea batatas), yam Japanese yam (Dioscorea japonica) and other yam (Dioscoreacesum var) porrum), Onion Onion (Allium cepa), Rakkyo Rakkyo (Allium chinense), Leek Welsh onion (Allium fistulosum), Garlic
  • Lotus root such as Lotus root (Nelumbo nucifera) (Nelumbonaceae), groundnut Peanut (Arachis hypogaea), chickpea Chickpea (Cicer arietinum), lentil Lentil (Lens culinaris), pea Pea (Pisum sativum) , Soybean Soybean (Glycine max), common bean Common bean (Phaseolus vulgaris), adzuki bean (Vigna angularis) adzuki bean, cowpea (Vigna unguiculata), legaceae (Fabaceae), aceae such as Hop Hop (Humulus lupulus) ), Fig Fig Tree (Ficus carica), Mulberry (Moraceae) such as Mulberry (Morus spp.), Mameaceae (Rhamnaceae) such as jujuba (Rhamnaceae), Strawberry Strawberry (Fragaria), Rose Rose (Rosa) s
  • Tougan Winter melon (Benincasa hispida), Watermelon Watermelon (Citrullus lanatus), Yuugao Bottle gourd (Lagenaria siceraria var. Hispida), Loofah Luffa (Luffa cylindrica), Pumpkin Pumpkin (Cucurbita spp. melon (Momordica charantia var. pavel), melon Muskmelon (Cucumis ⁇ melo), white candy Oriental pickling melon (Cucumis melo var. conomon), cucumber Oriental melon (Cucumis melo var.
  • Rutaceae Henruda subfamily (Rutoideae), Daidai Bitter orange (Citrus aurantium), Lime Lime (Citrus aurantifolia), Hassaku Hassaku orange (Citrus hassaku), Yuzu Yuzu (Citrusemons) Citrus limon), Natsumikan (Citrus natsudaidai), Grapefruit Grapefruit (Citrus x paradisi), Orange Orange (Citrus sinensis), Kavos Kabosu (Citrus sphaerocarpa), Sudachi Sudachi (Citrus sudachi), Ponkan Mandarin t Satsuma (Citrus unshiu), Kumquat Kumquat (Fortunella spp.), Etc. Rutaceae, Rutaceae (Aurantioideae).
  • Horseradish (Armoracia rusticana), mustard (Brassica juncea), Takana Takana (Brassica juncea var. Integrifolia), Brassica rapeseed (Brassica napus), cauliflower (Brassica oleraceaageractis capitata), brussels sprout (Brassica oleracea var. gemmifera), broccoli Broccoli (Brassica oleracea var. Brassica rapa var. Nippo-oleifera), Mizuna Potherb Mustard (Brassica rapa var. Nipposinica), Chinese cabbage Napa cabbage (Brassica rapa var.
  • Persimmon such as oyster Kaki Persimmon (Diospyros kaki); Azalea (Ericaceae) such as Blueberry (Vacciniumberryspp.), Cranberry (Vaccinium spp.), Rubiaceae such as Coffee ⁇ plants (Coffea spp.), Lemon balm Lemon balm (Melissa officinalis), Mint Mint (Mentha spp.), Basil Basil (Ocimum basilicum), Shiso Shiso (Perilla frutescens var. crispa), Sesame (Perilla frutescens var.
  • Sesame Pedaliaceae
  • Sesame Sesame (Sesamum indicum)
  • Oleaceae such as Olive Olive (Olea europaea)
  • Satsu Convolvulaceae Tomato (Solanum lycopersicum)
  • Eggplant Eggplant Solanum melongena
  • Potato Potato Solanum tuberosum
  • Pepper chili pepper Capsicum annuum
  • Carrot Dacus carota subsp.
  • plant in the present specification refers to an HPPD inhibitor such as isoxaflutol, an ALS inhibitor such as imazetapyr and thifensulfuron / methyl, an EPSP synthase inhibitor such as glyphosate, and a glutamine synthase such as glufosinate.
  • HPPD inhibitor such as isoxaflutol
  • ALS inhibitor such as imazetapyr and thifensulfuron / methyl
  • EPSP synthase inhibitor such as glyphosate
  • glutamine synthase such as glufosinate.
  • Resistant to inhibitors acetyl-CoA carboxylase inhibitors such as cetoxidim, PPO inhibitors such as flumioxazin, herbicides such as bromoxynil, dicamba and 2,4-D by classical breeding methods and gene recombination techniques Plants are also included.
  • Examples of “agricultural and horticultural plants” that have been given resistance by classical breeding methods include rapeseed, wheat, sunflower, rice, and corn that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapil. It has already been sold under the product name>. Similarly, there are soybeans resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron-methyl by classical breeding methods and are already sold under the trade name STS soybeans.
  • SR corn and the like are examples of agricultural and horticultural plants to which resistance has been imparted to acetyl CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods.
  • acetyl CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods.
  • Agro-horticultural plants tolerated by acetyl-CoA carboxylase inhibitors are the Proceedings of the National Academy of Sciences of the United States of America (Proc.Natl.Acad Sci. USA) 87, 7175-7179 (1990).
  • a mutant acetyl CoA carboxylase resistant to acetyl CoA carboxylase inhibitors has been reported in Weed Science 53, 728-746 (2005).
  • a plant resistant to the acetyl-CoA carboxylase inhibitor By introducing a mutation into the plant acetyl-CoA carboxylase by introducing into the plant by resistance or resistance, a plant resistant to the acetyl-CoA carboxylase inhibitor can be produced. Furthermore, a nucleic acid introduced with a base substitution mutation represented by chimera plastic technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318) is introduced into a plant cell to produce a crop (acetyl CoA carboxylase / herbicide). Plants that are resistant to acetyl-CoA carboxylase inhibitors / herbicides can be created by inducing site-specific amino acid substitution mutations in the target) gene.
  • Examples of agricultural and horticultural plants imparted with resistance by genetic recombination technology include glyphosate-resistant corn, soybean, cotton, rapeseed, sugar beet varieties, Roundup Ready (registered trademark), Aglisher GT ( (Agriculture GT) ⁇ registered trademark> and the like.
  • glyphosate-resistant corn, soybean, cotton, rapeseed, sugar beet varieties Roundup Ready (registered trademark)
  • Aglisher GT (Agriculture GT) ⁇ registered trademark>
  • bromoxynyl-resistant cotton by gene recombination technology is already sold under the trade name BXN.
  • the “agricultural and horticultural plant” includes a plant that can synthesize, for example, a selective toxin known in the genus Bacillus using a gene recombination technique.
  • insecticidal toxins expressed in such genetically modified plants include, for example, insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; Cry1Ab, Cry1Ac derived from Bacillus thuringiensis, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other ⁇ -endotoxins, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; nematode-derived insecticidal proteins; Toxins produced by animals such as neurotoxins; filamentous fungi toxins; plant lectins; agglutinins; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin,
  • toxins expressed in such transgenic plants insecticidal proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, ⁇ -endotoxin proteins, VIP1, VIP2, VIP3 or VIP3A
  • Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques.
  • Cry1Ab lacking a part Cry1Ab lacking a part of the amino acid sequence is known.
  • the modified toxin one or more amino acids of the natural toxin are substituted.
  • Examples of these toxins and recombinant plants capable of synthesizing these toxins include, for example, EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073, etc. It is described in the patent literature. Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Diptera pests, and Lepidoptera pests.
  • genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known and some are commercially available.
  • these genetically modified plants include Yieldgard (registered trademark) (a corn variety that expresses Cry1Ab toxin), YieldGuard rootworm (registered trademark) (a corn variety that expresses Cry3Bb1 toxin), YieldGuard Plus (registered trademark) (a corn variety expressing Cry1Ab and Cry3Bb1 toxin), Herculex I (registered trademark) (phosphino to confer resistance to Cry1Fa2 toxin and glufosinate Corn varieties expressing Tricine N-acetyltransferase (PAT)), NuCOTN33B ⁇ registered trademark> (cotton varieties expressing Cry1Ac toxin), Volgaard I (Bollgard I) ⁇ registered trademark> (cotton varieties expressing Cry1Ac toxin), Bolgard II (Bo
  • RNAi is an example of a gene recombination technique that provides nematode resistance.
  • the plants include those that have been imparted with the ability to produce anti-pathogenic substances having a selective action using genetic recombination techniques.
  • anti-pathogenic substances include PR proteins (described in PRPs, EP-A-0392225); sodium channel inhibitors, calcium channel inhibitors (virus-produced KP1, KP4, KP6 toxins, etc.) Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (called plant disease resistance genes) And the like, which are produced by microorganisms such as those described in WO 03/000906).
  • Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191, and the like.
  • the plants include crops to which useful traits such as oil component modification and amino acid content enhancing traits have been imparted using genetic recombination techniques. Examples include VISTIVE ⁇ (R)> (low linolenic soybean with reduced linolenic content) or high-lysine (high hoil) corn (corn with increased lysine or oil content).
  • VISTIVE ⁇ (R)> low linolenic soybean with reduced linolenic content
  • high hoil high hoil corn (corn with increased lysine or oil content).
  • the above-mentioned classic herbicide traits or herbicide resistance genes, insecticidal pest resistance genes, anti-pathogenic substance production genes, oil component modification and amino acid content enhancement traits Combined stack varieties are also included. Also included are plants into which RNAi technology has been introduced.
  • composition of the present invention can be used as it is as a mixture of at least one active compound I as the first active ingredient and at least one active compound II as the second active ingredient.
  • solid carrier examples include quartz, calcite, gypsum, dolomite, chalk, kaolinite, pyrophyllite, sericite, halosite, metahalosite, kibushi clay, glazed clay, porcelain stone, nostirite, and allophane.
  • Natural minerals such as shirasu, kira, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite and diatomaceous earth, for example, calcined clay, perlite, shirasu balloon, vermiculite, attapulgus clay and calcined diatomaceous earth
  • Baked products such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium bicarbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate and potassium chloride, such as glucose, fructose , And Sugars such as sugar and lactose, polysaccharides such as starch, powdered cellulose and dextrin, organic materials such as urea, urea derivatives, benzoic acid and benzoic acid salts, such as wood flour, cork flour, corn cobs, walnut shells and Examples include plants such
  • liquid carrier examples include xylene, alkyl (C 9 or C 10 etc.) benzene, phenyl xylyl ethane and alkyl (C 1 or C 3 etc.) naphthalene and other aromatic hydrocarbons, machine oil, normal paraffin, isoparaffin and Aliphatic hydrocarbons such as naphthene, mixtures of aromatic and aliphatic hydrocarbons such as kerosene, alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol and benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol , Polyhydric alcohols such as polyethylene glycol and polypropylene glycol, propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol Ethers such as ethyl monoethyl ether, propylene glycol mono
  • surfactant examples include polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene Ethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene oxide adduct of acetylene alcohol and alkyl
  • Nonionic surfactants such as glycosides, alkyl sulfate esters, alkylbenzene sulfonates, lignin sulfonates, alkyls Rufosuccinate, naphthalene sulfonate, alkyl naphthalene
  • formulation examples of the preparation when using the composition of the present invention are shown. However, the formulation examples of the present invention are not limited to these.
  • “parts” means parts by weight
  • “active ingredient compound” means active compound I as the first active ingredient and active compound II as the second active ingredient in the composition of the present invention. It is a generic name.
  • Surfactant 1 to 12 parts Others 0.01 to 30 parts Others include, for example, antifreezing agents and thickeners.
  • the wettable powder, emulsion, flowable powder and granular wettable powder are diluted 1 to 20000 times with water and sprayed so that the active ingredient is 0.005 to 50 kg per hectare (ha).
  • the composition of the present invention containing the active compound I as the first active ingredient and the active compound II as the second active ingredient can be formulated and used as described above, A drug containing each of active compound I and active compound II as active ingredients is prepared separately, and these drugs are used or treated or applied at the same time or close to each other in time to obtain a synergistic excellent control effect. You can also.
  • a leaf disk (3 cm in diameter) made of green beans was placed on the filter paper, and a leaf disk carrying the nymph mite larvae prepared in the above-described procedure was placed on the filter paper overnight to release the nymph mite larvae.
  • the compounds described in Tables 1 to 3 and the active ingredients described in Tables 4 to 29 were prepared according to formulation examples.
  • the preparation was diluted with water to prepare a chemical solution having a predetermined concentration. Using a spraying device, spraying solution was uniformly sprayed for each test container (2.5 ml / cup).
  • the survey was conducted 6 days after spraying, and the death rate and expected value were calculated using the formulas described in Test Example 1.
  • the test was conducted in a two ward system. The results regarding the mortality of each chemical solution are shown in Tables 54 to 65 below.
  • the compounds described in Tables 1 to 3 and the active ingredients described in Tables 4 to 29 were prepared according to formulation examples.
  • the preparation was diluted with water to prepare a chemical solution having a predetermined concentration.
  • spraying solution was uniformly sprayed for each test container (2.5 ml / cup).
  • the survey was conducted 6 days after spraying, and the death rate and expected value were calculated using the formulas described in Test Example 1.
  • the test was conducted in a two ward system. Tables 90 to 101 show the results regarding the death rate of each chemical solution.
  • composition of the present invention and the method of the present invention can be used for controlling various pests. It should be noted that all of the description, claims and abstract of Japanese Patent Application No. 2016-180834 filed on September 15, 2016 and Japanese Patent Application No. 2017-137176 filed on July 13, 2017. The contents of which are hereby incorporated herein by reference.

Abstract

L'invention concerne une nouvelle composition d'agent de lutte contre des nuisibles et un procédé de lutte contre des nuisibles. La composition d'agent de lutte contre des nuisibles contient au moins un composé actif I choisi parmi des composés hétérocycliques condensés représentés par la formule (1) : [Chim. 1] [Dans la formule, Q représente un cycle représenté par Q1 ou Q3, A1a représente un alkyle en C1-C6, A4 et A5 représentent chacun indépendamment un atome d'azote ou similaire, R1 représente un alkyle en C1-C6, R3 représente un halogénoalkyle en (C1-C6) ou similaire, Y2, Y3 et Y4 représentent chacun indépendamment un atome d'hydrogène, un atome d'halogène, ou similaire, et n représente un nombre entier de 0, 1, ou 2] ou des N-oxydes, ou leurs sels, et au moins un composé actif II choisi parmi des insecticides connus, etc.
PCT/JP2017/033541 2016-09-15 2017-09-15 Composition d'agent de lutte contre des nuisibles et procédé de lutte contre des nuisibles WO2018052136A1 (fr)

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WO2021170463A1 (fr) 2020-02-28 2021-09-02 BASF Agro B.V. Procédés et utilisations d'un mélange comprenant de l'alpha-cyperméthrine et du dinotéfurane permettant la régulation d'organismes nuisibles invertébrés dans le gazon
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