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WO2017073733A1 - Composition antiparasitaire et son utilisation - Google Patents

Composition antiparasitaire et son utilisation Download PDF

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Publication number
WO2017073733A1
WO2017073733A1 PCT/JP2016/082078 JP2016082078W WO2017073733A1 WO 2017073733 A1 WO2017073733 A1 WO 2017073733A1 JP 2016082078 W JP2016082078 W JP 2016082078W WO 2017073733 A1 WO2017073733 A1 WO 2017073733A1
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Prior art keywords
group
compound
halogen atoms
bipyridine
ring
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PCT/JP2016/082078
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English (en)
Japanese (ja)
Inventor
慎哉 西村
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住友化学株式会社
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Publication of WO2017073733A1 publication Critical patent/WO2017073733A1/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
    • 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
    • A01C—PLANTING; SOWING; FERTILISING
    • A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
    • A01C1/08—Immunising seed
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-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
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/74—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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4

Definitions

  • the present invention relates to a pest control composition and a pest control method.
  • Non-Patent Document 1 discloses many compounds as active ingredients of pest control compositions.
  • An object of the present invention is to provide a pest control composition having an excellent control effect against pests.
  • a pest control composition comprising one or more compounds selected from the group consisting of the following group (a) and the following group (b).
  • (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms (C1-C5 alkylsulfinyl) C2-C5 alkyl group, having one or more halogen atoms (C1-C5 alkylsulfonyl) C2-C5
  • R 2 represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group
  • R 3 each independently has a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group B, and one or more substituents selected from group D.
  • R 13 represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, one or more A (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having a halogen atom, a phenyl group optionally having one or more substituents selected from group D, or one or more selected from group D
  • R 14 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and one or more halogen atoms.
  • the optionally substituted (C3-C6 cycloalkyl) C1-C3 alkyl group or the phenyl C1-C3 alkyl group ⁇ the phenyl moiety in the phenyl C1-C3 alkyl group has one or more substituents selected from group D; You may do it.
  • R 15 and R 16 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms, n and y each independently represents 0, 1, or 2; x represents 0 or 1; p and q each independently represent 0, 1, 2, or 3, and when p is 2 or 3, a plurality of R 6 may be the same or different, and q is 2 or 3 In this case, the plurality of R 3 may be the same or different.
  • Group B C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms
  • Group D C1-C6 chain hydrocarbon group which may have one or more halogen atoms, hydroxy group, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms
  • a C3-C6 alkenyloxy group which may have one or more, a C3-C6 alkynyloxy group which may have one or more halogen atoms, a sulfanyl group, or a C1-C6 which may have one or more halogen atoms.
  • C6 alkylsulfanyl group C1-C6 alkylsulfinyl group optionally having one or more halogen atoms
  • C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, amino group, NHR 21 , NR A group consisting of 21 R 22 , C (O) R 21 , OC (O) R 21 , C (O) OR 21 , a cyano group, a nitro group, and a halogen atom.
  • ⁇ R 21 and R 22 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms ⁇
  • Group E C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms
  • Group F C1-C6 alkoxy group optionally having one or more halogen atoms, NHR 21 , NR 21 R 22 , cyano group, phenyl optionally having one or more substituents selected from Group D A group, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a group A group consisting of a 3-7-membered non-aromatic heterocyclic group which may have one or more substituents selected from C.
  • Group C C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A group consisting of an optionally substituted C3-C6 alkenyloxy group, an optionally substituted C3-C6 alkynyloxy group, and a halogen atom.
  • Group G A group consisting of a halogen atom and a C1-C6 haloalkyl group.
  • Subgroup a-1 Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, flupiradifurone, sulfoxafurol, triflumezopyrim, dichloromesothiaz and the following formula The group which consists of a compound shown by these.
  • Subgroup a-2 Acrinatrin, Aleslin, Bifenthrin, Kappabifenthrin, Bioarethrin, Bioresmethrin, Cycloproton, Cyfluthrin, Beta-Cyfluthrin, Cyhalothrin, Gamma Cyhalothrin, Lambdacyhalothrin, Cypermethrin, Alpha Cypermethrin, Betacypermethrin, Theta Permethrin, zeta-cypermethrin, sigma-permethrin, ciphenothrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenpropatoline, fenvalerate, flucitrinate, flumethrin, fluvinate, taufulvalinate, halfenprox, hepta Flutrin, imiprothrin, cadreslin, meperfluthrin, monfluor
  • Subgroup a-3 A group consisting of etiprol, fipronil, flufiprolol, afoxolanel, fluralanel, brofuranilide and floxamethamide.
  • Subgroup a-4 A group consisting of chlorantraniliprole, cyantranylprolol, cyclaniliprol, fulvendiamide, tetraniprolol and cyhalodiamide.
  • Subgroup a-5 Alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxym, butoxycarboxym, carbaryl, carbofuran, carbosulfan, ethiophene carb, fenobucarb, formethanate, furthiocarb, isoprocarb, methiocarb, mesomil, metolcarb, oxamyl, pyrimicarb, dioxycarb, propoxyl Group consisting of thiophanox, triazamate, trimetacarb, XMC and xylylcarb.
  • Subgroup a-6 A group consisting of abamectin, fluenesulfone, thioxazaphene and fluazaindolizine.
  • Subgroup a-7 Mycorrhizal fungi, Arthrobotris dacteroides, Bacillus thuringiensis, Bacillus films, Bacillus megaterium, Bacillus amyloliquefaciens, Hilstera rosiliensis, Hilstera minnesotensis, Monacrosporium fimatopagum, Pasteurian nisawae , Pasteuria penetrans, Pasteuria usgae, Verticillium chlamydosporium and Harpin protein.
  • Subgroup b-2 Azoxystrobin, cumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, phenaminestrobin, fluphenoxystrobin, floxastrobin, cresoxime-methyl, mandestrobin, methinostrobin, A group consisting of orissastrobin, picoxystrobin, pyraclostrobin, pyramethostrobin, pyroxystrobin, trifloxystrobin, pyribencarb, triclopyricarb, cyazofamide and amisulbrom.
  • Subgroup b-3 A group consisting of benalaxyl, benalaxyl M, furaxyl, metalaxyl, metalaxyl M, oxadixyl and oflase.
  • Subgroup b-4 Benodanyl, benzobindiflupyr, bixaphene, boscalid, carboxin, fenfram, fluopyram, flutolanil, fluxapyroxad, furametopyr, isophetamide, isopyrazam, mepronil, oxycarboxyl, pentiopyrad, penflufen, cedaxane, tifluzamide, pyradiflumide Phen, 3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazole-4-carboxamide, 3-difluoromethyl-1-methyl-N-[(3R) -1 , 1,3-Trimethylindan-4-yl
  • Subgroup b-5 The group consisting of benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, dietofencarb, zoxamide and ethaboxam.
  • Subgroup b-6 A group consisting of felbam, manzeb, manneb, methyle, propineb, thiuram, dineb, ziram, captan, captahol, holpet, chlorothalonil, tolylfluanid, guazatine, iminotadine, anilazine, dithianone, quinomethionate and fluorimide.
  • Subgroup b-7 A group consisting of dimethomorph, flumorph, pyrimorph, bench avaricarb, bench avaricarb isopropyl, iprovaricarb, varifenalate and mandipropamide.
  • Subgroup b-8 A group consisting of fenpiclonyl, fludioxonil, clozolinate, iprodione, procymidone and vinclozolin.
  • Subgroup b-9 The group consisting of toluclophosmethyl, oxathiapiproline, picalbutrazox, fluopicolide and silthiofam.
  • [2] A content of one or more compounds selected from the group (a), the compound represented by the formula (I) or an N oxide compound thereof, and one or more compounds selected from the group (a) The pesticidal composition according to [1], wherein the ratio of is 100: 1 to 1: 100 by weight.
  • [3] A content of one or more compounds selected from the group (a), the compound represented by the formula (I) or an N oxide compound thereof, and one or more compounds selected from the group (a) The pesticidal composition according to [1], wherein the weight ratio is 10: 1 to 1:10 by weight.
  • [4] A content of one or more compounds selected from the group (b), a compound represented by the formula (I) or an N oxide compound thereof, and one or more compounds selected from the group (b) The pesticidal composition according to [1], wherein the weight ratio is 10,000: 1 to 1: 100 by weight.
  • [5] A content of one or more compounds selected from the group (b), a compound represented by the formula (I) or an N oxide compound thereof, and one or more compounds selected from the group (b) The pest control composition according to [1], wherein the weight ratio is 1000: 1 to 1:10 by weight.
  • a pest control method comprising a step of applying an effective amount of the pest control composition according to any one of [1] to [5] to a pest or a habitat of the pest.
  • a method for controlling pests comprising a step of applying an effective amount of the pest control composition according to any one of [1] to [5] to a plant or soil for cultivating the plant.
  • a method for controlling pests which comprises a step of applying an effective amount of the pest control composition according to any one of [1] to [5] to seeds or bulbs.
  • [9] [1] A seed or bulb having an effective amount of the pesticidal composition according to any one of [1] to [5].
  • pests can be controlled.
  • the pest control composition of the present invention (hereinafter referred to as the present composition) comprises a compound represented by the formula (I) or an N oxide compound thereof (hereinafter referred to as a compound represented by the formula (I) and an N oxide thereof.
  • the compound is referred to as the present bipyridine compound) and one or more compounds selected from the group consisting of the group (a) and the group (b) (hereinafter referred to as the present compound).
  • halogen atoms when it has two or more halogen atoms, these halogen atoms may be the same or different from each other.
  • CX-CY means that the number of carbon atoms is X to Y.
  • C1-C6 means 1 to 6 carbon atoms.
  • a halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the “chain hydrocarbon group” represents an alkyl group, an alkenyl group, and an alkynyl group.
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, tert-butyl group, A pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group are mentioned.
  • alkenyl group examples include a vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1,1-dimethyl-2-propenyl group, 1-ethyl-1-propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group, 4-pentenyl group, 5-hexenyl group heptenyl group, octenyl group, nonenyl Group, and decenyl group.
  • alkynyl group examples include ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, Examples include 2-butynyl group, 4-pentynyl group, 5-hexynyl group, heptynyl group, octynyl group, nonynyl group, and decynyl group.
  • the “C2-C10 haloalkyl group” represents a group in which a hydrogen atom of a C2-C10 alkyl group is substituted with a halogen atom, and examples thereof include a chloroethyl group, a 2,2,2-trifluoroethyl group, 2-bromo-1 1,2,2,2-tetrafluoroethyl group, 2,2,3,3-tetrafluoropropyl group, 1-methyl-2,2,3,3-tetrafluoropropyl group, perfluorohexyl group and perfluorodecyl group Can be mentioned.
  • the “C3-C10 haloalkenyl group” represents a group in which one or more hydrogen atoms of the C3-C10 alkenyl group are substituted with a halogen atom, and examples thereof include a C3-C10 fluoroalkenyl group.
  • Examples of the “C3-C10 haloalkenyl group” include a 3,3,3-trifluoro-1-propenyl group and a 1-trifluoro-3-butenyl group.
  • the “C3-C10 haloalkynyl group” represents a group in which one or more hydrogen atoms of the C3-C10 alkynyl group are substituted with a halogen atom, and examples thereof include a C3-C10 fluoroalkynyl group.
  • Examples of the “C3-C10 haloalkynyl group” include a 3,3,3-trifluoro-1-propynyl group.
  • the “C1-C6 alkyl group optionally having one or more halogen atoms” represents, for example, a group in which one or more hydrogen atoms of the C1-C6 alkyl group are substituted with a halogen atom.
  • C1-C6 chain hydrocarbon group having one or more halogen atoms represents a C1-C6 alkyl group, a C2-C6 alkenyl group, or a C2-C6 alkynyl group having one or more halogen atoms.
  • the “C1-C6 alkyl group having one or more halogen atoms” refers to the “C1-C6 alkyl group optionally having one or more halogen atoms” and the “C2-C10 having one or more halogen atoms”.
  • C2-C6 alkenyl group having one or more halogen atoms and “C2-C6 alkynyl group having one or more halogen atoms” mean the above “C2-C10 chain hydrocarbon group having one or more halogen atoms”. Included in the definition of
  • cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • alkoxy group represents a monovalent group in which the alkyl group is bonded to an oxygen atom.
  • Examples of the C1-C6 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n- Examples include butoxy, t-butoxy, s-butoxy, and 3-methylbutoxy.
  • 3-7-membered non-aromatic heterocyclic group means an aziridine ring, azetidine ring, pyrrolidine ring, imidazoline ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidine Ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring, isothiazolidine ring, 1,3-thiazinane ring, thiomorpholine ring, or 1,4-thiazepane ring
  • Examples of the 3-7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from group E include the following groups.
  • N oxide compound examples include a compound represented by the formula (Id), a compound represented by the formula (Ie), and a compound represented by the formula (If). [Wherein the symbols have the same meaning as described above. ] [Wherein the symbols have the same meaning as described above. ] [Wherein the symbols have the same meaning as described above. ] [Wherein the symbols have the same meaning as described above. ]
  • Phenyl C1-C3 alkyl group ⁇ the phenyl moiety in the phenyl C1-C3 alkyl group may have one or more substituents selected from group D ⁇ includes, for example, a benzyl group, 2-fluorobenzyl Group, 4-chlorobenzyl group, 4- (trifluoromethyl) benzyl group, 2- [4- (trifluoromethyl) phenyl] ethyl group.
  • (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms refers to a group in which (C1-C5 alkoxy) and / or (C2-C5 alkyl) has one or more halogen atoms,
  • 2,2-difluoro-3- (2,2,2-trichloroethoxy) propyl group 2- (2,2,2-trichloroethoxy) ethyl group, 1,1,2-trifluoro-2- ( Trifluoromethoxy) ethyl group, 2,2-difluoro-3- (2,2,2-trifluoroethoxy) propyl group, 2- (2,2,2-trifluoroethoxy) ethyl group, 2,2-difluoro
  • An example is a -3-methoxypropyl group.
  • “(C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms” is a group in which (C1-C5 alkylsulfanyl) and / or (C2-C5 alkyl) has one or more halogen atoms.
  • a 2,2-difluoro-2- (trifluoromethylthio) ethyl group “(C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms” means a group in which (C1-C5 alkylsulfinyl) and / or (C2-C5 alkyl) has one or more halogen atoms.
  • 2,2-difluoro-2- (trifluoromethanesulfinyl) ethyl group can be mentioned.
  • “(C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms” means a group in which (C1-C5 alkylsulfonyl) and / or (C2-C5 alkyl) has one or more halogen atoms. Examples thereof include 2,2-difluoro-2- (trifluoromethanesulfonyl) ethyl group.
  • (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from group G means that (C3-C7 cycloalkyl) and / or (C1-C3 alkyl) is one or more groups Represents a group having one or more substituents selected from G, for example, (2,2-difluorocyclopropyl) methyl group, [1- (trifluoromethyl) cyclopropyl] methyl group, [2- (trifluoromethyl) ) Cyclopropyl] methyl group, 2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, and 2-cyclopropyl-3,3,3-trifluoropropyl group.
  • C3-C7 cycloalkyl group having one or more substituents selected from group G includes, for example, a 2,2-difluorocyclopropyl group, a 1- (2,2,2-trifluoroethyl) cyclopropyl group And 4- (trifluoromethyl) cyclohexyl group.
  • “5- or 6-membered aromatic heterocyclic group” represents a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group, and the 5-membered aromatic heterocyclic group is a pyrrolyl group, a furyl group, a thienyl group, or a pyrazolyl group.
  • “5-membered aromatic heterocyclic group containing 1 to 4 nitrogen atoms” means pyrrolyl group, pyrazolyl group, imidazolyl group, 1,2,4-triazolyl group, 1,2,3-triazolyl group, and tetrazolyl group Represents.
  • An alkylsulfanyl group, an alkylsulfinyl group, and an alkylsulfonyl group represent an S (O) z group having an alkyl group.
  • examples of the alkylsulfanyl group in which z is 0 include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, and an isopropylsulfanyl group.
  • examples of the alkylsulfinyl group in which z is 1 include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, and an isopropylsulfinyl group.
  • examples of the alkylsulfonyl group in which z is 2 include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and an isopropylsulfonyl group.
  • bipyridine compound examples include the following compounds.
  • bipyridine compound a compound wherein R 2 is a C1-C6 alkyl group optionally having one or more halogen atoms; In the bipyridine compound, a compound wherein R 2 is a C1-C6 alkyl group; In the bipyridine compound, a compound wherein R 2 is an ethyl group;
  • each R 3 is independently a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B ,
  • One 5-membered aromatic heterocyclic group selected from group Q (the 5-membered aromatic heterocyclic group may have one or more substituents selected from group D), OR 12 , NR 11 R 12 , NR 11a R 12a , NR 24 NR 11 R 12 , or a compound that is a halogen atom;
  • Group Q: ⁇ Drawing R 26 represents one or more halogen atoms which may have a C1-C6 alkyl group.
  • R 1 is a C2-C10 haloalkyl group, or one or more with a halogen atom (C1-C5 alkoxy) C2-C5 alkyl group
  • R 2 is a C1-C6 alkyl group
  • q is 0, 1, or 2
  • R 3 each independently has a C1-C6 alkyl group optionally having one or more substituents selected from group B, and may have one or more substituents selected from group B -C6 alkenyl group, one 5-membered aromatic heterocyclic group selected from group Q (the 5-membered aromatic heterocyclic group may have one or more substituents selected from group D), OR 12, NR 11 R 12, NR 11a R 12a, NR 24 NR 11 R 12, NR 11 C (O) R 13, NR 24 NR 11 C (O) R 13, NR 11 C (O) OR 14, NR 24 NR 11 C (O) OR 14 , NR 11 C (O) NR 15 R 16 , NR 24 NR 11
  • R 1 is a C2-C10 haloalkyl group, or one or more with a halogen atom (C1-C5 alkoxy) C2-C5 alkyl group
  • R 2 is a C1-C6 alkyl group
  • q is 0, 1, or 2
  • R 3 each independently has a C1-C6 alkyl group optionally having one or more substituents selected from group B, and may have one or more substituents selected from group B
  • a compound in which R 6 is each independently OR 18 , NR 18 R 19 , C (O) OR 25 , OC (O
  • R 1 is a C2-C6 alkyl group having 2 or more fluorine atoms, or a (C1-C5 alkoxy) C2-C5 alkyl group having 1 or more fluorine atoms
  • R 2 is a C1-C6 alkyl group
  • q is 0, 1, or 2
  • R 3 each independently has a C1-C6 alkyl group optionally having one or more substituents selected from group B, and may have one or more substituents selected from group B
  • R 1 is a C3-C5 alkyl group having 4 or more fluorine atoms, or a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group
  • R 2 is an ethyl group
  • q is 0, 1, or 2
  • R 3 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkenyl group optionally having one or more halogen atoms, one or more halogen atoms
  • a triazole group optionally having NR 11 R 12 , or a halogen atom
  • R 11 and R 12 are each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms, and p is 0;
  • R 1 is a C3-C5 alkyl group having 4 or more fluorine atoms
  • R 2 is an ethyl group
  • q is 0 or 1
  • R 3 each independently represents a C1-C6 alkyl group having one or more halogen atoms, an 1,2,4-triazol-1-yl group optionally having one or more halogen atoms, NR 11 R 12 or a halogen atom
  • R 11 and R 12 are each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms;
  • a compound wherein p is 0.
  • R 1 is a C2-C10 haloalkyl group or a C3-C7 cycloalkyl group having one or more substituents selected from Group G;
  • R 2 is a C1-C6 alkyl group optionally having one or more halogen atoms,
  • R 3 each independently has a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, NR 11 R 12 , NR 24 NR 11 R 12 , NR 24 NR 11 C (O) R 13 , or a halogen atom
  • R 11 , R 12 , R 13 and R 24 are a hydrogen atom or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms,
  • R 6 is a halogen atom, n is 2, q is 0, 1 or 2;
  • a compound wherein p is 0 or 1.
  • R 1 is a C2-C6 haloalkyl group or a C5-C7 cycloalkyl group having one or more halogen atoms
  • R 2 is a C1-C3 alkyl group
  • Each R 3 is independently a 5- or 6-membered aromatic heterocyclic group, NR 11 R 12 , NR 24 NR 11 R 12 , NR 24 NR 11 C (O) R 13 , or a halogen atom
  • R 11 , R 12 , R 13 and R 24 are a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms
  • R 6 is a halogen atom
  • n is 2
  • q is 0, 1 or 2
  • a compound wherein p is 0 or 1.
  • R 1 is a C2-C6 fluoroalkyl group or a C5-C7 cycloalkyl group having one or more fluorine atoms
  • R 2 is a C1-C3 alkyl group
  • R 3 is each independently a 5-membered heterocyclic group containing 1 to 4 nitrogen atoms, NR 11 R 12 , NR 24 NR 11 R 12 , NR 24 NR 11 C (O) R 13 , or a halogen atom Yes
  • R 11, R 12, R 13 and R 24 is hydrogen atom or a C1-C3 alkyl group
  • R 6 is a chlorine atom
  • n is 2
  • q is 0, 1 or 2
  • a compound wherein p is 0 or 1.
  • R 1 is a C3-C5 alkyl group having 2 or more fluorine atoms, or a cyclohexyl group having 1 or more fluorine atoms
  • R 2 is an ethyl group
  • R 3 each independently has a 1,2,4-triazol-1-yl group optionally having one or more halogen atoms, NR 11 R 12 , NR 24 NR 11 R 12 , NR 24 NR 11 C (O) R 13 , or a halogen atom
  • R 11 , R 12 , R 13 and R 24 are a hydrogen atom or a methyl group
  • R 6 is a chlorine atom
  • n is 2
  • q is 0, 1 or 2
  • a compound wherein p is 0 or 1.
  • R 1 is a C3-C5 alkyl group having two or more fluorine atoms, or a 4,4-difluorocyclohexyl group
  • R 2 is an ethyl group
  • Each R 3 independently represents a 1,2,4-triazol-1-yl group, NR 11 R 12 , NR 24 NR 11 R 12 , NR 24 NR 11 C (O) R 13 , a chlorine atom or a bromine atom
  • R 11 , R 12 and R 24 are a hydrogen atom or a methyl group, R 13 is a methyl group, R 6 is a chlorine atom, n is 2, q is 0, 1 or 2;
  • a compound wherein p is 0 or 1.
  • the bipyridine compound is the bipyridine compound 7, 8, 11, 12, 14, 15, 64, 69, 84, 104, 184, 204, 300, 303, 304, 306, 318, in the examples described below. 321 or 344.
  • Examples of the production method of the bipyridine compound include the following production methods.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons).
  • the oxidizing agent used in the reaction include m-chloroperbenzoic acid (hereinafter referred to as mCPBA).
  • mCPBA m-chloroperbenzoic acid
  • an oxidizing agent is usually used in an amount of 1 to 1.2 mol per 1 mol of the bipyridine compound (Ia).
  • the reaction temperature is usually in the range of ⁇ 20 to 80 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the obtained bipyridine compound (Ib) can be obtained by drying and concentrating the obtained organic layer.
  • a reducing agent for example, sodium sulfite or sodium thiosulfate
  • a base for example, sodium bicarbonate
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include halogenated hydrocarbons.
  • the oxidizing agent used in the reaction include mCPBA.
  • an oxidizing agent is usually used at a ratio of 1 to 2 moles with respect to 1 mole of the bipyridine compound (Ib).
  • the reaction temperature is usually in the range of ⁇ 20 to 80 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the reaction mixture After completion of the reaction, water is added to the reaction mixture, extraction is performed with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite or sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash with. By drying and concentrating the organic layer, the bipyridine compound (Ic) can be obtained.
  • a reducing agent for example, sodium sulfite or sodium thiosulfate
  • a base for example, sodium bicarbonate
  • this bipyridine compound (Ic) can be manufactured by one step reaction (one pot) by making this bipyridine compound (Ia) and an oxidizing agent react.
  • the reaction is carried out according to the method for producing the bipyridine compound (Ic) from the bipyridine compound (Ib) using an oxidizing agent in a proportion of usually 2 to 5 mol with respect to 1 mol of the bipyridine compound (Ia). be able to.
  • the bipyridine compound represented by the formula (Id) (hereinafter referred to as the present bipyridine compound (Id)), the bipyridine compound represented by the formula (Ie) (hereinafter referred to as the present bipyridine compound (Ie)), and the formula
  • the bipyridine compound represented by (If) (hereinafter referred to as the present bipyridine compound (If)) can be produced by reacting the bipyridine compound (Ic) with an oxidizing agent. [Wherein the symbols have the same meaning as described above. ]
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include halogenated hydrocarbons.
  • the oxidizing agent used in the reaction include mCPBA.
  • the reaction is usually used in a ratio of 1 to 10 mol per 1 mol of the bipyridine compound (Ic).
  • the reaction temperature is usually in the range of ⁇ 20 to 80 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • this bipyridine compound (Id), this bipyridine compound (Ie), and the mixture of this bipyridine compound (If) can be obtained.
  • This bipyridine compound (Id), this bipyridine compound (Ie), and this bipyridine compound (If) can be isolated by subjecting this mixture to chromatography, recrystallization, and the like.
  • the bipyridine compound (Ia) includes a compound represented by formula (M-1) (hereinafter referred to as compound (M-1)) and a compound represented by formula (R-1) (hereinafter referred to as compound (R-1)). And) in the presence of a base.
  • M-1 compound represented by formula (M-1)
  • R-1 compound represented by formula (R-1)
  • V represents a halogen atom, and other symbols have the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include aprotic polar solvents such as dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone (hereinafter referred to as NMP), and dimethyl sulfoxide (hereinafter referred to as DMSO).
  • DMF dimethylformamide
  • NMP N-methylpyrrolidone
  • DMSO dimethyl sulfoxide
  • aprotic polar solvent examples include alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides).
  • compound (R-1) is usually used at a ratio of 1 to 10 mol
  • base is usually used at a ratio of 1 to 10 mol.
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • the bipyridine compound (Ia) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • V is preferably a fluorine atom or a chlorine atom.
  • the bipyridine compound (Ia) includes a compound represented by formula (M-2) (hereinafter referred to as compound (M-2)) and a compound represented by formula (R-2) (hereinafter referred to as compound (R-2)). And) in the presence of a base.
  • M-2 a compound represented by formula
  • R-2 a compound represented by formula
  • V 1 represents a chlorine atom, a bromine atom or an iodine atom, and other symbols have the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include an aprotic polar solvent.
  • Examples of the base used in the reaction include alkali metal carbonates such as potassium carbonate and cesium carbonate (hereinafter referred to as alkali metal carbonates).
  • the compound (R-2) is usually used at a ratio of 1 to 10 moles, and the base is usually used at a ratio of 1 to 10 moles.
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • the bipyridine compound (Ia) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • the bipyridine compound represented by the formula (I) (hereinafter referred to as the present bipyridine compound (I)) is composed of the compound represented by the formula (M-3) (hereinafter referred to as the compound (M-3)) and the formula. It can be produced by reacting a compound represented by (R-3) (hereinafter referred to as compound (R-3)) in the presence of a base.
  • a compound represented by (R-3) hereinafter referred to as compound (R-3)
  • V 2 represents a C1-C10 perfluoroalkanesulfonyloxy group, and other symbols have the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include an aprotic polar solvent.
  • Examples of the base used in the reaction include alkali metal carbonates.
  • compound (R-3) is usually used in a proportion of 1 to 10 mol, and a base is usually used in a proportion of 0.1 to 5 mol with respect to 1 mol of compound (M-3).
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the bipyridine compound (I) can be obtained by performing post-treatment operations such as adding water of the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • the bipyridine compound (I) includes a compound represented by formula (M-4) (hereinafter referred to as compound (M-4)) and a compound represented by formula (R-4) (hereinafter referred to as compound (R-4)). And) in the presence of a base.
  • M-4 a compound represented by formula (M-4)
  • R-4 a compound represented by formula (R-4)
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include an aprotic polar solvent.
  • Examples of the base used in the reaction include alkali metal hydrides.
  • the compound (R-4) is usually used in a proportion of 1 to 10 mol
  • the base is usually used in a proportion of 1 to 10 mol.
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • the bipyridine compound (I) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • V is preferably a fluorine atom.
  • a compound represented by the formula (Ig) (hereinafter referred to as the present bipyridine compound (Ig)) can be produced according to the method described below.
  • R 34 , R 35 , and R 36 each independently represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, one or more atoms selected from group D, or Represents a phenyl group which may have a group, or a 5- or 6-membered aromatic heterocyclic group which may have one or more atoms or groups selected from group D, and other symbols have the same meanings as described above Represents.
  • R 34 , R 35 , and R 36 each independently represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, one or more atoms selected from group D, or Represents a phenyl group which may have a group, or a 5- or 6-membered aromatic heterocyclic group which may have one or more
  • Step 1 a compound represented by formula (M-5) (hereinafter referred to as compound (M-5)) and a compound represented by formula (R-5) (hereinafter referred to as compound (R-5)) And react.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include alcohols, aprotic polar solvents, and mixtures thereof.
  • compound (R-5) is usually used at a ratio of 1 to 10 mol per 1 mol of compound (M-5).
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, the residue obtained by concentrating the reaction mixture is directly used in Step 2.
  • the bipyridine compound (Ig) can be produced by reacting the residue obtained in Step 1, methanesulfonyl chloride and triethylamine.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include ethers (hereinafter referred to as ethers) such as tetrahydrofuran and methyl-tert-butyl ether (hereinafter referred to as MTBE).
  • ethers such as tetrahydrofuran and methyl-tert-butyl ether
  • MTBE methyl-tert-butyl ether
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the bipyridine compound (Ig) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • a compound represented by the formula (Ih) (hereinafter referred to as the present bipyridine compound (Ih)) can be produced, for example, according to the following method. [Wherein the symbols have the same meaning as described above. ] First, a method for producing a compound represented by the formula (M-6) (hereinafter referred to as compound (M-6)) from compound (M-5) will be described.
  • Compound (M-6) can be produced by reacting compound (M-5) with a compound represented by formula (R-6) (hereinafter referred to as compound (R-6)). The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons.
  • compound (R-6) is usually used at a ratio of 1 to 10 mol per 1 mol of compound (M-5).
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (M-6) can be isolated by performing post-treatment operations such as adding sodium bicarbonate water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. .
  • This bipyridine compound (Ih) can be produced by reacting compound (M-6) with a halogenating agent.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include halogenated hydrocarbons.
  • the halogenating agent used in the reaction include N-bromosuccinimide and N-chlorosuccinimide.
  • benzoyl peroxide may be added as necessary.
  • the halogenating agent is usually used in a proportion of 1 to 10 mol, and benzoyl peroxide is usually used in the proportion of 0.1 to 0.5 mol.
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • Step 1 A compound represented by formula (M-7) (hereinafter referred to as compound (M-7)) and a compound represented by formula (R-7) (hereinafter referred to as compound (R-7)) are prepared as bases. React in the presence.
  • Compound (R-7) can be produced according to the method described in WO2009 / 054742. The reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include halogenated hydrocarbons.
  • Examples of the base used in the reaction include organic bases such as triethylamine and pyridine (hereinafter referred to as organic bases).
  • organic bases such as triethylamine and pyridine (hereinafter referred to as organic bases).
  • compound (M-7) is usually used at a ratio of 1 to 10 mol
  • base is usually used at a ratio of 1 to 10 mol.
  • the reaction temperature is usually in the range of ⁇ 50 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, the residue obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer is used in Step 2.
  • the bipyridine compound (Ii) can be produced by reacting the residue obtained in Step 1 with ammonia.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include alcohols, water, and mixtures thereof.
  • As the ammonia used in the reaction an aqueous ammonia solution, an ammonia methanol solution, or the like can be used.
  • ammonia is usually used at a ratio of 1 to 100 mol per 1 mol of compound (M-7).
  • the reaction temperature is usually in the range of 0 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the bipyridine compound (Ii) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • the compound represented by the formula (Ij) (hereinafter referred to as the present bipyridine compound (Ij)) is composed of the compound (M-5) and the compound represented by the formula (R-8) (hereinafter referred to as the compound (R-8)). It can be manufactured by reacting. [Wherein the symbols have the same meaning as described above. ]
  • a solvent can be used as necessary. Examples of the solvent used in the reaction include an aprotic polar solvent.
  • compound (R-8) is usually used at a ratio of 1 to 10 mol per 1 mol of compound (M-5).
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the bipyridine compound (Ij) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • the compound represented by the formula (Ip) (hereinafter referred to as the present bipyridine compound (Ip)) is the same as the compound represented by the formula (Ik) (hereinafter referred to as the present bipyridine compound (Ik)) and the formula (R-12). ) (Hereinafter referred to as the compound (R-12)) is reacted in the presence of a base.
  • X 3 represents a fluorine atom, a chlorine atom, or S (O) 2 R 15 ; r represents 0, 1 or 2; and other symbols represent the same meaning as described above.
  • the reaction is usually performed in a solvent. Examples of the solvent used in the reaction include an aprotic polar solvent.
  • the base used in the reaction examples include alkali metal carbonates and alkali metal hydrides.
  • the compound (R-12) is usually used in a proportion of 1 to 10 moles, and the base is usually used in a proportion of 1 to 10 moles.
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the bipyridine compound (Ip) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • the compound represented by the formula (Im) (hereinafter referred to as the present bipyridine compound (Im)) is composed of the present bipyridine compound (Ik) and the compound represented by the formula (R-9) (hereinafter referred to as the compound (R-9)). It can be manufactured by reacting.
  • the compound represented by the formula (In) (hereinafter referred to as the present bipyridine compound (In)) is composed of the present bipyridine compound (Ik) and the compound represented by the formula (R-10) (hereinafter referred to as the compound (R-10)). It can be manufactured by reacting.
  • the compound represented by the formula (Io) (hereinafter referred to as the present bipyridine compound (Io)) is composed of the present bipyridine compound (Ik) and the compound represented by the formula (R-11) (hereinafter referred to as the compound (R-11)). It can be manufactured by reacting. [Wherein the symbols have the same meaning as described above. ] The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include ethers, nitriles such as acetonitrile (hereinafter referred to as nitriles), aprotic polar solvents, and mixtures thereof. The reaction can be carried out by adding a base as necessary.
  • Examples of the base used in the reaction include alkali metal carbonates, alkali metal hydrides, organic bases and the like.
  • the compound (R-9) is usually in a ratio of 1 to 10 mol and the base is usually 1 to 10 mol with respect to 1 mol of the bipyridine compound (Ik). It is used in the ratio.
  • the compound (R-10) is usually in a ratio of 1 to 10 mol and the base is usually in an amount of 1 to 10 per 1 mol of the bipyridine compound (Ik) compound. Used in molar proportions.
  • the compound (R-11) is usually in a ratio of 1 to 10 mol and the base is usually 1 to 10 per 1 mol of the bipyridine compound (Ik) compound. Used in molar proportions.
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound represented by the formula (Iq) (hereinafter referred to as the present bipyridine compound (Iq)) is composed of the present bipyridine compound (Ik) and the compound represented by the formula (R-13) (hereinafter referred to as the compound (R-13)).
  • a base In the presence of a base.
  • B 1 and B 2 each independently represent a nitrogen atom or CR 33
  • R 31 , R 32 , and R 33 each independently represent a hydrogen atom or one substituent selected from Group D And other symbols have the same meaning as described above.
  • This reaction can be carried out according to the method described in Production Method 11, using compound (R-13) instead of compound (R-12).
  • Manufacturing method 14 The compound represented by the formula (Is) (hereinafter referred to as the present bipyridine compound (Is)) and the compound represented by the formula (It) (hereinafter referred to as the present bipyridine compound (It)) are prepared according to the following method. Can be manufactured. [Wherein the symbols have the same meaning as described above. ]
  • a compound represented by formula (Ir) (hereinafter referred to as the present bipyridine compound (Ir)) and a compound represented by formula (R-14) (hereinafter referred to as compound (R-14)) are reacted.
  • a method for producing the present bipyridine compound (Is) is described.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include nitriles.
  • a base can be used as necessary.
  • Examples of the base used in the reaction include organic bases.
  • the compound (R-14) is usually used at a ratio of 1 to 5 moles and the base at a ratio of 0.1 to 5 moles.
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the bipyridine compound (Is) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • this bipyridine compound (It) it continues and describes the method of manufacturing this bipyridine compound (It) by making this bipyridine compound (Is) and a base react.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include alcohols, water, and mixtures thereof.
  • the base used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
  • the base is used in a proportion of 0.1 to 5 mol with respect to 1 mol of the bipyridine compound (Is).
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the bipyridine compound (It) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • This bipyridine compound (Ia) is obtained by reacting a compound represented by formula (M-22) (hereinafter referred to as compound (M-22)) with compound (R-2) in the presence of a base and a reducing agent.
  • M-22 a compound represented by formula (M-22)
  • R-2 a reducing agent
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include an aprotic polar solvent.
  • Examples of the base used in the reaction include alkali metal carbonates.
  • Examples of the reducing agent used in the reaction include sodium hydroxymethanesulfinate.
  • compound (R-2) is usually in a proportion of 1 to 10 mol
  • base is usually in a proportion of 1 to 10 mol
  • reducing agent is usually in a proportion of 1 to 10 mol. It is used in the ratio.
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • the bipyridine compound (Ia) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Compound (M-1) is a compound represented by formula (M-8) (hereinafter referred to as compound (M-8)) and a compound represented by formula (M-9) (hereinafter referred to as compound (M-9)).
  • M a compound represented by formula (M-8)
  • M-9 a compound represented by formula (M-9)
  • V 3 represents a chlorine atom, a bromine atom or an iodine atom
  • M represents Sn (n—C 4 H 9 ) 3
  • Compound (M-9) can be produced, for example, according to the method described in WO 03/024961 or the method described in Organic Process Research & Development, 2004, 8, 192-200.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene.
  • the metal catalyst used in the reaction include palladium catalysts such as tetrakis (triphenylphosphine) palladium (0) and 1,1′-bis (diphenylphosphino) ferrocenepalladium (II) dichloride.
  • the inorganic halide used in the reaction include alkali metal fluorides such as potassium fluoride and sodium fluoride, and alkali metal chlorides such as lithium chloride and sodium chloride.
  • the compound (M-9) is usually in a proportion of 1 to 10 moles
  • the metal catalyst is usually in a proportion of 0.01 to 0.5 mole, an inorganic halide. Is usually used in a proportion of 0.1 to 5 mol.
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • compound (M-1) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Reference production method 2 Compound (M-8) is produced by reacting a compound represented by formula (M-10) (hereinafter referred to as compound (M-10)) with compound (R-3) in the presence of a base. can do. [Wherein the symbols have the same meaning as described above. ] The method of reacting compound (M-10) and compound (R-3) is in accordance with the method described in Production Method 5.
  • Reference manufacturing method 3 Compound (M-3) can be produced by reacting a compound represented by formula (M-11) (hereinafter referred to as compound (M-11)) with an acid.
  • M-11 a compound represented by formula (M-11)
  • R x represents a methyl group or an ethyl group, and other symbols represent the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include halogenated hydrocarbons.
  • Examples of the acid used in the reaction include boron halides such as boron trichloride and boron tribromide.
  • an acid is usually used at a ratio of 0.1 to 10 mol per 1 mol of the compound (M-11).
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • compound (M-3) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic
  • Reference production method 4 In the compound (M-11), a compound in which n is 0 (hereinafter referred to as the compound (M-11a)), a compound in which n is 1 (hereinafter referred to as the compound (M-11b)), and n A compound in which is 2 (hereinafter referred to as compound (M-11c)) can be produced according to the following method. [Wherein the symbols have the same meaning as described above. ]
  • Compound (M-13) described in Reference Production Method 1 is a compound represented by formula (M-12) (hereinafter referred to as compound (M-12)) instead of compound (M-8). It can be produced according to the method.
  • Compound (M-12) can be obtained by production according to the method described in Heterocycles, 1990, 30, 875-884. A commercially available compound (M-12) may also be used.
  • Compound (M-11a) can be produced according to the method described in Production Method 3, using Compound (M-13) instead of Compound (M-1).
  • Compound (M-11b) and Compound (M-11c) can be produced according to the method described in Production Method 1 using Compound (M-11a) instead of Bipyridine Compound (Ia).
  • the compound represented by the formula (M-15) (hereinafter referred to as compound (M-15)) can be produced according to the method described below. [Wherein the symbols have the same meaning as described above. ]
  • compound (M-15) a compound represented by the formula (M-14) (hereinafter referred to as compound (M-14)) is used in place of the compound (M-5), and the method according to production method 7 is used. It can be manufactured according to.
  • a compound represented by formula (M-17) (hereinafter referred to as compound (M-17)) is a compound represented by formula (M-16) (hereinafter referred to as compound (M-16)) and a compound. It can be produced by reacting with (R-12) and then reacting with ammonia. [Wherein the symbols have the same meaning as described above. ] Compound (M-17) can be produced according to the method described in production method 9, using compound (M-16) in place of compound (M-7).
  • Reference manufacturing method 7 A compound represented by the formula (M-18) (hereinafter referred to as compound (M-18)) can be produced by reacting compound (M-14) with compound (R-8). [Wherein the symbols have the same meaning as described above. ] Compound (M-18) can be produced according to the method described in production method 10, using compound (M-14) instead of compound (M-5).
  • a compound represented by formula (M-19) (hereinafter referred to as compound (M-19)) is a compound represented by formula (M-20) (hereinafter referred to as compound (M-20)). It can be produced by reacting in the presence of an acid.
  • R 38 represents a halogen atom or OR 1 , and other symbols have the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, alcohols, aprotic polar solvents, water, and mixtures thereof.
  • the acid used in the reaction include hydrochloric acid and sulfuric acid.
  • an acid is usually used at a ratio of 0.1 to 5 mol with respect to 1 mol of the compound (M-17).
  • the reaction temperature is usually in the range of 0 ° C to 100 ° C.
  • the reaction time is usually in the range of 0.5 to 12 hours.
  • compound (M-19) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Compound (M-20) includes a compound represented by formula (M-21) (hereinafter referred to as compound (M-21)) and a compound represented by formula (R-16) (hereinafter referred to as compound (R-)). 16).) Can be reacted in the presence of a base. [Wherein the symbols have the same meaning as described above. ] The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include ethers, hexane, and mixtures thereof. An example of the base used in the reaction is n-butyllithium.
  • compound (M-21) In the reaction, with respect to 1 mol of compound (M-21), compound (R-16) is usually used at a ratio of 1 to 5 mol, and base is usually used at a ratio of 1 to 5 mol.
  • the reaction temperature is usually in the range of ⁇ 78 ° C. to 100 ° C.
  • the reaction time is usually in the range of 0.5 to 12 hours.
  • compound (M-20) After completion of the reaction, compound (M-20) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Compound (M-21) can be produced by a known method. A commercially available compound (M-21) may also be used.
  • Reference production method 10 Compound (M-2) and compound (M-22) can be produced by reacting compound (M-1) with a sulfurizing agent. [Wherein the symbols have the same meaning as described above. ]
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include an aprotic polar solvent.
  • the sulfurizing agent used in the reaction include sodium sulfide and sodium hydrogen sulfide.
  • a sulfurizing agent is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (M-1).
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • post-treatment operations such as addition of water to the reaction mixture, extraction with an organic solvent, drying and concentration of the organic layer, and the like are carried out to give compound (M-2) and compound (M-22).
  • V is preferably a fluorine atom or a chlorine atom.
  • Reference production method 11 In the compound (M-4), a compound in which V is a chlorine atom or a bromine atom (hereinafter referred to as compound (M-4a)), and a compound in which V is a fluorine atom or an iodine atom (hereinafter referred to as compound (M-4b) ) Can be produced according to the method described below.
  • V 4 represents a chlorine atom or a bromine atom
  • V 5 represents a fluorine atom or an iodine atom
  • other symbols represent the same meaning as described above.
  • Compound (M-4a) can be produced by reacting compound (M-3) with phosphorus oxychloride or phosphorus oxybromide.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include aromatic hydrocarbons.
  • phosphorus oxychloride can also be used as a solvent.
  • phosphorus oxychloride or phosphorus oxybromide is usually used at a ratio of 1 to 10 mol with respect to 1 mol of compound (M-3).
  • the reaction temperature is usually in the range of 0 ° C to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • the compound (M-4a) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Compound (M-4b) can be produced by reacting compound (M-4a) with an inorganic fluoride or inorganic iodide.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include nitriles, aprotic polar solvents, and mixtures thereof.
  • Examples of the inorganic fluoride used in the reaction include potassium fluoride.
  • Examples of the inorganic iodide used in the reaction include sodium iodide.
  • an inorganic fluoride or an inorganic iodide is usually used at a ratio of 1 to 10 mol with respect to 1 mol of the compound (M-4a).
  • reaction temperature is usually in the range of 0 ° C to 250 ° C.
  • reaction time is usually in the range of 0.5 to 24 hours.
  • compound (M-4b) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • R 201 represents R 1
  • R 202 represents R 2
  • R 203 , R 204 , and R 205 each independently represent a hydrogen atom or R 3
  • R 208 each independently represents a hydrogen atom or R 6
  • n represents 0, 1, or 2.
  • n 2
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are hydrogen atoms
  • R 201 and R 202 are Tables 1 to 11 Or a bipyridine compound (hereinafter referred to as compound group SX1).
  • n is 1, R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are hydrogen atoms, and R 201 and R 202 are Tables 1 to 11
  • the bipyridine compound (hereinafter referred to as compound group SX2), which is any combination described in 1.
  • n is 0, R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are hydrogen atoms, and R 201 and R 202 are Tables 1 to 11 Or a bipyridine compound (hereinafter referred to as compound group SX3).
  • n 2
  • R 201 is a 2,2,3,3-tetrafluoropropyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX4).
  • n 2
  • R 201 is a 2,2,3,3,3-pentafluoropropyl group
  • R 202 is an ethyl group
  • R 203 is an ethyl group
  • R 204 The present bipyridine compound wherein R 205 , R 206 , R 207 and R 208 are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX5).
  • R 201 is a 1,1,2,3,3,3-hexafluoropropyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are bipyridine compounds (hereinafter referred to as compound group SX6) in which any combination shown in Table 12 to Table 19 is combined.
  • n 2
  • R 201 is a 2,2,3,4,4,4-hexafluorobutyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are the present bipyridine compounds (hereinafter referred to as compound group SX7) in any combination of Tables 12-19.
  • n 2
  • R 201 is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any of the combinations described in Tables 12 to 19 (hereinafter referred to as compound group SX8).
  • n 2
  • R 201 is a 2,2,3,3-tetrafluoropropyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX9).
  • n 2
  • R 201 is a 2,2,3,3,3-pentafluoropropyl group
  • R 202 is a methyl group
  • R 203 is a methyl group
  • R 204 This bipyridine compound wherein R 205 , R 206 , R 207 and R 208 are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX10).
  • R 201 is a 1,1,2,3,3,3-hexafluoropropyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are bipyridine compounds (hereinafter referred to as compound group SX11) wherein any combination of Table 12 to Table 19 is combined.
  • n 2
  • R 201 is a 2,2,3,4,4,4-hexafluorobutyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are the present bipyridine compounds (hereinafter referred to as compound group SX12) in any combination of Tables 12-19.
  • n 2
  • R 201 is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any of the combinations described in Tables 12 to 19 (hereinafter referred to as compound group SX13).
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are hydrogen atoms, and R 201 and R 202 are any one of those shown in Tables 1 to 11.
  • This bipyridine compound as a combination hereinafter referred to as compound group SX14).
  • n 2
  • R 201 is a 2,2,3,3-tetrafluoropropyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are a combination of any of Tables 12 to 19 (hereinafter referred to as compound group SX15).
  • n 2
  • R 201 is a 2,2,3,3,3-pentafluoropropyl group
  • R 202 is an ethyl group
  • R 203 is an ethyl group
  • R 204 This bipyridine compound wherein R 205 , R 206 , R 207 and R 208 are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX16).
  • R 201 is a 1,1,2,3,3,3-hexafluoropropyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are the present bipyridine compounds (hereinafter referred to as compound group SX17) in any combination of Tables 12-19.
  • n 2
  • R 201 is a 2,2,3,4,4,4-hexafluorobutyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are bipyridine compounds of any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX18).
  • n 2
  • R 201 is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any of the combinations described in Tables 12 to 19 (hereinafter referred to as compound group SX19).
  • n 2
  • R 201 is a 2,2,3,3-tetrafluoropropyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX20).
  • n 2
  • R 201 is a 2,2,3,3,3-pentafluoropropyl group
  • R 202 is a methyl group
  • R 203 is a methyl group
  • R 204 is a present bipyridine compound wherein R 205 , R 206 , R 207 and R 208 are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX21).
  • R 201 is a 1,1,2,3,3,3-hexafluoropropyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are bipyridine compounds (hereinafter referred to as compound group SX22) in which any combination shown in Tables 12 to 19 is combined.
  • n 2
  • R 201 is a 2,2,3,4,4,4-hexafluorobutyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are the present bipyridine compounds (hereinafter referred to as compound group SX23) in any combination of Tables 12-19.
  • n 2
  • R 201 is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX24).
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are hydrogen atoms, and R 201 and R 202 are any one of those shown in Tables 1 to 11.
  • This bipyridine compound as a combination hereinafter referred to as compound group SX25).
  • n 2
  • R 201 is a 2,2,3,3-tetrafluoropropyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX26).
  • n 2
  • R 201 is a 2,2,3,3,3-pentafluoropropyl group
  • R 202 is an ethyl group
  • R 203 is an ethyl group
  • R 204 The present bipyridine compound wherein R 205 , R 206 , R 207 and R 208 are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX27).
  • R 201 is a 1,1,2,3,3,3-hexafluoropropyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are bipyridine compounds (hereinafter referred to as compound group SX28) in which any combination shown in Tables 12 to 19 is combined.
  • n 2
  • R 201 is a 2,2,3,4,4,4-hexafluorobutyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are the present bipyridine compounds (hereinafter referred to as compound group SX29) in any combination of Tables 12 to 19;
  • n 2
  • R 201 is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are present bipyridine compounds (hereinafter referred to as compound group SX30) in any combination of Tables 12 to 19.
  • n 2
  • R 201 is a 2,2,3,3-tetrafluoropropyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX31).
  • n 2
  • R 201 is a 2,2,3,3,3-pentafluoropropyl group
  • R 202 is a methyl group
  • R 203 is a methyl group
  • R 204 This bipyridine compound wherein R 205 , R 206 , R 207 and R 208 are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX32).
  • n 2
  • R 201 is a 1,1,2,3,3,3-hexafluoropropyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are the present bipyridine compounds (hereinafter referred to as compound group SX33) in any combination of Tables 12-19.
  • n 2
  • R 201 is a 2,2,3,4,4,4-hexafluorobutyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are bipyridine compounds (hereinafter referred to as compound group SX34) wherein any combination shown in Tables 12 to 19 is combined.
  • n 2
  • R 201 is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any of the combinations described in Tables 12 to 19 (hereinafter referred to as compound group SX35).
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are hydrogen atoms, and R 201 and R 202 are any one of those shown in Tables 1 to 11.
  • This bipyridine compound as a combination hereinafter referred to as compound group SX36).
  • n 2
  • R 201 is a 2,2,3,3-tetrafluoropropyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX37).
  • n 2
  • R 201 is a 2,2,3,3,3-pentafluoropropyl group
  • R 202 is an ethyl group
  • R 203 , R 204 The present bipyridine compound wherein R 205 , R 206 , R 207 and R 208 are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX38).
  • R 201 is a 1,1,2,3,3,3-hexafluoropropyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are the present bipyridine compounds (hereinafter referred to as compound group SX39) in any combination of Tables 12-19.
  • n 2
  • R 201 is a 2,2,3,4,4,4-hexafluorobutyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are bipyridine compounds (hereinafter referred to as compound group SX40) in which any combination shown in Tables 12 to 19 is combined.
  • n 2
  • R 201 is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group
  • R 202 is an ethyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any of the combinations shown in Tables 12 to 19 (hereinafter referred to as compound group SX41).
  • n 2
  • R 201 is a 2,2,3,3-tetrafluoropropyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any combination of Tables 12 to 19 and the present bipyridine compound (hereinafter referred to as compound group SX42).
  • n 2
  • R 201 is a 2,2,3,3,3-pentafluoropropyl group
  • R 202 is a methyl group
  • R 203 , R 204 This bipyridine compound wherein R 205 , R 206 , R 207 and R 208 are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX43).
  • n 2
  • R 201 is a 1,1,2,3,3,3-hexafluoropropyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any of the combinations described in Table 12 to Table 19 and the present bipyridine compound (hereinafter referred to as compound group SX44).
  • n 2
  • R 201 is a 2,2,3,4,4,4-hexafluorobutyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are bipyridine compounds (hereinafter referred to as compound group SX45) in which any combination shown in Table 12 to Table 19 is combined.
  • n 2
  • R 201 is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group
  • R 202 is a methyl group
  • R 203 , R 204 , R 205 , R 206 , R 207 and R 208 are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX46).
  • Group (a) is a group consisting of the following subgroups a-1, a-2, a-3, a-4, a-5, a-6 and a-7.
  • Subgroups a-1 include acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, fluradixurone, flupyradifurone ), Triflumezopyrim (triflumezopyrim), dichloromesothiaz (dicloromezotiaz) and a compound represented by the following formula (CAS registration number 1689566-03-7, hereinafter may be referred to as insecticidal compound ⁇ )
  • a group of competitive modulators of nicotinic acetylcholine receptors A group of competitive modulators of nicotinic acetylcholine receptors.
  • Subgroup a-2 includes acrinathrin, allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin ), Beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, sigma-cypermethrin, cyphenothrin, deltamethrin, Empentrin (empe nthrin), esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate
  • Subgroup a-3 is a group of GABAergic chloride channel blockers consisting of ethiprole, fipronil and flufiprole, as well as afoxolaner, fluralaner, broflanilide. And a group of GABAergic chloride channel allosteric modulators consisting of flaxametamide.
  • Subgroup a-4 consists of chlorantraniliprole, cyantraniliprole, cycloniliprole, flubendiamide, tetraniliprole and cyhalodiamide.
  • a group of ryanodine receptor modulators A group of ryanodine receptor modulators.
  • Subgroup a-5 is composed of alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl (NAC), Carbofuran, carbosulfan, ethiofencarb, fenobucarb (BPMC), formethanate, furathiocarb, isoprocarb (MIPC), methiocarb, methomyl , Metolcarb (MTMC), oxamyl (oxamyl), pirimicarb, propoxur (PHC), thiodicarb, thiofanox, triazamate, trimethacarb, XMC Fine xylylcarb: consisting (xylylcarb MPMC), a group of carbamates acetylcholinesterase (AChE) inhibitors.
  • Subgroup a-6 is a group of nematicidal active compounds consisting of abamectin, fluensulfone, tioxazafen, and fluazaindolizine.
  • Subgroup a-7 includes Mycorrhiza Fungi, Arthrobotrys dactyloides, Bacillus thuringiensis, Bacillus firmus, Bacillus megaterium.
  • Pasturia Microbial material consisting of Pasteuria penetrans, Pasturia usgae, Verticillium chlamydosporium and Harpin protein A group.
  • Dichloromesothiaz (CAS registration number: 1263629-39-5), tetraniliprole (CAS registration number: 1229654-66-3), floxamethamide (CAS registration number: 928783-29-3), afoxoranel (CAS registration number: 1093861-60-9), fluralanel (CAS registration number: 864731-61-3), brofuranilide (CAS registration number: 1207727-04-5), fluazaindolizine (CAS registration number: 1254304-22-7), tioxazafen (CAS registration number: 330459-31-9) and insecticidal compound ⁇ (CAS registration number: 1689566-03-7) are both known compounds and are disclosed in International Publication Nos.
  • Mycorrhiza Fungi Arthrobotrys dactyloides, Bacillus thuringiensis, Bacillus firmus, Bacillus megaterium, Bacillus amyloliquefaciens (Bacillus amyloliquefaciens), Hirsutella rhossiliensis, Hirsutella minnesotensis, Monacrosporium phymatopagus, Pasturiatransurie, Pasturiapass ⁇ Usugae (Pasteuria usgae), Verticillium chlamydosporium and Harpin protein are all known microbial materials Obtained from commercially available preparations or obtained by production using a known method.
  • these microbial materials can also be obtained from a fungus depository.
  • a fungus depository As the mycorrhizal fungi, Arbuscular mycorrhizal fungus is preferable, and in particular, bacteria belonging to the genus Gromus, such as Glomus intraradices, Glomus mosseae Glomus aggregatum and Glomus etunicatum are preferred.
  • these bacterium belonging to the genus Gromas may be used alone or as a mixture of two or more bacteria.
  • Group (b) is a group consisting of the following subgroups b-1, b-2, b-3, b-4, b-5, b-6, b-7, b-8 and b-9.
  • Subgroup b-1 includes azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole M, epoxy Conoxi (epoxiconazole), etaconazole (etaconazole), fenarimol (fenarimol), fenbuconazole (fenbuconazole), fluquinconazole ( fluquinconazole), quinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, Microbutanil, nuarimol, oxpoconazole, oxpoconazole fumarate
  • Subgroup b-2 includes azoxystrobin, coumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, fena Minstrobin, flufenoxystrobin, fluoxastrobin, cresoxim-methyl, mandestrobin, methminostrobin, oryastrobine, orysastrobin, Picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, pyribencarb and triclopyricar b) a group of Qo inhibitors (Quinone outside inhibitors) and a group of Qi inhibitors (Quinone inside inhibitors) consisting of cyazofamid and amisulbrom.
  • Subgroup b-3 consists of benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl and ofurace, A group of RNA polymerase I inhibitors.
  • Subgroup b-4 includes benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil , Fluxapyroxad, furametpyr, isofetamid, isopyrazam, mepronil, oxycarboxin, penthiopyrad, penflufen, sedaxane (sax) Thifluzamide, pyraziflumid, pydiflumetofen (CAS registration number 1228284-64-7), 3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4 -Yl) pyrazole-4-carboxami (CAS registration number 141573-94-6, hereinafter may be referred to as bactericidal compound ⁇ 1), 3-difluoromethyl-1-methyl-N-[(3R) -1,1,3-trimethylindan-4- Yl] pyrazole-4-carboxamide (CAS registration
  • Subgroup b-5 includes benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide and A group of ⁇ -tubulin polymerization inhibitors consisting of ethaboxam.
  • Subgroup b-6 includes ferbam, mancozeb, maneb, metyram, propineb, thiram, zineb, ziram, captan ), Captafol, folpet, chlorothalonil, tolylfluanid, guazatine, iminoctadine, anilazine, dithianon, quinomethionate or chinomethionat It is a group of multi-acting point contact active compounds consisting of quinomethionate and fluoroimide.
  • Subgroup b-7 includes dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthivalicarb-isopropyl, iprovalicarb, variphenate ( A group of cellulose synthesis inhibitors consisting of valifenalate and mandipropamid. .
  • Subgroup b-8 consists of fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone and vinclozolin in MAP (mitogen-activated protein) ) / Histidine kinase inhibitor group.
  • Subgroup b-9 is a group of other fungicides consisting of tolclofos-methyl, oxathiapiprolin, picarbutrazox, fluopicolide and silthiofam. is there.
  • Kemmitt and the like. These compounds can be obtained from commercially available preparations or produced by known methods.
  • the bactericidal compound ⁇ 1 and the bactericidal compound ⁇ 2 are both known compounds, and can be produced by the methods described in International Publication No. 2011/162397, respectively.
  • the bactericidal compound ⁇ 3 and the bactericidal compound ⁇ 4 are both known compounds and can be produced by the methods described in International Publication No. 2012/084812, respectively.
  • the bactericidal compound ⁇ 5 is a known compound and can be produced by the method described in International Publication No. 2013/160387.
  • the compound is an insecticidal compound ⁇ , clothianidin, dichloromezothiaz, flupirazifuron, imidacloprid, thiacloprid, thiamethoxam, triflumezopyrim, tefluthrin, brofuranilide, fipronil, floxamethamide, chlorantraniliprole, cyantraniliprole, tetra Niliprol, Abamectin, Fluazaindolizine, Thioxazafen, Bacillus amyloliquefaciens, Bacillus films, Difenoconazole, Flutriahol, Ipconazole, Metoconazole, Prothioconazole, Tebuconazole, Tetraconazole, Triazimenol, Tritico Nazole, azoxystrobin, phenamidon, floxastrobin, mandestrobin, picoxystrobin, pirak Strobin, trifloxystro
  • the compound is clothianidin, imidacloprid, thiamethoxam, difenoconazole, flutriahole, ipconazole, metconazole, prothioconazole, tebuconazole, triazimenol, triticonazole, azoxystrobin, floxastrobin, mandestrobin , Picoxystrobin, pyraclostrobin, trifloxystrobin, metalaxyl M, metalaxyl, fluopyram, flutolanil, fluxapyroxad, penflufen, penthiopyrad, bactericidal compound ⁇ 2, cedaxane, ethaboxam, fludioxonil and oxathiapiproline It is one or more types of compounds selected from.
  • the compound is an insecticidal compound ⁇ , clothianidin, dichloromezothiaz, flupirazifuron, imidacloprid, thiacloprid, thiamethoxam, triflumezopyrim, tefluthrin, brofuranilide, fipronil, floxamethamide, chlorantraniliprole, cyantraniliprole, tetra It is one or more compounds selected from the group consisting of niliprol, abamectin, fluazaindolizine, thioxazaphene, Bacillus amyloliquefaciens and Bacillus films.
  • the compound is one or more compounds selected from the group consisting of clothianidin, imidacloprid and thiamethoxam.
  • the compound is difenoconazole, flutriazole, ipconazole, metconazole, prothioconazole, tebuconazole, tetraconazole, triadimenol, triticonazole, azoxystrobin, fenamidone, floxastrobin, mandest Robin, picoxystrobin, pyraclostrobin, trifloxystrobin, metalaxyl M, metalaxyl, boscalid, fluopyram, flutolanil, fluxapyroxad, penflufen, penthiopyrad, bactericidal compound ⁇ 2, sedaxane, ethaboxam, thiabendazole, thiuram, fludioxonil, One or more compounds selected from the group consisting of
  • the compound is difenoconazole, flutriazole, ipconazole, metconazole, prothioconazole, tebuconazole, triazimenol, triticonazole, azoxystrobin, floxastrobin, mandestrobin, picoxystrobin, One or more selected from the group consisting of pyraclostrobin, trifloxystrobin, metalaxyl M, metalaxyl, fluopyram, flutolanil, floxapyroxad, penflufen, penthiopyrad, bactericidal compound ⁇ 2, sedaxane, ethaboxam, fludioxonil and oxathiapiproline It is a compound of this.
  • SX means “any one of the present bipyridine compounds selected from the compound group SX1 to SX46”.
  • composition of the present invention may be a simple mixture of the present bipyridine compound and the present compound, but usually the present bipyridine compound and the present compound are mixed with an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, Emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, obtained by adding surfactants and other formulation adjuvants as necessary.
  • the total content of the bipyridine compound and the compound in the composition of the present invention is usually in the range of 0.1 to 100% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80% by weight. .
  • solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur).
  • Polyester resins such as polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymers).
  • liquid carrier examples include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), n
  • gaseous carrier examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.
  • surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.
  • formulation adjuvants include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthesis Water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4-methoxyphenol and 3- Mention may be made of mixtures with tert-butyl-4-methoxyphenol.
  • fixing agents such as casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthesis Water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, 2,
  • Examples of the base material of the resin preparation include vinyl chloride polymers and polyurethanes. These base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.), adipic acid esters, if necessary. A plasticizer such as stearic acid may be added.
  • the resin preparation is obtained by kneading the bipyridine compound and the compound into the base material using a general kneading apparatus, and then performing molding such as injection molding, extrusion molding, press molding, and the like. It can be processed into a resin formulation having a plate shape, a film shape, a tape shape, a net shape, a string shape or the like through processing steps such as molding and cutting.
  • the bait base include cereal flour, vegetable oil, sugar, crystalline cellulose, and, if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, Additives such as pepper, powdered foods for children and pets, cheese flavor, onion flavor, peanut oil and other pest attractant flavors are added.
  • the content ratio of the present bipyridine compound and the present compound in the composition of the present invention is not particularly limited, but the composition of the present invention is one or more compounds selected from the group (a) (hereinafter referred to as the present compound). a), the ratio of the content of the bipyridine compound and the compound a is preferably in the range of 100: 1 to 1: 100 by weight, in particular 10: 1 to 1:10. The range of is preferable.
  • the ratio of the content of the bipyridine compound and the present compound b is preferably The weight ratio is in the range of 10,000: 1 to 1: 100, particularly preferably in the range of 1000: 1 to 1:10, and more preferably in the range of 1000: 1 to 1: 1.
  • the pest control method of the present invention is carried out by applying an effective amount of the composition of the present invention to pests directly and / or in the habitat of pests.
  • habitats for pests include plants, soil for cultivating plants, indoors, and animal bodies.
  • Examples of a method for applying an effective amount of the composition of the present invention to a plant or soil for cultivating a plant include, for example, a method of applying an effective amount of the composition of the present invention to a plant foliage, flower vase, seedling or ear, seed disinfection, A method of applying an effective amount of the composition of the present invention to seeds such as seed soaking and seed coats or bulbs such as seed pods, a method of applying an effective amount of the composition of the present invention to soil before or after planting Is mentioned.
  • the effective amount of the composition of the present invention is applied to the surface of the plant such as foliage spraying, tree spraying, etc.
  • a method of spraying an effective amount of the composition of the present invention to the vase or the whole plant in the flowering period including before flowering, during flowering, and after flowering is mentioned.
  • a method of spraying an effective amount of the composition of the present invention on the panicle or the whole plant is mentioned.
  • a method for controlling pests by applying an effective amount of the composition of the present invention to soil before or after planting is intended to protect against damage such as feeding by pests.
  • a method for directly controlling pests by applying an effective amount of the composition of the present invention to the rhizosphere of the crop to be cultivated, or by feeding an effective amount of the composition of the present invention into the plant body from the root or the like to feed the plant It is a method to control the pests.
  • Examples of a method for applying an effective amount of the composition of the present invention to soil before or after planting a plant include planting treatment (planting hole spraying, planting treatment soil admixture), plant source treatment (strain Former spraying, Strain source soil mixing, Strain source irrigation, Late seedling treatment, Soil planting treatment (Sprouting spray, Sprout soil mixing), Soil treatment (Striping spray, Soil mixing, Growing season crop) Striping), cropping treatment at sowing (spreading at sowing, mixing with soil at sowing), full treatment (spreading all soil, blending with whole soil), side treatment, water surface treatment (water surface application, water surface after flooding) Application), other soil spraying treatments (growth season granule foliar spraying, under-canopy or around trunk trunk, soil surface spraying, soil surface mixing, sowing hole spraying, buttocks surface spraying, inter-plant spraying), other irrigation processing (soil Irrigation, seedling irrigation, chemical infusion treatment, local irrigation, chemical drip irrigation, chemigesi ), Seed
  • the seed means the seed of the plant in a state before being sown in the soil or the culture medium
  • the bulb is a bulb, a bulb, or a tuber of the plant in a state before being planted in the soil or the culture medium.
  • Rhizome, stem fragment, seed pod and tuberous root a method for controlling pests by applying an effective amount of the composition of the present invention to seeds or bulbs is, for example, directly applied to seeds or bulbs of plants to be protected from damage such as feeding by pests.
  • An effective amount of the composition of the present invention is osmotically transferred inside the plant body to control pests that feed on the plant, and a method of applying the effective amount of the composition of the present invention to seeds or bulbs is, for example, , Spraying treatment, smearing treatment, dipping treatment, impregnation treatment, coating treatment, film coating treatment, and pellet coating treatment. Seeds or bulbs that retain an effective amount of the composition of the invention are prepared by these methods.
  • the application amount of the bipyridine compound is usually 0.001 to 100 g, preferably 0.02 to 20 g, per 1 kg of seeds or bulbs.
  • the amount is usually 0.000001 to 50 g, preferably 0.0001 to 30 g per kg of seeds or bulbs.
  • Examples of the pests for which the composition of the present invention is effective include harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and phytopathogenic fungi such as filamentous fungi and bacteria. Examples of such pests include the following.
  • Hemiptera pests Japanese green planthoppers (Laodelphax striatellus), Japanese brown planthoppers (Nilaparvata lugens), white planthoppers (Sogatella furcifera), corn planters (Peregrinus maidis), etc .; Nephotettix (Nephotettix nigropictus), Recipe dorsalis, Emporasca onukii, Potato reef hopper (Empoasca fabae), Corn leaf hopper (Dalbulus maidis), Sugarcane ugicine (Suhana) ), Leafhoppers (Cofana spectra), leafhoppers such as Nephotettix nigropictus; cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), daikona Aphid (Brevicoryne brassicae), snowy aphid (Aphis spiraecola), tulip beetle a
  • Lepidopterous insects Chilo suppressalis, Darkheaded stem borer (Chilo polychrysus), Trichomyceae (Tryporyza incertulas), Shiromecho (Scirpophaga innotata), Yellow stem borer (Scirpophaga incertulas (Cnaphalocrocis medinalis), Marasmia patnalis, Marasmia exigna, cotton moth (Notarcha derogata), puffer moth (Plodia ⁇ interpunctella), yellow moth (Ostrinia furnacalis), yellow moth (Hellulaedlus moth) depunctalis), Marasmia genus, Hop vine borer (Hydraecia immanis), European corn borer (Ostrinia nubilalis), Lesser cornstalk borer (Elasmopalpus lignosellus), Bean Shoot Borer (Epinotia aporema ersuger
  • Heliotis genus Anticarsia gammatalis Cotton leafworm (Alabama argillacea) and other moths; White butterflies such as Pieris rapae; Adoxofies genus, Grapholita molesta, and Leguminivora glyc inivorella), Azkiyamushiga (Matsumuraeses azukivora), Apple Kokukumonmonaki (Adoxophyes orana fasciata), Chanokokumonmonamiki (Adoxophyes honmai.
  • Citrus thrips (Frankliniella occidentalis), Thrips peri, Scirtothrips dorsalis, Thrips tabici Thrips such as rice thrips (Haplothrips aculeatus) and rice thrips (Stenchaetothrips biformis).
  • Diptera Pteris flies (Delia platura), onion flies (Delia antiqua), sugar beet root maggots (Tetanopsemyopaeformis), etc .; ), Leafworms (Liriomyzariotrifolii), leafworms (Chromatomyia horticola), etc .; (Hydrellia philippina) Hydrellia sasakii, etc .; Drosophila, Drosophila, Drosophila, such as Megaselia spiracularis; Drosophila, such as Clogmia albipunctata; Crab fly mushrooms; Hessian flies (Mayetiola destructor), Tamas flies such as Oreseolia oryzae; Diopsis macrophthalma etc .; Frogs such as Common cranefly (Tipula oleracea), European cranefly (Tipula gad)
  • Coleoptera Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm (Diabrotica virgifera zeae), Banded cumber rot balte ), San Antonio Beetle (Diabrotica speciosa), Cucurbit Beetle (Diabrotica speciosa), Bean Leaf Beetle (Cerotoma trifurcata), Cereal Leaf Beetle (Oulema melanopus), Scots beetle (Aulacophora femoralis), Psyllotata s cruciferae), Western black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), rice beetle
  • Insect pest Locusta migratoria, Kera (Gryllotalpa africana),ixie terrestrial grasshopper (Dociostaurus maroccanus), Australian terrestrial grasshopper (Chortoicetes terminifera), Red croaker (Nomadacris septemfasciaust ina, Loc) melanorhodon), Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus sanguinipes) Grasshopper (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Copaneago (Oxya yezoensis), Red-
  • Hymenopteran pests bees such as Athalia rosae and Athalia japonica; fire ants; Cockroach insects: German cockroach (Blattella germanica), Black cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Great cockroach (Periplaneta brunnea), Great cockroach (Blatta orientalis).
  • Termite pests Yamato termites (Reticulitermes speratus), termites (Coptotermes formosanus), American ants termites (Incisitermes minor), stag termites (Cryptotermes domesticus), ants, termites (Odontotermes eoformosaterm), ants Glypto termes amamianus), Miyatake termite (Reticulitermes miyatakei), Camellia termite (Reticulitermes kanmonensis), Takasago termite (Nasutitermes takasagoensis), Nitobe Roari (Pericapritermes nitobei), warrior termite (Sinocapritermes mushae), Cornitermes cumulans like.
  • Ticks spider mites (Tetranychus urticae), spider mites (Tetranychus kanzawai), mandarin spider mites (Panonychus citri), apple spider mites (Panonychus ulmi), spider mites, Southern Turkey spider mites (Brevipalpus phoenicis), etc .; Phyllocoptruta citri, Tomato rustic mite (Aculops lycopersici), Chinese rustic mite (Calacarus carinatus), Chinese cabbage mite (Acaphylla theavagrans), Green radish mite (Eriophyes chibaensis), Mite schist ticks Dust mites such as (Polyphagotarsonemus latus); spider mites such as the southern spider mite (Brevipalpus phoenicis); spider mites; Haemaphysalis longicornis; Tick (Dermacentor taiwanicus), American dog tick
  • Spiders Spiders such as Chiracanthium japonicum and Latrodectus hasseltii. Lips and legs: Gezi (Thereuonema hilgendorfi), Tobismkade (Scolopendra subspinipes), etc. Double-legged class: zelkova (Oxidus gracilis), red scallop (Nedyopus tambanus), etc. Isopods: Armadillidium vulgare, etc. Gastropoda: Limax marginatus, Limax flavus, Pomacea canaliculata, etc.
  • Nematode Aphelenchoides basseyi of Aphelenchoides sp .; Pratylenchusus p neglectus); Meloidogyne javanica, Meloidogyne incognita, Meloidogyne hapla; Heterodera deter (Globodera sp.) Potato cyst nematode (Globodera rostochiensis), Rotylenchulus reniformis, strawberry mesenchu (Nothotylenchus acris), Radopholus similis, Ditilencs gypsashi (Ditylenc) hus dipsaci), Tylenchulus semipenetrans; Longidorus sp .; Xiphinema sp .; Trichodols (Trichodorus sp.); Bursaphelenchus sp. Nematode (Bursaphelenchus xylophilus) etc.
  • Plant pathogens Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), yellow dwarf (Sclerophthora macrospora); wheat udon Disease (Erysiphe graminis), red mold disease (Fusarium graminearum, F. avenaceum, F. culmorum, Microdochium nivale), rust disease (Puccinia striiformis, P. graminis, P. recondita), red snow rot (Microdochium nivale, M.
  • plague (Phytophthora parasitica, Phytophthora citrophthora); apple monili Disease (Monilinia mali), rot (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), spotted leaf disease (Alternaria alternata apple pathotype), black spot disease (Venturia inaequalis), anthracnose (Glomerella cingulata), brown leaf disease ( Diplocarpon mali), ring rot (Botryosphaeria berengeriana), plague (Phytophtora cactorum); pear scab (Venturia nashicola, V.
  • pirina black spot (Alternaria alternata Japanese pear pathotype), red scab (Gymnosporangium haraeanum); Ascidian disease (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis sp.
  • Seed disease or early growth of various crops caused by Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, and Diplodia Disease.
  • Viral diseases of various crops mediated by Polymixa genus or Olpidium genus.
  • Rice seed blight (Burkholderia plantarii); Cucumber spotted bacterial disease (Pseudomonas syringae pv. Lachrymans); Eggplant blight (Ralstonia solanacearum); Citrus scab (Xanthomonas citiri); carotovora) etc.
  • the target harmful insects, harmful mites, harmful nematodes and phytopathogenic fungi are insects, mites, insecticides, acaricides, nematicides, fungicides with reduced drug sensitivity or developed drug resistance. Nematodes and phytopathogenic fungi may be used. However, if the drug sensitivity is significantly reduced or the drug resistance is greatly developed, insecticides, acaricides, nematicides and fungicides other than the target insecticides, acaricides, nematicides and fungicides.
  • a composition of the invention comprising
  • composition of the present invention can also be used to protect plants from plant diseases caused by insect-borne viruses.
  • Examples of plant diseases caused by insect-borne viruses having the control effect of the composition of the present invention include the following.
  • Rice dwarf disease (Rice waika virus), Tundra disease (Rice tungro spherical virus, Rice tungro bacilliform virus), Rice grassy stunt disease (Rice grassy stunt virus), Rice ragged stunt virus, rice stripe leaf blight Diseases (Rice stripe virus), rice black streaked dwarf virus, rice southern black-streaked dwarf virus, rice gall dwarf virus, rice leaf blight ( Rice hoja blanca virus), White leaf desease of rice, Yellow dwarf virus, Red disease (Rice penyakit merah virus), Rice yellow stunt virus, Transition yellowing Disease (Rice transitory yellowing virus), rice yellow disease (Rice Yellow Mottle Virus), rice necrosis mosaic virus, rice dwarf stunt virus, northern wheat mosaic disease (No rthern Cereal Mosaic Virus), Barley Yellow Dwarf Virus, Wheat yellow dwarf virus, Oat sterile dwarf (Oat sterile dwarf virus), Wheat streak mosaic (Wheat streak mosaic virus) Maize mosaic disease, Maize stripe disease (maize stripe tenuivirus), Mai
  • the application amount can vary widely depending on the application time, application place, application method, etc., but the total amount of the bipyridine compound and the compound is It is usually 1 to 10,000 g per 10,000 m 2 .
  • the composition of the present invention is a preparation such as an emulsion, wettable powder, flowable agent, etc.
  • the composition of the present invention is usually adjusted so that the total concentration of the bipyridine compound and the compound is 0.01 to 10,000 ppm. Is applied diluted with water, and in the case of granules, powders, etc., the composition of the present invention is usually applied as it is.
  • Eggplant vegetable eggplant, tomato, pepper, pepper, bell pepper, potato
  • cucumber vegetable cucumber, pumpkin, zucchini, watermelon, melon, squash, etc.
  • cruciferous vegetable radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.
  • Asteraceae vegetables burdock, garlic, artichoke, lettuce, etc.
  • liliaceae vegetables eg, leek, onion, garlic, asparagus
  • celery family vegetables carrot, parsley, celery
  • red crustacean vegetables spinach, chard, etc.
  • perilla vegetables shiso, mint, basil, lavender etc.
  • vegetables such as strawberry, sweet potato, yam, taro, Fruits (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (citrus oranges, orange
  • the above-described plant is not limited as long as it is a variety generally cultivated as a crop.
  • the above-mentioned plant may be a plant bred by a hybrid technique.
  • Plants bred by hybrid technology are first-generation hybrids obtained by crossing two different varieties of varieties and generally have a hybrid strength (generally, increased yield potential, It is a plant having the characteristics of improving resistance to biological and abiotic stress factors.
  • the aforementioned plants include genetically modified crops.
  • the genetically modified crops include HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutol, ALS (acetolactic acid synthase) inhibitors such as imazetapyr and thifensulfuron methyl, EPSP (5 -Classic breeding with resistance to herbicides such as -enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, dicamba Plants granted by law or genetic engineering techniques are also included.
  • HPPD 4-hydroxyphenylpyruvate dioxygenase enzyme
  • ALS acetolactic acid synthase
  • EPSP -Classic breeding with resistance to herbicides such as -enolpyruvylshikimate-3-phosphate synthase
  • glutamine synthetase inhibitors glutamine syntheta
  • the above plants can be synthesized by using genetic engineering techniques to synthesize selective toxins known in the genus Bacillus such as Bacillus thuringiensis, and from harmful insects. Also included are plants that can confer specific insecticidal activity by synthesizing gene fragments that partially match the endogenous gene and inducing gene silencing (RNAi; RNA interference) within the target harmful insect body .
  • RNAi gene silencing
  • a line provided with two or more traits related to herbicide resistance, pest resistance, disease resistance, etc. as described above using classical breeding technology or genetic recombination technology, and the like Alternatively, a line in which two or more kinds of properties possessed by the parent line are given by crossing genetically modified plants having different characteristics is also included. Examples of such plants include Smart stax (registered trademark).
  • reaction mixture was stirred at room temperature for 10 hours.
  • sodium sulfite and saturated aqueous sodium hydrogen carbonate solution were sequentially added, and the mixture was extracted with chloroform.
  • the obtained organic layer was washed with saturated sodium hydrogen carbonate, dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure.
  • the obtained residue was subjected to silica gel chromatography, so as to obtain 490 mg of intermediate 5 represented by the following formula.
  • This bipyridine compound 22 was used in place of this bipyridine compound 9, and the bipyridine compound 23 represented by the following formula and the bipyridine compound 24 represented by the following formula were obtained according to the method described in Production Example 2.
  • This bipyridine compound 23 1 H-NMR (CDCl 3 ) ⁇ : 8.75 (1H, dd), 8.65 (1H, dd), 8.61-8.56 (2H, m), 7.75 (1H, dd), 7.59 (1H, dd), 6.01 (1H , dt), 3.51-3.41 (1H, m), 2.96-2.86 (1H, m), 1.41 (3H, t).
  • the obtained organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • the obtained residue was diluted with 30 mL of ethanol, and 10 mL of 28% aqueous ammonia solution was added at room temperature. The mixture was heated and stirred at 60 ° C. for 2.5 hours, allowed to cool to room temperature, added to saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate.
  • the obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.
  • the obtained residue was subjected to silica gel chromatography to obtain 9.4 g of intermediate 17 represented by the following formula.
  • the obtained residue was subjected to silica gel chromatography to obtain 0.2 g of the present bipyridine compound 204 represented by the following formula, 0.6 g of the present bipyridine compound 214, and 0.2 g of the present bipyridine compound 224.
  • the bipyridine compound 204 1 H-NMR (CDCl 3 ) ⁇ : 8.93 (1H, dd), 8.37 (1H, dd), 8.04 (1H, d), 7.64 (1H, dd), 7.38 (1H, d), 7.05 (1H, dd ), 4.50 (2H, t), 3.76-3.64 (1H, m), 3.61-3.49 (1H, m), 1.35 (3H, t).
  • the bipyridine compound 214 1 H-NMR (CDCl 3 ) ⁇ : 8.50 (1H, dd), 8.43 (1H, d), 7.97 (1H, dd), 7.69 (1H, d), 7.50 (1H, dd), 7.43 (1H, dd ), 4.54 (2H, t), 3.44 (2H, q), 1.30 (3H, t).
  • the bipyridine compound 224 1 H-NMR (CDCl 3 ) ⁇ : 8.49 (1H, dd), 8.14 (1H, d), 7.91 (1H, dd), 7.57 (1H, dd), 7.42 (1H, d), 7.07 (1H, dd ), 4.51 (2H, t), 3.36-3.18 (2H, m), 1.28 (3H, t).
  • the obtained residue was subjected to silica gel chromatography to obtain 6.7 g of the present bipyridine compound 169 represented by the following formula and 0.07 g of the present bipyridine compound 194.
  • the bipyridine compound 169 1 H-NMR (CDCl 3 ) ⁇ : 8.86 (1H, dd), 8.49 (1H, dd), 7.86 (1H, d), 7.56 (1H, dd), 7.42 (1H, d), 4.56 (2H, t ), 3.98 (2H, q), 1.44 (3H, t).
  • the bipyridine compound 194 1 H-NMR (CDCl 3 ) ⁇ : 8.93 (1H, d), 7.47 (1H, d), 7.42 (1H, d), 7.39 (1H, d), 4.56 (2H, t), 3.70 (2H, q ), 1.40 (3H, t).
  • This bipyridine compound 109 was used in place of the present bipyridine compound 79, and was carried out according to the method described in Preparation Example 17 to obtain the present bipyridine compound 124 represented by the following formula.
  • This bipyridine compound 109 was used in place of the present bipyridine compound 79, and was carried out according to the method described in Preparation Example 19 to obtain the present bipyridine compound 139 represented by the following formula.
  • Production Example 39-1 The following intermediate 22 was obtained according to the method described in Production Example 10-1 using 5-chloro-2-cyanopyridine instead of 5-fluoro-2-cyanopyridine.
  • Production Example 40-1 The following intermediate 24 was obtained according to the method described in Production Example 10-1 using 2-cyano-5-bromopyridine instead of 5-fluoro-2-cyanopyridine.
  • Production Example 40-2 The following intermediate 25 was obtained according to the method described in Production Example 10-2 using the intermediate 24 instead of the intermediate 16.
  • Production Example 42-2 The bipyridine compound 8 was obtained according to the method described in Production Example 10-2 using the intermediate 26 instead of the intermediate 16.
  • Formulation Example 1 5 parts of one of the bipyridine compounds 1 to 347, 10 parts of clothianidin, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 100 parts by mixing water Then, each preparation is obtained by fine pulverization by a wet pulverization method.
  • Formulation Example 2 By thoroughly pulverizing and mixing 10 parts of the present bipyridine compounds 1 to 347, 10 parts of clothianidin, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 75 parts of synthetic silicon hydroxide, Get the agent.
  • Formulation Example 3 1 part of the bipyridine compounds 1 to 347, 0.5 part of clothianidin, 1 part of synthetic hydrous silicon oxide fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65.5 parts of kaolin clay are mixed. . Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each granule.
  • Formulation Example 4 One part of the present bipyridine compounds 1 to 347, 10 parts of clothianidin, 2 parts of sorbitan trioleate, and 28 parts of an aqueous solution containing 2 parts of polyvinyl alcohol were mixed and pulverized by a wet pulverization method. An aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added to make the total amount 90 parts, and further 10 parts of propylene glycol is added and stirred and mixed to obtain each preparation.
  • Formulation Examples 74-142 In Formulation Example 2, instead of 10 parts of clothianidin, the same operation as in Formulation Example 2 was carried out except that the respective compounds and amounts used in Table ii were used to obtain each formulation.
  • Formulation Examples 212 to 241 In Formulation Example 4, in place of 2 parts of clothianidin, the same operations as in Formulation Example 4 were carried out except that the respective compounds and amounts used in Table iv were used to obtain each formulation.
  • Formulation Example 242 After mixing 10 parts of the bipyridine compounds 1 to 347, 0.1 part of tebuconazole, 1.5 parts of sorbitan trioleate, and 28 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, the mixture is pulverized by a wet pulverization method. Into this, an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added to make a total amount of 90 parts, and further 10 parts of propylene glycol is added and stirred and mixed to obtain each preparation.
  • Formulation Examples 243 to 280 In Formulation Example 242, the same operation as in Formulation Example 242 was carried out except that each compound and the amount used in Table v were used instead of 0.1 part of tebuconazole to obtain each formulation.
  • each commercial preparation is mixed with water containing 0.02% by volume of a spreading agent, and the present compound is contained so that the concentration of the present compound becomes a predetermined concentration.
  • Prepare the drug solution A chemical solution containing the present bipyridine compound and a chemical solution containing the present compound are mixed to prepare a test chemical solution. Cucumber sativus cotyledon leaf pieces (1.5 cm in length) are accommodated in each well of a 24-well microplate, and 2 cotton aphid adults and 8 larvae are released per well for the test per well. Spray 20 ⁇ L of chemical solution. This is the treatment area.
  • xylene DMF: surfactant
  • Solpol 3005X manufactured by Toho Chemical Industry Co., Ltd.
  • 4: 4: 1 volume ratio
  • 0.02 vol% water containing a spreading agent (Cindine (registered trademark), manufactured by Sumitomo Chemical Co., Ltd.) is added, and a chemical solution containing the bipyridine compound is added so that the concentration of the bipyridine compound becomes a predetermined concentration.
  • a spreading agent Tine (registered trademark)
  • medical solution containing this compound was prepared.
  • the chemical solution containing the present bipyridine compound and the chemical solution containing the present compound were mixed to prepare a test chemical solution.
  • Cucumber sativus cotyledon leaf pieces (1.5 cm in length) are accommodated in each well of a 24-well microplate, and 2 cotton aphid adults and 8 larvae are released per well for the test per well.
  • 20 ⁇ L of chemical solution was sprayed. This was designated as a treatment zone.
  • medical solution for a test was made into the no-treatment group.
  • Control value (%) ⁇ 1 ⁇ (Tai) / (Cai) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • the pest control composition of the present invention can be used to control pests.

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  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Agronomy & Crop Science (AREA)
  • Soil Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne une composition antiparasitaire ayant un excellent effet antiparasitaire, contenant : un composé représenté par la formule (I) [dans la formule, chaque symbole de référence représente des définitions figurant dans la description] ou une composition d'oxyde d'azote de celui-ci; et au moins une composition choisie dans le groupe constitué par le groupe (a) et le groupe (b).
PCT/JP2016/082078 2015-10-30 2016-10-28 Composition antiparasitaire et son utilisation WO2017073733A1 (fr)

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Cited By (5)

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WO2018101424A1 (fr) * 2016-12-01 2018-06-07 住友化学株式会社 Composé hétérocyclique et agent de lutte contre les arthropodes nuisibles le contenant
WO2019004082A1 (fr) * 2017-06-26 2019-01-03 日本曹達株式会社 Composé hétéroarylpyrimidine, et agent de lutte contre les organismes nuisibles
CN109222202A (zh) * 2018-09-28 2019-01-18 河南中烟工业有限责任公司技术开发分公司 一种生物法制备低多环芳烃烟草薄片的方法
WO2020178789A1 (fr) 2019-03-07 2020-09-10 Pi Industries Ltd. Composés hétérocycliques condensés et leur utilisation en tant qu'agents de lutte contre les nuisibles
GB2608704A (en) * 2021-07-06 2023-01-11 Inst Of Economic Crops Hubei Academy Of Agricultural Sciences Fungicide combination for controlling mulberry fruit sclerotiniosis disease and control method

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JP2000026421A (ja) * 1998-01-29 2000-01-25 Kumiai Chem Ind Co Ltd ジアリ―ルスルフィド誘導体及び有害生物防除剤
JP2000198768A (ja) * 1998-04-27 2000-07-18 Kumiai Chem Ind Co Ltd ３―アリ―ルフェニルスルフィド誘導体及び殺虫、殺ダニ剤
WO2012106495A1 (fr) * 2011-02-03 2012-08-09 E. I. Du Pont De Nemours And Company Pesticides méso-ioniques
JP2013060420A (ja) * 2011-08-23 2013-04-04 Ishihara Sangyo Kaisha Ltd 有害生物防除剤
WO2016121969A1 (fr) * 2015-01-30 2016-08-04 住友化学株式会社 Composé bipyridine et son utilisation pour la lutte contre les arthropodes nuisibles
WO2016121970A1 (fr) * 2015-01-30 2016-08-04 住友化学株式会社 Composé bipyridine et son utilisation pour lutter contre les arthropodes nuisibles

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JP2000026421A (ja) * 1998-01-29 2000-01-25 Kumiai Chem Ind Co Ltd ジアリ―ルスルフィド誘導体及び有害生物防除剤
JP2000198768A (ja) * 1998-04-27 2000-07-18 Kumiai Chem Ind Co Ltd ３―アリ―ルフェニルスルフィド誘導体及び殺虫、殺ダニ剤
WO2012106495A1 (fr) * 2011-02-03 2012-08-09 E. I. Du Pont De Nemours And Company Pesticides méso-ioniques
JP2013060420A (ja) * 2011-08-23 2013-04-04 Ishihara Sangyo Kaisha Ltd 有害生物防除剤
WO2016121969A1 (fr) * 2015-01-30 2016-08-04 住友化学株式会社 Composé bipyridine et son utilisation pour la lutte contre les arthropodes nuisibles
WO2016121970A1 (fr) * 2015-01-30 2016-08-04 住友化学株式会社 Composé bipyridine et son utilisation pour lutter contre les arthropodes nuisibles

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018101424A1 (fr) * 2016-12-01 2018-06-07 住友化学株式会社 Composé hétérocyclique et agent de lutte contre les arthropodes nuisibles le contenant
US11632955B2 (en) 2016-12-01 2023-04-25 Sumitomo Chemical Company, Limited Heterocyclic compound and harmful arthropods control agent comprising the same
WO2019004082A1 (fr) * 2017-06-26 2019-01-03 日本曹達株式会社 Composé hétéroarylpyrimidine, et agent de lutte contre les organismes nuisibles
US11427564B2 (en) 2017-06-26 2022-08-30 Nippon Soda Co., Ltd. Heteroaryl pyrimidine compound and pest control agent
CN109222202A (zh) * 2018-09-28 2019-01-18 河南中烟工业有限责任公司技术开发分公司 一种生物法制备低多环芳烃烟草薄片的方法
CN109222202B (zh) * 2018-09-28 2021-04-09 河南中烟工业有限责任公司技术开发分公司 一种生物法制备低多环芳烃烟草薄片的方法
WO2020178789A1 (fr) 2019-03-07 2020-09-10 Pi Industries Ltd. Composés hétérocycliques condensés et leur utilisation en tant qu'agents de lutte contre les nuisibles
GB2608704A (en) * 2021-07-06 2023-01-11 Inst Of Economic Crops Hubei Academy Of Agricultural Sciences Fungicide combination for controlling mulberry fruit sclerotiniosis disease and control method

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