[go: up one dir, main page]

WO2017090654A1 - Composition antiparasitaire et son utilisation - Google Patents

Composition antiparasitaire et son utilisation Download PDF

Info

Publication number
WO2017090654A1
WO2017090654A1 PCT/JP2016/084737 JP2016084737W WO2017090654A1 WO 2017090654 A1 WO2017090654 A1 WO 2017090654A1 JP 2016084737 W JP2016084737 W JP 2016084737W WO 2017090654 A1 WO2017090654 A1 WO 2017090654A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
halogen atoms
compound
alkyl
atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2016/084737
Other languages
English (en)
Japanese (ja)
Inventor
慎哉 西村
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Publication of WO2017090654A1 publication Critical patent/WO2017090654A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/64—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
    • A01N43/84—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 use thereof.
  • 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.
  • the present inventor has found that the compound represented by the formula (1) and one selected from the group (a) or the group (b) It has been found that a composition containing the above compounds has an excellent control effect against pests.
  • a 1 represents a nitrogen atom or CR 4 ;
  • a 2 and A 3 are those in which A 2 represents a nitrogen atom and A 3 represents CR 3b , or A 2 represents CR 3a and A 3 represents a nitrogen atom,
  • Q represents an oxygen atom or a sulfur atom
  • G is a C2-C10 haloalkyl group, a C3-C10 haloalkenyl group, a C3-C10 haloalkynyl group, a (C1-C5 alkyl) -O- (C2-C5 alkyl) group having one or more halogen atoms, one or more (C3-C5 alkenyl) -O— (C2-C5 alkyl) group having a halogen atom, (C3-C5 alkynyl) -O— (C2-C5 alkyl) group having one or more halogen atoms, one or more halogen atoms, (C3-C5 al
  • 6-membered aromatic heterocyclic group (the 6-membered aromatic heterocyclic group may have one or more atoms or groups selected from group A), any one of groups 3- 7-membered non-aromatic heterocyclic group (The 3-7-membered non-aromatic heterocyclic group may have one or more atoms or groups selected from the group consisting of halogen atoms and C1-C6 alkyl groups.
  • R 4 represents a hydrogen atom or a halogen atom
  • R 3 , R 3a and R 3b each independently represent a hydrogen atom, a C1-C3 alkyl group optionally having one or more halogen atoms, or a halogen atom
  • R 7 has a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms.
  • a C3-C6 alkynyl group which may have one or more halogen atoms (C1-C3 alkyl) -O- (C1-C3 alkyl) group which has one or more halogen atoms (C1-C3 alkyl) -S (O) y- (C1-C3 alkyl) group which may have one or more halogen atoms C3-C7 cycloalkyl group which may have one or more halogen atoms
  • R 8 represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alken
  • R 9 has a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms.
  • a C3-C6 alkynyl group which may have one or more halogen atoms (C1-C3 alkyl) -O- (C1-C3 alkyl) group which has one or more halogen atoms (C1-C3 alkyl) -S (O) y- (C1-C3 alkyl) group which may have one or more halogen atoms C3-C7 cycloalkyl group which may have one or more halogen atoms (C3-C7 cycloalkyl)-(C1-C3 alkyl) group, C1-C6 alkyl group having one cyano group, phenyl C1-C3 alkyl group (the phenyl of the phenyl C1-C3 alkyl group)
  • the minute may have one or more atoms or groups selected from group A), or (5- or 6-membered heteroaryl) C1-C6 alkyl group (the (5- or 6-membered heteroary
  • R 12 and R 13 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms,
  • R 14 represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, or one or more halogen atoms
  • Group A C1-C6 alkyl group optionally having one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, and one or more halogen atoms
  • Group B Group C: Group D: ] (Hereinafter referred to as the present pyrimidinone compound), A pest control composition (hereinafter referred to as the present invention composition) containing one or more compounds selected from the following group (a) or the following group (b) (hereinafter referred to as the present compound).
  • Subgroup a-1 Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, flupyrifurone, flupyradifurone ), Dichloromesothiaz (dicloromezotiaz) and a compound represented by the following formula (CAS registration number 1689566-03-7, hereinafter sometimes referred to as “insecticidal compound ⁇ ”) A group of competitive modulators of nicotinic acetylcholine receptors.
  • Subgroup a-2 Acrinathrin, allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin, beta beta-cyfluthrin), cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, betacypermethrin ( beta-cypermethrin), theta-cypermethrin, theta-cypermethrin, sigma-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esf Enfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin,
  • Subgroup a-3 GABAergic chloride channel blocker consisting of ethiprole, fipronil and flufiprole, and GABA consisting of afoxalaner, fluralaner, broflanilide and fluxametamide
  • Subgroup a-4 Group of ryanodine receptor modulators consisting of chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, tetraniliprole and cyhalodiamide .
  • Subgroup a-5 Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl (NAC), carbofuran, carbofuran Fan (carbosulfan), ethiofencarb (fthiobucarb), fenobucarb (BPMC), formethanate (formetanate), furathiocarb (furathiocarb), isoprocarb (isoprocarb: MIPC), methiocarb (methiocarb), methomyl (methomyl), metolcarb (MTMC) , Oxamyl, pirimicarb, propoxur (PHC), thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylica Bed (xylylcarb: MPMC) consists, the group of carbamates acetylcholinesterase (AChE) inhibitors.
  • Subgroup a-6 A group of nematicidal active compounds consisting of abamectin, fluensulfone, tioxazafen, and fluazaindolizine.
  • Subgroup a-7 Mycorrhiza Fungi, Arthrobotrys dactyloides, Bacillus thuringiensis, Bacillus firmus, Bacillus megaterium, Bacillus amyloliquefaciens (Bacillus amyloliquefaciens), Hirsutella rhossiliensis, Hirsutella minnesotensis, Monacrosporium phymatopagus, Pasturiatransurie, Pasturiapass A group of microbial materials consisting of Pasteuria usgae, Verticillium chlamydosporium and Harpin protein.
  • Group (b) 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 Azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diiconazole, diniconazole-M, epiconconazole, ethaconazole (Etaconazole), fenarimol, fenbuconazole, fluquinconazole, quinconazole, flusilazole, flutriafol, hexaconazole, imazaril ( imazalil), imibenconazole, ipconazole, metconazole, microbutanil, nuarimol, oxpoconazole, o Spoconazole fumarate, pefurazoate, penconazole, prochloraz, propiconazole
  • Subgroup b-2 Azoxystrobin, coumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, fenaminstrobin, full Phenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metinominostrobin, orysastrobin, picoxystrobin , Pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, pyribencarb, triclopyricarb, triazopyricarb Consisting de (cyazofamid) and amisulbrom (amisulbrom), the group of Qo inhibitors (Quinone outside inhibitors).
  • Subgroup b-3 A group of RNA polymerase I inhibitors consisting of benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl and ofurace .
  • Subgroup b-4 Benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad ), Furametpyr, isofetamid, isoprazam, mepronil, oxycarboxin, penthiopyrad, penflufen, sedaxane, thifluzamide, thifluamide (Pyraziflumid), pydiflumetofen (CAS registration number 1228284-64-7), 3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazole-4- Carboxamide (CAS registration No.
  • bacteria 141573-94-6 hereinafter referred to as “bactericidal compound ⁇ 1”
  • 3-difluoromethyl-1-methyl-N-[(3R) -1,1,3-trimethylindan-4-yl] pyrazole -4-carboxamide CAS registration number 1352994-67-2, hereinafter sometimes referred to as “bactericidal compound ⁇ 2”
  • 3-difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4- Yl) -1-methylpyrazole-4-carboxamide CAS Registry Number 1383809-87-7, hereinafter sometimes referred to as “bactericidal compound ⁇ 3”
  • 3-difluoromethyl-N-[(3R) -7-fluoro- 1,1,3-trimethylindan-4-yl] -1-methylpyrazole-4-carboxamide CAS registration number 1513466-73-3, hereinafter sometimes referred to as “bactericidal compound ⁇ 4”
  • Subgroup b-5 It consists of benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide and ethaboxam.
  • a group of ⁇ -tubulin polymerization inhibitors It consists of benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide and ethaboxam.
  • Subgroup b-6 Ferbam, mancozeb, manneb, maneb, metiram, propineb, thiram, zineb, ziram, captan, captafol ), Folpet, chlorothalonil, tolylfluanid, guazatine, iminoctadine, anilazine, dithianon, chinomethionate or quinomethionate fluoride
  • Subgroup b-7 Dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthivalicarb-isopropyl, iprovalicarb, valifenalate and mandipropamid
  • cellulose synthesis inhibitors A group of cellulose synthesis inhibitors.
  • Subgroup b-8 MAP (mitogen-activated protein) / histidine kinase inhibitor in osmotic signal transduction consisting of fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone and vinclozolin group.
  • Subgroup b-9 A group of other fungicides consisting of tolclofos-methyl, oxathiapiproline, picarbutrazox, fluopicolide and silthiofam.
  • 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, plant seed, bulb or soil for cultivating a plant.
  • pests can be controlled.
  • composition of the present invention contains the present pyrimidinone compound and the present compound.
  • the notation “may have one or more atoms or groups selected from group A” means that when it has two or more atoms or groups selected from group A, atoms selected from those groups ⁇ Alternatively, the groups may be the same as or different from each other.
  • the expression “which may have one or more halogen atoms” means that when two or more halogen atoms are present, the halogen atoms may be the same as or different from each other.
  • the expression “having one or more halogen atoms”, when having two or more halogen atoms, may be the same as or different from each other.
  • Heterocyclic group means a group containing at least one selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom in addition to a carbon atom as a ring-constituting atom, an aromatic heterocyclic group and a non-aromatic group Represents a heterocyclic group.
  • aromatic heterocyclic group examples include 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 3-pyrazolyl group, 4-pyrazolyl group, 5-pyrazolyl group, 1-pyrrolyl.
  • 5-membered aromatic heterocyclic groups such as 1-pyrazolyl group, 1-imidazolyl group, 1,2,4-triazol-1-yl group; and 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, etc.
  • non-aromatic heterocyclic group examples include aziridin-1-yl group, azetidin-1-yl group, pyrrolidin-1-yl group, 3,3,4,4-tetrafluoropyrrolidin-1-yl group , Non-aromatic heterocycles such as tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl group, piperidin-1-yl group, morpholin-4-yl group, thiomorpholin-4-yl group, azepan-1-yl group Groups.
  • “5- or 6-membered heteroaryl” represents a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group.
  • C2-C10 haloalkyl group examples include 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group , Heptafluoroisopropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2,3,4,4,4-hexafluorobutyl group Etc.
  • C3-C10 haloalkenyl group examples include 3,3-difluoro-2-propenyl group, 3,3-difluoro-2-propenyl group, 4,4-difluoro-3-butenyl group and the like.
  • C3-C10 haloalkynyl group examples include 3-chloro-2-propynyl group, 3-fluoro-2-propynyl group, 4,4,4-trifluoro-2-butynyl group and the like.
  • (C1-C5 alkyl) -O— (C2-C5 alkyl) group having one or more halogen atoms means a group having one or more halogen atoms in a C1-C5 alkyl moiety and / or a C2-C5 alkyl moiety. And examples thereof include 2- (2,2,2-trifluoroethoxy) ethyl group and 1,1,1-trifluoro-3-methoxypropan-2-yl group.
  • (C3-C5 alkenyl) -O— (C2-C5 alkyl) having one or more halogen atoms means a group having one or more halogen atoms in the C3-C5 alkenyl moiety and / or C2-C5 alkyl moiety. For example, 2- (3,3-difluoro-2-propenyloxy) ethyl group.
  • (C3-C5 alkynyl) -O— (C2-C5 alkyl) group having one or more halogen atoms means a group having one or more halogen atoms in the C3-C5 alkynyl moiety and / or C2-C5 alkyl moiety. For example, a 2- (4,4,4-trifluoro-2-butynyloxy) ethyl group.
  • “(C1-C5 alkyl) -S (O) m — (C2-C5 alkyl) group having one or more halogen atoms” means one or more halogen atoms in the C1-C5 alkyl portion and / or the C2-C5 alkyl portion. Represents a group having an atom, and examples thereof include a 2- (trifluoromethylthio) ethyl group, a 2- (trifluoromethylsulfinyl) ethyl group, and a 2- (trifluoromethylsulfonyl) ethyl group.
  • (C3-C5 alkenyl) -S (O) m — (C2-C5 alkyl) group having one or more halogen atoms means one or more halogen atoms in the C3-C5 alkenyl moiety and / or C2-C5 alkyl moiety. Represents a group having an atom, and examples thereof include a 2- (3,3-difluoro-2-propenylthio) ethyl group.
  • (C3-C5 alkynyl) -S (O) m — (C2-C5 alkyl) group having one or more halogen atoms means one or more halogen atoms in the C3-C5 alkenyl moiety and / or C2-C5 alkyl moiety. Represents a group having an atom, for example, 2- (4,4,4-trifluoro-2-butynylthio) ethyl group.
  • (C1-C5 alkyl) -C (O)-(C1-C5 alkyl) group having one or more halogen atoms means any one C1-C5 alkyl moiety or both C1-C5 alkyl group moieties Represents a group having one or more halogen atoms, and examples thereof include a 3,3,3-trifluoro-2-oxopropyl group.
  • (C1-C3 alkyl) -O— (C1-C3 alkyl) group optionally having one or more halogen atoms refers to any one C1-C3 alkyl moiety or both C1-C3 alkyl
  • a group having one or more halogen atoms in the group part is represented, and examples thereof include a methoxymethyl group, a trifluoromethoxymethyl group, a difluoro (methoxy) methyl group, and a difluoro (trifluoromethoxy) methyl group.
  • C1-C6 chain hydrocarbon group optionally having one or more halogen atoms include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, pentyl group, hexyl group, trifluoromethyl
  • a C1-C6 alkyl group optionally having one or more halogen atoms such as a group, a trichloromethyl group, a 2,2,2-trifluoroethyl group and a pentafluoroethyl group; It has one or more halogen atoms such as vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 1-pentenyl group, 1-hexenyl group, 1,1-difluoroallyl group and pentafluoroallyl group.
  • a C2-C6 alkenyl group which may optionally have one or more halogen atoms such as an ethynyl group, a propargyl group, a 1-hexynyl group and a 4,4,4-trifluoro-2-butynyl group.
  • a C6 alkynyl group is mentioned.
  • phenyl group optionally having one or more atoms or groups selected from group A examples include a phenyl group, a 2-fluorophenyl group, a 4-fluorophenyl group, a 2,3-difluorophenyl group, 2,3,4,5,6-pentafluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl group, 4- (trifluoromethyl) phenyl group, 4- (trifluoromethoxy) phenyl Groups, 4- (trifluoromethylsulfanyl) phenyl group, 4-cyanophenyl group, 4- (methylsulfinyl) phenyl group, and 4- (methylsulfonyl) phenyl group.
  • any five-membered aromatic heterocyclic group selected from group B (the 5-membered aromatic heterocyclic group may have one or more atoms or groups selected from group A)".
  • pyrrol-1-yl group 2-chloropyrrol-1-yl group, pyrazol-1-yl group, 3- (trifluoromethyl) pyrazol-1-yl group, 4-chloroimidazol-1-yl group, 1,2,4-triazol-1-yl group, 3-methoxy-1,2,4-triazol-1-yl group, 3-methylthio-1,2,4-triazol-1-yl group, 1,2 , 3-Triazol-1-yl group, oxazol-2-yl group, thiazol-2-yl group, 1,3,4-oxadiazol-2-yl group, 1,3,4-thiadiazol-2-yl And 1,2,4-oxadiazol-3-yl And the like.
  • any 6-membered aromatic heterocyclic group selected from group C (the 6-membered aromatic heterocyclic group may have one or more atoms or groups selected from group A)”.
  • any 3-7 membered non-aromatic heterocyclic group selected from group D (the 3-7 membered non-aromatic heterocyclic group is one or more selected from the group consisting of a halogen atom and a C1-C6 alkyl group)
  • the group may have an atom or a group ”as, for example, aziridin-1-yl group, azetidin-1-yl group, pyrrolidin-1-yl group, 3,3,4,4-tetrafluoropyrrolidine-1 -Yl group, piperidin-1-yl group, 4,4-dimethylpiperidin-1-yl group, azepan-1-yl group.
  • C3-C7 cycloalkyl group optionally having one or more halogen atoms examples include a cyclopropyl group, a 2,2-difluorocyclopropan-1-yl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, A cycloheptyl group etc. are mentioned.
  • (C3-C7 cycloalkyl)-(C1-C3 alkyl) group optionally having one or more halogen atoms represents a group having one or more halogen atoms in the C3-C7 cycloalkyl moiety; Examples thereof include a cyclopropylmethyl group, a 2- (cyclopropyl) ethyl group, a (2,2-difluorocyclopropyl) methyl group, and a cyclopentylmethyl group.
  • Examples of the “phenyl C1-C3 alkyl group include, for example, a benzyl group, 2-fluoro Examples include benzyl group, 4-chlorobenzyl group, 4- (trifluoromethyl) benzyl group, 2- (4- (trifluoromethyl) phenyl) ethyl group and the like.
  • “(5- or 6-membered heteroaryl) C1-C6 alkyl group (the 5- or 6-membered heteroaryl) of the (5- or 6-membered heteroaryl) C1-C6 alkyl group has one or more atoms or groups selected from group A; For example, (1-methylpyrrol-3-yl) methyl group, (oxazol-2-yl) methyl group, (tetrahydrofuran-3-yl) methyl group, (tetrahydrofuran-2).
  • Halogen atom represents a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • C2-C6 alkoxycarbonyl group examples include a methoxycarbonyl group and an ethoxycarbonyl group.
  • Examples of the “C1-C6 alkoxy group optionally having one or more halogen atoms” include a trifluoromethoxy group and a 2,2,2-trifluoroethoxy group.
  • C1-C3 alkyl) -S (O) y — (C1-C3 alkyl) group optionally having one or more halogen atoms means a C1-C3 alkyl moiety and / or a C1-C3 alkyl moiety Represents a group which may have one or more halogen atoms, for example, methylthiomethyl group, trifluoromethylthiomethyl group, methanesulfinylmethyl group, trifluoromethanesulfonylmethyl group, methanesulfonylmethyl group, 2- (methylthio) ethyl Group and ethylthiomethyl group.
  • the “C1-C6 fluoroalkyl group” represents a C1-C6 alkyl group having one or more fluorine atoms, and examples thereof include a fluoromethyl group, a trifluoromethyl group, and a 2,2,2-trifluoroethyl group. .
  • Examples of the pyrimidinone compound include the following compounds.
  • G is a C2-C10 haloalkyl group, a C3-C10 haloalkenyl group, a C3-C10 haloalkynyl group, or a (C1-C5 alkyl) -O— (C2- C5 alkyl) group, or one or more with a halogen atom (C1-C5 alkyl) -S (O) m - (a C2-C5 alkyl) group, R 1 is a C1-C6 alkyl group optionally having one or more halogen atoms, R 2 is a C1-C6 alkyl group which may have one or more halogen atoms, and any 5-membered aromatic heterocyclic group selected from the group consisting of groups B-1 to B-4 (the 5 The membered aromatic heterocyclic group may have one or more halogen atoms), any non-aromatic heterocyclic group selected from the group consisting of groups
  • R 8 is a hydrogen atom or a C1-C6 alkyl group
  • R 9 is a hydrogen atom, a C1-C6 alkyl group, a (5-membered heteroaryl) C1-C6 alkyl group (the 5-membered heteroaryl part of the (5-membered heteroaryl) C1-C6 alkyl group is selected from group A 1 (It may have the above atoms or groups.)
  • p is 0 or 1;
  • a compound in which y is 0, 1 or 2.
  • a compound according to Aspect 1 wherein G is a C2-C10 haloalkyl group or a C3-C10 haloalkenyl group, and R 3 is a hydrogen atom.
  • G is a C2-C10 haloalkyl group or a C3-C10 haloalkenyl group
  • R 1 is a C1-C6 alkyl group
  • p is 0 or 1
  • R 2 is one or more halogen atoms optionally may C1-C6 alkyl group which may have one or more halogen atoms which may have a 1,2,4-triazol-1-yl group, 1 or more
  • a pyrrolidin-1-yl group optionally having a halogen atom, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkyl optionally having one or more halogen atoms Sulfanyl group, C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, di (C1
  • Q is an oxygen atom
  • G is a C2-C6 haloalkyl
  • R 1 is a C1-C6 alkyl group
  • p is 1
  • R 2 is a C1-C6 fluoroalkyl group
  • Aspect 8 A compound according to Aspects 1 to 6, wherein A 1 is CH, A 2 is CR 3a , R 3a is a hydrogen atom or a C1-C3 alkyl group, and A 3 is a nitrogen atom.
  • Aspect 9 A compound according to Aspects 1 to 6, wherein A 1 is a nitrogen atom, A 2 is CR 3a , and A 3 is a nitrogen atom.
  • Aspect 11 A compound according to Aspects 1 to 6, wherein A 1 is CH, A 2 is a nitrogen atom, and A 3 is CR 3b .
  • a 1 is CH, A 2 is nitrogen atom, A 3 is CR 3b, compounds R 3b is a hydrogen atom or a C1-C3 alkyl group.
  • the present pyrimidinone compound and intermediate compound can be produced, for example, by the following (Production Method 1) to (Production Method 18).
  • the reaction is usually performed in the presence of 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
  • the oxidizing agent is usually used in a proportion of 1 to 1.2 mol per 1 mol of the pyrimidinone compound (1a).
  • 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.
  • water is added to the reaction mixture and extracted with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary.
  • a reducing agent for example, sodium sulfite, sodium thiosulfate
  • a base for example, sodium bicarbonate
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used for the reaction include halogenated hydrocarbons.
  • the oxidizing agent used in the reaction include mCPBA.
  • the reaction temperature is usually in the range of ⁇ 20 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • aqueous solution of a reducing agent for example, sodium sulfite, sodium thiosulfate
  • a base for example, sodium bicarbonate
  • this pyrimidinone compound (1c) can be manufactured by one-step reaction (one pot) by making this pyrimidinone compound (1a) and an oxidizing agent react.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used for the reaction include halogenated hydrocarbons.
  • the oxidizing agent used in the reaction include mCPBA.
  • the oxidizing agent is usually used at a ratio of 2 to 3 moles per 1 mole of the pyrimidinone compound (1a).
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • aqueous solution of a reducing agent for example, sodium sulfite, sodium thiosulfate
  • a base for example, sodium bicarbonate
  • the pyrimidinone compound (1a) is a base composed of a compound represented by formula (M1) (hereinafter referred to as compound (M1)) and a compound represented by formula (R1) (hereinafter referred to as compound (R1)). It can manufacture by making it react in presence of. [Wherein V represents a fluorine atom or a chlorine atom, and other symbols represent the same meaning as described above. ] The reaction is usually performed in the presence of a solvent.
  • Examples of 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), dimethyl sulfoxide (hereinafter referred to as DMSO), and the like. (Hereinafter referred to as aprotic polar solvent).
  • Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates), and alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides).
  • compound (R1) is usually used at a ratio of 1 to 10 moles and base is usually used at a ratio of 1 to 10 moles relative to 1 mole of compound (M1).
  • 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 pyrimidinone compound (1a) 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 pyrimidinone compound represented by the formula (1z) (hereinafter referred to as the present pyrimidinone compound (1z)) is represented by the compound represented by the formula (M2) (hereinafter referred to as the compound (M2)) and the formula (R2).
  • the compound shown below (hereinafter referred to as compound (R2)) can be produced by reacting in the presence of a base.
  • V 2 represents a chlorine atom, a bromine atom, an iodine atom, or a C1-C10 perfluoroalkanesulfonyloxy group, and other symbols have the same meanings as described above.
  • the reaction is usually performed in the presence of a solvent.
  • Examples of the solvent used for the reaction include halogenated hydrocarbons and aprotic polar solvents.
  • Examples of the base used in the reaction include organic bases such as triethylamine, diisopropylpyrroleamine, pyridine, 4-dimethylaminopyridine (hereinafter referred to as organic bases), alkali metal hydrides, or alkali metal carbonates. Examples include salts.
  • the compound (R2) is usually used in a proportion of 1 to 10 mol and the base is usually used in a proportion of 0.1 to 5 mol with respect to 1 mol of the compound (M2).
  • 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 pyrimidinone compound (1) 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.
  • Compound (M1) can be produced by reacting a compound represented by formula (M3) (hereinafter referred to as compound (M3)) with compound (R2) in the presence of a base. [Wherein the symbols have the same meaning as described above. ] In this reaction, compound (M1) can be produced according to the reaction described in Production Method 3 by using compound (M3) instead of compound (M2).
  • Compound (M2a) can be produced by reacting compound (M3) with compound (R1) in the presence of a base. [Wherein the symbols have the same meaning as described above. ] In this reaction, compound (M2a) can be produced according to the method described in production method 2, using compound (M3) instead of compound (M1).
  • Manufacturing method 7 Compound (M3) can be produced, for example, according to the following method.
  • R represents a C1-C3 alkyl group
  • M represents —B (OH) 2 , 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, —SnBu 3 , -ZnCl, -MgCl, or -MgBr, and other symbols have the same meanings as described above.
  • R represents a C1-C3 alkyl group
  • M represents —B (OH) 2 , 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, —SnBu 3 , -ZnCl, -MgCl, or -MgBr, and other symbols have the same meanings as described above.
  • R represents a C1-C3 alkyl group
  • M represents —B (OH) 2 , 4,4,5,5-tetramethyl-1,3,2-
  • the compound (M9) includes a compound represented by the formula (M10) (hereinafter referred to as the compound (M10)) and a compound represented by the formula (M11) (hereinafter referred to as the compound (M11)) as a metal catalyst. It can manufacture by making it react in presence of. The reaction is usually performed in the presence of a solvent.
  • solvent used in the reaction examples include ethers such as ethylene glycol dimethyl ether (hereinafter referred to as DME) and tetrahydrofuran (hereinafter referred to as ethers), and aromatics such as toluene and xylene.
  • ethers such as ethylene glycol dimethyl ether (hereinafter referred to as DME) and tetrahydrofuran (hereinafter referred to as THF) (hereinafter referred to as ethers)
  • aromatics such as toluene and xylene.
  • Group hydrocarbons hereinafter referred to as aromatic hydrocarbons
  • aprotic polar solvents aprotic polar solvents
  • Examples of the metal catalyst used in the reaction include tetrakistriphenylphosphine palladium (0), 1,1′-bis (diphenylphosphino) ferrocene-palladium (II) dichloride, tris (dibenzylideneacetone) dipalladium (0), acetic acid.
  • Palladium catalysts such as palladium (II), nickel catalysts such as bis (cyclooctadiene) nickel (0), nickel (II) chloride, copper catalysts such as copper (I) iodide, copper (I) chloride, etc.
  • a ligand, a base and an inorganic halide may be added as necessary.
  • Examples of the ligand used in the reaction include triphenylphosphine, xanthophos, 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl, 1,1′-bis (diphenylphosphino) ferrocene, 2- Dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl, 1,2-bis (diphenylphosphino) ethane, 2,2′-bipyridine 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline and the like.
  • Examples of the base used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases.
  • examples of the inorganic halide used in the reaction include alkali metal fluorine salts such as potassium fluoride and sodium fluoride, and alkali metal chlorine salts such as lithium chloride and sodium chloride.
  • the compound (M11) is usually in a proportion of 1 to 10 mol
  • the metal catalyst is usually in a proportion of 0.01 to 0.5 mol
  • the ligand is usually in a proportion of 0.00.
  • a proportion of 01 to 1 mol, a base of usually 0.1 to 5 mol, and an inorganic halide of usually 0.1 to 5 mol are used.
  • 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.
  • the compound (M9) 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.
  • Compound (M3) can be produced by reacting compound (M9) in the presence of an acid.
  • the reaction is performed in the presence of a solvent.
  • the solvent used in the reaction include halogenated hydrocarbons, aromatic hydrocarbons, alcohols such as methanol and ethanol (hereinafter referred to as alcohols), acetic acid, water, and mixtures thereof.
  • the acid used for the reaction include mineral acids such as hydrochloric acid.
  • an acid is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (M9).
  • Mineral acids can also be used as a solvent.
  • the reaction temperature is usually in the range of ⁇ 20 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (M3) can be isolated by collecting by
  • Manufacturing method 8 Compound (M2a) can be produced, for example, according to the following method. [Wherein the symbols have the same meaning as described above. ]
  • compound (M12) can be produced by reacting compound (M9) with compound (R1) in the presence of a base. In this reaction, compound (M12) can be used in place of compound (M1), and compound (M12) can be produced according to the method described in Production Method 2.
  • Compound (M2a) can be produced by reacting compound (M12) in the presence of an acid. In this reaction, compound (M2a) can be produced according to the method described in production method 7 using compound (M12) instead of compound (M9).
  • compound (M3-1) in which A 2 is CR 3a and A 3 is a nitrogen atom (hereinafter referred to as compound (M3-1)) can be produced, for example, according to the following method. It can. [Wherein the symbols have the same meaning as described above. ]
  • Compound (M5) can be produced by reacting a compound represented by formula (M6) (hereinafter referred to as compound (M6)) with a carbonate in the presence of a base.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used in the reaction include ethers, aliphatic halogenated hydrocarbons, and aprotic polar solvents.
  • Examples of the base used in the reaction include alkali metal hydrides, or alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide (hereinafter referred to as alkali metal alkoxides).
  • Examples of the carbonate ester used in the reaction include dimethyl carbonate, diethyl carbonate, and dipropyl carbonate.
  • the ester carbonate is usually used in a proportion of 1 to 10 mol
  • the base is usually used in a proportion of 0.1 to 5 mol.
  • Carbonic acid esters can also be used as a solvent.
  • 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.
  • the compound (M5) 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.
  • Compound (M5) is obtained by reacting compound (M7) with a compound represented by the formula (R3) (hereinafter referred to as compound (R3)) in the presence of magnesium chloride and a base, and then reacting with an acidic aqueous solution. It can be produced by reacting.
  • the reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers and aprotic polar solvents. Examples of the base used in the reaction include organic bases.
  • the acidic aqueous solution used for the reaction examples include aqueous solutions of mineral acids such as hydrochloric acid and sulfuric acid.
  • the compound (R3) is usually 1 to 10 moles
  • the magnesium chloride is usually 1 to 10 moles
  • the base is usually 0.1 to 10 moles
  • As the acidic aqueous solution 1N to 12N acidic aqueous solution is used at a ratio of 1 to 100 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.
  • the compound (M5) 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.
  • Compound (M4) can be produced by reacting compound (M5) with ammonium acetate.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used for the reaction include an aprotic polar solvent.
  • ammonium acetate is usually used at a ratio of 1 to 10 mol per 1 mol of compound (M5).
  • 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.
  • the compound (M4) 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.
  • Compound (M3-1) can be produced by reacting compound (M4) with a compound represented by formula (R6) (hereinafter referred to as compound (R6)) in the presence of a base.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used for the reaction include alcohols, ethers, and aprotic polar solvents.
  • the base used in the reaction include alkali metal hydrides and alkali metal alkoxides.
  • compound (R6) 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 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (M3-1) can be isolated by post-treatment such as addition of water to the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer.
  • the compound represented by the formula (M2a-1) (hereinafter referred to as the compound (M2a-1)) can be produced, for example, according to the following method. [Wherein the symbols have the same meaning as described above. ]
  • a compound represented by the formula (M16) (hereinafter referred to as the compound (M16)) is used in place of the compound (M7), or a compound (M15) is used instead of the compound (M6).
  • the compound can be produced according to the method described in Production Method 9 (hereinafter referred to as Compound (M15)).
  • a compound represented by the formula (M14) (hereinafter referred to as the compound (M14)) was used instead of the compound (M5). It can be produced according to the method described in production method 9.
  • Compound (M2a-1) can be produced according to the method described in production method 9, using compound (M13) instead of compound (M4).
  • Manufacturing method 11 The compound represented by the formula (M2a-2) (hereinafter referred to as the compound (M2a-2)) can be produced, for example, according to the following method. [Wherein the symbols have the same meaning as described above. ]
  • Compound (M21) can be produced according to the method described in Production Method 9, using a compound represented by the formula (R4) (hereinafter, referred to as compound (R4)) instead of carbonate ester.
  • Compound (M3-2) can be produced by reacting compound (M21) with urea.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used in the reaction include alcohols, aprotic polar solvents, acetic acid, water, and mixtures thereof.
  • urea is usually used at a ratio of 1 to 10 moles with respect to 1 mole of the compound (M21).
  • 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.
  • the compound (M3-2) 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.
  • Compound (M22) can be produced by reacting compound (M6) with a compound represented by formula (R5) (hereinafter referred to as compound (R5)).
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used in the reaction include an aprotic polar solvent and a mixture thereof.
  • compound (R5) is usually used at a ratio of 1 to 100 mol per 1 mol of compound (M6).
  • compound (R5) can also be used as a solvent.
  • 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.
  • the compound (M22) 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.
  • Compound (M3-2) can be produced by reacting compound (22) with urea in the presence of a base.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used in the reaction include alcohols and aprotic polar solvents.
  • the base used for the reaction include alkali metal alkoxides.
  • urea is usually used at a ratio of 1 to 10 moles
  • the base is usually used at a ratio of 1 to 5 moles.
  • 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.
  • the compound (M3-2) 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.
  • Compound (M2a-2) can be produced by reacting compound (M3-2) with compound (R1) in the presence of a base. In this reaction, compound (M2a-2) can be produced according to the method described in Production Method 2 by using compound (M3-2) instead of compound (M1).
  • Production method 12 Compound (M2a-2) can be produced, for example, according to the following method. [Wherein the symbols have the same meaning as described above. ]
  • the present pyrimidinone compound represented by formula (1e) (hereinafter referred to as the present pyrimidinone compound (1e)) and the present pyrimidinone compound represented by formula (1d) (hereinafter referred to as the present pyrimidinone compound (1d)) and formula It can be produced by reacting a compound represented by (R16) (hereinafter referred to as compound (R16)) in the presence of a base.
  • a compound represented by (R16) hereinafter referred to as compound (R16)
  • X 2 represents a fluorine atom, a chlorine atom, or S (O) 2 R 1 , and other symbols have the same meaning as described above.
  • Examples of the solvent used in the reaction include alcohols and aprotic polar solvents.
  • Examples of the base used for the reaction include alkali metal hydrides.
  • the compound (R16) 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 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the pyrimidinone compound (1e) 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 pyrimidinone compound (hereinafter referred to as the present pyrimidinone compound (1f)) in which Q is an oxygen atom, p is 1, and R 2 is NR 5 R 6 is referred to as the present pyrimidinone compound ( It can be produced by reacting 1d) with a compound represented by the formula (R15) (hereinafter referred to as compound (R15)). [Wherein the symbols have the same meaning as described above. ] The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers, aprotic polar solvents, water, and mixtures thereof. This reaction can also be performed by adding a base as necessary.
  • Examples of the base used for the reaction include alkali metal carbonates, alkali metal hydrides, organic bases and the like.
  • the compound (R15) is usually used at a ratio of 1 to 10 moles
  • the base is usually used at a ratio 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 pyrimidinone compound (1f) 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 pyrimidinone compound (1g) can be produced by reacting the pyrimidinone compound (1d) with a compound represented by the formula (R18) (hereinafter referred to as compound (R18)) in the presence of a base. it can.
  • this pyrimidinone compound (1 g) can be produced according to the method described in Production Method 13 by using compound (R18) instead of compound (R16).
  • This pyrimidinone compound (1h) can be manufactured by making this pyrimidinone compound (1g) and an oxidizing agent react. In this reaction, compound (1h) can be produced according to the method described in production method 1 by using compound (1g) instead of compound (1a).
  • the pyrimidinone compound (1i) can be produced by reacting the pyrimidinone compound (1h) with an oxidizing agent. In this reaction, compound (1i) can be produced according to the method described in production method 1 by using compound (1h) instead of compound (1b).
  • the present pyrimidinone compound represented by the formula (1y) (hereinafter referred to as the present pyrimidinone compound (1y)) is sulfided with the present pyrimidinone compound represented by the formula (1z) (hereinafter referred to as the present pyrimidinone compound (1z)). It can manufacture by making an agent react. [Wherein the symbols have the same meaning as described above. ] The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, and aliphatic halogenated hydrocarbons.
  • Examples of the sulfurizing agent used in the reaction include 2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphatan-2,4-disulfide.
  • the sulfurizing agent is usually used in a ratio of 1 to 10 mol per 1 mol of the pyrimidinone compound (1z).
  • the reaction temperature is usually in the range of ⁇ 20 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the pyrimidinone compound (1y) 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 pyrimidinone compound represented by the formula (1L) (hereinafter referred to as the present pyrimidinone compound (1L)) is composed of the present pyrimidinone compound (1d) and a compound represented by the formula (R28) (hereinafter referred to as the compound (R28)). .) In the presence of a base.
  • B 1 and B 2 each independently represent a nitrogen atom or CH
  • R 11 represents a hydrogen atom, or one atom or group selected from group A, and the other symbols have the same meaning as described above.
  • compound (R28) can be used instead of compound (R16), and this pyrimidinone compound (1L) can be produced according to the method described in Production Method 13.
  • This pyrimidinone compound represented by the formula (1m) (hereinafter referred to as the present pyrimidinone compound (1m)) is composed of the present pyrimidinone compound (1d) and a compound represented by the formula (R29) (hereinafter referred to as the compound (R29)). .) Can be made to react. [Wherein t represents an integer of 0 to 4, and other symbols have the same meaning as described above. ] In this reaction, compound (R29) can be used instead of compound (R15), and this pyrimidinone compound (1m) can be produced according to the method described in Production Method 14.
  • PI represents a piperidin-1-yl group
  • PY represents a pyrrolidin-1-yl group
  • MO represents a morpholin-4-yl group
  • TH represents a thiomorpholine-4 -Represents an yl group.
  • R 3 and R 3a are hydrogen atoms
  • R 21 , R 22 and R 23 are hydrogen atoms
  • R 1 , G and n are the present pyrimidinones according to [Table 1] to [Table 4]
  • Compound hereinafter referred to as compound group SX1).
  • R 3 and R 3a are hydrogen atoms
  • R 21 and R 23 are hydrogen atoms
  • R 22 is a trifluoromethyl group
  • R 1 , G, and n are [Tables] 1] to [Table 4]
  • the pyrimidinone compounds hereinafter referred to as compound group SX2).
  • R 3 is a hydrogen atom
  • R 21 , R 22 , and R 23 are hydrogen atoms
  • R 3a is CH 3
  • R 1 , G, and n are [Table 1 ]
  • the pyrimidinone compounds hereinafter referred to as compound group SX3
  • R 3 is a hydrogen atom
  • R 21 and R 23 are hydrogen atoms
  • R 22 is a trifluoromethyl group
  • R 3a is CH 3
  • n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX4).
  • R 3 is a hydrogen atom
  • R 21 , R 22 , and R 23 are hydrogen atoms
  • R 3a is a fluorine atom
  • R 1 , G, and n are [Table 1 ]
  • the pyrimidinone compounds (hereinafter referred to as compound group SX5).
  • R 3 is a hydrogen atom
  • R 21 and R 23 are hydrogen atoms
  • R 22 is a trifluoromethyl group
  • R 3a is a fluorine atom
  • n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX6).
  • R 3 is a hydrogen atom
  • R 21 , R 22 , and R 23 are hydrogen atoms
  • R 3a is a chlorine atom
  • R 1 , G, and n are [Table 1 ]
  • the pyrimidinone compounds (hereinafter referred to as compound group SX7).
  • R 3 is a hydrogen atom
  • R 21 and R 23 are hydrogen atoms
  • R 22 is a trifluoromethyl group
  • R 3a is a chlorine atom
  • n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX8).
  • R 3a is a hydrogen atom
  • R 21 , R 22 , and R 23 are hydrogen atoms
  • R 3 is CH 3
  • R 1 , G, and n are [Table 1 ]
  • the pyrimidinone compounds hereinafter referred to as compound group SX9.
  • R 3a is a hydrogen atom
  • R 21 and R 23 are hydrogen atoms
  • R 22 is a trifluoromethyl group
  • R 3 is CH 3 , R 1 , G
  • n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX10).
  • R 3 and R 3a are hydrogen atoms, and R 1 , G, n, R 21 , R 22 , and R 23 are combinations shown in [Table 5] to [Table 13].
  • a certain pyrimidinone compound hereinafter referred to as compound group SX11). [Table 1]
  • R 3 and R 3a are hydrogen atoms
  • R 21 , R 22 and R 23 are hydrogen atoms
  • R 1 , G and n are the present pyrimidinones according to [Table 1] to [Table 4]
  • Compound hereinafter referred to as compound group SX12
  • R 3 and R 3a are hydrogen atoms
  • R 21 and R 23 are hydrogen atoms
  • R 22 is a trifluoromethyl group
  • R 1 , G, and n are [Table 1] to [Table 4]
  • the pyrimidinone compounds hereinafter referred to as compound group SX13).
  • R 3 is a hydrogen atom
  • R 21 , R 22 , and R 23 are hydrogen atoms
  • R 3a is CH 3
  • R 1 , G, and n are [Table 1 ]
  • the pyrimidinone compounds hereinafter referred to as compound group SX14.
  • R 3 is a hydrogen atom
  • R 21 and R 23 are hydrogen atoms
  • R 22 is a trifluoromethyl group
  • R 3a is CH 3
  • n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX15).
  • R 3 is a hydrogen atom
  • R 21 , R 22 , and R 23 are hydrogen atoms
  • R 3a is a fluorine atom
  • R 1 , G, and n are [Table 1]
  • the pyrimidinone compounds described in [Table 4] (hereinafter referred to as compound group SX16).
  • R 3 is a hydrogen atom
  • R 21 and R 23 are hydrogen atoms
  • R 22 is a trifluoromethyl group
  • R 3a is a fluorine atom
  • n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX17).
  • R 3 is a hydrogen atom
  • R 21 , R 22 , and R 23 are hydrogen atoms
  • R 3a is a chlorine atom
  • R 1 , G, and n are [Table 1 ]
  • the pyrimidinone compounds hereinafter referred to as compound group SX18.
  • R 3 is a hydrogen atom
  • R 21 and R 23 are hydrogen atoms
  • R 22 is a trifluoromethyl group
  • R 3a is a chlorine atom
  • n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX19).
  • R 3a is a hydrogen atom
  • R 21 , R 22 , and R 23 are hydrogen atoms
  • R 3 is CH 3
  • R 1 , G, and n are [Table 1 ]
  • the pyrimidinone compounds hereinafter referred to as compound group SX20.
  • R 3a is a hydrogen atom
  • R 21 and R 23 are hydrogen atoms
  • R 22 is a trifluoromethyl group
  • R 3 is CH 3 , R 1 , G
  • n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX21).
  • R 3 and R 3a are hydrogen atoms, and R 1 , G, n, R 21 , R 22 , and R 23 are combinations shown in [Table 5] to [Table 13].
  • a certain pyrimidinone compound hereinafter referred to as compound group SX22).
  • R 3 and R 3b are hydrogen atoms
  • R 21 , R 22 , and R 23 are hydrogen atoms
  • R 1 , G, and n are the combinations described in [Table 1] to [Table 4]
  • a certain pyrimidinone compound hereinafter referred to as compound group SX23.
  • R 3 and R 3b are hydrogen atoms
  • R 21 and R 23 are hydrogen atoms
  • R 22 is a trifluoromethyl group
  • R 1 , G, and n are [ The pyrimidinone compounds (hereinafter referred to as compound group SX24) which are combinations described in Table 1] to [Table 4].
  • R 3 and R 3b are hydrogen atoms, and R 1 , G, n, R 21 , R 22 , and R 23 are combinations shown in [Table 5] to [Table 13].
  • a certain pyrimidinone compound hereinafter referred to as compound group SX25).
  • R 3 and R 3b are hydrogen atoms, R 21 , R 22 , and R 23 are hydrogen atoms, and R 1 , G, and n are the combinations described in [Table 1] to [Table 4]
  • a certain pyrimidinone compound hereinafter referred to as compound group SX26).
  • R 3 and R 3b are hydrogen atoms, R 21 and R 23 are hydrogen atoms, R 22 is a trifluoromethyl group, and R 1 , G, and n are [ The pyrimidinone compounds (hereinafter referred to as compound group SX27) which are combinations described in Table 1] to [Table 4].
  • R 3 and R 3b are hydrogen atoms, and R 1 , G, n, R 21 , R 22 , and R 23 are combinations shown in [Table 5] to [Table 13].
  • a certain pyrimidinone compound hereinafter referred to as compound group SX28).
  • R 3 and R 3b are hydrogen atoms, R 21 , R 22 , and R 23 are hydrogen atoms, and R 1 , G, and n are the combinations described in [Table 1] to [Table 4]
  • a certain pyrimidinone compound hereinafter referred to as compound group SX29).
  • R 3 and R 3b are hydrogen atoms
  • R 21 and R 23 are hydrogen atoms
  • R 22 is a trifluoromethyl group
  • R 1 , G, and n are [ The pyrimidinone compounds (hereinafter referred to as compound group SX30) which are combinations described in Table 1] to [Table 4].
  • R 3 and R 3b are hydrogen atoms, and R 1 , G, n, R 21 , R 22 , and R 23 are combinations shown in [Table 5] to [Table 13].
  • a certain pyrimidinone compound hereinafter referred to as compound group SX31).
  • Examples of the compound of group (a) include compounds of subgroups a-1, a-2, a-3, a-4, a-5, a-6 and a-7.
  • Subgroup a-1 Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, flupyrifurone, flupyradifurone ), Dichloromesothiaz (dicloromezotiaz) and a compound represented by the following formula (CAS registration number 1689566-03-7)
  • a group of competitive modulators of nicotinic acetylcholine receptors A group of competitive modulators of nicotinic acetylcholine receptors.
  • Subgroup a-2 Acrinathrin, allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin, beta beta-cyfluthrin), cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, betacypermethrin ( beta-cypermethrin), theta-cypermethrin, theta-cypermethrin, sigma-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esf Enfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin,
  • Subgroup a-3 GABAergic chloride channel blocker consisting of ethiprole, fipronil and flufiprole, and GABA consisting of afoxalaner, fluralaner, broflanilide and fluxametamide
  • Subgroup a-4 Group of ryanodine receptor modulators consisting of chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, tetraniliprole and cyhalodiamide .
  • Subgroup a-5 Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl (NAC), carbofuran, carbofuran Fan (carbosulfan), ethiofencarb (fthiobucarb), fenobucarb (BPMC), formethanate (formetanate), furathiocarb (furathiocarb), isoprocarb (isoprocarb: MIPC), methiocarb (methiocarb), methomyl (methomyl), metolcarb (MTMC) , Oxamyl, pirimicarb, propoxur (PHC), thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylica Bed (xylylcarb: MPMC) consists, the group of carbamates acetylcholinesterase (AChE) inhibitors.
  • Subgroup a-6 A group of nematicidal active compounds consisting of abamectin, fluensulfone, tioxazafen, and fluazaindolizine.
  • Subgroup a-7 Mycorrhiza Fungi, Arthrobotrys dactyloides, Bacillus thuringiensis, Bacillus firmus, Bacillus megaterium, Bacillus amyloliquefaciens (Bacillus amyloliquefaciens), Hirsutella rhossiliensis, Hirsutella minnesotensis, Monacrosporium phymatopagus, Pasturiatransurie, Pasturiapass A group of microbial materials consisting of Pasteuria usgae, Verticillium chlamydosporium and Harpin protein.
  • acetamiprid clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, fluradifurone, fluradifurone , Triflumezopyrim, acrinathrin, allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, cycloresin, prothrin (Cyfluthrin), beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, Permethrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, sigma-cypermethrin , Cy
  • Dichloromesothiaz (CAS registration number: 1263629-39-5), tetraniliprolol (CAS registration number: 1229654-66-3), floxamethamide (CAS registration number: 928783-29-3, afoxoranel) used in the present invention (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 all known compounds, such as International Publication No.
  • Mycorrhiza Fungi Arthrobotrys dactyloides, Bacillus thuringiensis, Bacillus firmus, Bacillus megaterium used in the present invention, Bacillus amyloliquefaciens, Hirsutella rhossiliensis, Hirsutella minnesotensis, Monacrosporium phymatopagus, Monacrosporium phymatopagus, Pasteuria e (Pasteuria penetrans), Pasturia usgae, Verticillium chlamydosporium and Harpin protein are all public A microbial materials, obtained from commercially available preparations or obtained by production using a known method.
  • Examples of the compound of the group (b) include compounds of subgroups b-1, b-2, b-3, b-4, b-5, b-6, b-7, b-8 and b-9 below. Is mentioned.
  • Subgroup b-1 Azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diiconazole, diniconazole-M, epiconconazole, ethaconazole (Etaconazole), fenarimol, fenbuconazole, fluquinconazole, quinconazole, flusilazole, flutriafol, hexaconazole, imazaril ( imazalil), imibenconazole, ipconazole, metconazole, microbutanil, nuarimol, oxpoconazole, o Spoconazole fumarate, pefurazoate, penconazole, prochlora
  • Subgroup b-2 Azoxystrobin, coumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, fenaminstrobin, full Phenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metinominostrobin, orysastrobin, picoxystrobin , Pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, pyribencarb, triclopyricarb, triazopyricarb Consisting de (cyazofamid) and amisulbrom (amisulbrom), the group of Qo inhibitors (Quinone outside inhibitors).
  • Subgroup b-3 A group of RNA polymerase I inhibitors consisting of benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl and ofurace .
  • Subgroup b-4 Benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad ), Furametpyr, isofetamid, isoprazam, mepronil, oxycarboxin, penthiopyrad, penflufen, sedaxane, thifluzamide, thifluamide (Pyraziflumid), pydiflumetofen (CAS registration number 1228284-64-7), 3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazole-4- Carboxamide (CAS registration No.
  • Subgroup b-5 It consists of benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide and ethaboxam.
  • a group of ⁇ -tubulin polymerization inhibitors It consists of benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide and ethaboxam.
  • Subgroup b-6 Ferbam, mancozeb, manneb, maneb, metiram, propineb, thiram, zineb, ziram, captan, captafol ), Folpet, chlorothalonil, tolylfluanid, guazatine, iminoctadine, anilazine, dithianon, chinomethionate or quinomethionate fluoride
  • Subgroup b-7 Dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthivalicarb-isopropyl, iprovalicarb, valifenalate and mandipropamid
  • cellulose synthesis inhibitors A group of cellulose synthesis inhibitors.
  • Subgroup b-8 MAP (mitogen-activated protein) / histidine kinase inhibitor in osmotic signal transduction consisting of fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone and vinclozolin group.
  • Subgroup b-9 A group of other fungicides consisting of tolclofos-methyl, oxathiapiproline, picarbutrazox, fluopicolide and silthiofam.
  • Pyraziflumid used in the present invention is a known compound and can be produced, for example, by the method described in International Publication No. 2007/072999.
  • Pidiflumetofen used in the present invention is a known compound and can be produced, for example, by the method described in WO2010 / 063700.
  • Methyl-1-methyl-N-[(3R) -1,1,3-trimethylindan-4-yl] pyrazole-4-carboxamide (CAS Registry Number 1352994-67-2) is a known compound, For example, it can be produced by the method described in International Publication No. 2011/162397, respectively.
  • 3-Difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4-yl) -1-methylpyrazole-4-carboxamide (CAS registration number 1383809-87-7) used in the present invention 3-difluoromethyl-N-[(3R) -7-fluoro-1,1,3-trimethylindan-4-yl] -1-methylpyrazole-4-carboxamide (CAS Registry Number 1513466-73-3) is All are known compounds and can be produced, for example, by the methods described in International Publication No. 2012/084812.
  • N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide (CAS registration number) used in the present invention 1255734-28-1) is a known compound and can be produced, for example, by the method described in International Publication No. 2013/160387.
  • SX means “any one of the present pyrimidinone compounds selected from the compound group SX1 to SX31”.
  • composition of the present invention may be a simple mixture of the present pyrimidinone compound and the present compound, but usually the present pyrimidinone compound and the present compound are mixed with an inert carrier such as a solid carrier, a liquid carrier or a gaseous carrier. If necessary, add surfactants and other formulation adjuvants, emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smokers, poison baits , Resin preparations, shampoos, paste preparations, foams, carbon dioxide preparations, tablets and the like.
  • an inert carrier such as a solid carrier, a liquid carrier or a gaseous carrier.
  • the total amount of the pyrimidinone 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.
  • adjuvants for preparation include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
  • fixing agents such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (is
  • 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 formulation is obtained by kneading the pyrimidinone 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, if necessary. 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.
  • These resin preparations are processed into, for example, animal collars, animal ear tags, sheet preparations, attraction strings, and horticultural supports.
  • 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 chili powder, anti-fouling agents by children and pets, cheese flavor, onion flavor, peanut oil and other pest-attracting flavors.
  • the content ratio of the present pyrimidinone compound and the present compound in the composition of the present invention is not particularly limited, but the ratio of the content of the present pyrimidinone compound and one or more compounds selected from the group (a) Is preferably in the range of 100: 1 to 1: 100 by weight, particularly preferably in the range of 10: 1 to 1:10, and one or more compounds selected from the present pyrimidinone compound and the group (b)
  • the ratio by weight is preferably in the range of 10,000: 1 to 1: 100 by weight, particularly preferably in the range of 1000: 1 to 1:10.
  • the pest control method of the present invention is performed by applying an effective amount of the composition of the present invention to pests directly and / or to pest habitats (plants, soil, households, animal bodies, etc.). .
  • Examples of the application method of the composition of the present invention include application to plants, application to soil where plants are cultivated, application to plant seeds or bulbs.
  • Examples of application to plants include application to plant foliage, flower vases, seedlings or ears.
  • Examples of the application to soil for cultivating plants include application to soil before planting or after planting.
  • Examples of application to plant seeds or bulbs include seed disinfection, seed soaking, and seed coating.
  • the pyrimidinone compound and the compound may be applied separately. Before and after planting seeds or bulbs to which either the pyrimidinone compound or the compound is attached to the soil, the remaining one is applied to the soil. Also good.
  • Specific examples of application to plant stems and leaves, flower vases, seedlings or ears include application methods applied to the surface of plants such as foliage spraying, trunk spraying, etc., and before flowering, during flowering, after flowering. Examples include a method of spraying the entire vase or the whole plant at the flowering time, and a method of spraying the head or the whole plant at the heading time for cereals.
  • the method of applying to the soil before or after planting is, for example, by applying the composition of the present invention to the rhizosphere of a crop to be protected from damage such as feeding by pests. It is a method for controlling pests directly, or a method for controlling pests such as feeding plants by osmotically transferring the present pyrimidinone compound and the present compound from the root to the inside of the plant body.
  • planting treatment planting hole spraying, planting hole treatment soil mixing
  • plant source processing stock source spraying, strain source soil mixing, strain source irrigation, late seedling stage plant source processing
  • planting groove processing planting groove processing
  • cropping treatment growing sprinkling, cropping soil blending, growing season cropping spraying
  • sowing cropping treatment sowing cropping spraying, sowing cropping soil blending
  • Whole surface treatment overall soil application, whole surface soil admixture
  • side strip treatment water surface treatment (water surface application, water surface application after submergence), other soil application treatment (growth season foliar leaf surface application, under the crown or around the trunk
  • irrigation treatments irrigation, seedling irrigation, chemical solution injection treatment, local irrigation, chemical drip irrigation, chemical ligation
  • Nursery box processing noursery box spraying, seedling box irrigation,
  • the plant seed means plant seed in a state before being sown in the soil or the culture medium
  • the bulb is a bulb of the plant in a state before being planted in the soil or the culture medium. It means tubers, rhizomes, stem fragments, seed pods and tuberous roots.
  • the method of applying the composition of the present invention to plant seeds or bulbs is, for example, a method of controlling pests by applying the composition of the present invention directly to plant seeds or bulbs to be protected from damage such as feeding by pests.
  • the plant seed or bulb of the present invention is a plant seed or bulb obtained by attaching an effective amount of the composition of the present invention by these methods, and retains an effective amount of the composition of the present invention.
  • the amount of the pyrimidinone compound applied is usually 0.001 to 100 g, preferably 0.02 to 20 g, per 1 kg of plant seeds or bulbs.
  • the dose is usually 0.000001 to 50 g, preferably 0.0001 to 30 g per kg of plant seeds or bulbs.
  • pests for which the composition of the present invention is effective include harmful insects, harmful mites, harmful nematodes, and phytopathogenic fungi such as filamentous fungi and bacteria. Specific 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), Rice leafroller (Marasmia) patnalis), Inatake maki (Marasmia exigua), Cottontail moth (Notarcha derogata), Plodia interpunctella, Awa no Mei teri ), Rice case worms (Nymphula depunctalis), Marasmia, Hop vine borer (Hydraecia immanis), European corn borer (Ostrinia nubilalis), Lesser cornstalk borer (Elasmopalpus lignosellus), Bean Shootpiborer aigasaccharalis), Giant Sugarcane borer (Tel
  • 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 ee Beetle (Diabrotica speciosa), Bean Leaf Beetle (Cerotoma trifurcata), Cereal Leaf Beetle (Oulema melanopus), Woolly horn beetle (Aulacophora femoralis), Pterol hamde (Phylolta) ), Rice beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn flare beetle (Chaetocnema pulicaria), potato flare beetle (Ep) itrix ⁇ cu
  • Weevil Echinocnemus squameus
  • rice weevil Loevil (Lissorhoptrus oryzophilus), weevil (Sphenophorus venatus), etc .
  • us subsignatus and Sphenophorus levis and other genus Sphenophorus
  • epicarunas such as Epilachna vigintioctopunctata; Lyctus brunneus; Japanese beetles; longhorn beetles (Anoplophora malasiaca), longhorn beetles such as Migdolus fryanus; sp., Anchastus sp., Melanotus sp., Limonius sp., Conoderus sp., Ctenicera sp.); Swan beetles, such as Paederus fuscipes, and Coffee Berry Borer (Hypothenemus hampei).
  • 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.
  • Lip and limb class Thereuonema hilgendorfi, Scolopendra subspinipes, etc. Double-legged class: Japanese red millipede (Oxidus gracilis), Japanese red millipede (Nedyopus tambanus).
  • 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 (Fusarium graminearum, F.avenaceum, F.culmorum, Microdochium nivale), rust (Puccinia striiformis, P.graminis, P. recondita), red snow rot (Microdochium nivale, M.
  • 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.
  • 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, insecticidal, acaricidal, nematicidal, bactericidal agents other than the target insecticidal, acaricidal, nematicidal, bactericidal agents The use of 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), Tungue disease (Rice tungro spherical virus, Rice tungro bacilliform virus), rice grassy stunt disease (Rice grassy stunt virus), rice rugged stunt disease (Rice ragged stunt virus), rice stripe leaf blight Disease (Rice stripe virus), black stripe atrophy (Rice black streaked dwarf virus), rice southern black stripe atrophy (Southern rice black-streaked dwarf virus), rice hump dwarf disease (Rice gall dwarf virus), rice leaf blight ( Rice hoja blanca virus), white leaf disease (White leaf desease of rice), yellowing dwarf disease (Yellow dwarf virus), Red disease (Rice penyakit merah virus), rice yellow leaf disease (Rice yellow stunt virus), transition yellowing Disease (Rice transitory yellowing virus), rice yellow spot (Rice Yellow Mottle Virus), rice necrotic mosaic virus (Rice necrosis mosaic virus), rice dwarf disease (Rice) dwarf stunt virus), northern wheat mosaic disease (Northern Cereal Mosaic Virus), barley yellow
  • the application amount can vary widely depending on the application time, application location, application method, etc., but in general, the pyrimidinone compound and the compound The total amount of is usually 1 to 10,000 g per 10,000 m 2 .
  • the composition of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc.
  • the present pyrimidinone compound and the present compound are usually adjusted so that the total concentration thereof is 0.01 to 10,000 ppm. It is diluted with water and applied, and granules, powders and the like are usually applied as they are.
  • 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 that is generally cultivated.
  • Such varieties of plants include plants to which one or more useful traits have been conferred by genetic breeding techniques or genetic recombination techniques (genetically modified plants) and stack varieties in which they are crossed.
  • useful traits include herbicide resistance, pest resistance, disease resistance, stress resistance, and quality improvement of fatty acid residue composition modified crops of fats and oils.
  • Examples of such a genetically modified plant include, for example, genetic recombination in the electronic information site (http://www.isaaa.org/) of the International Agri-Bio Corporation (INTERRNATIN SERVICE for the ACQUISITION of AGRI-BIOTECH APPLICATIONS, ISAAA). Plants listed in the crop registration database (GM APPROVAL DATABASE). More specifically, plants that have been given environmental stress resistance, disease resistance, herbicide resistance, pest resistance, etc. by genetic recombination techniques, or traits related to growth and yield, product quality, fertility traits, etc. It may be a modified plant.
  • Plants that have been given herbicide tolerance by genetic recombination technology include protoporphyrinogen oxidase (hereinafter abbreviated as PPO) herbicides such as flumioxazin, 4-hydroxyphenylpyruvate diacids such as isoxaflutol and mesotrione.
  • PPO protoporphyrinogen oxidase
  • HPPD Oxygenase
  • ALS acetolactate synthase
  • EPSP 5-enolpyruvylshikimate-3-phosphate synthase
  • glutamine synthase inhibitors such as glufosinate
  • auxin-type herbicides such as 2,4-D and dicamba
  • Examples of plants to which herbicide tolerance has been imparted by gene recombination technology include glyphosate-resistant EPSPS gene (CP4 epsps) derived from Agrobacterium tumefaciens strain CP4, glyphosate metabolizing enzyme derived from Bacillus licheniformis (Glyphosate N-acetyltransferase) gene whose activity is enhanced by shuffling technology, glyphosate metabolic enzyme genes (gat4601, gt6421), glyphosate metabolic enzyme (glyphosate oxidase gene, goxv247) derived from Ochrobacterum strain LBAA Or maize-derived glyphosate tolerance mutation EPSPS gene (mepsps, 2mepsps) having has one or more of the introduced glyphosate tolerant transgenic plants and the like.
  • CP4 epsps glyphosate-resistant EPSPS gene
  • CP4 epsps glyphos
  • Maize (Zea mays L.), Soybean (Glycine max L.), Cotton (Gossypium hirsutum L.), Sugar beet (Beta vulgaris), Canola (Brassica napus, Brassica rapaed), Alfalfa .), Wheat (Triticum aestivum), creeping bentgrass (Agrossis tolonifera) and other plants, there are glyphosate-resistant genetically modified varieties. Several glyphosate-tolerant transgenic plants are commercially available.
  • genetically modified plants that express glyphosate-resistant EPSPS derived from Agrobacterium are trade names including Roundup Ready (registered trademark) and express glyphosate-metabolizing enzyme derived from Bacillus with enhanced metabolic activity by shuffling technology
  • Genetically modified plants are trade names such as Optimum (registered trademark) GAT (registered trademark), Optimum (registered trademark) Gly canola, and transgenic plants expressing EPSPS having a glyphosate-resistant mutation derived from corn are GlyTol (registered trademark). ) Is already sold under the product name.
  • phosphinothricin N-acetyltransferase As an example of a plant to which herbicide tolerance has been imparted by genetic recombination technology, phosphinothricin N-acetyltransferase, a glufosinate metabolizing enzyme derived from Streptomyces hygroscopicus, Phosphinothricin N-acetyltransferase, A gene (bar), a phosphinothricin N-acetyltransferase gene (pat), which is a glufosinate metabolizing enzyme derived from Streptomyces virochromogenes, or a glufosinate-tolerant transgenic plant introduced with a synthesized pat gene or the like There is.
  • glufosinate-resistant transgenic varieties such as corn, soybean, cotton, canola, rice (Oryza sativa L.), sugar beet, chicory (Cichorium intybus) and the like.
  • glufosinate-tolerant transgenic plants are commercially available.
  • Genetically modified plants that express glufosinate metabolizing enzymes (bar, pat) derived from Streptomyces are already sold under trade names including LibertyLink (registered trademark).
  • bromoxynyl-tolerant gene recombination in which a nitrilase gene (bxn), which is a bromoxynyl-metabolizing enzyme derived from Klebsiella pneumoniae subsp. Ozaenae, has been introduced.
  • bxn a nitrilase gene
  • Bromoxinyl-resistant genetically modified varieties are produced in plants such as canola, cotton, tobacco (Nicotiana tabacum L.), and are already sold under trade names including Navigator (registered trademark) canola or BXN (registered trademark) .
  • a genetically modified carnation into which an ALS herbicide-tolerant ALS gene (surB, S4-HrA) derived from tobacco has been introduced as a selection marker
  • a transgenic flax Lium usitistisumum L.
  • CDC Trifid Flax a transgenic flax into which an ALS herbicide-resistant ALS gene derived from Arabidopsis thaliana has been introduced.
  • a genetically modified soybean introduced with an ALS herbicide-resistant ALS gene (csr1-2) derived from Arabidopsis thaliana has been developed under the name of Culture (registered trademark).
  • transgenic corn resistant to sulfonylurea and imidazolinone herbicides introduced with corn-derived ALS herbicide-resistant ALS gene (zm-hra), soybean-derived ALS herbicide-resistant ALS gene (gm-
  • gm- soybean-derived ALS herbicide-resistant ALS gene
  • HPPD herbicide-resistant HPPD gene hppdPFW336
  • allyloxyalkanoate dioxygenase which is a 2,4-D metabolizing enzyme derived from Sphingobium herbicidovorans, is exemplified.
  • examples of plants that have been rendered tolerant to two or more herbicides by genetic engineering techniques include transgenic cotton that is resistant to both glyphosate and glufosinate, and genetically modified maize that is GlyTol® LibertyLink. (Registered trademark), Round Ready (registered trademark) LibertyLink (registered trademark) Maize is already sold under the trade name.
  • GlyTol® LibertyLink (Registered trademark), Round Ready (registered trademark) LibertyLink (registered trademark) Maize is already sold under the trade name.
  • a genetically modified soybean resistant to both glufosinate and 2,4-D was developed under the trade name of Enlist (registered trademark) Soybean, and genetically modified cotton resistant to both glufosinate and 2,4-D. There is also.
  • a genetically modified soybean that is resistant to both glyphosate and dicamba has been developed under the trade name Genuity (R) Roundup Ready (R) 2 Xtend (R).
  • Genetically modified maize, soybean, which is resistant to both glyphosate and ALS inhibitors has been developed under the trade name Optimum® GAT®.
  • transgenic cotton resistant to both glufosinate and dicamba transgenic corn resistant to both glyphosate and 2,4-D
  • transgenic soybean resistant to both glyphosate and HPPD herbicide has also been developed.
  • genetically modified soybeans that are resistant to three herbicides, glyphosate, glufosinate and 2,4-D have also been developed.
  • Plants to which pest resistance has been imparted by gene recombination technology include plants to which resistance to lepidopterous insects, Coleoptera insects, multiple order insects, nematodes and the like are imparted.
  • a plant that has been given resistance to lepidopteran insects by genetic recombination technology it encodes delta-endotoxin, which is an insecticidal protein derived from soil bacteria Bacillus thuringiensis (hereinafter abbreviated as Bt) And transgenic plants such as corn, soybean, cotton, rice, Populus (Populus sp.), Tomato (Lycopersicon esculentum) and eggplant (Solanum melongena).
  • Bt Bacillus thuringiensis
  • transgenic plants such as corn, soybean, cotton, rice, Populus (Populus sp.), Tomato (Lycopersicon esculentum) and eggplant (Solanum melongena).
  • Cry1A, Cry1Ab, modified Cry1Ab (partially deleted Cry1Ab), Cry1Ac, Cry1Ab-Ac a hybrid protein in which Cry1Ab and Cry1Ac are fused
  • Cry1C, Cry1F , Cry1Fa2 modified cry1F
  • moCry1F modified Cry1F
  • 105 a hybrid protein in which Cry1Ab, Cry1Ac, and Cry1F are fused
  • Cry2Ab2Ae, Cry9C, Vip3A, Vip3Aa20, and the like a hybrid protein in which Cry1Ab, Cry1Ac, and Cry1F are fused
  • Examples of delta-endotoxins that confer resistance to Coleoptera insects include Cry3A, mCry3A (modified Cry3A), Cry3Bb1, Cry34Ab1, and Cry35Ab1.
  • Insecticidal proteins that impart pest resistance to plants include hybrid proteins of the above-mentioned insecticidal proteins, partially missing proteins, and modified proteins.
  • the hybrid protein is produced by a combination of different domains of a plurality of insecticidal proteins using genetic recombination technology, and Cry1Ab-Ac or Cry1A. 105 etc. are known.
  • Cry1Ab and the like lacking a part of the amino acid sequence are known.
  • the modified protein include proteins in which one or more amino acids of the natural delta-endotoxin are substituted, and Cry1Fa2, moCry1F, mCry3A and the like are known.
  • insecticidal proteins that impart pest resistance to plants by genetic recombination technology
  • insecticidal proteins derived from Bacillus cereus and Bacillus popilliae insecticidal protein Vip1 derived from Bt bacteria , Vip2, Vip3, nematode-derived insecticidal protein, scorpion toxin, spider toxin, bee toxin or insect-specific neurotoxin-produced toxin, filamentous fungal toxin, plant lectin, agglutinin, trypsin inhibitor, serine Protease inhibitor, protease inhibitor such as patatin, cystatin, papain inhibitor, lysine, corn-RIP, ribosome inactivating protein (RIP) such as abrin, ruffin, saporin, bryodin, 3-hydroxysterloy Oxidase, ecdysteroid-UDP-glucosyltransferase, steroid metabolic enzymes such as cholesterol oxidase, ecdy
  • transgenic plants imparted with pest resistance by introducing one or two or more insecticidal protein genes are already known, and some genetically modified plants are commercially available.
  • transgenic cotton imparted with pest resistance include Bollgard (registered trademark) cotton that expresses the insecticidal protein Cry1Ac derived from Bt bacteria, and Bollgard II (registered trademark) that expresses the insecticidal proteins Cry1Ac and Cry2Ab derived from Bt bacteria.
  • Examples of genetically modified maize imparted with pest resistance include Yieldgard® Rootworm RW that expresses the insecticidal protein Cry3Bb1 derived from Bt, YieldGard Plus that expresses the insecticidal proteins Cry1Ab and Cry3Bb1 derived from Bt Trademark), insecticidal protein Cry1A. YieldGard (registered trademark) VT Pro (registered trademark) and the like that express 105 and Cry2Ab2 are commercially available.
  • Agrisure (registered trademark) RW expressing insecticidal protein mCry3A derived from Bt bacteria, Agrisure (registered trademark) Viptera expressing insecticidal protein Vip3Aa20 derived from Bt bacteria, Agrisure expressing insecticidal protein eCry3.1 Ab derived from Bt bacteria (Registered trademark) Duracade (registered trademark) and the like are also commercially available.
  • As examples of genetically modified potatoes imparted with pest resistance Atlantic NewLeaf (registered trademark) potato, NewLeaf (registered trademark) Russet Burbank poto, etc. that express the insecticidal protein Cry3A derived from Bt bacteria are commercially available.
  • Plants to which disease resistance has been imparted by gene recombination techniques include common bean (Phaseolus vulgaris), papaya (Carica papaya), plum (Prunus domestica), potato, and Cucurbita pepo. , Sweet pepper (Capsicum annuum), tomato and the like.
  • a genetically modified plant imparted with resistance to plant viral diseases specifically, a gene set in which a gene that generates double-stranded RNA of a replica protein of Bean golden mosaic virus is introduced.
  • a genetically modified potato imparted with resistance to a plant viral disease a genetically modified potato with a trade name including Newleaf (registered trademark) is commercially available.
  • Plants imparted with disease resistance also include plants imparted with the ability to produce anti-pathogenic substances having a selective action using genetic engineering techniques.
  • anti-pathogenic substances PR proteins and the like are known (PRPs, EP392225). Such anti-pathogenic substances and genetically modified plants that produce them are described in EP392225, WO199533818, EP353191, and the like.
  • anti-pathogenic substances include, for example, ion channel inhibitors such as sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.), stilbene synthase, Microorganisms such as benzyl synthase, chitinase, glucanase, peptide antibiotics, heterocyclic antibiotics, and protein factors involved in plant disease resistance (referred to as plant disease resistance genes and described in WO2003010906) are produced. And anti-pathogenic substances.
  • ion channel inhibitors such as sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.)
  • stilbene synthase such as benzyl synthase, chitinase, glucanase, peptide antibiotics, heterocyclic antibiotics, and protein factors involved in plant disease resistance (referred to as plant disease resistance genes and described in WO2003010906) are produced.
  • anti-pathogenic substances include,
  • Alfalfa-derived S-adenosyl-L-methionine involved in lignin production Trans-caffeoyl CoA
  • a gene that generates double-stranded RNA of 3-methyltransferase (ccomt) gene was introduced to reduce lignin content by RNA interference.
  • a transgenic canola whose triacylglyceride content, including lauric acid, has been increased by introducing a 12: 0 ACP thioesterase gene derived from Laurel (Umbellaria californica) involved in fatty acid synthesis under the trade name Laurical (registered trademark) Canola. has been developed.
  • phyA 3-phytase gene
  • Dihydroflavonol-4-reductase gene from Petunia hybrida an enzyme that produces the blue pigment delphinidin and its derivatives, and petunia, pansy (Viola wittrockiana), salvia (Salvia splendens), or flavonoid from carnation
  • a genetically modified carnation in which the flower color is controlled to be blue by introducing a -3 ′, 5′-hydroxylase gene is known.
  • the genetically modified carnations in which the flower color is controlled to blue are Moondust (registered trademark), Moonshadow (registered trademark), Moonshade (registered trademark), Moonlite (registered trademark), Moonaqua (registered trademark), Moonvista (registered trademark), Moonique ( It has been developed under trade names such as (registered trademark), Moonpearl (registered trademark), Moonberry (registered trademark), and Moonvelvet (registered trademark).
  • anthocyanin-5-acyltransferase gene derived from Torenia sp. An enzyme that produces the blue pigment delphinidin and its derivatives, and a flavonoid-3 ′, 5′-hydroxylase gene derived from pansy A genetically modified rose whose flower color is controlled to blue has also been developed.
  • a genetically modified maize that has enhanced bioethanol production by introducing a thermostable alpha-amylase gene (amy797E) of Thermococcales sp. For starch degradation under the trade name of Enogen (R) Has been developed.
  • cordapA dihydrodipicolinate synthase gene
  • Mavera® Developed under the trade name.
  • Genetically modified melons and genetically modified tomatoes have been developed that have improved shelf life by introducing the S-adenosylmethion hydrolase gene (sam-K) derived from E. coli bacteriophage T3 related to ethylene production of plant hormones .
  • a gene lacking a part of the ACC synthase gene derived from tomato involved in ethylene production of plant hormones an ACC deaminase gene derived from Pseudomonas chlororaphis that degrades ethylene precursor ACC, and pectin on the cell wall Tomato-derived polygalacturonase gene double-stranded RNA or a tomato-derived ACC oxidase gene involved in ethylene production has been introduced to improve genetic shelf tomatoes.
  • a genetically modified tomato improved in shelf life by introducing a gene that generates double-stranded RNA of a polygalacturonase gene derived from tomato has been developed under the trade name FLAVR SAVR (registered trademark).
  • a genetically modified potato having a reduced amylose content by introducing an antisense gene of starch synthase derived from potato has been developed under the trade name of Amflora (registered trademark).
  • Genetically modified rice has been developed that has an immunotolerant effect and a hay fever alleviating effect by introducing a modified cedar pollen antigen protein gene (7crp).
  • a modified cedar pollen antigen protein gene (7crp) By introducing a partial gene (gm-fad2-1) of soybean-derived ⁇ -6 desaturase derived from soybean, which is a fatty acid desaturase, genetically modified soybean that suppresses the gene expression and enhances the oleic acid content is known as Plenish ( (Registered trademark) or Treus (registered trademark).
  • a gene that produces double-stranded RNA of soybean-derived acyl-acyl carrier protein thioesterase gene (fatb1-A) and a double-stranded RNA of soybean-derived ⁇ -12 desaturase gene (fad2-1A) Genetically modified soybeans having a reduced saturated fatty acid content by introducing a gene to be produced have been developed under the trade name of Visual Gold (registered trademark).
  • a genetically modified soybean in which the content of ⁇ 3 fatty acid is enhanced by introducing a ⁇ -6 desaturase gene (Pj.D6D) derived from primrose and a ⁇ -12 desaturase gene (Nc.Fad3) derived from red bread fungus has been developed. Yes.
  • a genetically modified tobacco having a reduced nicotine content by introducing an antisense gene of tobacco-derived quinolinate phosphoribosyltransferase gene has been developed.
  • a phytoene synthase gene (psy) derived from Narcissus pseudonarcissus and a carotene desaturase gene (crt1) derived from a soil bacterium that synthesizes carotenoids (Erwinia uredovora) is introduced into ⁇ -endosperm tissue and expressed in the endosperm tissue.
  • psy phytoene synthase gene
  • crt1 carotene desaturase gene
  • -Golden rice a genetically modified rice that can produce carotene and harvest rice containing vitamin A, has also been developed.
  • Plants whose fertility traits and the like have been modified by gene recombination techniques include genetically modified plants in which the plants are given male sterility and fertility recovery traits.
  • genetically modified maize and genetically modified chicory imparted with male sterility by expressing a ribonuclease gene (barnase) derived from Bacillus amyloliquefaciens in cocoon tapetum cells.
  • barnase ribonuclease gene
  • ms45 alpha-amylase gene
  • ms45 ms45 protein gene
  • a gene set in which fertility traits are controlled by expressing a ribonuclease gene (barnase) derived from Bacillus that gives male sterile traits and a ribonuclease inhibitor protein gene (barstar) derived from Bacillus that gives fertility recovery traits There is also a replacement canola.
  • Examples of plants that have been imparted with environmental stress tolerance by genetic recombination technology include genetically modified plants with drought tolerance.
  • a drought-tolerant corn introduced with a cold shock protein gene (cspB) derived from Bacillus subtilis has been developed under the trade name of Genuity (registered trademark) DraughtGard (registered trademark).
  • cspB cold shock protein gene
  • DraughtGard registered trademark
  • a drought-resistant sugarcane into which a choline dehydrogenase gene (RmBetA) derived from alfalfa rhizobia (Rhizobium meliloti) or Escherichia coli has been developed.
  • Examples of plants whose growth and yield traits have been modified by genetic engineering techniques include genetically modified plants with enhanced growth ability.
  • the plant in the present invention may be a plant modified using a technique other than the genetic recombination technique. More specifically, it may be a plant imparted with environmental stress resistance, disease resistance, herbicide resistance, pest resistance, etc. by classical breeding technology, genetic marker breeding technology, genome editing technology, or the like.
  • Examples of plants to which herbicide tolerance has been imparted by classical or genetic marker breeding techniques include corn, rice, wheat, sunflower (Helianthus annuus), canola, which are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapill, Lentils (Lens culinaris) and the like are sold under the trade name of Clearfield (registered trademark).
  • Clearfield registered trademark
  • SR corn which is cetoxydim-resistant maize, is an example of a plant to which tolerance is imparted to acetyl CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical or genetic marker breeding techniques. is there.
  • An example of a plant to which pest resistance is imparted by classical or genetic marker breeding techniques is soybean having a Rag1 (Resistance Aphid Gene 1) gene that is an aphid resistance gene.
  • soybean having a Rag1 (Resistance Aphid Gene 1) gene that is an aphid resistance gene.
  • a plant imparted with nematode tolerance by a classical breeding method soybean imparted with resistance to cyst nematode, cotton imparted with resistance to root knot nematode, and the like can be mentioned.
  • As a plant to which disease resistance has been imparted by classical or genetic marker breeding techniques resistance to corn and gray leaf spot that have been imparted resistance to anthracnose disease is given.
  • Resistant corn resistant to Goss's wilt, resistant to Fusarium stalk rot, resistant to Asian soybean rust Soybeans, Peptotolerant to Phytophathora, Lettuce tolerant to powdery mildew, Tomato tolerant to Bacterial wilt And tomatoes with resistance to geminivirus, lettuce with resistance against downy mildew, and the like.
  • drought-tolerant maize has been developed under the trade names of Agurisure Artesian (registered trademark) and Optimum AQUAmax (registered trademark).
  • a sulfonylurea herbicide is introduced by a rapid variety development technology that introduces a sulfonylurea herbicide resistance mutation into an ALS gene via a DNA and RNA chimeric oligonucleotide.
  • a canola imparted with resistance has been developed under the trade name SU Canola®.
  • genetically modified soybeans such as Intatta (registered trademark) Roundup Ready (registered trademark) 2 Pro have been developed.
  • Intatta registered trademark
  • Roundup Ready registered trademark 2 Pro
  • products such as Widestrike (registered trademark) Cotton, Twinlink (registered trademark) Cotton, Fibermax (registered trademark) LibertyLink (registered trademark) Bollgard II (registered trademark) Named genetically modified cotton has been developed.
  • Agriure (registered trademark) CB / LL Agriure (registered trademark) CB / LL / RW, Agriure (registered trademark) Viptera (registered trademark) 2100, Agriure (registered trademark) Viptera (registered trademark) 3100, Bt Xtra (registered trademark).
  • a genetically modified plant provided with disease resistance and pest resistance.
  • a genetically modified plant imparted with resistance to potato virus Y (Potato virus Y) and pest resistance Hi-Lite NewLeaf (registered trademark) Y Potato, NewLeaf (registered trademark) Y Russet Burbank Potato, SheepodyNe (Trademark) Y Potato, or a genetically modified plant imparted with resistance to potato leaf roll virus and pest resistance, and a gene group with a trade name such as NewLeaf (registered trademark) Plus Russset Burbank Potato Replacement potatoes have been developed.
  • An example of a line provided with two or more of the above-mentioned plural traits is a genetically modified plant provided with herbicide resistance and modified product quality.
  • genetically modified canola and genetically modified maize imparted with glufosinate resistance and fertile traits have been developed under the trade names of InVigor (registered trademark) Canola and InVigor (registered trademark) Maize.
  • An example of a line provided with two or more of the above-mentioned plural traits is a genetically modified plant imparted with pest resistance and modified product quality.
  • genetically modified maize imparted with traits that enhance resistance to lepidopterous pests and lysine production has been developed under the trade name of Mavera (registered trademark) Yieldgard (registered trademark) Maize.
  • a genetically modified plant provided with herbicide tolerance and a modified fertility trait a gene provided with herbicide tolerance and environmental stress tolerance Recombinant plants, genetically modified plants with herbicide resistance and modified growth and yield traits, genetically modified plants with herbicide resistance, pest resistance, and modified product quality, herbicides Genetically modified plants imparted with resistance, pest resistance, and environmental stress resistance have been developed.
  • Production Example 1 (1) 1.28 g of 4-chloro-6-methoxypyrimidine, 1.48 g of [2-fluoro-4- (trifluoromethyl) phenyl] boronic acid pinacol ester, 0.28 g of tetrakis (triphenylphosphine) palladium (0), sodium carbonate A mixture of 6.3 mL of aqueous solution (2M) and 15 mL of DME was stirred at 80 degrees for 3 hours. After completion of the reaction, water was added to the reaction mixture allowed to cool to room temperature, extracted with ethyl acetate, and then the organic layer was dried over anhydrous sodium sulfate.
  • the present pyrimidinone compound 8 and by-product 8 represented by the following formula were obtained.
  • Production Example 13 (1) To a mixture of 10 g of 3,6-dichloropyridine-2-carboxylic acid and 52 mL of toluene, 9.8 mL of thionyl chloride was added at room temperature. The reaction mixture was heated and stirred at 110 ° C. for 4 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to give an oily substance.
  • Production Example 13 (2) To a mixture of 6.9 g of anhydrous magnesium chloride and 104 mL of THF, 11 g of methyl potassium malonate was added at room temperature. The reaction mixture was stirred at room temperature for 2 hours. To this reaction mixture, the whole amount of the oily substance obtained in Production Example 13 (1) and 14 mL of triethylamine were sequentially added under ice cooling. The reaction mixture was warmed to room temperature and stirred at room temperature for 12 hours. 300 mL of 2N hydrochloric acid was added to the obtained reaction mixture under ice cooling, and the mixture was stirred at room temperature for 3 hours. The resulting reaction mixture was extracted with ethyl acetate.
  • Production Example 19 (2) A mixture of 2.36 g of intermediate (19-1), 0.72 g of urea, 4.1 g of sodium ethoxide (20% ethanol solution) and 10 mL of ethanol was stirred with heating under reflux for 2 hours. The reaction mixture allowed to cool to room temperature was concentrated under reduced pressure, water and concentrated hydrochloric acid were added, the mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate. After the organic layer was concentrated under reduced pressure, the resulting residue was subjected to silica gel column chromatography to obtain 2.52 g of compound A.
  • the pyrimidinone compound 22 represented by the following formula was obtained according to the above method.
  • Production Example 26 The method described in Production Example 12 (7) using 1,1,1,2,2,3,3-heptafluoro-5-iodopentane instead of 1,1,3-trichloro-1-propene In this manner, the present pyrimidinone compound 32 represented by the following formula was obtained.
  • Production Example 29 (2) To a mixture of 22 g of anhydrous magnesium chloride and 270 mL of THF, 32 g of methyl potassium malonate was added at room temperature. The reaction mixture was stirred at 50 ° C. for 1 hour. To this reaction mixture, the whole amount of the oily substance obtained in Production Example 28 (1) and 65 mL of triethylamine were sequentially added under ice cooling. The reaction mixture was warmed to room temperature and stirred at room temperature for 12 hours. 400 mL of 2N hydrochloric acid was added to the obtained reaction mixture under ice cooling, and the mixture was stirred at room temperature for 2 hours. The resulting reaction mixture was extracted with ethyl acetate.
  • compositions of the composition of the present invention will be described below.
  • the composition which has the combination as described in [Table A] is attached
  • the composition of No. 1 in [Table A] is referred to as the present composition 1.
  • * described in the column of component 1 represents any one of the pyrimidinone compounds 1 to 57, and the numbers described in [] in the column of each component are the numbers in the present invention.
  • the amount (part) of each component relative to 100 parts of the composition is meant.
  • “ ⁇ 2” represents the bactericidal compound ⁇ 2.
  • compositions 841-1680 In each of Compositions 1 to 840 described in [Table A], a composition using 2 parts of tebuconazole instead of 2 parts of metconazole.
  • composition 2521-3360 In each of Compositions 1 to 840 described in [Table A], a composition using 2 parts of triticonazole instead of 2 parts of metconazole.
  • composition 3361-4200 A composition using 2 parts of prothioconazole instead of 2 parts of metconazole in each of the present compositions 1 to 840 described in [Table A].
  • composition 4201-5040 In each of Compositions 1 to 840 described in [Table A], a composition using 2 parts of diniconazole instead of 2 parts of metconazole.
  • composition 5041-5880 In each of Compositions 1 to 840 described in [Table A], a composition using 2 parts of diniconazole M instead of 2 parts of metconazole.
  • composition 5881-6720 In each of Compositions 1 to 840 described in [Table A], a composition using 2 parts of ipconazole instead of 2 parts of metconazole.
  • compositions 6721-7560 A composition using 2 parts of prochloraz in place of 2 parts of metconazole in each of the present compositions 1 to 840 described in [Table A].
  • composition 7561-8400 A composition using 2 parts of fluquinconazole instead of 2 parts of metconazole in each of the present compositions 1 to 840 described in [Table A].
  • composition 8401-9240 In each of Compositions 1 to 840 described in [Table A], a composition using 2 parts of triazimenol instead of 2 parts of metconazole.
  • compositions A1 to A9240 A composition further comprising 10 parts clothianidin and 10 parts chlorantraniliprol in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions B1 to B9240 A composition further containing 10 parts clothianidin and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions C1 to C9240 A composition comprising 10 parts of clothianidin and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions D1 to D9240 A composition comprising 10 parts of imidacloprid and 10 parts of chlorantraniliprol in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions E1 to E9240 A composition further containing 10 parts imidacloprid and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions F1 to F9240 A composition further comprising 10 parts of imidacloprid and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions G1 to G9240 A composition further comprising 10 parts thiamethoxam and 10 parts chlorantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions further comprising 10 parts thiamethoxam and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions I1 to I9240 A composition further comprising 10 parts thiamethoxam and 10 parts fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions J1 to J9240 A composition further comprising 10 parts thiacloprid and 10 parts chlorantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions K1 to K9240 A composition further comprising 10 parts thiacloprid and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions L1 to L9240 A composition further comprising 10 parts of thiacloprid and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions M1 to M9240 A composition further comprising 10 parts of furpyraziflon and 10 parts of chlorantraniliprol in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • composition N1 to N9240 A composition further comprising 10 parts of flupiradiflon and 10 parts of cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • composition O1-O9240 A composition further comprising 10 parts of furpyradiflon and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions P1 to P9240 A composition further comprising 20 parts of clothianidin in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions Q1 to Q9240 A composition further comprising 10 parts of the insecticidal compound ⁇ and 10 parts of chlorantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions R1 to R9240 A composition comprising 10 parts of the insecticidal compound ⁇ and 10 parts of cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • compositions S1 to S9240 A composition comprising 10 parts of insecticidal compound ⁇ and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)
  • Formulation Example 1 5 parts of one of the pyrimidinone compounds 1 to 57, 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 pulverizing and mixing 10 parts of the pyrimidinone compounds 1 to 57, 10 parts of clothianidin, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate and 75 parts of synthetic hydrous silicon oxide, Get the agent.
  • Formulation Example 3 1 part of the present pyrimidinone compounds 1 to 57, 0.5 part of clothianidin, 1 part of synthetic silicon hydrous 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 After mixing 10 parts of the present pyrimidinone compounds 1 to 57, 2 parts of clothianidin, 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. 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, in place of 10 parts of clothianidin, the same operations as in Formulation Example 2 are carried out except that the present compounds and amounts used in [Table ii] are used to obtain respective formulations.
  • Formulation Examples 212 to 241 In Formulation Example 4, in place of 2 parts of clothianidin, the same operation as in Formulation Example 4 is carried out except that the present compound and the amount used described in [Table iv] are used to obtain each formulation.
  • Formulation Example 242 After mixing 10 parts of this pyrimidinone compound 1-57, 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 procedure as in Formulation Example 242 was performed except that 0.1 part of tebuconazole was used and the present compound and the amount used described in [Table v] were used to obtain each formulation.
  • Formulation Example 281 The present compositions 1-9240, A1 ⁇ , obtained by adding 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water so that the total amount becomes 100 parts.
  • Each flowable preparation is obtained by pulverizing any one of N1 to N9240, O1 to O9240, P1 to P9240, Q1 to Q9240, R1 to R9240, and S1 to S9240 by a wet pulverization method.
  • Formulation Example 282 The present compositions 1 to 9240, A1 to A9240, B1 to B9240, C1 to C3, obtained by adding 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and synthetic silicon hydroxide so that the total amount becomes 100 parts C9240, D1 to D9240, E1 to E9240, F1 to F9240, G1 to G9240, H1 to H9240, I1 to I9240, J1 to J9240, K1 to K9240, L1 to L9240, M1 to M9240, N1 to N9240, O1 to O9240, Each wettable powder is obtained by thoroughly pulverizing and mixing any one of P1 to P9240, Q1 to Q9240, R1 to R9240, and S1 to S9240.
  • Formulation Example 283 Compositions 1 to 9240, A1 to A15 obtained by adding 15 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water so that the total amount becomes 100 parts.
  • Each flowable preparation is obtained by pulverizing any one of N1 to N9240, O1 to O9240, P1 to P9240, Q1 to Q9240, R1 to R9240, and S1 to S9240 by a wet pulverization method.
  • Application example 1 200 kg of any one of the flowable preparations obtained by the method described in Preparation Example 281 or 283 is smeared on 100 kg of dried sorghum seeds using a rotary seed processor (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained. In addition, 180 grams of oxabetalinyl is added to 200 ml of any one of the flowable formulations obtained by the method described in Formulation Example 281 or 283, and each treated seed is obtained by a smearing treatment as described above.
  • Application example 3 Apply 10 ml of any flowable formulation obtained by the method described in Formulation Example 281 or 283 to 10 kg of dried corn seed using a rotary seed processing machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.
  • a genetically modified corn containing a glyphosate resistance gene or a Bt crystal toxin protein gene is used.
  • Each treated seed is obtained by subjecting 10 kg of dried corn seed to 50 g of any one of the wettable powders obtained by the method described in Formulation Example 282.
  • Application example 8 100 kg of any one of the flowable preparations obtained by the method described in Formulation Example 281 or 283 is smeared on 10 kg of dried soybean seeds using a rotary seed processor (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.
  • Application Example 10 Apply 50 ml of any flowable formulation obtained by the method described in Formulation Example 281 or 283 to 10 kg of dried oilseed rape using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). Each treated seed is obtained by treatment.
  • oilseed rape a genetically modified oilseed rape including a glyphosate resistance gene or a Bt crystal toxin protein gene is used.
  • Application Example 11 Apply 10 ml of any flowable formulation obtained by the method described in Formulation Example 281 or 283 to 10 kg of dried oilseed rape seeds using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH). Each treated seed is obtained by treatment.
  • Application Example 12 Apply 50 ml of any one of the flowable formulations obtained by the method described in Formulation Example 281 or 283 to 10 kg of dry wheat seeds using a rotary seed processor (seed dresser, Hans-Ulrich Hege GmbH). To obtain each treated seed
  • a chemical solution containing the present compound is prepared so that the concentration of the present compound becomes a predetermined concentration.
  • each commercial preparation is mixed with water containing 0.02% by volume of a spreading agent, and a chemical solution containing the present compound so that the concentration of the present compound is a predetermined concentration.
  • a chemical solution containing the present pyrimidinone 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 housed 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.
  • medical solution for a test be an untreated section.
  • the upper part of the microplate is covered with a gas permeable film sheet (trade name: AeroSeal, manufactured by Excel Scientific Inc.), and the number of viable insects in each well is examined 5 days after release.
  • Control value (%) ⁇ 1 ⁇ (Tai) / (Cai) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Cai Number of surviving insects at the time of the survey in the untreated area
  • Tai Number of surviving insects at the time of the survey in the treated area
  • Test example 2 By seeding any one of the treated seeds of corn obtained by the method described in Application Example 3 at a depth of 5 cm using a seeder at an interval of 15 cm, Rhizotonia solani and Pythium spp. ), High control effect can be obtained against Negusare nematode. When seeds treated with a preparation containing an insecticide are used, it is possible to obtain a high control effect against pests having the control effect of the insecticide.
  • Test example 3 By sowing any one of soybean treated seeds obtained by the method described in Application Example 7, high control against Fusarium oxysporum, Rhizoctonia solani, and soybean cyst nematode An effect can be obtained. When seeds treated with a preparation containing an insecticide are used, it is possible to obtain a high control effect against pests having the control effect of the insecticide.
  • Test example 4 By sowing any one of the oilseed rape treated seeds obtained by the method described in Application Example 10, it is possible to obtain a high control effect against Rhizotonia solani and Negusale nematode. When seeds treated with a preparation containing an insecticide are used, it is possible to obtain a high control effect against pests having the control effect of the insecticide.
  • the pest control composition of the present invention can be used to control pests.

Landscapes

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

Abstract

La présente invention concerne une composition antiparasitaire qui comprend un composé représenté par la formule (1) (dans la formule, chaque symbole est tel que défini dans la description), et au moins un composé sélectionné dans le groupe a) ou le groupe b), et qui présente une excellente efficacité antiparasitaire.
PCT/JP2016/084737 2015-11-26 2016-11-24 Composition antiparasitaire et son utilisation Ceased WO2017090654A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015-230328 2015-11-26
JP2015230328 2015-11-26

Publications (1)

Publication Number Publication Date
WO2017090654A1 true WO2017090654A1 (fr) 2017-06-01

Family

ID=58047129

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2016/084737 Ceased WO2017090654A1 (fr) 2015-11-26 2016-11-24 Composition antiparasitaire et son utilisation

Country Status (2)

Country Link
JP (1) JP2017036339A (fr)
WO (1) WO2017090654A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109504638A (zh) * 2018-12-29 2019-03-22 贵州大学 解淀粉芽孢杆菌gual210及其应用
WO2020174096A1 (fr) 2019-02-28 2020-09-03 Syngenta Crop Protection Ag Dérivés hétérocycliques à action pesticide comprenant des substituants contenant du soufre
CN111712497A (zh) * 2017-12-22 2020-09-25 住友化学株式会社 杂环化合物和含有该杂环化合物的有害节肢动物防除剂
JP2021521150A (ja) * 2018-04-13 2021-08-26 バイエル・アクチエンゲゼルシヤフト 殺虫性、殺菌性及び殺ダニ性を有する活性成分組み合わせ

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116426444B (zh) * 2023-06-06 2023-08-15 广东省农业科学院植物保护研究所 一种斜纹夜蛾准霍氏肠杆菌XWc1菌株及其应用
WO2025215578A1 (fr) * 2024-04-10 2025-10-16 Priya Rani Composition pesticide synergique stable

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0543555A (ja) * 1991-08-13 1993-02-23 Nissan Chem Ind Ltd ウラシル誘導体及び有害生物防除剤
JPH06220023A (ja) * 1993-01-22 1994-08-09 Nippon Soda Co Ltd 含窒素複素環誘導体、その製法及び有害生物防除剤
WO2000029387A1 (fr) * 1998-11-12 2000-05-25 Sagami Chemical Research Center Derives de 2- anilino (3h)- pyrimidone, intermediaires dans la production de ces derniers, procede de production de ces derniers et pesticides contenant ces derniers comme ingredient actif
WO2001068613A1 (fr) * 2000-03-17 2001-09-20 Nissan Chemical Industries, Ltd. Dérivés pyrimidinone et herbicides
WO2010093595A1 (fr) * 2009-02-10 2010-08-19 E. I. Du Pont De Nemours And Company 2‑pyridones fongicides
JP2014065675A (ja) * 2012-09-25 2014-04-17 Sumitomo Chemical Co Ltd 有害生物防除組成物およびその用途
JP2014111558A (ja) * 2013-05-15 2014-06-19 Sumitomo Chemical Co Ltd 有害生物防除組成物およびその用途
WO2014125651A1 (fr) * 2013-02-13 2014-08-21 Sumitomo Chemical Company, Limited Composition de lutte contre les organismes nuisibles et utilisation de celle-ci
WO2016052247A1 (fr) * 2014-10-03 2016-04-07 住友化学株式会社 Composé pyrimidinone

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0543555A (ja) * 1991-08-13 1993-02-23 Nissan Chem Ind Ltd ウラシル誘導体及び有害生物防除剤
JPH06220023A (ja) * 1993-01-22 1994-08-09 Nippon Soda Co Ltd 含窒素複素環誘導体、その製法及び有害生物防除剤
WO2000029387A1 (fr) * 1998-11-12 2000-05-25 Sagami Chemical Research Center Derives de 2- anilino (3h)- pyrimidone, intermediaires dans la production de ces derniers, procede de production de ces derniers et pesticides contenant ces derniers comme ingredient actif
WO2001068613A1 (fr) * 2000-03-17 2001-09-20 Nissan Chemical Industries, Ltd. Dérivés pyrimidinone et herbicides
WO2010093595A1 (fr) * 2009-02-10 2010-08-19 E. I. Du Pont De Nemours And Company 2‑pyridones fongicides
JP2014065675A (ja) * 2012-09-25 2014-04-17 Sumitomo Chemical Co Ltd 有害生物防除組成物およびその用途
WO2014125651A1 (fr) * 2013-02-13 2014-08-21 Sumitomo Chemical Company, Limited Composition de lutte contre les organismes nuisibles et utilisation de celle-ci
JP2014111558A (ja) * 2013-05-15 2014-06-19 Sumitomo Chemical Co Ltd 有害生物防除組成物およびその用途
WO2016052247A1 (fr) * 2014-10-03 2016-04-07 住友化学株式会社 Composé pyrimidinone

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111712497A (zh) * 2017-12-22 2020-09-25 住友化学株式会社 杂环化合物和含有该杂环化合物的有害节肢动物防除剂
CN111712497B (zh) * 2017-12-22 2022-10-18 住友化学株式会社 杂环化合物和含有该杂环化合物的有害节肢动物防除剂
JP2021521150A (ja) * 2018-04-13 2021-08-26 バイエル・アクチエンゲゼルシヤフト 殺虫性、殺菌性及び殺ダニ性を有する活性成分組み合わせ
JP2023154066A (ja) * 2018-04-13 2023-10-18 バイエル・アクチエンゲゼルシヤフト 殺虫性、殺菌性及び殺ダニ性を有する活性成分組み合わせ
JP7437318B2 (ja) 2018-04-13 2024-02-22 バイエル・アクチエンゲゼルシヤフト 殺虫性、殺菌性及び殺ダニ性を有する活性成分組み合わせ
JP7636484B2 (ja) 2018-04-13 2025-02-26 バイエル・アクチエンゲゼルシヤフト 殺虫性、殺菌性及び殺ダニ性を有する活性成分組み合わせ
CN109504638A (zh) * 2018-12-29 2019-03-22 贵州大学 解淀粉芽孢杆菌gual210及其应用
CN109504638B (zh) * 2018-12-29 2022-07-05 贵州大学 贝莱斯芽胞杆菌gual210及其应用
WO2020174096A1 (fr) 2019-02-28 2020-09-03 Syngenta Crop Protection Ag Dérivés hétérocycliques à action pesticide comprenant des substituants contenant du soufre

Also Published As

Publication number Publication date
JP2017036339A (ja) 2017-02-16

Similar Documents

Publication Publication Date Title
US11905271B2 (en) Pyrazine compound
KR102443010B1 (ko) 복소환 화합물 및 그것을 함유하는 유해 절족 동물 방제제
WO2017090654A1 (fr) Composition antiparasitaire et son utilisation
WO2017090655A1 (fr) Composition antiparasitaire et son utilisation
JP7644005B2 (ja) アクリル酸エステル誘導体、その用途及びその製造中間体
WO2017073733A1 (fr) Composition antiparasitaire et son utilisation
JP7675024B2 (ja) フェニル酢酸誘導体、その用途及びその製造中間体
EP4299557A1 (fr) Dérivé d'acide phénylacétique, utilisation associée et intermédiaire de production associé
JP7787870B2 (ja) フェニル酢酸誘導体、その用途及びその製造中間体
JP2016222720A (ja) 有害生物防除組成物およびその用途
JP2017039751A (ja) 有害生物防除組成物およびその用途
CN116997542A (zh) 苯基乙酸衍生物、其用途及其制造中间体
WO2022186377A1 (fr) Composé à cycles condensés et son utilisation
JP2017031193A (ja) 有害生物防除組成物およびその用途
JP2018016593A (ja) 有害生物防除組成物及び有害生物防除方法
JP2017043627A (ja) 有害生物防除組成物およびその用途

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16868597

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16868597

Country of ref document: EP

Kind code of ref document: A1