WO2022186377A1 - Fused ring compound and use thereof - Google Patents

Fused ring compound and use thereof Download PDF

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Publication number
WO2022186377A1
WO2022186377A1 PCT/JP2022/009401 JP2022009401W WO2022186377A1 WO 2022186377 A1 WO2022186377 A1 WO 2022186377A1 JP 2022009401 W JP2022009401 W JP 2022009401W WO 2022186377 A1 WO2022186377 A1 WO 2022186377A1
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group
compound
aromatic heterocyclic
substituted
substituents selected
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PCT/JP2022/009401
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French (fr)
Japanese (ja)
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吉彦 野倉
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住友化学株式会社
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Publication of WO2022186377A1 publication Critical patent/WO2022186377A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01C—PLANTING; SOWING; FERTILISING
    • A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
    • A01C1/08—Immunising seed
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G13/00—Protecting plants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01M—CATCHING, TRAPPING OR SCARING OF ANIMALS; APPARATUS FOR THE DESTRUCTION OF NOXIOUS ANIMALS OR NOXIOUS PLANTS
    • A01M1/00—Stationary means for catching or killing insects
    • A01M1/20—Poisoning, narcotising, or burning insects
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01M—CATCHING, TRAPPING OR SCARING OF ANIMALS; APPARATUS FOR THE DESTRUCTION OF NOXIOUS ANIMALS OR NOXIOUS PLANTS
    • A01M21/00—Apparatus for the destruction of unwanted vegetation, e.g. weeds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01M—CATCHING, TRAPPING OR SCARING OF ANIMALS; APPARATUS FOR THE DESTRUCTION OF NOXIOUS ANIMALS OR NOXIOUS PLANTS
    • A01M29/00—Scaring or repelling devices, e.g. bird-scaring apparatus
    • A01M29/12—Scaring or repelling devices, e.g. bird-scaring apparatus using odoriferous substances, e.g. aromas, pheromones or chemical agents
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/12—Asteraceae or Compositae [Aster or Sunflower family], e.g. daisy, pyrethrum, artichoke, lettuce, sunflower, wormwood or tarragon
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/02—Acaricides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom

Definitions

  • Patent Document 1 describes a condensed ring compound.
  • the purpose of the present invention is to provide a compound that has excellent control efficacy against pests.
  • Group A C1-C6 alkoxy group, C1-C6 alkylthio group ⁇ the C1-C6 alkoxy group and the C1-C6 alkylthio group may be substituted with one or more substituents selected from group F ⁇ , C3 -C10 alicyclic hydrocarbon group, 3-10 membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10 membered aromatic heterocyclic group ⁇ the C3-C10 alicyclic hydrocarbon group, the 3-
  • the 10-membered non-aromatic heterocyclic group, the C6-C10 aryl group, and the 5-10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group D ⁇ , cyano group , a nitro group, a hydroxy group, a halogen atom, an oxo group, and a thioxo group.
  • Group B an oxo group, a thioxo group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group ⁇ the C1-C6 chain hydrocarbon group and the C1-C6 alkoxy group are substituted with one or more halogen atoms; optionally], a halogen atom, and a cyano group.
  • Group C a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylthio group ⁇ the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, and the C1-C6 alkylthio group are optionally substituted with one or more substituents selected from group F ⁇ , optionally substituted with one or more substituents selected from group B C3-C6 cycloalkyl group, cyano group, nitro group, halogen A group consisting of an atom and a hydroxy group.
  • Group D C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylthio group, C2-C6 alkoxycarbonyl group, ⁇ said C1-C6 chain hydrocarbon group, said C1-C6 alkoxy group, said C1-C6 alkylthio group and said C2-C6 alkoxycarbonyl group optionally substituted with one or more substituents selected from group G ⁇ , C3-C10 alicyclic hydrocarbon group, 3-10 membered non- aromatic heterocyclic group ⁇ the C3-C10 alicyclic hydrocarbon group and the 3-10-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B ⁇ , C6 -C10 aryl group, 5-10 membered aromatic heterocyclic group ⁇ the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C good ⁇ , the group consisting
  • L3 represents an oxygen atom or S ( O) m , m represents 0, 1, or 2;
  • R 24 is a C6-C10 aryl group or a 5-10 membered aromatic heterocyclic group ⁇ the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group are one or more substituents selected from Group C; may be substituted ⁇ .
  • Group F from a C1-C6 alkoxy group, a C3-C6 cycloalkyl group ⁇ the C1-C6 alkoxy group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms ⁇ , and a halogen atom the group.
  • Group G C1-C6 alkoxy group, C3-C6 cycloalkyl group ⁇ the C1-C6 alkoxy group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms ⁇ , C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group ⁇ the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C ⁇ , and a group consisting of halogen atoms.
  • the compound represented by (hereinafter referred to as the compound N of the present invention), or its N oxide or a salt thereof (hereinafter, the compound represented by formula (I), or its N oxide or a salt thereof is referred to as the compound of the present invention ).
  • J is a group represented by J1
  • E is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, one or more substituents selected from group D a C6-C10 aryl group optionally substituted with a group, a 5-10 membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group D, or C(O)OR 25 , the compound according to any one of [1] to [3], its N oxide, or a salt thereof.
  • J is a group represented by J2
  • a halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • a substituent is substituted with two or more halogen atoms, each of those halogen atoms may be the same or different.
  • substituent is substituted with two or more groups or atoms selected from a specific group (for example, the group consisting of C1-C3 alkyl groups and halogen atoms), each of these groups or atoms may be the same or different.
  • alkyl groups include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, and hexyl groups.
  • alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 3- butenyl, 4-pentenyl, and 5-hexenyl groups.
  • alkynyl groups examples include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 4-pentynyl, and A 5-hexynyl group can be mentioned.
  • Alkoxy groups include, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy groups.
  • Alkylthio groups include, for example, methylthio, ethylthio, isopropylthio, and hexylthio groups.
  • Alkoxycarbonyl groups include, for example, methoxycarbonyl, isopropoxycarbonyl, and hexyloxycarbonyl groups.
  • Alicyclic hydrocarbon groups include, for example, cycloalkyl groups and cycloalkenyl groups.
  • Cycloalkyl groups include, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, bicyclo[6.5.0]nonyl, and bicyclo[6.6.0]decyl groups.
  • Cycloalkenyl groups include, for example, cyclopentenyl and cyclohexenyl groups.
  • the cycloalkenyl group may be condensed with a benzene ring, and examples thereof include an indanyl group and a tetrahydronaphthyl group.
  • Aryl groups include, for example, phenyl and naphthyl groups.
  • aromatic heterocyclic groups include pyrrolyl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl and thiadiazolyl groups.
  • 6-membered aromatic heterocyclic groups such as pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group and tetrazinyl group; 9-membered aromatic heterocyclic groups such as indazolyl group, indolizinyl group and imidazopyridyl group; Cyclic groups; 10-membered aromatic heterocyclic groups such as quinolyl, isoquinolyl, quinazolinyl, naphthyridinyl, and benzopyranyl groups.
  • Non-aromatic heterocyclic groups include, for example, aziridinyl, oxiranyl, thiiranyl, azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothienyl, pyrazolinyl, pyrazolidinyl, imidazolinyl and imidazolidinyl.
  • soybean rust fungus having an F129L amino acid substitution in the mitochondrial cytochrome b protein has a mutation in the mitochondrial cytochrome b gene that encodes the mitochondrial cytochrome protein, and as a result of the mutation, the F129L amino acid substitution occurred, resulting in QoI It is a fungicide-resistant soybean rust fungus (scientific name: Phakopsora pachyrhizi).
  • Stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • the present invention includes each stereoisomer and mixtures of stereoisomers in any proportion.
  • Geometric isomers include, for example, the following structures.
  • Compound N of the present invention or its N oxide can be mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid and benzoic acid to obtain hydrochloride, sulfate, nitrate, phosphate, acetate and benzoate. may form an acid addition salt such as
  • Embodiments of the compound N of the present invention include the following compounds.
  • R 1 , R 2 and R 3 are the same or different, a C1-C6 alkyl group, a C3-C6 cycloalkyl group ⁇ the C1-C6 alkyl group and the C3-C6 A cycloalkyl group may be substituted with one or more halogen atoms ⁇ , a cyano group, a nitro group, a halogen atom, or a hydrogen atom.
  • R 1 , R 2 and R 3 are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a halogen atom or a hydrogen atom
  • a compound that is [Aspect 7] A compound N in which R 1 , R 2 and R 3 are the same or different and are a methyl group, a halogen atom or a hydrogen atom in the compound N of the present invention.
  • J is a group represented by J1.
  • J is a group represented by J2.
  • X 3 is CR 4 or a nitrogen atom
  • X 4 is CR 5
  • X 5 is CR 6 or a nitrogen atom
  • X 3 is CR 4
  • X 4 is CR 5
  • X 5 is CR 6
  • a compound N of the present invention wherein J is a group represented by J2, X 5 is CR 6 and X 6 is *--C(R 8 ) C(R 9 )--.
  • E is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A. .
  • Aspect 17 The compound in any one of Aspects 1 to 15 and the compound N of the present invention, wherein E is a C1-C6 chain hydrocarbon group.
  • E is a C3-C10 alicyclic hydrocarbon group optionally substituted with one or more substituents selected from Group D. Compound.
  • Aspect 19 The compound in any one of Aspects 1 to 15 and the compound N of the present invention, wherein E is a C3-C10 alicyclic hydrocarbon group.
  • Aspect 20 A compound in which E is a C6-C10 aryl group optionally substituted with one or more substituents selected from Group D in any one of Aspects 1 to 15 and Compound N of the present invention.
  • E is a 5- to 10-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group D.
  • J is a group represented by J1
  • E is C(O)OR 25 , C(O)R 26 or C(O)NR 27 R 28 .
  • Aspect 26 A compound in which J is a group represented by J2 and E is CH 2 -L 1 -R 12 in any one of Aspects 1 to 7, Aspect 14, Aspect 15 and Compound N of the present invention.
  • Aspect 29 In any one of Aspects 1 to 7, Aspect 14, Aspect 15, and Compound N of the present invention, J is a group represented by J2, E is L 2 R 23 , and L 2 is an oxygen atom. some compound.
  • the combination of J and E is C1-C6, wherein J is a group represented by J1, and E is optionally substituted with one or more substituents selected from Group A.
  • C6-C10 aryl group optionally substituted with one or more substituents selected from group D, C(O)OR 25 , C(O)R 26 , or C(O)NR 27 or
  • J is a group represented by J2
  • E is a C1- C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, or Group D
  • the combination of J and E is such that J is a group represented by J1, and E is a C1-C6 chain hydrocarbon group, a C6-C10 aryl group, or C(O) or a combination that is OR 25 ; or J is a group represented by J2, and E is a C1-C6 chain hydrocarbon group, or optionally substituted with one or more substituents selected from group D 5- A compound that is a combination of 10-membered aromatic heterocyclic groups.
  • the combination of J and E is C1-C6, wherein J is a group represented by J1, and E is optionally substituted with one or more substituents selected from Group A.
  • the compound represented by formula (A1) (hereinafter referred to as compound (A1)) is a compound represented by formula (B1) (hereinafter referred to as compound (B1)) and the compound represented by formula (M1) (hereinafter referred to as It can be produced by reacting a compound (M1)) in the presence of a base.
  • E 1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C10 alicyclic hydrocarbon group, a 3- to 10-membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10 membered aromatic heterocyclic group ⁇ said C3-C10 alicyclic hydrocarbon group, said 3-10 membered non-aromatic heterocyclic group, said C6-C10 aryl group and
  • the 5- to 10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group D ⁇
  • X 51 is a chlorine atom, a bromine atom, an iodine atom, or a triflyloxy group and other symbols have the same meanings as above.
  • the reaction is usually carried out in a solvent.
  • Solvents used in the reaction include, for example, hydrocarbons such as hexane, toluene, and xylene (hereinafter referred to as hydrocarbons); methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), Ethers such as dimethoxyethane (hereinafter referred to as ethers); Halogenated hydrocarbons such as chloroform and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); Dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone and the like amides (hereinafter referred to as amides); esters such as methyl acetate and ethyl acetate (hereinafter referred to as esters); nitriles such as acetonitrile and propionitrile (hereinafter referred to as
  • bases examples include organic bases such as triethylamine and pyridine (hereinafter referred to as organic bases); alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); sodium hydrogen carbonate and hydrogen carbonate. alkali metal hydrogen carbonates such as potassium (hereinafter referred to as alkali metal hydrogen carbonates); sodium hydride and tripotassium phosphate.
  • organic bases such as triethylamine and pyridine
  • alkali metal carbonates such as sodium carbonate and potassium carbonate
  • sodium hydrogen carbonate and hydrogen carbonate alkali metal hydrogen carbonates
  • alkali metal hydrogen carbonates such as potassium (hereinafter referred to as alkali metal hydrogen carbonates); sodium hydride and tripotassium phosphate.
  • a metal catalyst and/or a ligand may be used for the reaction, if necessary.
  • Metal catalysts include copper (I) iodide, copper (I) bromide, copper (I) chloride, copper (I) oxide, copper (I) trifluoromethanesulfonate benzene complex, tetrakis(acetonitrile) copper (I) copper catalysts such as hexafluorophosphate and copper (I) 2-thiophenecarboxylate; and nickel catalysts such as bis(cyclooctadiene)nickel (0) and nickel chloride (II).
  • the metal catalyst is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B1).
  • ligands include triphenylphosphine, xantphos, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,1′-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphos Phino-2′,4′,6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2′-bipyridine, 2 -aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, N,N'-dimethylethylenediamine, and N , N-dimethylglycine hydrochloride.
  • the ligand When a ligand is used in the reaction, the ligand is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B1).
  • the compound (M1) In the reaction, the compound (M1) is generally used in an amount of 1 to 10 mol, and the base is generally used in an amount of 1 to 10 mol, per 1 mol of the compound (B1).
  • the reaction temperature is usually in the range of 0-150°C.
  • the reaction time is usually in the range of 0.1 to 48 hours.
  • compound (A1) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
  • Compound (B1) and compound (M1) are known or can be produced according to known methods.
  • the compound represented by formula (A2) (hereinafter referred to as compound (A2)) is obtained by reacting compound (B1) and a compound represented by formula (M2) (hereinafter referred to as compound (M2)) in the presence of a base. It can be produced by reacting with [In the formula, E 2 represents C(O)OR 25 , C(O)R 26 , or C(O)NR 27 R 28 , and other symbols have the same meanings as above. ]
  • the reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
  • Bases include, for example, organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
  • the compound (M2) is usually used in an amount of 1 to 10 mol, and the base is usually used in an amount of 1 to 10 mol, per 1 mol of the compound (B1).
  • the reaction temperature is usually in the range of -50 to 100°C.
  • the reaction time is usually in the range of 0.1 to 48 hours.
  • compound (A2) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
  • Compound (M2) is known or can be produced according to known methods.
  • the compound represented by formula (A3) (hereinafter referred to as compound (A3)) is obtained by reacting the compound represented by formula (B2) (hereinafter referred to as compound (B2)) and compound (M1) with a palladium catalyst and a base. It can be produced by reacting in the presence.
  • M 1 represents B(OH) 2 or 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, and other symbols have the same meanings as above.
  • the reaction is usually carried out in a solvent.
  • Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water, and mixtures of two or more thereof.
  • Palladium catalysts used in the reaction include, for example, palladium(II) acetate and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.
  • bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium fluoride and tripotassium phosphate.
  • the compound (M1) is usually used in an amount of 0.5 to 2 mol
  • the palladium catalyst is usually used in an amount of 0.01 to 1 mol
  • the base is usually used in an amount of 1 to 10 mol, relative to 1 mol of the compound (B2). Used in proportion.
  • the reaction temperature is usually in the range of 0-150°C.
  • the reaction time is usually in the range of 0.1 to 120 hours.
  • the compound (A3) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
  • Compound (A3) is prepared by reacting a compound represented by formula (B3) (hereinafter referred to as compound (B3)) and a compound represented by formula (M3) (hereinafter referred to as compound (M3)) with a palladium catalyst and a base. It can also be produced by reacting in the presence. [In the formula, the symbols have the same meanings as described above. ] The reaction can be carried out according to production method C using compound (M3) instead of compound (B2) and compound (B3) instead of compound (M1). Compound (M3) is known or can be produced according to known methods.
  • the compound represented by formula (A4) (hereinafter referred to as compound (A4)) is a compound represented by formula (B4) (hereinafter referred to as compound (B4)) and the compound represented by formula (M4) (hereinafter referred to as , compound (M4)) or a salt thereof.
  • R 51 is a C1-C6 chain hydrocarbon group, a C3-C10 alicyclic hydrocarbon group ⁇ the C1-C6 chain hydrocarbon group and the C3-C10 alicyclic hydrocarbon group are 1 or more; or a hydrogen atom
  • R 52 represents OR 15 , N ⁇ CR 17 R 18 or NR 20 R 21 , and other symbols have the same meanings as above.
  • Salts of compound (M4) include, for example, hydrochloride and sulfate.
  • the reaction is usually carried out in a solvent.
  • Solvents used in the reaction include, for example, hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; alcohols such as methanol and ethanol (hereinafter referred to as alcohols); and mixtures of two or more of A base may be used for the reaction, if necessary.
  • bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
  • the base When a base is used in the reaction, the base is generally used in a proportion of 1 to 10 mol per 1 mol of compound (B4).
  • compound (M4) In the reaction, compound (M4) is generally used in a proportion of 1 to 10 mol per 1 mol of compound (B4).
  • the reaction temperature is usually in the range of 0-150°C.
  • the reaction time is usually in the range of 0.1 to 120 hours.
  • compound (A4) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
  • Compound (M4) is known or can be produced according to known methods.
  • the compound represented by formula (A5) (hereinafter referred to as compound (A5)) is a compound represented by formula (B5) (hereinafter referred to as compound (B5)) and the compound represented by formula (M5) (hereinafter referred to as compound (M5)) in the presence of a base.
  • L 51 represents an oxygen atom or a sulfur atom, and other symbols have the same meanings as above.
  • the reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
  • Bases include, for example, organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
  • the compound (M5) is usually used in an amount of 1 to 10 mol, and the base is usually used in an amount of 1 to 10 mol, per 1 mol of the compound (B5).
  • the reaction temperature is usually in the range of -20 to 150°C.
  • the reaction time is usually in the range of 0.1 to 48 hours.
  • compound (A5) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
  • Compound (M5) is known or can be produced according to known methods.
  • the compound represented by formula (A6) (hereinafter referred to as compound (A6)) is a compound represented by formula (B6) (hereinafter referred to as compound (B6)) and the compound represented by formula (M6) (hereinafter referred to as compound (M6)) in the presence of a base.
  • the symbols have the same meanings as described above.
  • the reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
  • Bases include, for example, organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
  • a metal catalyst and/or a ligand may be used for the reaction, if necessary.
  • Metal catalysts include copper (I) iodide, copper (I) bromide, copper (I) chloride, copper (I) oxide, copper (I) trifluoromethanesulfonate benzene complex, tetrakis(acetonitrile) copper (I) copper catalysts such as hexafluorophosphate and copper (I) 2-thiophenecarboxylate; and nickel catalysts such as bis(cyclooctadiene)nickel (0) and nickel chloride (II).
  • the metal catalyst is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B6).
  • ligands triphenylphosphine, xantphos, 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-amino ethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, N,N'
  • the ligand is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B6).
  • the compound (M6) is generally used in an amount of 1 to 10 mol
  • the base is generally used in an amount of 1 to 10 mol, per 1 mol of the compound (B6).
  • the reaction temperature is usually in the range of -20 to 150°C.
  • the reaction time is usually in the range of 0.1 to 48 hours.
  • compound (A6) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
  • Compound (M6) is known or can be produced according to known methods.
  • the compound represented by formula (A7) (hereinafter referred to as compound (A7)) is a compound represented by formula (B7) (hereinafter referred to as compound (B7)) and the compound represented by formula (M7) (hereinafter referred to as a compound (M7)) in the presence of a base to obtain a compound represented by formula (B8) (hereinafter referred to as compound (B8)) (hereinafter referred to as step (H-1)) , and a step of reacting compound (B8) with a compound represented by formula (M8) (hereinafter referred to as compound (M8)) in the presence of a base (hereinafter referred to as step (H-2)).
  • step (H-2) a compound represented by formula (H-2)
  • R 53 represents a C1-C4 alkyl group
  • X 52 represents an iodine atom, a methoxysulfonyloxy group, a mesyloxy group, or a tosyloxy group, and other symbols have the same meanings as above.
  • Step (H-1) is usually carried out in a solvent.
  • Solvents used in the reaction include, for example, ethers, amides, and mixtures of two or more thereof.
  • bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
  • the compound (M7) is generally used in an amount of 1 mol to 10 mol, and the base is generally used in an amount of 0.5 mol to 5 mol, per 1 mol of the compound (B7).
  • the reaction time is usually in the range of 5 minutes to 72 hours.
  • the reaction temperature is usually in the range of -50°C to 100°C.
  • compound (B8) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
  • Compound (M7) is a commercially available compound, or can be produced according to a known method.
  • Step (H-2) is usually carried out in a solvent.
  • Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
  • bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
  • the compound (M8) is generally used in an amount of 1 to 10 mol
  • the base is generally used in an amount of 1 to 20 mol, per 1 mol of the compound (B8).
  • the reaction temperature is usually in the range of -50 to 100°C.
  • the reaction time is usually in the range of 0.1 to 48 hours.
  • compound (A7) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
  • Compound (M8) is a commercially available compound, or can be produced according to a known method.
  • the compound represented by formula (A8) (hereinafter referred to as compound (A8)) is obtained by reacting compound (B7) and compound represented by formula (M9) (hereinafter referred to as compound (M9)) in the presence of a base.
  • step (I-2) [In the formula, R 54 represents a tert-butyl group or an isopentyl group, and other symbols have the same meanings as above. ]
  • Step (I-1) is usually carried out in a solvent.
  • Solvents used in the reaction include, for example, ethers, amides, alcohols, and mixtures of two or more thereof.
  • Bases used in the reaction include, for example, sodium hydride; and alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide.
  • the compound (M9) is generally used in an amount of 1 mol to 10 mol, and the base is generally used in an amount of 1 mol to 5 mol, per 1 mol of the compound (B7).
  • the reaction time is usually in the range of 5 minutes to 72 hours.
  • the reaction temperature is usually in the range of -20°C to 100°C.
  • compound (B9) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
  • Compound (M9) is a commercially available compound.
  • the step (I-2) can be carried out according to the step (H-2) of the manufacturing method H, using the compound (B9) instead of the compound (B8).
  • the compound represented by formula (A10) (hereinafter referred to as compound (A10)) can be produced by reacting the compound represented by formula (A9) (hereinafter referred to as compound (A9)) with methylamine. can be done.
  • the reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, alcohols, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
  • a base may be used in the reaction, if necessary.
  • Bases used in the reaction include, for example, organic bases; alkali metal carbonates; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide (hereinafter referred to as alkali metal hydroxides); and sodium hydride is mentioned.
  • the base is usually used in a proportion of 0.1 to 10 mol per 1 mol of compound (A8).
  • Methylamine is usually used as a solution. Solutions of methylamine include, for example, methanol solutions and aqueous solutions.
  • methylamine is generally used in a proportion of 1 to 100 mol per 1 mol of compound (A9).
  • the reaction temperature is usually in the range of -50 to 50°C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • compound (A10) can be isolated by post-treatment such as mixing the reaction mixture with water, extracting with an organic solvent, drying and concentrating the organic layer.
  • step (K-1) a compound represented by formula (B10)
  • step (K-2) compound represented by formula (M10)
  • step (K-2) compound represented by formula (M10)
  • X 53 represents a chlorine atom, a bromine atom or an iodine atom, and other symbols have the same meanings as above.
  • Step (K-1) can be carried out according to production method J using compound (A8) instead of compound (A9) and hydroxylamine instead of methylamine.
  • Step (K-2) is usually carried out in a solvent.
  • Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water and mixtures of two or more thereof.
  • Bases include, for example, organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
  • the compound (M10) is generally used in an amount of 1 to 10 mol, and the base is generally used in an amount of 1 to 10 mol, per 1 mol of the compound (B10).
  • 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 48 hours.
  • compound (A11) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
  • Compound (M10) is a commercially available compound.
  • the compound represented by formula (A12) is a compound represented by formula (B11) (hereinafter referred to as compound (B11)) and methyl 2-iodo-3-methoxyacrylate.
  • B11 a compound represented by formula (B11)
  • compound (B11) methyl 2-iodo-3-methoxyacrylate
  • the reaction can be carried out according to Production Method C using compound (B11) in place of compound (B2) and methyl 2-iodo-3-methoxyacrylate in place of compound (M1).
  • Compound (B11) and methyl 2-iodo-3-methoxyacrylate can be produced according to known methods.
  • N-oxide of the compound of formula (I) can be prepared by reacting the compound of formula (I) with an oxidizing agent.
  • the reaction can be carried out, for example, according to the method described in US Patent Application Publication No. 2018/0009778 or International Publication No. 2016/121970.
  • Reference manufacturing method a Compound (B1) can be produced by reacting compound (A2) with an acid.
  • the reaction is usually carried out in a solvent.
  • Solvents used in the reaction include, for example, alcohols; hydrocarbons; ethers; halogenated hydrocarbons; amides; Acids used in the reaction include, for example, acetic acid, trifluoroacetic acid, hydrochloric acid, sulfuric acid, and montmorillonite.
  • an acid is usually used in a proportion of 0.1 to 5 mol per 1 mol of compound (A2).
  • the reaction temperature is usually in the range of 0-150°C.
  • the reaction time is usually in the range of 0.1 to 48 hours.
  • the compound (B1) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
  • Reference manufacturing method b The compound represented by formula (B51) (hereinafter referred to as compound (B51)) can be produced by reacting compound (B3) with bis(pinacolato)diboron in the presence of a base and a palladium catalyst. [In the formula, the symbols have the same meanings as described above. ] The reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; Nitriles and mixtures of two or more thereof are included. Examples of bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates and tripotassium phosphate.
  • Palladium catalysts include, for example, [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.
  • bis(pinacolato)diboron is usually used at a ratio of 1 to 5 mol
  • a base is usually used at a ratio of 1 to 5 mol
  • a palladium catalyst is usually used at a ratio of 0.01 to 0.5 mol. used at a rate of
  • the reaction temperature is usually in the range of 0-150°C.
  • the reaction time is usually in the range of 0.1 to 48 hours.
  • compound (B51) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
  • Reference manufacturing method c A compound represented by formula (B52) (hereinafter referred to as compound (B52)) is produced by reacting compound (B3) with a compound represented by formula (M11) (hereinafter referred to as compound (M11)). can do.
  • R 55 represents a methyl group or an ethyl group, and other symbols have the same meanings as above.
  • the reaction can be carried out, for example, according to the method described in WO2016/123253.
  • Compound (M11) is a commercially available compound, or can be produced according to a known method.
  • Reference manufacturing method d Compound (B5) is prepared by reacting compound (B3) with N-formylsaccharin in the presence of a palladium catalyst, a ligand, triethylsilane and a base to obtain a compound represented by formula (B53) (hereinafter referred to as compound (B53) (hereinafter referred to as step (d-1)), a compound represented by formula (B54) by reacting compound (B53) with sodium borohydride (hereinafter referred to as compound (B54) ) (hereinafter referred to as step (d-2)), and a step of reacting compound (B54) with carbon tetrachloride, carbon tetrabromide, or iodine in the presence of triphenylphosphine (hereinafter referred to as It can be produced by the step (d-3)).
  • step (d-1) a compound represented by formula (B53)
  • step (d-2) a compound represented by formula (B54) by
  • step (d-1) Angew. Chem. Int. Ed. , 2013, 52, 8611-8615 and the like.
  • Step (d-2) can be carried out according to the method described in Chemistry-A European Journal, 2019, 25(15), 3950-3956 and the like.
  • step (d-3) J. Org. Synth. , 1974, 54, 63 and the like.
  • a compound represented by formula (B55) (hereinafter referred to as compound (B55)) can be produced by reacting compound (B2) with an oxidizing agent.
  • the reaction is usually carried out in a solvent.
  • Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water and mixtures of two or more thereof.
  • the oxidizing agent used in the reaction includes, for example, meta-chloroperbenzoic acid and hydrogen peroxide solution. When using hydrogen peroxide water as the oxidizing agent, a base may be used as necessary.
  • Bases used in the reaction include alkali metal hydroxides.
  • the base is usually used in a proportion of 0.1 to 5 mol per 1 mol of compound (B2).
  • the oxidizing agent is generally used in a proportion of 1 to 5 mol per 1 mol of compound (B2).
  • the reaction temperature is usually in the range of -20 to 120°C, and the reaction time is usually in the range of 0.1 to 48 hours.
  • water and a reducing agent such as sodium thiosulfate are added to the reaction mixture, the mixture is extracted with an organic solvent, and the organic layer is dried and concentrated to isolate compound (B55). can do.
  • Reference manufacturing method f The compound represented by formula (B56) (hereinafter referred to as compound (B56)) is prepared by reacting the compound represented by formula (B57) (hereinafter referred to as compound (B57)) with bis(pinacolato)diboron as a base and a palladium catalyst. can be produced by reacting in the presence of [In the formula, symbols have the same meanings as described above. ] The reaction can be carried out according to Reference Production Method b using compound (B57) in place of compound (B3). Compound (B57) can be produced according to known methods.
  • the compound of the present invention can be mixed or used in combination with one or more components (hereinafter referred to as the present component) selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) below. can be done.
  • the mixed use or combined use means using the compound of the present invention and this component at the same time, separately or with a time interval.
  • the compound of the present invention and the component of the present invention may be contained in separate formulations or may be contained in one formulation.
  • composition A One aspect of the present invention is one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) (that is, the present component), and the compound of the present invention It is a composition containing (hereinafter referred to as composition A).
  • Group (a) includes acetylcholinesterase inhibitors (e.g. carbamate insecticides, organophosphorus insecticides), GABAergic chloride ion channel blockers (e.g. phenylpyrazole insecticides), sodium channel modulators (e.g. pyrethroid insecticides).
  • acetylcholinesterase inhibitors e.g. carbamate insecticides, organophosphorus insecticides
  • GABAergic chloride ion channel blockers e.g. phenylpyrazole insecticides
  • sodium channel modulators e.g. pyrethroid insecticides.
  • nicotinic acetylcholine receptor competitive modulators e.g., neonicotinoid insecticides
  • nicotinic acetylcholine receptor allosteric modulators glutamatergic chloride channel allosteric modulators (e.g., macrolide insecticides)
  • nereistoxin insecticides chitin synthesis inhibitors, moulting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, inhibitors of mitochondrial electron transport chain complexes I, II, III and IV, voltage dependent from sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal modulators, microbial insecticides, and other insecticidal, acaricidal and nematicidal active ingredients. It is a group of They are described in the IRAC mechanism-based classification.
  • Group (b) includes nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeletal inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides).
  • nucleic acid synthesis inhibitors e.g., phenylamide fungicides, acyl amino acid fungicides
  • cell division and cytoskeletal inhibitors e.g., MBC fungicides
  • respiratory inhibitors e.g., QoI fungicides
  • QiI fungicides amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyridine-based fungicides), signal transduction inhibitors, lipid and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMIs such as triazoles) fungicides), cell wall synthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-site contact active fungicides, microbial fungicides, and other fungicidal active ingredients. They are described in the FRAC mechanism-based classification.
  • Group (c) is a group of plant growth-regulating components (including mycorrhizal fungi and rhizobia).
  • Group (d) is a group of repellent ingredients.
  • alanycarb + SX means the combination of alanycarb and SX.
  • the abbreviation SX means any one compound of the present invention selected from the compound group SX1 to SX90 described in Examples.
  • all of the components described below are known components and can be obtained from commercially available formulations or produced by known methods. If this component is a microorganism, it can also be obtained from a bacteria depository.
  • the numbers in parentheses represent CAS RN (registered trademark).
  • a combination of this component of group (a) above and a compound of the present invention abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acynonapyr + SX, aphidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha endosulfan -endosulfan + SX, aluminum phosphide + SX, amitraz + SX, azadirachtin + SX, azamethiphos + SX, azinphos-ethyl + SX, azinphos- methyl) + SX, azocyclotin + SX, bark of Celastrus angulatus + SX, bendi
  • Kurstaki strain HD-1 + SX Bacillus Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype strain H-14 + SX, Bacillus thuringiensis var.
  • japonensis strain buibui + SX Bacillus thuringien sis var. san diego strain M-7 + SX, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var.
  • SX Beauveria bassiana strain GHA + SX, Beauveria brongniartii + SX, Burkholderia rinojensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dectylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var.
  • pumilus strain AQ717 + SX Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB/BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002/AQ30002 + SX, Bacillus subtilis strain QST30004/AQ30004 + SX, Bacillus subtilis strain QST71
  • the ratio of the compound of the present invention to the component is not particularly limited, but the weight ratio (compound of the present invention:the component) is 1000:1 to 1:1000, 500:1 to 1:500, 100:1. ⁇ 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1 : 1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, etc. .
  • the compound of the present invention has efficacy against pests.
  • pests include phytopathogenic microorganisms, harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks.
  • the compound of the present invention can control plant diseases caused by phytopathogenic microorganisms such as fungi, Oomycete, Phytomyxea, and bacteria.
  • Fungi include, for example, Ascomycota, Basidiomycota, Blasocladiomycota, Chytridiomycota, Mucoromycota and Olpidiomycota. Specifically, the following are mentioned, for example. Parentheses indicate the scientific name of the phytopathogenic microorganism that causes each disease.
  • Rice diseases Pyricularia oryzae, Cochliobolus miyabeanus, Rhizoctonia solani, Gibberella fujikuroi, Sclerophthora macrospora, Sclerophthora macrospora, and Epicoccum nigrum, Trichoderma viride, Rhizopus oryzae, pseudocolonial blight (Waitea circinata, Ceratobasidium setariae, Thanatephorus cucumeris)); Wheat diseases: Powdery mildew (Blumeria graminis), Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale, Yellow rust (Puccinia striiformis), Black rust (Puccinia graminis), Red rust (Puccinia recondita) ), red snow rot (Microdochium nivale, Microdochium majus), snow rot (Typhula
  • Polymyxa betae and Polymyxa graminis Diseases caused by bacteria: Burkholderia plantarii in rice, Pantoea ananatis in rice, Xanthomonas oryzae pv. oryzae in rice, bacterial spot in cucumber (Pseudomonas syringae pv.
  • harmful arthropods examples include the following.
  • Hemiptera Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodes orizicolus, etc.
  • Delphacidae Leafhopper (Nephotettix cincticeps), Leafhopper (Nephotettix virescens), Leafhopper (Nephotettix nigropictus), Leafhopper (Recilia dorsalis), Leafhopper (Empoasca onukii), Potato Leafhopper (Empoasca fabae) , Corn leaf hopper (Dalbulus maidis), White leafhopper (Cofana spectra), Amrasca biguttula biguttula, etc. Cicadellidae; European Spittle Bug (Philaenus spumarius), etc.
  • Aphis fabae Aphis glycines, Aphis gossypii, Aphis pomi, Aphis spiraecola, Green peach aphid ( Myzus persicae), Brachycaudus helichrysi, Brevicoryne brassicae, rosy apple aphid (Dysaphis plantaginea), Lipaphis erysimi, Macrosiphum euphorbiae, potato aphid Aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), wheat neck aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus aphid (Toxoptera citricida), peach aphid (Hyalopterus pruni), hienoaphis (Melanaphis) Aphididae such as sacchari, Tetraneura
  • Cicadidae such as Quesada gigas
  • Reduviidae such as Triatoma infestans, Triatoma rubrofasciata, Triatoma dimidiata, and Rhodonius prolixus.
  • Lepidoptera Chilo suppressalis, Chilo polychrysus, White stem borer (Scirpophaga innotata), Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis, Rice hare moth (Marasmia exigua), cotton moth (Notarcha derogata), corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), high spotted moth (Hellula undalis), monkey crocodile moth (Herpetogramma luctuosale), Shibatutoga (Parapediasia teterrellus) , Rice case worm (Nymphula depunctalis), Sugar cane borer (Diatraea saccharalis), Egg plant fruit borer (Leucinodes orbonalis), etc.; Pyralidae such as Euzophera
  • Heliothis virescens Helicoverpa spp. such as Helicoverpa armigera and Helicoverpa zea, Velvet bean caterpillar (Anticarsia gemmatalis), Cotton leaf worm (Alabama argillacea), Hop wine borer (Hydraecia immanis) and other noctuids (Noctuidae); Pieridae such as Pieris rapae; orana fasciata), Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus, Cydia pomonella, Tetramoera schistaceana, Epinotia aporema , Citrus Fruit Borer (Citripestis sagittiferella), Tortricidae, such as European grape wine moss (Lobesia botrana); Gracillariidae, such as Caloptilia theivora and Phyllonorycter ringoniella; Lyon
  • Thysanoptera Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips , Echinothrips americanus, Scirtothrips perseae, etc.; Phlaeothripidae, such as Haplothrips aculeatus.
  • Anthomyiidae such as Delia platura, Delia antiqua, and Pegomya cunicularia
  • Ulidiidae such as Tetanops myopaeformis Agromyzidae, such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, and Chromatomyia horticola
  • Chloropidae such as Chlorops oryzae
  • Bactrocera cucurbitae Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, Ceratitis capitata, Rhagoletis pomonella, Rjapachla fruit fly ), etc.
  • Drosophilidae such as Drosophila melanogaster
  • Phoridae such as Megaselia spiracularis
  • Psychodidae such as Clogmia albipunctata
  • Culicidae such as Prosimulium yezoensis and Simulium ornatum
  • Tabanidae such as Tabanus trigonus
  • Musca domestica and Muscinasta bulans marbling Muscidae such as Stomoxys calcitrans and Haematobia irritans
  • Calliphoridae Sarcophagidae
  • Chironomus plumosus Chironomus yoshimatsui
  • Glyptotendipes tokunagai of Chironomidae Chironomidae
  • Diabrotica spp. e.g. Western Corn Rootworm (Diabrotica virgifera virgifera), Southern Corn Rootworm (Diabrotica undecimpunctata howardi), Northern Corn Rootworm (Diabrotica barberi), Mexican Corn Rootworm (Diabrotica virgifera zeae)), banded cucumber beetle (Diabrotica balteata), cucumber beetle (Diabrotica speciosa) and other bean leaf beetles (Cerotoma trifurcata), neck beetle (Oulema melanopus), cucumber beetle (Aulacophora femoralis), cucumber beetle (Phyllotreta striolata), cabbage-free beetle (Phyllotreta cruciferae), western black-free beetle (Phyllotreta pusilla), cabbage stem-free beetle (Psylliodes chrysocephala), hop-free bee
  • Tribolium castaneum Tribolium confusum, Tenebrionidae such as Alphitobius diaperinus; Coccinellidae such as Epilachna vigintioctopunctata; Lyctus brunneus, Bostrychidae, such as Rhizopertha dominica; Ptinidae; Cerambycidae such as Anoplophora malasiaca, Migdolus fryanus, Aromia bungii; Melanotus okinawensis, Agriotes fuscicollis, Click beetles such as Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., Limonius spp., Aeolus spp.
  • Hymenoptera Tenthredinidae, such as Athalia rosae and Athalia japonica; Solenopsis spp., such as Solenopsis invicta and Solenopsis geminata, brown leaf-cutting ants (Atta capiguara), Acromyrmex spp., Paraponera clavata, Ochetellus glaver, Monomorium pharaonis, Linepithema humile , Formica japonica, Pristomyrmex punctutus, Pheidole noda, Pheidole megacephala, Camponotus japonicus, Camponotus obscuripes, etc., Camponotus spp.
  • Pogonomyrmex spp. such as Pogonomyrmex occidentalis, Wasmania spp. such as Wasmania auropunctata, Formicidae such as Anoplolepis gracilipes; Vespa mandarinia ), Vespa simillima, Vespa analis, Vespa velutina, Polistes jokahamae, etc.; Siricidae, such as Urocerus gigas ; Bethylidae.
  • Blattodea Ectobiidae, such as Blattella germanica; Blatta orientalis); Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis, Reticulitermes amamianus, Reticutermes miyatakei), Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, and Cornitermes cumulans.
  • Siphonaptera Pulicidae, such as Pulex irritans, Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, and Echidnophaga gallinacea; Hectopsyllidae, such as penetrans; Ceratophyllidae, such as the European rat flea (Nosopsyllus fasciatus).
  • Pulicidae such as Pulex irritans, Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, and Echidnophaga gallinacea
  • Hectopsyllidae such as penetrans
  • Ceratophyllidae such as the European rat flea (Nosopsyllus fasciatus).
  • Psocodae Pediculidae, such as head lice (Pediculus humanus capitis); Pthiridae, such as pubic lice (Pthirus pubis); Haematopinidae); Linognathidae, such as Linognathus vituli, Linognathus ovillus, Solenopotes capillatus; Bovicola bovis, Bovicola forvis, Bovicola breviceps, Damalin Bovicoliidae, such as Werneckiella spp.; Trichodectidae, such as Trichodectes canis and Felicola subrostratus; Menopon gallinae, Menacanthus stramineus ), Menoponidae such as Trinoton spp.; Trimenoponidae such as Cummingsia spp.; Trogiidae such as Trogium pulsatorium; Liposcelidae or Liposcelidida
  • Thysanura Lepismatidae, such as Ctenolepisma villosa and Lepisma saccharina.
  • Araneae Eutichuridae, such as Cheiracanthium japonicum; Theridiidae, such as Latrodectus hasseltii.
  • Polydesmida Paradoxosomatidae, such as Oxidus gracilis and Nedyopus tambanus.
  • Isopoda Armadillidiidae, such as Armadillidium vulgare.
  • Chilopoda Scutigeridae, such as Thereuonema hilgendorfi; Scolopendridae, such as Scolopendra subspinipes; Ethopolyidae, such as Bothropolys rugosus.
  • Gastropoda Limacidae, such as Limax marginatus and Limax flavus; Philomycidae, such as Meghimatium bilineatum; Pomacea canaliculata, etc. Lymnaeidae, such as Austropeplea ollula.
  • Nematoda Aphelenchoididae such as Aphelenchoides besseyi; Pratylenchidae; Meloidogyne javanica, Meloidogyne incognita, guava root-knot nematodes (Meloidogyne enterolobii), Meloidogyne hapla, Heterodera glycines, potato cyst nematode ( Heteroderidae such as Globodera rostochiensis and Globodera pallida; Hoplolimidae such as Rotylenchus reniformis; Anguinidae); Tylenchulidae, such as citrus nematode (Tylenchulus semipenetrans); Longidoridae, such as Xiphinema index; Trichodoridae; Aphelenx family (Parasitaphelenchidae).
  • Harmful insects, harmful arthropods such as harmful mites, harmful molluscs and harmful nematodes have reduced drug sensitivity or drug resistance to insecticides, acaricides, molluscicides and nematicides. It may be developed harmful insects, harmful arthropods such as harmful mites, harmful mollusks, and harmful nematodes.
  • an effective amount of the compound of the present invention or composition A is applied directly to pests and/or to habitats of pests (plants, soil, indoors, animals, etc.). It is done by Examples of the pest control method of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, smoking treatment, water surface treatment and seed treatment.
  • the compound or composition A of the present invention is usually prepared by mixing an inert carrier such as a solid carrier, a liquid carrier, or a gaseous carrier with a surfactant or the like, and optionally adding a binder, a dispersant, a stabilizer, or the like for formulation.
  • solid carriers examples include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice stone, silica sand, chemical fertilizers. fine powders and granules of (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.) and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).
  • clay pyrophyllite clay, kaolin clay, etc.
  • talc calcium carbonate
  • diatomaceous earth zeolite
  • bentonite acid clay
  • attapulgite white carbon
  • ammonium sulfate vermiculite
  • perlite perlite
  • pumice stone pumice
  • liquid carriers examples include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylylethane, methyl naphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides ( N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethylsulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic
  • gaseous carriers examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.
  • surfactants examples include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkylsulfonates, alkylarylsulfonates , alkyl sulfates, etc.).
  • formulation adjuvants include binders, dispersants, colorants, stabilizers, etc.
  • Specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, Examples include water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acidic isopropyl phosphate, and dibutylhydroxytoluene.
  • an adjuvant can be used as a component that enhances or assists the efficacy of the compound of the present invention.
  • plants include whole plants, foliage, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs and seedlings.
  • the vegetative reproductive organ means the plant's roots, stems, leaves, etc. that have the ability to grow when the part is separated from the main body and placed in the soil.
  • Vegetative reproductive organs include, for example, tuberous root, creeping root, bulb, corm or solid bulb, tuber, rhizome, stolon , rhizophore, cane cuttings, propagule and vine cuttings.
  • the stolons are sometimes called runners, and the mukago is also called buds, which are divided into broad buds and bulbils.
  • a vine means a shoot (collective term for leaves and stems, shoot) of sweet potato, yamanoimo, and the like. Bulbs, corms, tubers, rhizomes, stem fragments, rhizophores or tuberous roots are collectively called bulbs. Cultivation of potatoes begins by planting tubers in the soil, and the tubers used are generally called seed potatoes.
  • an effective amount of the compound of the present invention or composition A is applied to soil before or after planting plants. and the method of applying. More specifically, for example, planting hole treatment (planting hole spraying, planting hole treatment soil mixing), stock base treatment (stock base spraying, stock base soil mixing, stock irrigation, late seedling period stock base treatment), planting groove Treatment (ditch spraying, ditch soil mixing), cropping treatment (cropping spraying, cropping soil mixing, growing season cropping), cropping treatment at the time of sowing (crop spraying at the time of sowing, cropping soil mixing at the time of sowing) ), full surface treatment (overall soil spraying, full soil mixing), side row treatment, water surface treatment (water surface application, water surface application after flooding), other soil spraying treatments (granule spraying during the growing season, foliar spraying, under the canopy or around the trunk) , soil surface spraying, soil surface mixing, sowing hole spraying, furrow ground surface spray
  • Seed treatment includes, for example, the treatment of seeds or vegetative reproductive organs with the compound of the present invention or composition A. Specifically, for example, a suspension of the compound of the present invention or composition A is atomized and applied to the seed surface. Alternatively, a spraying treatment in which the surface of the vegetative reproductive organs is sprayed, a smearing treatment in which the compound of the present invention or composition A is applied to seeds or vegetative reproductive organs, and an immersion treatment in which seeds are immersed in a chemical solution of the compound of the present invention or composition A for a certain period of time. , a method of coating seeds or vegetative reproductive organs with a carrier containing the compound of the present invention or composition A (film coating, pellet coating, etc.).
  • the vegetative and reproductive organs mentioned above include, in particular, seed potatoes.
  • the seed or the vegetative reproductive organ can be treated with the composition A as a single formulation, or the composition A can be divided into a plurality of different formulations and applied to the seeds. Alternatively, it can be processed into vegetative and reproductive organs.
  • a method of treating composition A in a plurality of times as different formulations for example, a formulation containing only the compound of the present invention as an active ingredient is treated, seeds or vegetative reproductive organs are air-dried, and then this component is added.
  • the seed or vegetative reproductive organ retaining the compound of the present invention or composition A in the present invention means a state in which the compound of the present invention or composition A is attached to the surface of the seed or vegetative reproductive organ. .
  • the seed or vegetative reproductive organ holding the compound of the present invention or composition A described above is treated with a compound other than the compound of the present invention or composition A before or after the compound of the present invention or composition A is attached to the seed or vegetative reproductive organ. Materials may be attached.
  • the layer when the composition A adheres to the surface of a seed or vegetative reproductive organ in a layer, the layer consists of one layer or multiple layers. Also, when it consists of a plurality of layers, each layer is a layer containing one or more active ingredients, or a layer containing one or more active ingredients and a layer not containing an active ingredient. Become. Seeds or vegetative reproductive organs retaining the compound of the present invention or composition A are obtained, for example, by applying a formulation containing the compound of the present invention or composition A to seeds or vegetative reproductive organs by the method of seed treatment described above. be able to.
  • the application rate is usually 1 to 10,000 g of the compound of the invention per 10,000 m 2 .
  • the amount of the compound of the present invention is usually applied in the range of 0.001 to 100 g per 1 kg of seeds or vegetative reproductive organs.
  • the compound of the present invention or composition A is formulated as an emulsion, wettable powder, flowable powder, etc., it is usually applied after being diluted with water so that the concentration of the active ingredient is 0.01 to 10,000 ppm. , granules, powders and the like are usually applied as they are.
  • It can also be treated by wrapping a sheet-shaped or string-shaped resin formulation around crops, spreading it around crops, or laying it on the soil at the base of the plant.
  • the amount of application is the amount of the compound of the present invention per 1 m 2 of the treated area when the surface is treated.
  • the amount is 0.01 to 1,000 mg
  • the amount of the compound of the present invention per 1 m 3 of space to be treated is usually 0.01 to 500 mg.
  • the compound of the present invention or composition A is formulated as an emulsion, wettable powder, flowable powder, etc., it is usually applied after being diluted with water so that the concentration of the active ingredient is 0.1 to 10,000 ppm. , oils, aerosols, smoke agents, poison baits, etc., are applied as they are.
  • composition A When the compound of the present invention or composition A is used for controlling ectoparasites of domestic animals such as cattle, horses, pigs, sheep, goats, chickens, etc., and small animals such as dogs, cats, rats, mice, etc., veterinary known methods are used. Can be used on animals with As a specific method of use, for the purpose of systemic suppression, for example, it is administered by tablet, feed, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), and non-systemic suppression is intended.
  • systemic suppression for example, it is administered by tablet, feed, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), and non-systemic suppression is intended.
  • the amount of the compound of the present invention or composition A when administered to an animal is generally in the range of 0.1 to 1,000 mg per kg body weight of the animal.
  • the compound or composition A of the present invention can be used as a pest control agent in agricultural lands such as fields, paddy fields, lawns, and orchards. Examples of plants include the following.
  • the above plants are not particularly limited as long as they are commonly cultivated varieties.
  • the above plants also include plants that can be produced by natural crossing, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops.
  • genetically modified crops include HPPD (4-hydroxyphenylpyruvate dioxygenase) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron-methyl, and EPSP (5 - enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or plants tolerant to herbicides such as dicamba ;Plants capable of synthesizing selective toxins, etc.
  • HPPD 4-hydroxyphenylpyruvate dioxygenase
  • ALS acetolactate synthase
  • Bacillus such as Bacillus thuringiensis
  • Gene fragments, etc. that partially match endogenous genes derived from harmful insects Plants capable of synthesizing and conferring specific insecticidal activity by inducing gene silencing (RNAi; RNA interference) in target pests.
  • RNAi gene silencing
  • Me represents a methyl group
  • Et represents an ethyl group
  • Pr represents a propyl group
  • i-Pr represents an isopropyl group
  • i-Bu represents an isobutyl group
  • t-Bu represents tert- represents a butyl group
  • c-Pr represents a cyclopropyl group
  • c-Bu represents a cyclobutyl group
  • c-Pen represents a cyclopentyl group
  • c-Hex represents a cyclohexyl group
  • Ph represents a phenyl group
  • 2 -Py represents a 2-pyridyl group
  • 3-Py represents a 3-pyridyl group
  • 4-Py represents a 4-pyridyl group.
  • 2-F-Ph represents 2-fluorophenyl
  • 2-OCF 3 -Ph represents a 2-(trifluoromethoxy)phenyl group
  • 2-Ph-Ph represents a 2-phenylphenyl group
  • 3-Cl- 2-Py represents a 3-chloro-2-pyridyl group.
  • CH(CH 3 )c-Pr represents a 1-cyclopropylethyl group
  • CH 2 (2-F-3-F-Ph) represents a (2,3-difluorophenyl)methyl group
  • O(3 -CF 3 -5-CF 3 -Ph) represents a [3,5-bis(trifluoromethyl)phenyl]oxy group
  • OCH 2 (2-OPh-Ph) represents a (2-phenoxyphenyl)methoxy group.
  • Oi-Pr represents an isopropyloxy group.
  • LCMS liquid chromatography/mass spectrometry
  • RT write the measured molecular ion value [M+H] + or [M ⁇ H] ⁇ and retention time
  • LC liquid chromatography/mass spectrometry
  • MS mass spectrometry
  • Production Example 1-1 The compounds produced according to Production Example 1 and their physical properties are shown below.
  • Production example 2-1 The compounds produced according to Production Example 2 and their physical properties are shown below.
  • Invention compound 1-5 1 H-NMR (CDCl 3 ) ⁇ : 7.62-7.57 (2H, m), 7.29 (1H, s), 7.09-7.01 (2H, m), 6.44 (1H, d), 3.89 (2H, d), 3.85 (3H, s), 3.74 (3H, s), 2.23-2.14 (1H, m), 0.92 (6H, d).
  • Invention compound 1-6 1 H-NMR (CDCl 3 ) ⁇ : 7.65 (1H, d), 7.57 (1H, s), 7.53-7.49 (5H, m), 7.36-7.31 (2H, m), 7.11 (1H, dd), 6.65 (1H, dd), 3.83 (3H, s), 3.72 (3H, s).
  • Invention compound 1-9 1 H-NMR ( CDCl3 ) ⁇ : 7.93 (1H, s), 7.60 (1H, s), 7.51 (1H, d), 7.40 (1H, s), 6.48 (1H, d), 3.83 (3H, s) , 3.70 (3H, s), 2.25 (3H, s), 1.64 (9H, s).
  • Invention compound 1-16 1 H-NMR (CDCl 3 ) ⁇ : 7.64 (1H, d), 7.56 (1H, s), 7.49-7.26 (9H, m), 7.10-7.08 (3H, m), 6.62 (1H, dd), 5.13 (2H, s), 3.82 (3H, s), 3.72 (3H, s).
  • the resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • 80 mL of methanol was added to the obtained residue, 16.2 mL of 28% sodium methoxide methanol solution was added to the mixture, and the mixture was stirred at 40° C. for 7 hours.
  • a saturated aqueous ammonium chloride solution was added to the resulting mixture, and the mixture was extracted with ethyl acetate.
  • the resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • Invention compound 1-14 1 H-NMR (CDCl 3 ) ⁇ : 8.31 (1H, br s), 7.64 (1H, d), 7.58 (1H, d), 7.31 (1H, dd), 6.81 (1H, s), 6.57 (1H, d), 3.99 (3H, s), 2.96 (3H, d), 1.66 (9H, s).
  • Production Example 4-1 The compounds produced according to Production Example 4 and their physical properties are shown below.
  • Compound 1-15 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.78 (2H, d), 7.73 (1H, s), 7.71 (1H, d), 7.63 (2H, d), 7.40 (1H, d ), 7.28 (1H, dd), 6.87 (1H, br s), 6.73 (1H, dd), 3.98 (3H, s), 2.95 (3H, d).
  • Group X Me, Et, Pr, i-Pr, c-Pr, c-Bu, c-Pen, c-Hex, ( CH2 ) 3CH3 , CH2CH ( CH3 ) 2 , CH( CH3 ) CH2CH3 , t-Bu,CH2c-Pr,( CH2 ) 4CH3 ,( CH2 ) 2CH ( CH3 ) 2 ,CH ( CH3 ) ( CH2 ) 2 CH3 , CH ( CH2CH3 ) CH2CH3 , CH2CH ( CH3 ) CH2CH3 , C ( CH3 ) 2CH2CH3 , CH2t -Bu,CH2c - Bu, CH2Py , ( CH2 )2c-Pr, CH2 (1-methylcyclopropyl), CH2 ( 2 -methylcyclopropyl),CH( CH3 )c-Pr,( CH2 ) 3c - Pr,( CH2 ) 5CH3 ,( CH
  • X 1 is CH
  • X 2 is C(O)NHCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 and X 4 are CH
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX2).
  • X 1 is CH
  • X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 and X 4 are CH
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX3).
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 and X 4 are CH
  • Compounds in which E is any one of the substituents described in Group X and Group Y hereinafter referred to as Compound Group SX4.
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 and X 4 are CH
  • Compounds in which E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX5).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 and X 4 are CH
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX6).
  • X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 and X 4 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX7);
  • X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 and X 4 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX8);
  • X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, X 3 and X 4
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 3 and X 4 is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX10).
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 3 and X 4 is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX11).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • X 3 and X 4 are CH
  • E is any one of substituents described in groups X and Y
  • X 1 is CH
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is chlorine atom
  • X 3 and X 4 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX13)
  • X 1 is CH
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is chlorine atom
  • X 3 and X 4 are a
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a chlorine atom
  • X 3 and X 4 is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX16).
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a chlorine atom
  • X 3 and X 4 is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX17).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • X 3 and X 4 are CH
  • E is any one of the substituents described in groups X and Y
  • X 1 is CH
  • X 2 is C(O)OCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 is nitrogen atom
  • X 4 is a compound in which CH is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX19);
  • X 1 is CH
  • X 2 is C(O)NHCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 is nitrogen atom
  • X 4 is a compound in which CH is CH and E is any one of the substituent
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 is a nitrogen atom
  • X 4 is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX22).
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 is a nitrogen atom
  • X 4 is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX23).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 is a nitrogen atom
  • X 4 is CH
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX24).
  • X 1 is CH
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 3 is a nitrogen atom.
  • X 1 is CH
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 3 is a nitrogen atom
  • X 4 is CH
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX26).
  • X 1 is CH
  • X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X3 is a nitrogen atom
  • X4 is CH
  • E is any one of the substituents described in Groups X and Y (hereinafter referred to as Compound Group SX27).
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 3 is a nitrogen atom and X 4 is CH
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX28).
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 3 is a nitrogen atom and X 4 is CH
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX29).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • X 3 is a nitrogen atom
  • X 4 is CH
  • E is any one of the substituents described in groups X and Y
  • X 1 is CH
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is chlorine atom
  • X 3 is nitrogen atom and X 4 is CH
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX31).
  • X 1 is CH
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is chlorine atom
  • X 3 is nitrogen atom
  • X 4 is CH
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX32).
  • X 1 is CH
  • X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a chlorine atom
  • X3 is a nitrogen atom
  • X4 is CH
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX33).
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a chlorine atom
  • X 3 is a nitrogen atom and X 4 is CH
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX34).
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a chlorine atom
  • X 3 is a nitrogen atom and X 4 is CH
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX35).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • X 3 is a nitrogen atom
  • X 4 is CH
  • E is any one of the substituents described in groups X and Y
  • X 1 is CH
  • X 2 is C(O)OCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 is CH
  • X 4 is CCl
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX37).
  • X 1 is CH
  • X 2 is C(O)NHCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 is CH
  • X 4 is CCl
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX38).
  • X 1 is CH
  • X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 is CH
  • X 4 is CCl
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX39).
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 is CH
  • X 4 is CCl and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX40).
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 is CH
  • X 4 is CCl and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX41).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 3 is CH
  • X 4 is CCl
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX42).
  • X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 is CH , X 4 is CCl, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX43).
  • X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 is CH , X 4 is CCl, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX44).
  • X 1 is CH
  • X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 3 is CH
  • X 4 is CCl
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX45).
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 3 is CH.
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 3 is CH
  • X 4 is CCl
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX47).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • X 3 is CH
  • X 4 is CCl
  • E is any one of the substituents described in groups X and Y (hereinafter referred to as compound group SX48);
  • compound (1A) is CH
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is chlorine atom
  • X 3 is CH
  • X 4 is CCl
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX49).
  • X 1 is CH
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is chlorine atom
  • X 3 is CH
  • X 4 is CCl
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX50).
  • X 1 is CH
  • X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a chlorine atom
  • X 3 is CH
  • X 4 is CCl
  • E is any one of the substituents described in Groups X and Y (hereinafter referred to as Compound Group SX51).
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a chlorine atom
  • X 3 is CH.
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a chlorine atom
  • X 3 is CH
  • X 4 is CCl
  • E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX53).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • X 3 is CH
  • X 4 is CCl
  • E is any one of the substituents described in groups X and Y (hereinafter referred to as compound group SX54);
  • Group Z CH2OPh, CH2O ( 2 -F-Ph), CH2O (3-F-Ph), CH2O (4-F-Ph), CH2O (2-Cl-Ph), CH2 O(3-Cl-Ph), CH2O (4-Cl-Ph), CH2O (2-Br-Ph), CH2O (3-Br-Ph), CH2O (4-Br- Ph), CH2O (2-I-Ph), CH2O (3-I-Ph), CH2O (4-I-Ph), CH2O (2-Me-Ph), CH2O (3-Me-Ph), CH2O (4-Me-Ph), CH2O (2- CF3 -Ph), CH2O (3- CF3 -Ph), CH2O (4-CF 3 -Ph), CH2O (2-OMe-Ph), CH2O (3-OMe-Ph), CH2O (4-OMe-Ph), CH2O (2- OCF3 -Ph), CH2
  • X 1 is CH
  • X 2 is C(O)NHCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 5 and X 6 are CH
  • E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX56).
  • X 1 is CH
  • X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 5 and X 6 are CH
  • E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX57).
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 5 and X 6 are CH
  • Compound Group SX58 Compounds in which E is any one of the substituents described in Groups X and Z
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 5 and X 6 are CH
  • Compounds in which E is any one of the substituents described in Groups X and Z (hereinafter referred to as Compound Group SX59).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 5 and X 6 are CH
  • E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX60).
  • X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 5 and X 6 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX61);
  • X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 5 and X 6 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX62);
  • X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R 2 is a methyl group, X 5 and X 6 are
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 5 and X 6 is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX64).
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 5 and X 6 is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX65).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • X 5 and X 6 are CH
  • E is any one of the substituents described in groups X and Z
  • X 1 is CH
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is chlorine atom
  • X 5 and X 6 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Z
  • Compound Group SX67 In compound (1B), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is chlorine atom, and X 5 and X 6 are a compound
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a chlorine atom
  • X 5 and X 6 is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX70).
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a chlorine atom
  • X 5 and X 6 is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX71).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • X 5 and X 6 are CH
  • E is any one of the substituents described in groups X and Z
  • X 1 is CH
  • X 2 is C(O)OCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 5 is CH
  • X 6 is nitrogen
  • Compound Group SX73 A compound in which E is any one of the substituents described in Groups X and Z
  • X 1 is CH
  • X 2 is C(O)NHCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 5 is CH
  • X 6 is nitrogen
  • Compound Group SX74 A compound in which E is any one of the substituents described in Groups X and Z (hereinafter referred to as Compound Group SX74).
  • X 1 is CH
  • X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 5 is CH
  • X 6 is a nitrogen atom
  • E is any one of the substituents described in Group X and Group Z
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 5 is CH
  • X 6 is a compound which is a nitrogen atom and in which E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX76);
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 , R 2 and R 3 are hydrogen atoms
  • X 5 is CH
  • X 6 is a compound which is a nitrogen atom and in which E is any one of the substituents described in groups X and Z
  • compound group SX77 In compound (1B), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 , R 2 and R 3 are hydrogen atoms; and
  • X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 5 is CH , X 6 is a nitrogen atom, and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX79).
  • compound group SX79 X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 5 is CH , X 6 is a nitrogen atom, and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX80).
  • X 1 is CH
  • X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 5 is CH
  • X 6 is a nitrogen atom
  • E is any one of the substituents described in Groups X and Z (hereinafter referred to as Compound Group SX81).
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 5 is CH.
  • X 1 is a nitrogen atom
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a methyl group
  • X 5 is CH
  • X6 is a nitrogen atom
  • E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX83).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • X 5 is CH
  • X 6 is a nitrogen atom
  • E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX84);
  • compound (1B) is CH
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is chlorine atom
  • X 5 is CH
  • X 6 is a nitrogen atom
  • E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX85).
  • X 1 is CH
  • X 2 is C(O)NHCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is chlorine atom
  • X 5 is CH
  • X 6 is a nitrogen atom
  • E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX86).
  • X 1 is CH
  • X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a chlorine atom
  • X5 is CH
  • X6 is a nitrogen atom
  • E is any one of the substituents described in Groups X and Z (hereinafter referred to as Compound Group SX87 ).
  • X 1 is a nitrogen atom
  • X 2 is C(O)OCH 3
  • R 1 and R 3 are hydrogen atoms
  • R 2 is a chlorine atom
  • X 5 is CH.
  • X6 is a nitrogen atom and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX88 ).
  • compound (1B) X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom, and X 5 is CH. and X 6 is a nitrogen atom, and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX89).
  • X 1 is a nitrogen atom
  • X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group
  • R 1 and R 3 are hydrogen atoms
  • X 5 is CH
  • X 6 is a nitrogen atom
  • E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX90);
  • the compound S of the present invention represents compounds described in the compound groups SX1 to SX90.
  • Formulation example 1 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and silica (weight ratio 1:1), 10 parts of any one of the compounds S of the present invention, and 55 parts of water are mixed and finely pulverized by a wet pulverization method. By doing so, a formulation is obtained.
  • Formulation example 2 A preparation is obtained by pulverizing and mixing 50 parts of any one compound S of the present invention, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of silica.
  • Formulation example 3 5 parts of any one of the compounds S of the present invention, 9 parts of polyoxyethylene styryl phenyl ether, 5 parts of polyoxyethylene decyl ether (number of ethylene oxide additions: 5), 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene are mixed. By doing so, a formulation is obtained.
  • Formulation example 4 2 parts of any one of the compound S of the present invention, 1 part of silica, 2 parts of calcium ligninsulfonate, 30 parts of bentonite, and 65 parts of kaolin clay are pulverized and mixed, kneaded with an appropriate amount of water, and granulated. After granulating with, the formulation is obtained by drying.
  • Formulation example 5 10 parts of any one of the compounds S of the present invention are mixed with a mixture of 18 parts of benzyl alcohol and 9 parts of DMSO, to which 6.3 parts of GERONOL® TE250, Ethylan® NS-500LQ2 are added. Add .7 parts and 54 parts solvent naphtha and mix to obtain a formulation.
  • Formulation example 6 0.1 part of any one of the compound S of the present invention and 39.9 parts of kerosene are mixed and dissolved, placed in an aerosol container, and liquefied petroleum gas (propane, butane and isobutane mixture; saturated vapor pressure: 0.47 MPa (25 C))) to obtain a formulation by filling 60 parts.
  • liquefied petroleum gas propane, butane and isobutane mixture; saturated vapor pressure: 0.47 MPa (25 C)
  • Formulation example 7 0.2 parts of any one of the compounds S of the present invention, 50 parts of pyrethrum extract lees powder, 30 parts of tab powder and 19.8 parts of wood powder are mixed, kneaded by adding an appropriate amount of water, and extruded into a plate shape.
  • the formulation is obtained by sheeting and coiling with a punch.
  • Test Examples 1 to 7 The untreated section in Test Examples 1 to 7 is a test section performed under the same conditions as described in each Test Example except that DMSO is dispensed instead of the DMSO diluted solution containing the compound of the present invention. represents Further, "no treatment" in Test Examples 8 to 14 means that the water-diluted formulation containing the compound of the present invention was not sprayed.
  • Test Example 1 Control test against wheat leaf blight fungus (Septoria tritici) 1 ⁇ L of the medium was added to a titer plate (96 wells), and then 150 ⁇ L of YBG medium previously inoculated with spores of the wheat leaf blight fungus was added. After culturing this plate at 18° C. for 3 days to grow the wheat leaf blight fungus, the absorbance at 550 nm of each well of the titer plate was measured, and the value was defined as the growth rate of the wheat leaf blight fungus. As a result, the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
  • Test Example 2 Control test against corn smut (Ustilago maydis) Compound 1-6, 1-7, 1-9, 1-10, or 2-1 of the present invention was diluted with DMSO to contain 150 ppm, and a titer plate ( 96 wells), and then 150 ⁇ L of a potato decoction liquid medium (PDB medium) previously inoculated with corn smut spores was dispensed. This plate was cultured at 18° C. for 4 days to grow the corn smut fungus, and then the absorbance at 550 nm of each well of the titer plate was measured to determine the growth rate of the corn smut fungus. As a result, the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
  • PDB medium potato decoction liquid medium
  • Test Example 3 Control test against Rhynchosporium secalis Compounds of the present invention 1-1, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1- Dilute with DMSO to contain 13, 1-15, 1-17, 2-1, or 2-2 at 150 ppm, dispense 1 ⁇ L into a titer plate (96 wells), and inoculate in advance with spores of barley 150 ⁇ L of a potato decoction liquid medium (PDB medium) was dispensed. After culturing this plate at 18° C.
  • PDB medium potato decoction liquid medium
  • the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of the barley cloud.
  • the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
  • Test Example 4 Control test against cucumber gray mold (Botrytis cinerea) Compounds 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-15, or 1-17 was diluted with DMSO so as to contain 150 ppm, 1 ⁇ L was dispensed into a titer plate (96 wells), and then 150 ⁇ L of complete medium previously inoculated with spores of Botrytis cucumber was dispensed. After culturing this plate at 18° C. for 4 days to grow the cucumber botrytis, the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of the cucumber botrytis. As a result, the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
  • Test Example 5 Control test against peach scab (Cladosporium carpophilum) Compounds of the present invention 1-1, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1- Dilute with DMSO to contain 13, 1-15, 1-16, 1-17, or 2-1 at 150 ppm, dispense 1 ⁇ L into a titer plate (96 well), and inoculate peach scab spores in advance. 150 ⁇ L of a potato decoction liquid medium (PDB medium) was dispensed. This plate was cultured at 18° C.
  • PDB medium potato decoction liquid medium
  • the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
  • Test Example 6 Control test against rice sesame leaf blight fungus (Cochliobolus miyabeanus) Compounds of the present invention 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-13, 1-15, 1-16, 1-17, or 2-1 diluted with DMSO to contain 150 ppm, titer plate (96 well) After 1 ⁇ L was dispensed, 150 ⁇ L of YB liquid medium previously inoculated with spores of the rice sesame leaf blight fungus was dispensed. After culturing this plate at 23° C.
  • the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of the rice and sesame leaf blight fungus.
  • the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
  • Test Example 7 Prevention test against soybean rust (Phakopsora pachyrhizi) A leaf disc having a diameter of 1 cm was cut out from a true leaf of soybean (variety: Kurosengoku). After 1 mL of agar medium (agar concentration: 1.2%) was dispensed into each well of a 24-well microplate, one leaf disk was placed on each well of the agar medium. To a mixture of 0.5 ⁇ L of Sorpol® 1200KX, 4.5 ⁇ L of DMSO and 5 ⁇ L of xylene, 20 ⁇ L of DMSO solution containing 10000 ppm of the test compound was added and mixed.
  • the obtained mixture was diluted with ion-exchanged water to prepare a mixture containing the test compound at a predetermined concentration. 10 ⁇ L of the resulting mixture was spread on each leaf disc.
  • an aqueous spore suspension (1.0 ⁇ 10 5 /mL) of Phakopsora pachyrhizi having an amino acid substitution of F129L in the mitochondrial cytochrome b protein was spray-inoculated onto the leaf discs. After inoculation, the plants were placed in an artificial climate chamber (6 hours light, 18 hours light off, temperature 23°C, humidity 60%). After one day, the leaf disc was air-dried until no water droplets were left on the surface, and placed again in the climate chamber for 12 days.
  • the lesion area of soybean rust was investigated.
  • the predetermined concentration was set to 50 ppm, and the present invention compounds 1-1, 1-2, 1-3, 1-4, 1-6, 1-7, 1-8, 1-9, 1-
  • the lesion area of leaf discs treated with any one of 10, 1-12, 1-13, 1-14, or 1-15 is 30% or less of the lesion area of untreated leaf discs. there were.
  • Test Example 8 Pyrenophora teres Control Test A plastic pot was filled with soil, and barley (cultivar: Nishinohoshi) was seeded therein and cultivated in a greenhouse for 7 days. Compound 1-4, 1-6, 1-7, 1-10, 1-15, or 2-1 of the present invention formulated according to the method described in Formulation Example 1, so that the concentration is 200 ppm Mixed with water. The resulting mixture was foliarly sprayed so as to sufficiently adhere to the foliage of the barley. After spraying, the barley was air-dried, and one day later, an aqueous suspension of spores of barley net spot fungus was inoculated by spraying.
  • the barley was placed in a greenhouse at 23° C. during the day and 20° C. at night under high humidity for 3 days, then cultivated in the greenhouse for 7 days, and then the lesion area was examined.
  • the lesion area in barley treated with each compound of the present invention was 30% or less of the lesion area in untreated barley.
  • Test Example 9 Control Test against Wheat Rust (Puccinia recondita) A plastic pot was filled with soil, wheat (cultivar: Shirogane) was sown therein, and cultivated in a greenhouse for 9 days. Compound 1-6, 1-7, 1-9, 1-13, 1-15, 1-16, or 2-1 of the present invention formulated according to the method described in Formulation Example 1 at a concentration of 200 ppm The resulting mixture was foliarly sprayed so that it adhered sufficiently to the leaves of the above wheat. After spraying, the wheat was air-dried, cultivated under lighting at 20° C. for 5 to 7 days, and then inoculated with spores of wheat rust.
  • the wheat was placed under darkness and high humidity at 23°C for 1 day, then cultivated under illumination at 20°C for 8 days, and the lesion area was investigated.
  • the lesion area in the wheat treated with each compound of the present invention was 30% or less of the lesion area in the untreated wheat.
  • Test Example 10 Control Test Against Wheat Leaf Blight (Septoria tritici) Plastic pots were filled with soil, wheat (cultivar: Apogee) was sown therein, and cultivated in a greenhouse for 10 days. Compounds 1-1, 1-2, 1-3, 1-6, 1-8, 1-9, 1-11, 1-12 and 1 of the present invention formulated according to the method described in Formulation Example 1 -14 or 1-15 was mixed with water to a concentration of 200 ppm, and the resulting mixture was foliarly sprayed so that it adhered sufficiently to the leaves of the above wheat.
  • the wheat After spraying, the wheat was air-dried, and four days later, an aqueous suspension containing spores of the wheat leaf blight fungus was inoculated by spraying. After inoculation, the wheat was placed under high humidity at 18°C for 3 days, then cultivated under lighting for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the wheat treated with each compound of the present invention was 30% or less of the lesion area in the untreated wheat.
  • Test Example 11 Prevention test against soybean rust (Phakopsora pachyrhizi) Plastic pots were filled with soil, soybeans (cultivar: Kurosengoku) were seeded therein, and grown in a greenhouse for 10 to 14 days.
  • Compound 1-6, 1-9, or 1-17 of the present invention formulated according to the method described in Formulation Example 1 was mixed with water to a concentration of 200 ppm, and the resulting mixture was added to the soybean. It was sprayed on the foliage so that it would adhere sufficiently to the leaf surfaces of . After spraying, the soybeans were air-dried, and 2 to 5 days later, an aqueous suspension of soybean rust spores was inoculated by spraying.
  • the soybeans were placed in a greenhouse at 23° C. during the day and 20° C. at night under high humidity for 1 to 2 days, then cultivated in the greenhouse for 12 days, and then the lesion area was examined.
  • the lesion area in the soybeans treated with each compound of the present invention was 30% or less of the lesion area in the untreated soybeans.
  • Test Example 12 Control test against soybean rust (Phakopsora pachyrhizi) A plastic pot was filled with soil, soybeans (cultivar: Kurosengoku) were sown there, grown in a greenhouse for 10 days, and water suspension containing spores of soybean rust fungus. The suspension was spray inoculated. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under high humidity for 1 day, and then cultivated in the greenhouse for 2 days. -4, 1-5, 1-6, 1-10, or 2-1 is mixed with water so that the concentration is 200 ppm, and the resulting mixture is attached to the foliage of the soybean. disseminated.
  • the soybeans were air-dried, cultivated in a greenhouse for 8 days, and then the lesion area was investigated. As a result, the lesion area in the soybeans treated with each compound of the present invention was 30% or less of the lesion area in the untreated soybeans.
  • Test Example 13 Control test against soybean spot (Cercospora sojina) Plastic pots were filled with soil, soybeans (cultivar: Tachinagaha) were sown there, and grown in a greenhouse for 13 days.
  • Compound 1-1, 1-6, 1-7, 1-9, or 1-10 of the present invention formulated according to the method described in Formulation Example 1 is mixed with water to a concentration of 200 ppm, The resulting mixture was foliarly sprayed so that it adhered sufficiently to the foliage of the soybean. After spraying, the soybeans were air-dried, and one day later, they were inoculated by spraying an aqueous suspension of spores of the soybean leaf spot fungus.
  • the soybeans were placed in a greenhouse at 23° C. during the day and 20° C. at night under high humidity for 3 days, then cultivated in the greenhouse for 16 days, and then the lesion area was examined.
  • the lesion area in the soybeans treated with each compound of the present invention was 30% or less of the lesion area in the untreated soybeans.
  • Test Example 14 Control test against tomato ring spot (Alternaria solani) Plastic pots were filled with soil, tomatoes (cultivar: patio) were seeded therein, and grown in a greenhouse for 20 days.
  • Compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8 and 1 of the present invention formulated according to the method described in Formulation Example 1 -9, 1-11, 1-13, 1-14, 1-15, 1-16, 1-17, 2-1, or 2-2 is mixed with water so that the concentration is 200 ppm, and the resulting The resulting mixture was foliarly sprayed so as to sufficiently adhere to the leaf surface of the tomato.
  • the tomatoes After spraying, the tomatoes were air-dried, and one day later, they were inoculated by spraying an aqueous suspension of spores of tomato ring-blight fungus. After the inoculation, the tomato was placed at 18° C. and high humidity for 6 days, and then the lesion area was examined. As a result, the lesion area on tomatoes treated with the compounds of the present invention was 30% or less of the lesion area on untreated tomatoes.
  • Test example 15 The results of tests performed according to test method 15 are shown below. As a result of using the following compounds of the present invention as test compounds with a predetermined period of one day, all showed a mortality rate of 70% or more.
  • Test example 16 The results of tests performed according to test method 16 are shown below. As a result of using the following compound of the present invention as a test compound with a predetermined time of 1 day, the mortality rate was 70%. Compounds of the present invention: 1-7
  • Test example 17 The results of tests performed according to test method 17 are shown below. Using the following compound of the present invention as a test compound with a predetermined time of 2 days, the mortality rate was 100%.
  • the compound of the present invention has a controlling effect on pests and can be used for controlling pests.

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Abstract

The present invention provides a compound, or a salt thereof, which exhibits an excellent controlling effect against pests and which is represented by formula (I) [in the formula, a combination of J and E is such that J is a group represented by J1 and E is a C1-C6 chain-like hydrocarbon group or the like that may be substituted with one or more substituent groups selected from among group A, X1 denotes CH or a nitrogen atom, X2 denotes C(O)OCH3 or the like, R1, R2 and R3 may be the same as, or different from, each other, and each denote a C1-C6 alkyl group, a group represented by J1 is a group represented by the formula below, X3 denotes CR4 or a nitrogen atom, X4 denotes CR5 or a nitrogen atom, # denotes a site of bonding to E, R4 and R5 may be the same as, or different from, each other, and each denote a C1-C6 alkyl group or the like]; or an N-oxide thereof.

Description

縮合環化合物及びその用途Condensed ring compound and use thereof
　本特許出願は、日本国特許出願２０２１－０３５００３号（２０２１年３月５日出願）及び日本国特許出願２０２１－１２４５５２号（２０２１年７月２９日出願）に基づくパリ条約上の優先権および利益を主張するものであり、ここに引用することによって、上記出願に記載された内容の全体が本明細書中に組み込まれるものとする。
　本発明は縮合環化合物及びその用途に関する。 This patent application is based on Japanese Patent Application No. 2021-035003 (filed on March 5, 2021) and Japanese Patent Application No. 2021-124552 (filed on July 29, 2021). Priority and benefits under the Paris Convention and the entire contents of the above application are incorporated herein by reference.
The present invention relates to a condensed ring compound and uses thereof.
　特許文献１には、縮合環化合物が記載されている。 Patent Document 1 describes a condensed ring compound.
中国特許出願公開第１０８８２１９７４号明細書Chinese Patent Application Publication No. 108821974
　本発明は、有害生物に対して優れた防除効力を有する化合物を提供することを目的とする。 The purpose of the present invention is to provide a compound that has excellent control efficacy against pests.
　本発明者は、有害生物に対する優れた防除効力を有する化合物を見出すべく検討の結果、下記式（Ｉ）で示される化合物が、有害生物に対して優れた防除効力を有することを見出した。
　すなわち、本発明は以下のとおりである。
〔１〕　式（Ｉ）：
Figure JPOXMLDOC01-appb-C000003
 〔式中、
　Ｘ１は、ＣＨ又は窒素原子を表し、
　Ｘ２は、Ｃ（Ｏ）ＯＣＨ３、Ｃ（Ｏ）ＮＨＣＨ３、又は５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基を表し、
　Ｒ１、Ｒ２、及びＲ３は、同一又は相異なり、Ｃ１－Ｃ６アルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルコキシカルボニル基｛該Ｃ１－Ｃ６アルキル基、該Ｃ１－Ｃ６アルコキシ基、該Ｃ３－Ｃ６シクロアルキル基、及び該Ｃ２－Ｃ６アルコキシカルボニル基は、１以上のハロゲン原子で置換されていてもよい｝、シアノ基、ニトロ基、ハロゲン原子、又は水素原子を表し、
　Ｊ及びＥの組合せは、
　　Ｊが、Ｊ１で示される基であり、
　　Ｅが、群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、Ｃ３－Ｃ１０脂環式炭化水素基、３－１０員非芳香族複素環基、Ｃ６－Ｃ１０アリール基、５－１０員芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基、該３－１０員非芳香族複素環基、該Ｃ６－Ｃ１０アリール基及び該５－１０員芳香族複素環基は、群Ｄより選ばれる１以上の置換基で置換されていてもよい｝、Ｃ（Ｏ）ＯＲ２５、Ｃ（Ｏ）Ｒ２６、又はＣ（Ｏ）ＮＲ２７Ｒ２８である組合せ；又は、
　　Ｊが、Ｊ２で示される基であり、
　　Ｅが、群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、Ｃ３－Ｃ１０脂環式炭化水素基、３－１０員非芳香族複素環基、Ｃ６－Ｃ１０アリール基、５－１０員芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基、該３－１０員非芳香族複素環基、該Ｃ６－Ｃ１０アリール基及び該５－１０員芳香族複素環基は、群Ｄより選ばれる１以上の置換基で置換されていてもよい｝、ＣＨ２－Ｌ１－Ｒ１２、ＣＨ２－Ｏ－Ｎ＝ＣＲ１３Ｒ１４、Ｃ（Ｒ１６）＝Ｎ－Ｏ－Ｒ１５、Ｃ（Ｒ１９）＝Ｎ－Ｎ＝ＣＲ１７Ｒ１８、Ｃ（Ｒ２２）＝Ｎ－ＮＲ２０Ｒ２１、Ｌ２Ｒ２３、シアノ基、ニトロ基、又はハロゲン原子である組合せを表し、
　Ｊ１で示される基、及びＪ２で示される基は、下式で示される基であり、
Figure JPOXMLDOC01-appb-C000004
 　＃は、Ｅとの結合位置を表し、
　Ｘ3は、ＣＲ４又は窒素原子を表し、
　Ｘ4は、ＣＲ５又は窒素原子を表し、
　Ｘ5は、ＣＲ６又は窒素原子を表し、
　Ｘ6は、酸素原子、硫黄原子、Ｎ（Ｒ７）、＊－Ｃ（Ｒ８）＝Ｃ（Ｒ９）－、＊－Ｃ（Ｒ１０）＝Ｎ－、又は＊－Ｎ＝Ｃ（Ｒ１１）－を表し、
　＊は、Ｘ５との結合位置を表し、
　Ｒ４、Ｒ５、Ｒ６、Ｒ８、Ｒ９、Ｒ１０、及びＲ１１は、同一又は相異なり、Ｃ１－Ｃ６アルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルコキシカルボニル基｛該Ｃ１－Ｃ６アルキル基、該Ｃ１－Ｃ６アルコキシ基、該Ｃ３－Ｃ６シクロアルキル基、及び該Ｃ２－Ｃ６アルコキシカルボニル基は、１以上のハロゲン原子で置換されていてもよい｝、シアノ基、ニトロ基、ハロゲン原子、又は水素原子を表し、
　Ｒ７は、Ｃ１－Ｃ６アルキル基、Ｃ３－Ｃ６シクロアルキル基｛該Ｃ１－Ｃ６アルキル基及び該Ｃ３－Ｃ６シクロアルキル基は、１以上のハロゲン原子で置換されていてもよい｝、又は水素原子を表し、
　Ｌ１及びＬ２は、同一又は相異なり、酸素原子又はＳ（Ｏ）ｎを表し、
　ｎは、０、１、又は２を表し、
　Ｒ１２、Ｒ１３、Ｒ１５、Ｒ１７、Ｒ２０、Ｒ２３、Ｒ２５、Ｒ２６、及びＲ２７は、同一又は相異なり、群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、Ｃ３－Ｃ１０脂環式炭化水素基、３－１０員非芳香族複素環基、Ｃ６－Ｃ１０アリール基、又は５－１０員芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基、該３－１０員非芳香族複素環基、該Ｃ６－Ｃ１０アリール基、及び該５－１０員芳香族複素環基は、群Ｄより選ばれる１以上の置換基で置換されていてもよい｝を表し、
　Ｒ１４、Ｒ１６、Ｒ１８、Ｒ１９、Ｒ２１、Ｒ２２、及びＲ２８は、同一又は相異なり、Ｃ１－Ｃ６鎖式炭化水素基、Ｃ３－Ｃ１０脂環式炭化水素基｛該Ｃ１－Ｃ６鎖式炭化水素基及び該Ｃ３－Ｃ１０脂環式炭化水素基は、１以上のハロゲン原子で置換されていてもよい｝、又は水素原子を表し、
　Ｒ１３及びＲ１４は、それらが結合する炭素原子と一緒になって、Ｃ３－Ｃ１０脂環式炭化水素基又は３－１０員非芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基及び該３－１０員非芳香族複素環基は、群Ｄより選ばれる１以上の置換基で置換されていてもよい｝を形成していてもよく、
　Ｒ１７及びＲ１８は、それらが結合する炭素原子と一緒になって、Ｃ３－Ｃ１０脂環式炭化水素基又は３－１０員非芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基及び該３－１０員非芳香族複素環基は、群Ｄより選ばれる１以上の置換基で置換されていてもよい｝を形成していてもよい。
　群Ａ：Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６アルキルチオ基｛該Ｃ１－Ｃ６アルコキシ基及び該Ｃ１－Ｃ６アルキルチオ基は、群Ｆより選ばれる１以上の置換基で置換されていてもよい｝、Ｃ３－Ｃ１０脂環式炭化水素基、３－１０員非芳香族複素環基、Ｃ６－Ｃ１０アリール基、５－１０員芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基、該３－１０員非芳香族複素環基、該Ｃ６－Ｃ１０アリール基、及び該５－１０員芳香族複素環基は、群Ｄより選ばれる１以上の置換基で置換されていてもよい｝、シアノ基、ニトロ基、ヒドロキシ基、ハロゲン原子、オキソ基、及びチオキソ基からなる群。
　群Ｂ：オキソ基、チオキソ基、Ｃ１－Ｃ６鎖式炭化水素基、Ｃ１－Ｃ６アルコキシ基｛該Ｃ１－Ｃ６鎖式炭化水素基及び該Ｃ１－Ｃ６アルコキシ基は、１以上のハロゲン原子で置換されていてもよい｝、ハロゲン原子、及びシアノ基からなる群。
　群Ｃ：Ｃ１－Ｃ６鎖式炭化水素基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６アルキルチオ基｛該Ｃ１－Ｃ６鎖式炭化水素基、該Ｃ１－Ｃ６アルコキシ基、及び該Ｃ１－Ｃ６アルキルチオ基は、群Ｆより選ばれる１以上の置換基で置換されていてもよい｝、群Ｂより選ばれる１以上の置換基で置換されていてもよいＣ３－Ｃ６シクロアルキル基、シアノ基、ニトロ基、ハロゲン原子、及びヒドロキシ基からなる群。
　群Ｄ：Ｃ１－Ｃ６鎖式炭化水素基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ２－Ｃ６アルコキシカルボニル基、｛該Ｃ１－Ｃ６鎖式炭化水素基、該Ｃ１－Ｃ６アルコキシ基、該Ｃ１－Ｃ６アルキルチオ基、及び該Ｃ２－Ｃ６アルコキシカルボニル基は、群Ｇより選ばれる１以上の置換基で置換されていてもよい｝、Ｃ３－Ｃ１０脂環式炭化水素基、３－１０員非芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基及び該３－１０員非芳香族複素環基は、群Ｂより選ばれる１以上の置換基で置換されていてもよい｝、Ｃ６－Ｃ１０アリール基、５－１０員芳香族複素環基｛該Ｃ６－Ｃ１０アリール基及び該５－１０員芳香族複素環基は、群Ｃより選ばれる１以上の置換基で置換されていてもよい｝、Ｌ３Ｒ２４、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、及びアミノ基からなる群。
　Ｌ３は、酸素原子又はＳ（Ｏ）ｍを表し、
　ｍは、０、１、又は２を表し、
　Ｒ２４は、Ｃ６－Ｃ１０アリール基又は５－１０員芳香族複素環基｛該Ｃ６－Ｃ１０アリール基及び該５－１０員芳香族複素環基は、群Ｃより選ばれる１以上の置換基で置換されていてもよい｝を表す。
　群Ｆ：Ｃ１－Ｃ６アルコキシ基、Ｃ３－Ｃ６シクロアルキル基｛該Ｃ１－Ｃ６アルコキシ基及び該Ｃ３－Ｃ６シクロアルキル基は、１以上のハロゲン原子で置換されていてもよい｝、及びハロゲン原子からなる群。
　群Ｇ：Ｃ１－Ｃ６アルコキシ基、Ｃ３－Ｃ６シクロアルキル基｛該Ｃ１－Ｃ６アルコキシ基及び該Ｃ３－Ｃ６シクロアルキル基は、１以上のハロゲン原子で置換されていてもよい｝、Ｃ６－Ｃ１０アリール基、５－１０員芳香族複素環基｛該Ｃ６－Ｃ１０アリール基及び該５－１０員芳香族複素環基は、群Ｃより選ばれる１以上の置換基で置換されていてもよい｝、及びハロゲン原子からなる群。〕
で示される化合物（以下、本発明化合物Ｎと記す）、若しくはそのＮオキシド又はそれらの塩（以下、式（Ｉ）で示される化合物、若しくはそのＮオキシド又はそれらの塩を、本発明化合物と記す）。
〔２〕　Ｘ１がＣＨであり、Ｒ１、Ｒ２、及びＲ３が、同一又は相異なり、Ｃ１－Ｃ６アルキル基、ハロゲン原子、又は水素原子である、〔１〕に記載の化合物、若しくはそのＮオキシド又はそれらの塩。
〔３〕　Ｘ１が窒素原子であり、Ｒ１、Ｒ２、及びＲ３が、同一又は相異なり、Ｃ１－Ｃ６アルキル基、ハロゲン原子、又は水素原子である、〔１〕に記載の化合物、若しくはそのＮオキシド又はそれらの塩。
〔４〕　ＪがＪ１で示される基であり、Ｅが群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、群Ｄより選ばれる１以上の置換基で置換されていてもよいＣ６－Ｃ１０アリール基、群Ｄより選ばれる１以上の置換基で置換されていてもよい５－１０員芳香族複素環基、又はＣ（Ｏ）ＯＲ２５である、〔１〕～〔３〕のいずれかに記載の化合物、若しくはそのＮオキシド又はそれらの塩。
〔５〕　ＪがＪ２で示される基であり、Ｅが群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、群Ｄより選ばれる１以上の置換基で置換されていてもよいＣ６－Ｃ１０アリール基、群Ｄより選ばれる１以上の置換基で置換されていてもよい５－１０員芳香族複素環基、ＣＨ２－Ｌ１－Ｒ１２、ＣＨ２－Ｏ－Ｎ＝ＣＲ１３Ｒ１４、Ｃ（Ｒ１６）＝Ｎ－Ｏ－Ｒ１５、Ｃ（Ｒ１９）＝Ｎ－Ｎ＝ＣＲ１７Ｒ１８、Ｃ（Ｒ２２）＝Ｎ－ＮＲ２０Ｒ２１、Ｌ２Ｒ２３、又はハロゲン原子である、〔１〕～〔３〕のいずれかに記載の化合物、若しくはそのＮオキシド又はそれらの塩。
〔６〕　〔１〕～〔５〕のいずれかに記載の化合物、若しくはそのＮオキシド又はそれらの塩と不活性担体とを含有する農薬組成物。
〔７〕　群（ａ）、群（ｂ）、群（ｃ）及び群（ｄ）からなる群より選ばれる１以上の成分、並びに、〔１〕～〔５〕のいずれかに記載の化合物、若しくはそのＮオキシド又はそれらの塩を含有する組成物：
　　群（ａ）：殺虫活性成分、殺ダニ活性成分及び殺線虫活性成分からなる群；
　　群（ｂ）：殺菌活性成分；
　　群（ｃ）：植物成長調整成分；
　　群（ｄ）：忌避成分。
〔８〕　〔１〕～〔５〕のいずれかに記載の化合物、若しくはそのＮオキシド若しくはそれらの塩の有効量又は〔７〕に記載の組成物の有効量を植物又は土壌に処理することによる有害生物防除方法。
〔９〕　〔１〕～〔５〕のいずれかに記載の化合物、若しくはそのＮオキシド若しくはそれらの塩の有効量又は〔７〕に記載の組成物の有効量をダイズ又はダイズを生育する土壌に施用することによる、ミトコンドリアチトクロームｂタンパク質にＦ１２９Ｌのアミノ酸置換を有するダイズさび病菌の防除方法。
〔１０〕　有害生物を防除するための、〔１〕～〔５〕のいずれかに記載の化合物、若しくはそのＮオキシド若しくはそれらの塩又は〔７〕に記載の組成物の使用。
〔１１〕　〔１〕～〔５〕のいずれかに記載の化合物、若しくはそのＮオキシド若しくはそれらの塩の有効量又は〔７〕に記載の組成物の有効量を保持している種子又は栄養生殖器官。 [Means for Solving the Problems] As a result of investigations aimed at discovering compounds having excellent control efficacy against pests, the present inventors have found that the compound represented by the following formula (I) has excellent control efficacy against pests.
That is, the present invention is as follows.
[1] Formula (I):
Figure JPOXMLDOC01-appb-C000003
 [In the formula,
X 1 represents CH or a nitrogen atom,
X 2 represents a C(O)OCH 3 , C(O)NHCH 3 , or 5,6-dihydro-1,4,2-dioxazin-3-yl group;
R 1 , R 2 , and R 3 are the same or different and are a C1-C6 alkyl group, a C1-C6 alkoxy group, a C3-C6 cycloalkyl group, a C2-C6 alkoxycarbonyl group {the C1-C6 alkyl group, the The C1-C6 alkoxy group, the C3-C6 cycloalkyl group, and the C2-C6 alkoxycarbonyl group may be substituted with one or more halogen atoms}, a cyano group, a nitro group, a halogen atom, or a hydrogen atom represents
The combination of J and E is
J is a group represented by J1,
E is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C10 alicyclic hydrocarbon group, a 3-10 membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10 membered aromatic heterocyclic group {the C3-C10 alicyclic hydrocarbon group, the 3-10 membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10 The membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group D}, C(O)OR 25 , C(O)R 26 , or C(O)NR 27 R 28 or
J is a group represented by J2,
E is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C10 alicyclic hydrocarbon group, a 3-10 membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10 membered aromatic heterocyclic group {the C3-C10 alicyclic hydrocarbon group, the 3-10 membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10 The membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D}, CH 2 —L 1 —R 12 , CH 2 —O—N=CR 13 R 14 , C( R 16 )=NO-R 15 , C(R 19 )=NN=CR 17 R 18 , C(R 22 )=N-NR 20 R 21 , L 2 R 23 , cyano group, nitro group, or represents a combination that is a halogen atom,
The group represented by J1 and the group represented by J2 are groups represented by the following formulae,
Figure JPOXMLDOC01-appb-C000004
 # represents the bonding position with E,
X3 represents CR4 or a nitrogen atom ,
X4 represents CR5 or a nitrogen atom;
X5 represents CR6 or a nitrogen atom,
X 6 is an oxygen atom, a sulfur atom, N(R 7 ), *-C(R 8 )=C(R 9 )-, *-C(R 10 )=N-, or *-N=C(R 11 ) represents -,
* represents the binding position with X5 ,
R 4 , R 5 , R 6 , R 8 , R 9 , R 10 and R 11 are the same or different, C1-C6 alkyl group, C1-C6 alkoxy group, C3-C6 cycloalkyl group, C2-C6 an alkoxycarbonyl group {the C1-C6 alkyl group, the C1-C6 alkoxy group, the C3-C6 cycloalkyl group, and the C2-C6 alkoxycarbonyl group may be substituted with one or more halogen atoms}; represents a cyano group, a nitro group, a halogen atom, or a hydrogen atom,
R 7 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group {the C1-C6 alkyl group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, or a hydrogen atom represents
L 1 and L 2 are the same or different and represent an oxygen atom or S(O) n ,
n represents 0, 1, or 2;
R 12 , R 13 , R 15 , R 17 , R 20 , R 23 , R 25 , R 26 and R 27 are the same or different and may be substituted with one or more substituents selected from group A A good C1-C6 chain hydrocarbon group, C3-C10 alicyclic hydrocarbon group, 3-10 membered non-aromatic heterocyclic group, C6-C10 aryl group, or 5-10 membered aromatic heterocyclic group {the C3 -C10 alicyclic hydrocarbon group, said 3-10 membered non-aromatic heterocyclic group, said C6-C10 aryl group, and said 5-10 membered aromatic heterocyclic group are substituted with one or more selected from group D may be substituted with a group],
R 14 , R 16 , R 18 , R 19 , R 21 , R 22 and R 28 are the same or different and are C1-C6 chain hydrocarbon groups, C3-C10 alicyclic hydrocarbon groups {the C1- The C6 chain hydrocarbon group and the C3-C10 alicyclic hydrocarbon group may be substituted with one or more halogen atoms}, or represent a hydrogen atom,
R 13 and R 14 together with the carbon atom to which they are attached are a C3-C10 alicyclic hydrocarbon group or a 3-10 membered non-aromatic heterocyclic group {the C3-C10 alicyclic hydrocarbon group and the 3- to 10-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from group D} may be formed,
R 17 and R 18 together with the carbon atom to which they are attached are a C3-C10 alicyclic hydrocarbon group or a 3-10 membered non-aromatic heterocyclic group {the C3-C10 alicyclic hydrocarbon group and said 3- to 10-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from Group D}.
Group A: C1-C6 alkoxy group, C1-C6 alkylthio group {the C1-C6 alkoxy group and the C1-C6 alkylthio group may be substituted with one or more substituents selected from group F}, C3 -C10 alicyclic hydrocarbon group, 3-10 membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10 membered aromatic heterocyclic group {the C3-C10 alicyclic hydrocarbon group, the 3- The 10-membered non-aromatic heterocyclic group, the C6-C10 aryl group, and the 5-10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group D}, cyano group , a nitro group, a hydroxy group, a halogen atom, an oxo group, and a thioxo group.
Group B: an oxo group, a thioxo group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group and the C1-C6 alkoxy group are substituted with one or more halogen atoms; optionally], a halogen atom, and a cyano group.
Group C: a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylthio group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, and the C1-C6 alkylthio group are optionally substituted with one or more substituents selected from group F}, optionally substituted with one or more substituents selected from group B C3-C6 cycloalkyl group, cyano group, nitro group, halogen A group consisting of an atom and a hydroxy group.
Group D: C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylthio group, C2-C6 alkoxycarbonyl group, {said C1-C6 chain hydrocarbon group, said C1-C6 alkoxy group, said C1-C6 alkylthio group and said C2-C6 alkoxycarbonyl group optionally substituted with one or more substituents selected from group G}, C3-C10 alicyclic hydrocarbon group, 3-10 membered non- aromatic heterocyclic group {the C3-C10 alicyclic hydrocarbon group and the 3-10-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B}, C6 -C10 aryl group, 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C good}, the group consisting of L 3 R 24 , a halogen atom, a cyano group, a nitro group, a hydroxy group, and an amino group.
L3 represents an oxygen atom or S ( O) m ,
m represents 0, 1, or 2;
R 24 is a C6-C10 aryl group or a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group are one or more substituents selected from Group C; may be substituted}.
Group F: from a C1-C6 alkoxy group, a C3-C6 cycloalkyl group {the C1-C6 alkoxy group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, and a halogen atom the group.
Group G: C1-C6 alkoxy group, C3-C6 cycloalkyl group {the C1-C6 alkoxy group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C}, and a group consisting of halogen atoms. ]
The compound represented by (hereinafter referred to as the compound N of the present invention), or its N oxide or a salt thereof (hereinafter, the compound represented by formula (I), or its N oxide or a salt thereof is referred to as the compound of the present invention ).
[2] the compound of [1], wherein X 1 is CH, and R 1 , R 2 , and R 3 are the same or different and are a C1-C6 alkyl group, a halogen atom, or a hydrogen atom, or N-oxides thereof or salts thereof.
[3] the compound of [1], wherein X 1 is a nitrogen atom, and R 1 , R 2 and R 3 are the same or different and are a C1-C6 alkyl group, a halogen atom or a hydrogen atom; or its N-oxide or a salt thereof.
[4] J is a group represented by J1, E is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, one or more substituents selected from group D a C6-C10 aryl group optionally substituted with a group, a 5-10 membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group D, or C(O)OR 25 , the compound according to any one of [1] to [3], its N oxide, or a salt thereof.
[5] J is a group represented by J2, E is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, one or more substituents selected from group D a C6-C10 aryl group optionally substituted with a group, a 5-10 membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group D, CH 2 -L 1 -R 12 , CH 2 —O—N=CR 13 R 14 , C(R 16 )=N—O—R 15 , C(R 19 )=N—N=CR 17 R 18 , C(R 22 )=N—NR 20 The compound according to any one of [1] to [3], which is R 21 , L 2 R 23 , or a halogen atom, or its N oxide, or a salt thereof.
[6] An agricultural chemical composition containing the compound according to any one of [1] to [5], or its N oxide or salt thereof, and an inert carrier.
[7] one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound according to any one of [1] to [5], or a composition containing its N-oxide or salt thereof:
Group (a): a group consisting of an insecticidal active ingredient, an acaricidal active ingredient and a nematicidal active ingredient;
Group (b): fungicidal active ingredient;
Group (c): plant growth regulating ingredients;
Group (d): repellent ingredients.
[8] By treating plants or soil with an effective amount of the compound according to any one of [1] to [5], or its N oxide or salt thereof, or an effective amount of the composition according to [7] pest control method.
[9] adding an effective amount of the compound according to any one of [1] to [5], or its N oxide or salt thereof, or an effective amount of the composition according to [7] to soybeans or soil for growing soybeans; A method for controlling a soybean rust fungus having an F129L amino acid substitution in the mitochondrial cytochrome b protein by applying.
[10] Use of the compound according to any one of [1] to [5], its N-oxide or salt thereof, or the composition according to [7] for controlling pests.
[11] A seed or vegetative reproduction that retains an effective amount of the compound according to any one of [1] to [5], or its N oxide or salt thereof, or an effective amount of the composition according to [7] organ.
　本発明により、有害生物を防除することができる。 With the present invention, pests can be controlled.
　本発明における置換基について説明する。
　ハロゲン原子とは、フッ素原子、塩素原子、臭素原子、又はヨウ素原子を意味する。
　置換基が２以上のハロゲン原子で置換されている場合、それらのハロゲン原子は各々同一でも異なっていてもよい。
　置換基が特定の群（例えばＣ１－Ｃ３アルキル基及びハロゲン原子からなる群）より選ばれる２以上の基又は原子で置換されている場合、それらの基又は原子は各々同一であっても異なっていてもよい。
　本明細書における「群Ｘより選ばれる１以上の置換基で置換されていてもよい」（ＸはＡ、Ｂ、Ｃ、Ｄ、Ｅ、Ｆ、およびＧのいずれか１つを意味する）との表記は、群Ｘより選ばれる置換基が２つ以上存在する場合、それらの置換基は各々同一でも異なっていてもよい。
　本明細書における「ＣＸ－ＣＹ」との表記は、炭素原子数がＸ乃至Ｙであることを意味する。例えば「Ｃ１－Ｃ６」との表記は、炭素原子数が１乃至６であることを意味する。
　鎖式炭化水素基とは、アルキル基、アルケニル基又はアルキニル基を表す。
　アルキル基としては、例えばメチル基、エチル基、プロピル基、イソプロピル基、１，１－ジメチルプロピル基、１，２－ジメチルプロピル基、ブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基、ペンチル基、及びヘキシル基が挙げられる。
　アルケニル基としては、例えばビニル基、１－プロペニル基、２－プロペニル基、１－メチル－１－プロペニル基、１－メチル－２－プロペニル基、１，２－ジメチル－１－プロペニル基、３－ブテニル基、４－ペンテニル基、及び５－ヘキセニル基が挙げられる。
　アルキニル基としては、例えばエチニル基、１－プロピニル基、２－プロピニル基、１－メチル－２－プロピニル基、１，１－ジメチル－２－プロピニル基、２－ブチニル基、４－ペンチニル基、及び５－ヘキシニル基が挙げられる。
　アルコキシ基としては、例えばメトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、ｔｅｒｔ－ブトキシ基、ペンチルオキシ基、及びヘキシルオキシ基が挙げられる。
　アルキルチオ基としては、例えば、メチルチオ基、エチルチオ基、イソプロピルチオ基、及びヘキシルチオ基が挙げられる。
　アルコキシカルボニル基としては、例えばメトキシカルボニル基、イソプロポキシカルボニル基、及びヘキシルオキシカルボニル基が挙げられる。
　脂環式炭化水素基としては、例えばシクロアルキル基又はシクロアルケニル基が挙げられる。
　シクロアルキル基としては、例えばシクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、ビシクロ［６．５．０］ノニル基、及びビシクロ［６．６．０］デシル基が挙げられる。
　シクロアルケニル基としては、例えばシクロペンテニル基及びシクロヘキセニル基が挙げられる。また、該シクロアルケニル基はベンゼン環が縮合していてもよく、例えばインダニル基及びテトラヒドロナフチル基が挙げられる。
　アリール基としては、例えばフェニル基及びナフチル基が挙げられる。
　芳香族複素環基としては、例えばピロリル基、フラニル基、チエニル基、ピラゾリル基、イミダゾリル基、トリアゾリル基、テトラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、オキサジアゾリル基及びチアジアゾリル基等の５員芳香族複素環基；ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基及びテトラジニル基の６員芳香族複素環基；インダゾリル基、インドリジニル基、及びイミダゾピリジル基等の９員芳香族複素環基；キノリル基、イソキノリル基、キナゾリニル基、ナフチリジニル基、及びベンゾピラニル基等の１０員芳香族複素環基が挙げられる。
　非芳香族複素環基としては、例えば、アジリジニル基、オキシラニル基、チイラニル基、アゼチジニル基、オキセタニル基、チエタニル基、ピロリジニル基、テトラヒドロフラニル基、テトラヒドロチエニル基、ピラゾリニル基、ピラゾリジニル基、イミダゾリニル基、イミダゾリジニル基、オキサゾリニル基、チアゾリニル基、オキサゾリジニル基、チアゾリジニル基、イソオキサゾリニル基、イソオキサゾリジニル基、イソチアゾリニル基、イソチアゾリジニル基、ジオキソラニル基、ジオキサニル基、ピペリジル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ピラニル基、ジヒドロピラニル基、テトラヒドロピラニル基、テトラヒドロチオピラニル基、アゼパニル基、オキセパニル基、チエパニル基、ジヒドロベンゾフラニル基、１，３－ベンゾジオキソリル基、及びジヒドロベンゾピラニル基が挙げられる。 The substituents in the present invention will be explained.
A halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
When a substituent is substituted with two or more halogen atoms, each of those halogen atoms may be the same or different.
When the substituent is substituted with two or more groups or atoms selected from a specific group (for example, the group consisting of C1-C3 alkyl groups and halogen atoms), each of these groups or atoms may be the same or different. may
In the present specification, "optionally substituted with one or more substituents selected from group X" (X means any one of A, B, C, D, E, F, and G) When there are two or more substituents selected from group X, the notation of may be the same or different.
The notation "CX-CY" used herein means that the number of carbon atoms is from X to Y. For example, the notation "C1-C6" means 1 to 6 carbon atoms.
A chain hydrocarbon group represents an alkyl group, an alkenyl group or an alkynyl group.
Examples of alkyl groups include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, and hexyl groups.
Examples of alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 3- butenyl, 4-pentenyl, and 5-hexenyl groups.
Examples of alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 4-pentynyl, and A 5-hexynyl group can be mentioned.
Alkoxy groups include, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy groups.
Alkylthio groups include, for example, methylthio, ethylthio, isopropylthio, and hexylthio groups.
Alkoxycarbonyl groups include, for example, methoxycarbonyl, isopropoxycarbonyl, and hexyloxycarbonyl groups.
Alicyclic hydrocarbon groups include, for example, cycloalkyl groups and cycloalkenyl groups.
Cycloalkyl groups include, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, bicyclo[6.5.0]nonyl, and bicyclo[6.6.0]decyl groups.
Cycloalkenyl groups include, for example, cyclopentenyl and cyclohexenyl groups. Moreover, the cycloalkenyl group may be condensed with a benzene ring, and examples thereof include an indanyl group and a tetrahydronaphthyl group.
Aryl groups include, for example, phenyl and naphthyl groups.
Examples of aromatic heterocyclic groups include pyrrolyl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl and thiadiazolyl groups. 6-membered aromatic heterocyclic groups such as pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group and tetrazinyl group; 9-membered aromatic heterocyclic groups such as indazolyl group, indolizinyl group and imidazopyridyl group; Cyclic groups; 10-membered aromatic heterocyclic groups such as quinolyl, isoquinolyl, quinazolinyl, naphthyridinyl, and benzopyranyl groups.
Non-aromatic heterocyclic groups include, for example, aziridinyl, oxiranyl, thiiranyl, azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothienyl, pyrazolinyl, pyrazolidinyl, imidazolinyl and imidazolidinyl. group, oxazolinyl group, thiazolinyl group, oxazolidinyl group, thiazolidinyl group, isoxazolinyl group, isoxazolidinyl group, isothiazolinyl group, isothiazolidinyl group, dioxolanyl group, dioxanyl group, piperidyl group, piperazinyl group, morpholinyl group , thiomorpholinyl group, pyranyl group, dihydropyranyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, azepanyl group, oxepanyl group, thiepanyl group, dihydrobenzofuranyl group, 1,3-benzodioxolyl group, and dihydro A benzopyranyl group is mentioned.
　本明細書における用語について説明する。
　ミトコンドリアチトクロームｂタンパク質にＦ１２９Ｌのアミノ酸置換を有するダイズさび病菌とは、ミトコンドリアチトクロームタンパク質をコードするミトコンドリアチトクロームｂ遺伝子中に変異を有し、該変異の結果としてＦ１２９Ｌのアミノ酸置換が起こったことにより、ＱｏＩ殺菌剤に抵抗性を示すダイズさび病菌（学名：Phakopsora pachyrhizi）である。 Terms used in this specification will be explained.
The soybean rust fungus having an F129L amino acid substitution in the mitochondrial cytochrome b protein has a mutation in the mitochondrial cytochrome b gene that encodes the mitochondrial cytochrome protein, and as a result of the mutation, the F129L amino acid substitution occurred, resulting in QoI It is a fungicide-resistant soybean rust fungus (scientific name: Phakopsora pachyrhizi).
　本発明化合物は、一つ以上の立体異性体が存在する場合がある。立体異性体としては、エナンチオマー、ジアステレオマー、アトロプ異性体及び幾何異性体が挙げられる。本発明には各立体異性体及び任意の比率の立体異性体混合物が含まれる。
　幾何異性体としては、例えば以下の構造が挙げられる。
Figure JPOXMLDOC01-appb-C000005
 Compounds of the present invention may exist in one or more stereoisomers. Stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. The present invention includes each stereoisomer and mixtures of stereoisomers in any proportion.
Geometric isomers include, for example, the following structures.
Figure JPOXMLDOC01-appb-C000005
　本発明化合物Ｎ又はそのＮオキシドは、塩酸、硫酸、硝酸、リン酸、酢酸、安息香酸等の酸と混合することにより、塩酸塩、硫酸塩、硝酸塩、リン酸塩、酢酸塩、安息香酸塩等の酸付加塩を形成することがある。 Compound N of the present invention or its N oxide can be mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid and benzoic acid to obtain hydrochloride, sulfate, nitrate, phosphate, acetate and benzoate. may form an acid addition salt such as
　本発明化合物Ｎの態様としては、以下の化合物が挙げられる。 Embodiments of the compound N of the present invention include the following compounds.
〔態様１〕本発明化合物Ｎにおいて、Ｘ１がＣＨである化合物。
〔態様２〕本発明化合物Ｎにおいて、Ｘ１が窒素原子である化合物。
〔態様３〕本発明化合物Ｎにおいて、Ｘ１がＣＨであり、Ｘ２が、Ｃ（Ｏ）ＯＣＨ３、又はＣ（Ｏ）ＮＨＣＨ３である化合物。
〔態様４〕本発明化合物Ｎにおいて、Ｘ１が窒素原子であり、Ｘ２が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基である化合物。
〔態様５〕本発明化合物Ｎにおいて、Ｒ１、Ｒ２、及びＲ３が、同一又は相異なり、Ｃ１－Ｃ６アルキル基、Ｃ３－Ｃ６シクロアルキル基｛該Ｃ１－Ｃ６アルキル基及び該Ｃ３－Ｃ６シクロアルキル基は、１以上のハロゲン原子で置換されていてもよい｝、シアノ基、ニトロ基、ハロゲン原子、又は水素原子である化合物。
〔態様６〕本発明化合物Ｎにおいて、Ｒ１、Ｒ２、及びＲ３が、同一又は相異なり、１以上のハロゲン原子で置換されていてもよいＣ１－Ｃ６アルキル基、ハロゲン原子、又は水素原子である化合物。
〔態様７〕本発明化合物Ｎにおいて、Ｒ１、Ｒ２、及びＲ３が、同一又は相異なり、メチル基、ハロゲン原子、又は水素原子である化合物。
〔態様８〕本発明化合物Ｎにおいて、ＪがＪ１で示される基である化合物。
〔態様９〕本発明化合物Ｎにおいて、ＪがＪ２で示される基である化合物。
〔態様１０〕本発明化合物Ｎにおいて、Ｘ３がＣＲ４又は窒素原子であり、Ｘ４がＣＲ５であり、Ｘ５がＣＲ６又は窒素原子であり、Ｘ６が、酸素原子、硫黄原子、Ｎ（Ｒ7）、又は＊－Ｃ（Ｒ8）＝Ｃ（Ｒ9）－である化合物。
〔態様１１〕本発明化合物Ｎにおいて、Ｘ３がＣＲ４であり、Ｘ４がＣＲ５であり、Ｘ５がＣＲ６であり、Ｘ６が＊－Ｃ（Ｒ8）＝Ｃ（Ｒ9）－である化合物。
〔態様１２〕本発明化合物Ｎにおいて、ＪがＪ１で示される基であり、Ｘ３がＣＲ４又は窒素原子であり、Ｘ4がＣＲ5である化合物。
〔態様１３〕本発明化合物Ｎにおいて、ＪがＪ１で示される基であり、Ｘ３がＣＲ４であり、Ｘ４がＣＲ６である化合物。
〔態様１４〕本発明化合物Ｎにおいて、ＪがＪ２で示される基であり、Ｘ５がＣＲ６又は窒素原子であり、Ｘ6が、酸素原子、硫黄原子、Ｎ（Ｒ７）、又は＊－Ｃ（Ｒ８）＝Ｃ（Ｒ９）－である化合物。
〔態様１５〕本発明化合物Ｎにおいて、ＪがＪ２で示される基であり、Ｘ5がＣＲ6であり、Ｘ6が＊－Ｃ（Ｒ8）＝Ｃ（Ｒ9）－である化合物。
〔態様１６〕態様１～１５、又は本発明化合物Ｎのいずれかにおいて、Ｅが、群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基である化合物。
〔態様１７〕態様１～１５、又は本発明化合物Ｎのいずれかにおいて、ＥがＣ１－Ｃ６鎖式炭化水素基である化合物。
〔態様１８〕態様１～１５、又は本発明化合物Ｎのいずれかにおいて、Ｅが、群Ｄより選ばれる１以上の置換基で置換されていてもよいＣ３－Ｃ１０脂環式炭化水素基である化合物。
〔態様１９〕態様１～１５、又は本発明化合物Ｎのいずれかにおいて、Ｅが、Ｃ３－Ｃ１０脂環式炭化水素基である化合物。
〔態様２０〕態様１～１５、又は本発明化合物Ｎのいずれかにおいて、Ｅが、群Ｄより選ばれる１以上の置換基で置換されていてもよいＣ６－Ｃ１０アリール基である化合物。
〔態様２１〕態様１～１５、又は本発明化合物Ｎのいずれかにおいて、Ｅが、群Ｄより選ばれる１以上の置換基で置換されていてもよい５－１０員芳香族複素環基である化合物。
〔態様２２〕態様１～１５、又は本発明化合物Ｎのいずれかにおいて、Ｅが、Ｃ６－Ｃ１０アリール基である化合物。
〔態様２３〕態様１～７、態様１２、態様１３、又は本発明化合物Ｎのいずれかにおいて、ＪがＪ１で示される基であり、Ｅが、Ｃ（Ｏ）ＯＲ２５、Ｃ（Ｏ）Ｒ２６、又はＣ（Ｏ）ＮＲ２７Ｒ２８である化合物。
〔態様２４〕態様１～７、態様１２、態様１３、又は本発明化合物Ｎのいずれかにおいて、ＪがＪ１で示される基であり、Ｅが、Ｃ（Ｏ）ＯＲ２５である化合物。〔態様２５〕態様１～７、態様１４、態様１５、又は本発明化合物Ｎのいずれかにおいて、ＪがＪ２で示される基であり、Ｅが、ＣＨ２－Ｌ１－Ｒ１２、又はＣＨ２－Ｏ－Ｎ＝ＣＲ１３Ｒ１４である化合物。
〔態様２６〕態様１～７、態様１４、態様１５、又は本発明化合物Ｎのいずれかにおいて、ＪがＪ２で示される基であり、ＥがＣＨ２－Ｌ１－Ｒ１２である化合物。
〔態様２７〕態様１～７、態様１４、態様１５、又は本発明化合物Ｎのいずれかにおいて、ＪがＪ２で示される基であり、ＥがＣＨ２－Ｏ－Ｎ＝ＣＲ１３Ｒ１４である化合物。
〔態様２８〕態様１～７、態様１４、態様１５、又は本発明化合物Ｎのいずれかにおいて、ＪがＪ２で示される基であり、ＥがＣ（Ｒ１６）Ｎ＝Ｏ－Ｒ１５である化合物。
〔態様２９〕態様１～７、態様１４、態様１５、又は本発明化合物Ｎのいずれかにおいて、ＪがＪ２で示される基であり、ＥがＬ2Ｒ23であり、Ｌ2が酸素原子である化合物。
〔態様３０〕態様１～７、態様１４、態様１５、又は本発明化合物Ｎのいずれかにおいて、ＪがＪ２で示される基であり、Ｅがハロゲン原子である化合物。
〔態様３１〕本発明化合物Ｎにおいて、Ｊ及びＥの組合せが、ＪがＪ１で示される基であり、Ｅが、群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、群Ｄより選ばれる１以上の置換基で置換されていてもよいＣ６－Ｃ１０アリール基、Ｃ（Ｏ）ＯＲ２５、Ｃ（Ｏ）Ｒ２６、又はＣ（Ｏ）ＮＲ２７Ｒ２８である組合せ；又は、ＪがＪ２で示される基であり、Ｅが、群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、又は群Ｄより選ばれる１以上の置換基で置換されていてもよいＣ６－Ｃ１０アリール基である組合せである化合物。
〔態様３２〕本発明化合物Ｎにおいて、Ｊ及びＥの組合せが、ＪがＪ１で示される基であり、Ｅが、Ｃ１－Ｃ６鎖式炭化水素基、Ｃ６－Ｃ１０アリール基、又はＣ（Ｏ）ＯＲ２５である組合せ；又は、ＪがＪ２で示される基であり、Ｅが、Ｃ１－Ｃ６鎖式炭化水素基、又は群Ｄより選ばれる１以上の置換基で置換されていてもよい５－１０員芳香族複素環基である組合せである化合物。
〔態様３３〕本発明化合物Ｎにおいて、Ｊ及びＥの組合せが、ＪがＪ１で示される基であり、Ｅが、群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、群Ｄより選ばれる１以上の置換基で置換されていてもよいＣ６－Ｃ１０アリール基、Ｃ（Ｏ）ＯＲ２５、Ｃ（Ｏ）Ｒ２６、又はＣ（Ｏ）ＮＲ２７Ｒ２８である組合せ；又は、ＪがＪ２で示される基であり、Ｅが、群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、又は群Ｄより選ばれる１以上の置換基で置換されていてもよいＣ６－Ｃ１０アリール基である組合せであり、Ｘ１がＣＨであり、Ｒ１、Ｒ２、及びＲ３が、水素原子であり、Ｘ３がＣＲ４であり、Ｘ４がＣＲ５であり、Ｘ５がＣＲ６であり、Ｘ６が＊－Ｃ（Ｒ８）＝Ｃ（Ｒ９）－である化合物。
〔態様３４〕本発明化合物Ｎにおいて、Ｊ及びＥの組合せが、ＪがＪ１で示される基であり、Ｅが、Ｃ１－Ｃ６鎖式炭化水素基、Ｃ６－Ｃ１０アリール基、又はＣ（Ｏ）ＯＲ２５である組合せ；又は、ＪがＪ２で示される基であり、Ｅが、Ｃ１－Ｃ６鎖式炭化水素基、又はＣ６－Ｃ１０アリール基である組合せであり、Ｘ１がＣＨであり、Ｘ２が、Ｃ（Ｏ）ＯＣＨ３、又はＣ（Ｏ）ＮＨＣＨ３であり、Ｒ１、Ｒ２、及びＲ３が、水素原子であり、Ｘ３がＣＲ４であり、Ｘ４がＣＲ５であり、Ｘ５がＣＲ６であり、Ｘ６が＊－Ｃ（Ｒ８）＝Ｃ（Ｒ９）－である化合物。 [Aspect 1] A compound in which X 1 is CH in the compound N of the present invention.
[Aspect 2] A compound N in which X 1 is a nitrogen atom in the compound N of the present invention.
[Aspect 3] Compound N of the present invention, wherein X 1 is CH and X 2 is C(O)OCH 3 or C(O)NHCH 3 .
[Aspect 4] A compound N in which X 1 is a nitrogen atom and X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group in the compound N of the present invention.
[Aspect 5] In the compound N of the present invention, R 1 , R 2 and R 3 are the same or different, a C1-C6 alkyl group, a C3-C6 cycloalkyl group {the C1-C6 alkyl group and the C3-C6 A cycloalkyl group may be substituted with one or more halogen atoms}, a cyano group, a nitro group, a halogen atom, or a hydrogen atom.
[Aspect 6] In the compound N of the present invention, R 1 , R 2 and R 3 are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a halogen atom or a hydrogen atom A compound that is
[Aspect 7] A compound N in which R 1 , R 2 and R 3 are the same or different and are a methyl group, a halogen atom or a hydrogen atom in the compound N of the present invention.
[Embodiment 8] In the compound N of the present invention, J is a group represented by J1.
[Aspect 9] In the compound N of the present invention, J is a group represented by J2.
[Aspect 10] In the compound N of the present invention, X 3 is CR 4 or a nitrogen atom, X 4 is CR 5 , X 5 is CR 6 or a nitrogen atom, X 6 is an oxygen atom, a sulfur atom, N(R 7 ), or *-C(R 8 )=C(R 9 )-.
[Embodiment 11] In the compound N of the present invention, X 3 is CR 4 , X 4 is CR 5 , X 5 is CR 6 , and X 6 is *-C(R 8 )=C(R 9 ) - is a compound.
[Aspect 12 ] The compound N of the present invention, wherein J is a group represented by J1 , X3 is CR4 or a nitrogen atom, and X4 is CR5.
[Aspect 13 ] The compound N of the present invention, wherein J is a group represented by J1, X3 is CR4 , and X4 is CR6 .
[Aspect 14] In the compound N of the present invention, J is a group represented by J2, X 5 is CR 6 or a nitrogen atom, X 6 is an oxygen atom, a sulfur atom, N(R 7 ), or *- A compound in which C(R 8 )=C(R 9 )—.
[Aspect 15] A compound N of the present invention wherein J is a group represented by J2, X 5 is CR 6 and X 6 is *--C(R 8 )=C(R 9 )--.
[Aspect 16] In any one of Aspects 1 to 15 and Compound N of the present invention, E is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A. .
[Aspect 17] The compound in any one of Aspects 1 to 15 and the compound N of the present invention, wherein E is a C1-C6 chain hydrocarbon group.
[Aspect 18] In any of Aspects 1 to 15 and Compound N of the present invention, E is a C3-C10 alicyclic hydrocarbon group optionally substituted with one or more substituents selected from Group D. Compound.
[Aspect 19] The compound in any one of Aspects 1 to 15 and the compound N of the present invention, wherein E is a C3-C10 alicyclic hydrocarbon group.
[Aspect 20] A compound in which E is a C6-C10 aryl group optionally substituted with one or more substituents selected from Group D in any one of Aspects 1 to 15 and Compound N of the present invention.
[Aspect 21] In any of Aspects 1 to 15 and Compound N of the present invention, E is a 5- to 10-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group D. Compound.
[Aspect 22] A compound in which E is a C6-C10 aryl group in any one of Aspects 1 to 15 and the compound N of the present invention.
[Aspect 23] In any one of Aspects 1 to 7, Aspect 12, Aspect 13, and the compound N of the present invention, J is a group represented by J1, and E is C(O)OR 25 , C(O)R 26 or C(O)NR 27 R 28 .
[Aspect 24] A compound in which J is a group represented by J1 and E is C(O)OR 25 in any one of Aspects 1 to 7, Aspect 12, Aspect 13, and Compound N of the present invention. [Aspect 25] In any one of Aspects 1 to 7, Aspect 14, Aspect 15, and Compound N of the present invention, J is a group represented by J2, and E is CH 2 —L 1 —R 12 or CH 2 Compounds wherein -ON=CR 13 R 14 .
[Aspect 26] A compound in which J is a group represented by J2 and E is CH 2 -L 1 -R 12 in any one of Aspects 1 to 7, Aspect 14, Aspect 15 and Compound N of the present invention.
[Aspect 27] In any one of Aspects 1 to 7, Aspect 14, Aspect 15, and Compound N of the present invention, J is a group represented by J2, and E is CH 2 —O—N=CR 13 R 14 Compound.
[Aspect 28] In any one of Aspects 1 to 7, Aspect 14, Aspect 15, and Compound N of the present invention, J is a group represented by J2, and E is C(R 16 )N=OR 15 Compound.
[Aspect 29] In any one of Aspects 1 to 7, Aspect 14, Aspect 15, and Compound N of the present invention, J is a group represented by J2, E is L 2 R 23 , and L 2 is an oxygen atom. some compound.
[Aspect 30] A compound in which J is a group represented by J2 and E is a halogen atom in any one of Aspects 1 to 7, Aspect 14, Aspect 15, and Compound N of the present invention.
[Aspect 31] In the compound N of the present invention, the combination of J and E is C1-C6, wherein J is a group represented by J1, and E is optionally substituted with one or more substituents selected from Group A. chain hydrocarbon group, C6-C10 aryl group optionally substituted with one or more substituents selected from group D, C(O)OR 25 , C(O)R 26 , or C(O)NR 27 or, J is a group represented by J2, and E is a C1- C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, or Group D A compound which is a combination of C6-C10 aryl groups optionally substituted with one or more substituents selected from the above.
[Aspect 32] In the compound N of the present invention, the combination of J and E is such that J is a group represented by J1, and E is a C1-C6 chain hydrocarbon group, a C6-C10 aryl group, or C(O) or a combination that is OR 25 ; or J is a group represented by J2, and E is a C1-C6 chain hydrocarbon group, or optionally substituted with one or more substituents selected from group D 5- A compound that is a combination of 10-membered aromatic heterocyclic groups.
[Aspect 33] In the compound N of the present invention, the combination of J and E is C1-C6, wherein J is a group represented by J1, and E is optionally substituted with one or more substituents selected from Group A. chain hydrocarbon group, C6-C10 aryl group optionally substituted with one or more substituents selected from group D, C(O)OR 25 , C(O)R 26 , or C(O)NR 27 or, J is a group represented by J2, and E is a C1- C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, or Group D a combination of C6-C10 aryl groups optionally substituted with one or more substituents selected from X 1 is CH, R 1 , R 2 and R 3 are hydrogen atoms; A compound wherein 3 is CR 4 , X 4 is CR 5 , X 5 is CR 6 , and X 6 is *-C(R 8 )=C(R 9 )-.
[Aspect 34] In the compound N of the present invention, the combination of J and E is such that J is a group represented by J1, and E is a C1-C6 chain hydrocarbon group, a C6-C10 aryl group, or C(O) or a combination wherein J is a group represented by J2, E is a C1- C6 chain hydrocarbon group or a C6-C10 aryl group, X 1 is CH, and X 2 is C(O)OCH 3 or C(O)NHCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 3 is CR 4 and X 4 is CR 5 wherein X 5 is CR 6 and X 6 is *-C(R 8 )=C(R 9 )-.
　次に、本発明化合物の製造法について説明する。 Next, the method for producing the compound of the present invention will be explained.
製造法Ａ
　式（Ａ１）で示される化合物（以下、化合物（Ａ１）と記す）は、式（Ｂ１）で示される化合物（以下、化合物（Ｂ１）と記す）と式（Ｍ１）で示される化合物（以下、化合物（Ｍ１）と記す）とを塩基の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000006
 〔式中、Ｅ１は群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、Ｃ３－Ｃ１０脂環式炭化水素基、３－１０員非芳香族複素環基、Ｃ６－Ｃ１０アリール基、５－１０員芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基、該３－１０員非芳香族複素環基、該Ｃ６－Ｃ１０アリール基及び該５－１０員芳香族複素環基は、群Ｄより選ばれる１以上の置換基で置換されていてもよい｝を表し、Ｘ51は塩素原子、臭素原子、ヨウ素原子、又はトリフリルオキシ基を表し、その他の記号は前記と同じ意味を表す。〕
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、ヘキサン、トルエン、キシレン等の炭化水素（以下、炭化水素類と記す）；メチルｔｅｒｔ－ブチルエーテル（以下、ＭＴＢＥと記す）、テトラヒドロフラン（以下、ＴＨＦと記す）、ジメトキシエタン等のエーテル（以下、エーテル類と記す）；クロロホルム、クロロベンゼン等のハロゲン化炭化水素（以下、ハロゲン化炭化水素類と記す）；ジメチルホルムアミド（以下、ＤＭＦと記す）、Ｎ－メチルピロリドン等のアミド（以下、アミド類と記す）；酢酸メチル、酢酸エチル等のエステル（以下、エステル類と記す）；アセトニトリル、プロピオニトリル等のニトリル（以下、ニトリル類と記す）；水；及びこれらの２つ以上の混合物が挙げられる。
　塩基としては例えば、トリエチルアミン、ピリジン等の有機塩基（以下、有機塩基類と記す）；炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩（以下、アルカリ金属炭酸塩類と記す）；炭酸水素ナトリウム、炭酸水素カリウム等のアルカリ金属炭酸水素塩（以下、アルカリ金属炭酸水素塩類と記す）；水素化ナトリウム及びリン酸三カリウムが挙げられる。
　反応には必要に応じて、金属触媒、及び／又は配位子を用いてもよい。
　金属触媒としては、ヨウ化銅（Ｉ）、臭化銅（Ｉ）、塩化銅（Ｉ）、酸化銅（Ｉ）、トリフルオロメタンスルホン酸銅（Ｉ）ベンゼンコンプレックス、テトラキス（アセトニトリル）銅（Ｉ）ヘキサフルオロホスファート、２－チオフェンカルボン酸銅（Ｉ）等の銅触媒；ビス（シクロオクタジエン）ニッケル（０）、塩化ニッケル（ＩＩ）等のニッケル触媒が挙げられる。反応に金属触媒を用いる場合、化合物（Ｂ１）１モルに対して、金属触媒は通常０．０１～１モルの割合で用いられる。
　配位子としては、例えば、トリフェニルホスフィン、キサントホス、２，２’－ビス（ジフェニルホスフィノ）－１，１’－ビナフチル、１，１’－ビス（ジフェニルホスフィノ）フェロセン、２－ジシクロヘキシルホスフィノ－２’，４’，６’－トリイソプロピルビフェニル、２－ジシクロヘキシルホスフィノ－２’，６’－ジメトキシビフェニル、１，２－ビス（ジフェニルホスフィノ）エタン、２，２’－ビピリジン、２－アミノエタノール、８－ヒドロキシキノリン、１，１０－フェナントロリン、ｔｒａｎｓ－１，２－シクロヘキサンジアミン、ｔｒａｎｓ－Ｎ，Ｎ’－ジメチルシクロヘキサン－１，２－ジアミン、Ｎ，Ｎ’－ジメチルエチレンジアミン、及びＮ，Ｎ－ジメチルグリシン塩酸塩が挙げられる。反応に配位子を用いる場合、化合物（Ｂ１）１モルに対して、配位子は通常０．０１～１モルの割合で用いられる。
　反応には、化合物（Ｂ１）１モルに対して、化合物（Ｍ１）が通常１～１０モルの割合、塩基が通常１～１０モルの割合で用いられる。
　反応温度は通常０～１５０℃の範囲である。反応時間は通常０．１～４８時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ａ１）を単離することができる。
　化合物（Ｂ１）及び化合物（Ｍ１）は、公知であるか、公知の方法に準じて製造することができる。 Manufacturing method A
The compound represented by formula (A1) (hereinafter referred to as compound (A1)) is a compound represented by formula (B1) (hereinafter referred to as compound (B1)) and the compound represented by formula (M1) (hereinafter referred to as It can be produced by reacting a compound (M1)) in the presence of a base.
Figure JPOXMLDOC01-appb-C000006
 [Wherein, E 1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C10 alicyclic hydrocarbon group, a 3- to 10-membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10 membered aromatic heterocyclic group {said C3-C10 alicyclic hydrocarbon group, said 3-10 membered non-aromatic heterocyclic group, said C6-C10 aryl group and The 5- to 10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group D}, X 51 is a chlorine atom, a bromine atom, an iodine atom, or a triflyloxy group and other symbols have the same meanings as above. ]
The reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons such as hexane, toluene, and xylene (hereinafter referred to as hydrocarbons); methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), Ethers such as dimethoxyethane (hereinafter referred to as ethers); Halogenated hydrocarbons such as chloroform and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); Dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone and the like amides (hereinafter referred to as amides); esters such as methyl acetate and ethyl acetate (hereinafter referred to as esters); nitriles such as acetonitrile and propionitrile (hereinafter referred to as nitriles); Mixtures of two or more are included.
Examples of bases include organic bases such as triethylamine and pyridine (hereinafter referred to as organic bases); alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); sodium hydrogen carbonate and hydrogen carbonate. alkali metal hydrogen carbonates such as potassium (hereinafter referred to as alkali metal hydrogen carbonates); sodium hydride and tripotassium phosphate.
A metal catalyst and/or a ligand may be used for the reaction, if necessary.
Metal catalysts include copper (I) iodide, copper (I) bromide, copper (I) chloride, copper (I) oxide, copper (I) trifluoromethanesulfonate benzene complex, tetrakis(acetonitrile) copper (I) copper catalysts such as hexafluorophosphate and copper (I) 2-thiophenecarboxylate; and nickel catalysts such as bis(cyclooctadiene)nickel (0) and nickel chloride (II). When a metal catalyst is used for the reaction, the metal catalyst is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B1).
Examples of ligands include triphenylphosphine, xantphos, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,1′-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphos Phino-2′,4′,6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2′-bipyridine, 2 -aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, N,N'-dimethylethylenediamine, and N , N-dimethylglycine hydrochloride. When a ligand is used in the reaction, the ligand is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B1).
In the reaction, the compound (M1) is generally used in an amount of 1 to 10 mol, and the base is generally used in an amount of 1 to 10 mol, per 1 mol of the compound (B1).
The reaction temperature is usually in the range of 0-150°C. The reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, compound (A1) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
Compound (B1) and compound (M1) are known or can be produced according to known methods.
製造法Ｂ
　式（Ａ２）で示される化合物（以下、化合物（Ａ２）と記す）は、化合物（Ｂ１）と式（Ｍ２）で示される化合物（以下、化合物（Ｍ２）と記す）とを、塩基の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000007
 〔式中、Ｅ２は、Ｃ（Ｏ）ＯＲ２５、Ｃ（Ｏ）Ｒ２６、又はＣ（Ｏ）ＮＲ２７Ｒ２８を表し、その他の記号は前記と同じ意味を表す。〕
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類及びこれらの２つ以上の混合物が挙げられる。
　塩基としては例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、水素化ナトリウム及びリン酸三カリウムが挙げられる。
　反応には、化合物（Ｂ１）１モルに対して、化合物（Ｍ２）が通常１～１０モルの割合、塩基が通常１～１０モルの割合で用いられる。
　反応温度は通常－５０～１００℃の範囲である。反応時間は通常０．１～４８時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ａ２）を単離することができる。
　化合物（Ｍ２）は、公知であるか、公知の方法に準じて製造することができる。 Manufacturing method B
The compound represented by formula (A2) (hereinafter referred to as compound (A2)) is obtained by reacting compound (B1) and a compound represented by formula (M2) (hereinafter referred to as compound (M2)) in the presence of a base. It can be produced by reacting with
Figure JPOXMLDOC01-appb-C000007
 [In the formula, E 2 represents C(O)OR 25 , C(O)R 26 , or C(O)NR 27 R 28 , and other symbols have the same meanings as above. ]
The reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
Bases include, for example, organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
In the reaction, the compound (M2) is usually used in an amount of 1 to 10 mol, and the base is usually used in an amount of 1 to 10 mol, per 1 mol of the compound (B1).
The reaction temperature is usually in the range of -50 to 100°C. The reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, compound (A2) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
Compound (M2) is known or can be produced according to known methods.
製造法Ｃ
　式（Ａ３）で示される化合物（以下、化合物（Ａ３）と記す）は、式（Ｂ２）で示される化合物（以下、化合物（Ｂ２）と記す）と化合物（Ｍ１）とをパラジウム触媒及び塩基の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000008
 〔式中、Ｍ1はＢ（ＯＨ）２又は４，４，５，５－テトラメチル－１，３，２－ジオキサボロラン－２－イル基を表し、その他の記号は前記と同じ意味を表す。〕
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類、水、及びこれらの２つ以上の混合物が挙げられる。
　反応に用いられるパラジウム触媒としては、例えば、酢酸パラジウム（ＩＩ）、及び［１，１’－ビス（ジフェニルホスフィノ）フェロセン］パラジウム（ＩＩ）ジクロリドが挙げられる。
　反応に用いられる塩基としては例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、フッ化ナトリウム及びリン酸三カリウムが挙げられる。
　反応には、化合物（Ｂ２）１モルに対して、化合物（Ｍ１）が通常０．５～２モルの割合、パラジウム触媒が通常０．０１～１モルの割合、塩基が通常１～１０モルの割合で用いられる。
　反応温度は通常０～１５０℃の範囲である。反応時間は通常０．１～１２０時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物（Ａ３）を単離することができる。 Manufacturing method C
The compound represented by formula (A3) (hereinafter referred to as compound (A3)) is obtained by reacting the compound represented by formula (B2) (hereinafter referred to as compound (B2)) and compound (M1) with a palladium catalyst and a base. It can be produced by reacting in the presence.
Figure JPOXMLDOC01-appb-C000008
 [In the formula, M 1 represents B(OH) 2 or 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, and other symbols have the same meanings as above. ]
The reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water, and mixtures of two or more thereof.
Palladium catalysts used in the reaction include, for example, palladium(II) acetate and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.
Examples of bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium fluoride and tripotassium phosphate.
In the reaction, the compound (M1) is usually used in an amount of 0.5 to 2 mol, the palladium catalyst is usually used in an amount of 0.01 to 1 mol, and the base is usually used in an amount of 1 to 10 mol, relative to 1 mol of the compound (B2). Used in proportion.
The reaction temperature is usually in the range of 0-150°C. The reaction time is usually in the range of 0.1 to 120 hours.
After completion of the reaction, the compound (A3) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
製造法Ｄ
　化合物（Ａ３）は、式（Ｂ３）で示される化合物（以下、化合物（Ｂ３）と記す）と式（Ｍ３）で示される化合物（以下、化合物（Ｍ３）と記す）とをパラジウム触媒及び塩基の存在下で反応させることにより製造することもできる。
Figure JPOXMLDOC01-appb-C000009
 〔式中、記号は前記と同じ意味を表す。〕
　反応は、化合物（Ｂ２）に代えて化合物（Ｍ３）を用い、化合物（Ｍ１）に代えて化合物（Ｂ３）を用い、製造法Ｃに準じて実施することができる。
　化合物（Ｍ３）は、公知であるか、公知の方法に準じて製造することができる。 Manufacturing method D
Compound (A3) is prepared by reacting a compound represented by formula (B3) (hereinafter referred to as compound (B3)) and a compound represented by formula (M3) (hereinafter referred to as compound (M3)) with a palladium catalyst and a base. It can also be produced by reacting in the presence.
Figure JPOXMLDOC01-appb-C000009
 [In the formula, the symbols have the same meanings as described above. ]
The reaction can be carried out according to production method C using compound (M3) instead of compound (B2) and compound (B3) instead of compound (M1).
Compound (M3) is known or can be produced according to known methods.
製造法Ｅ
　式（Ａ４）で示される化合物（以下、化合物（Ａ４）と記す）は、式（Ｂ４）で示される化合物（以下、化合物（Ｂ４）と記す）と、式（Ｍ４）で示される化合物（以下、化合物（Ｍ４）と記す）又はその塩とを反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000010
 〔式中、Ｒ５１はＣ１－Ｃ６鎖式炭化水素基、Ｃ３－Ｃ１０脂環式炭化水素基｛該Ｃ１－Ｃ６鎖式炭化水素基及び該Ｃ３－Ｃ１０脂環式炭化水素基は、１以上のハロゲン原子で置換されていてもよい｝、又は水素原子を表し、Ｒ５２はＯＲ１５、Ｎ＝ＣＲ１７Ｒ１８、又はＮＲ２０Ｒ２１を表し、その他の記号は前記と同じ意味を表す。〕
　化合物（Ｍ４）の塩としては、例えば、塩酸塩及び硫酸塩が挙げられる。
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類；エーテル類；ハロゲン化炭化水素類；アミド類；エステル類；ニトリル類；メタノール、エタノール等のアルコール（以下、アルコール類と記す）；水及びこれらの２つ以上の混合物が挙げられる。
　反応には必要に応じて、塩基を用いてもよい。反応に用いられる塩基としては、例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、水素化ナトリウム及びリン酸三カリウムが挙げられる。
　反応に塩基が用いられる場合、化合物（Ｂ４）１モルに対して、塩基は通常１～１０モルの割合で用いられる。
　反応には、化合物（Ｂ４）１モルに対して、化合物（Ｍ４）が通常１～１０モルの割合で用いられる。
　反応温度は通常０～１５０℃の範囲である。反応時間は通常０．１～１２０時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物（Ａ４）を単離することができる。
　化合物（Ｍ４）は、公知であるか、公知の方法に準じて製造することができる。 Manufacturing method E
The compound represented by formula (A4) (hereinafter referred to as compound (A4)) is a compound represented by formula (B4) (hereinafter referred to as compound (B4)) and the compound represented by formula (M4) (hereinafter referred to as , compound (M4)) or a salt thereof.
Figure JPOXMLDOC01-appb-C000010
 [In the formula, R 51 is a C1-C6 chain hydrocarbon group, a C3-C10 alicyclic hydrocarbon group {the C1-C6 chain hydrocarbon group and the C3-C10 alicyclic hydrocarbon group are 1 or more; or a hydrogen atom, R 52 represents OR 15 , N═CR 17 R 18 or NR 20 R 21 , and other symbols have the same meanings as above. ]
Salts of compound (M4) include, for example, hydrochloride and sulfate.
The reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; alcohols such as methanol and ethanol (hereinafter referred to as alcohols); and mixtures of two or more of
A base may be used for the reaction, if necessary. Examples of bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
When a base is used in the reaction, the base is generally used in a proportion of 1 to 10 mol per 1 mol of compound (B4).
In the reaction, compound (M4) is generally used in a proportion of 1 to 10 mol per 1 mol of compound (B4).
The reaction temperature is usually in the range of 0-150°C. The reaction time is usually in the range of 0.1 to 120 hours.
After completion of the reaction, compound (A4) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
Compound (M4) is known or can be produced according to known methods.
製造法Ｆ
　式（Ａ５）で示される化合物（以下、化合物（Ａ５）と記す）は、式（Ｂ５）で示される化合物（以下、化合物（Ｂ５）と記す）と式（Ｍ５）で示される化合物（以下、化合物（Ｍ５）と記す）とを塩基の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000011
 〔式中、Ｌ５１は酸素原子又は硫黄原子を表し、その他の記号は前記と同じ意味を表す。〕
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類及びこれらの２つ以上の混合物が挙げられる。
　塩基としては、例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、水素化ナトリウム及びリン酸三カリウムが挙げられる。
　反応には、化合物（Ｂ５）１モルに対して、化合物（Ｍ５）が通常１～１０モルの割合、塩基が通常１～１０モルの割合で用いられる。
　反応温度は通常－２０～１５０℃の範囲である。反応時間は通常０．１～４８時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ａ５）を単離することができる。
　化合物（Ｍ５）は、公知であるか、公知の方法に準じて製造することができる。 Manufacturing method F
The compound represented by formula (A5) (hereinafter referred to as compound (A5)) is a compound represented by formula (B5) (hereinafter referred to as compound (B5)) and the compound represented by formula (M5) (hereinafter referred to as compound (M5)) in the presence of a base.
Figure JPOXMLDOC01-appb-C000011
 [In the formula, L 51 represents an oxygen atom or a sulfur atom, and other symbols have the same meanings as above. ]
The reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
Bases include, for example, organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
In the reaction, the compound (M5) is usually used in an amount of 1 to 10 mol, and the base is usually used in an amount of 1 to 10 mol, per 1 mol of the compound (B5).
The reaction temperature is usually in the range of -20 to 150°C. The reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, compound (A5) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
Compound (M5) is known or can be produced according to known methods.
製造法Ｇ
　式（Ａ６）で示される化合物（以下、化合物（Ａ６）と記す）は、式（Ｂ６）で示される化合物（以下、化合物（Ｂ６）と記す）と式（Ｍ６）で示される化合物（以下、化合物（Ｍ６）と記す）とを、塩基の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000012
 〔式中、記号は前記と同じ意味を表す。〕
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類及びこれらの２つ以上の混合物が挙げられる。
　塩基としては、例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、水素化ナトリウム及びリン酸三カリウムが挙げられる。
　反応には必要に応じて、金属触媒、及び／又は配位子を用いてもよい。
　金属触媒としては、ヨウ化銅（Ｉ）、臭化銅（Ｉ）、塩化銅（Ｉ）、酸化銅（Ｉ）、トリフルオロメタンスルホン酸銅（Ｉ）ベンゼンコンプレックス、テトラキス（アセトニトリル）銅（Ｉ）ヘキサフルオロホスファート、２－チオフェンカルボン酸銅（Ｉ）等の銅触媒；ビス（シクロオクタジエン）ニッケル（０）、塩化ニッケル（ＩＩ）等のニッケル触媒が挙げられる。反応に金属触媒を用いる場合、化合物（Ｂ６）１モルに対して、金属触媒は通常０．０１～１モルの割合で用いられる。
　配位子としては、トリフェニルホスフィン、キサントホス、２，２’－ビス（ジフェニルホスフィノ）－１，１’－ビナフチル、１，１’－ビス（ジフェニルホスフィノ）フェロセン、２－ジシクロヘキシルホスフィノ－２’，４’，６’－トリイソプロピルビフェニル、２－ジシクロヘキシルホスフィノ－２’，６’－ジメトキシビフェニル、１，２－ビス（ジフェニルホスフィノ）エタン、２，２’－ビピリジン、２－アミノエタノール、８－ヒドロキシキノリン、１，１０－フェナントロリン、ｔｒａｎｓ－１，２－シクロヘキサンジアミン、ｔｒａｎｓ－Ｎ，Ｎ’－ジメチルシクロヘキサン－１，２－ジアミン、Ｎ，Ｎ’－ジメチルエチレンジアミン、Ｎ，Ｎ－ジメチルグリシン塩酸塩等が挙げられる。反応に配位子を用いる場合、化合物（Ｂ６）１モルに対して、配位子は通常０．０１～１モルの割合で用いられる。
　反応には、化合物（Ｂ６）１モルに対して、化合物（Ｍ６）が通常１～１０モルの割合、塩基が通常１～１０モルの割合で用いられる。
　反応温度は通常－２０～１５０℃の範囲である。反応時間は通常０．１～４８時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ａ６）を単離することができる。
　化合物（Ｍ６）は、公知であるか、公知の方法に準じて製造することができる。 Manufacturing method G
The compound represented by formula (A6) (hereinafter referred to as compound (A6)) is a compound represented by formula (B6) (hereinafter referred to as compound (B6)) and the compound represented by formula (M6) (hereinafter referred to as compound (M6)) in the presence of a base.
Figure JPOXMLDOC01-appb-C000012
 [In the formula, the symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
Bases include, for example, organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
A metal catalyst and/or a ligand may be used for the reaction, if necessary.
Metal catalysts include copper (I) iodide, copper (I) bromide, copper (I) chloride, copper (I) oxide, copper (I) trifluoromethanesulfonate benzene complex, tetrakis(acetonitrile) copper (I) copper catalysts such as hexafluorophosphate and copper (I) 2-thiophenecarboxylate; and nickel catalysts such as bis(cyclooctadiene)nickel (0) and nickel chloride (II). When a metal catalyst is used for the reaction, the metal catalyst is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B6).
As ligands, triphenylphosphine, xantphos, 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-amino ethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, N,N'-dimethylethylenediamine, N,N- dimethylglycine hydrochloride and the like. When a ligand is used in the reaction, the ligand is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B6).
In the reaction, the compound (M6) is generally used in an amount of 1 to 10 mol, and the base is generally used in an amount of 1 to 10 mol, per 1 mol of the compound (B6).
The reaction temperature is usually in the range of -20 to 150°C. The reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, compound (A6) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
Compound (M6) is known or can be produced according to known methods.
製造法Ｈ
　式（Ａ７）で示される化合物（以下、化合物（Ａ７）と記す）は、式（Ｂ７）で示される化合物（以下、化合物（Ｂ７）と記す）と式（Ｍ７）で示される化合物（以下、化合物（Ｍ７）と記す）とを塩基の存在下で反応させて式（Ｂ８）で示される化合物（以下、化合物（Ｂ８）と記す）を得る工程（以下、工程（Ｈ－１）と記す）、及び化合物（Ｂ８）と式（Ｍ８）で示される化合物（以下、化合物（Ｍ８）と記す）とを塩基の存在下で反応させる工程（以下、工程（Ｈ－２）と記す）により製造することができる。
Figure JPOXMLDOC01-appb-C000013
 〔式中、Ｒ５３はＣ１－Ｃ４アルキル基を表し、Ｘ５２はヨウ素原子、メトキシスルホニルオキシ基、メシルオキシ基、又はトシルオキシ基を表し、その他の記号は前記と同じ意味を表す。〕 Manufacturing method H
The compound represented by formula (A7) (hereinafter referred to as compound (A7)) is a compound represented by formula (B7) (hereinafter referred to as compound (B7)) and the compound represented by formula (M7) (hereinafter referred to as a compound (M7)) in the presence of a base to obtain a compound represented by formula (B8) (hereinafter referred to as compound (B8)) (hereinafter referred to as step (H-1)) , and a step of reacting compound (B8) with a compound represented by formula (M8) (hereinafter referred to as compound (M8)) in the presence of a base (hereinafter referred to as step (H-2)). be able to.
Figure JPOXMLDOC01-appb-C000013
 [In the formula, R 53 represents a C1-C4 alkyl group, X 52 represents an iodine atom, a methoxysulfonyloxy group, a mesyloxy group, or a tosyloxy group, and other symbols have the same meanings as above. ]
　工程（Ｈ－１）は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、エーテル類、アミド類及びこれらの２つ以上の混合物が挙げられる。
　反応に用いられる塩基としては、例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、水素化ナトリウム及びリン酸三カリウムが挙げられる。
　反応には、化合物（Ｂ７）１モルに対して、化合物（Ｍ７）が通常１モル～１０モルの割合、塩基が通常０．５モル～５モルの割合で用いられる。
　反応時間は、通常５分間～７２時間の範囲である。反応温度は、通常－５０℃～１００℃の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物（Ｂ８）を得ることができる。
　化合物（Ｍ７）は、市販の化合物であるか、公知の方法に準じて製造することができる。 Step (H-1) is usually carried out in a solvent. Solvents used in the reaction include, for example, ethers, amides, and mixtures of two or more thereof.
Examples of bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
In the reaction, the compound (M7) is generally used in an amount of 1 mol to 10 mol, and the base is generally used in an amount of 0.5 mol to 5 mol, per 1 mol of the compound (B7).
The reaction time is usually in the range of 5 minutes to 72 hours. The reaction temperature is usually in the range of -50°C to 100°C.
After completion of the reaction, compound (B8) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
Compound (M7) is a commercially available compound, or can be produced according to a known method.
　工程（Ｈ－２）は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類及びこれらの２つ以上の混合物が挙げられる。
　反応に用いられる塩基としては例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、水素化ナトリウム及びリン酸三カリウムが挙げられる。
　反応には、化合物（Ｂ８）１モルに対して、化合物（Ｍ８）が通常１～１０モルの割合、塩基が通常１～２０モルの割合で用いられる。
　反応温度は通常－５０～１００℃の範囲である。反応時間は通常０．１～４８時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ａ７）を単離することができる。
　化合物（Ｍ８）は、市販の化合物であるか、公知の方法に準じて製造することができる。 Step (H-2) is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
Examples of bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
In the reaction, the compound (M8) is generally used in an amount of 1 to 10 mol, and the base is generally used in an amount of 1 to 20 mol, per 1 mol of the compound (B8).
The reaction temperature is usually in the range of -50 to 100°C. The reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, compound (A7) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
Compound (M8) is a commercially available compound, or can be produced according to a known method.
製造法Ｉ
　式（Ａ８）で示される化合物（以下、化合物（Ａ８）と記す）は、化合物（Ｂ７）と式（Ｍ９）で示される化合物（以下、化合物（Ｍ９）と記す）とを塩基の存在下で反応させて式（Ｂ９）で示される化合物（以下、化合物（Ｂ９）と記す）を得る工程（以下、工程（Ｉ－１）と記す）、及び化合物（Ｂ９）と化合物（Ｍ８）とを塩基の存在下で反応させる工程（以下、工程（Ｉ－２）と記す）により製造することができる。
Figure JPOXMLDOC01-appb-C000014
 〔式中、Ｒ５４はｔｅｒｔ－ブチル基又はイソペンチル基を表し、その他の記号は前記と同じ意味を表す。〕 Manufacturing method I
The compound represented by formula (A8) (hereinafter referred to as compound (A8)) is obtained by reacting compound (B7) and compound represented by formula (M9) (hereinafter referred to as compound (M9)) in the presence of a base. a step of reacting to obtain a compound represented by formula (B9) (hereinafter referred to as compound (B9)) (hereinafter referred to as step (I-1)), and compound (B9) and compound (M8) with a base It can be produced by a step of reacting in the presence of (hereinafter referred to as step (I-2)).
Figure JPOXMLDOC01-appb-C000014
 [In the formula, R 54 represents a tert-butyl group or an isopentyl group, and other symbols have the same meanings as above. ]
　工程（Ｉ－１）は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、エーテル類、アミド類、アルコール類及びこれらの２つ以上の混合物が挙げられる。
　反応に用いられる塩基としては、例えば、水素化ナトリウム；及び、ナトリウムメトキシド、ナトリウムエトキシド、カリウムｔ－ブトキシド等のアルカリ金属アルコキシドが挙げられる。
　反応には、化合物（Ｂ７）１モルに対して、化合物（Ｍ９）が通常１モル～１０モルの割合、塩基が通常１モル～５モルの割合で用いられる。
　反応時間は、通常５分間～７２時間の範囲である。反応温度は、通常－２０℃～１００℃の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物（Ｂ９）を得ることができる。
　化合物（Ｍ９）は、市販の化合物である。 Step (I-1) is usually carried out in a solvent. Solvents used in the reaction include, for example, ethers, amides, alcohols, and mixtures of two or more thereof.
Bases used in the reaction include, for example, sodium hydride; and alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide.
In the reaction, the compound (M9) is generally used in an amount of 1 mol to 10 mol, and the base is generally used in an amount of 1 mol to 5 mol, per 1 mol of the compound (B7).
The reaction time is usually in the range of 5 minutes to 72 hours. The reaction temperature is usually in the range of -20°C to 100°C.
After completion of the reaction, compound (B9) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
Compound (M9) is a commercially available compound.
　工程（Ｉ－２）は、化合物（Ｂ８）に代えて化合物（Ｂ９）を用い、製造法Ｈの工程（Ｈ－２）に準じて実施することができる。 The step (I-2) can be carried out according to the step (H-2) of the manufacturing method H, using the compound (B9) instead of the compound (B8).
製造法Ｊ
　式（Ａ１０）で示される化合物（以下、化合物（Ａ１０）と記す）は、式（Ａ９）で示される化合物（以下、化合物（Ａ９）と記す）とメチルアミンとを反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000015
 〔式中、記号は前記と同じ意味を表す。〕
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、アルコール類、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類及びこれらの２つ以上の混合物が挙げられる。
　反応には、必要に応じて塩基を用いてもよい。反応に用いられる塩基としては、例えば、有機塩基類；アルカリ金属炭酸塩類；水酸化ナトリウム、水酸化カリウム等のアルカリ金属水酸化物（以下、アルカリ金属水酸化物類と記す）；及び水素化ナトリウムが挙げられる。反応に塩基が用いられる場合、化合物（Ａ８）１モルに対して、塩基が通常０．１～１０モルの割合で用いられる。
　メチルアミンは、通常、溶液として用いられる。メチルアミンの溶液としては、例えば、メタノール溶液及び水溶液が挙げられる。
　反応には、化合物（Ａ９）１モルに対して、メチルアミンが通常１～１００モルの割合で用いられる。
　反応温度は通常－５０～５０℃の範囲である。反応時間は通常０．１～２４時間の範囲である。
　反応終了後は、反応混合物に水を混合した後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物（Ａ１０）を単離することができる。 Manufacturing method J
The compound represented by formula (A10) (hereinafter referred to as compound (A10)) can be produced by reacting the compound represented by formula (A9) (hereinafter referred to as compound (A9)) with methylamine. can be done.
Figure JPOXMLDOC01-appb-C000015
 [In the formula, symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, alcohols, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
A base may be used in the reaction, if necessary. Bases used in the reaction include, for example, organic bases; alkali metal carbonates; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide (hereinafter referred to as alkali metal hydroxides); and sodium hydride is mentioned. When a base is used in the reaction, the base is usually used in a proportion of 0.1 to 10 mol per 1 mol of compound (A8).
Methylamine is usually used as a solution. Solutions of methylamine include, for example, methanol solutions and aqueous solutions.
In the reaction, methylamine is generally used in a proportion of 1 to 100 mol per 1 mol of compound (A9).
The reaction temperature is usually in the range of -50 to 50°C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, compound (A10) can be isolated by post-treatment such as mixing the reaction mixture with water, extracting with an organic solvent, drying and concentrating the organic layer.
製造法Ｋ
　式（Ａ１１）で示される化合物（以下、化合物（Ａ１１）と記す）は、化合物（Ａ８）とヒドロキシルアミンとを塩基の存在下で反応させて式（Ｂ１０）で示される化合物（以下、化合物（Ｂ１０）と記す）を得る工程（以下、工程（Ｋ－１）と記す）、及び化合物（Ｂ１０）と式（Ｍ１０）で示される化合物（以下、化合物（Ｍ１０）と記す）とを塩基の存在下で反応させる工程（以下、工程（Ｋ－２）と記す）により製造することができる。
Figure JPOXMLDOC01-appb-C000016
 〔式中、Ｘ５３は、塩素原子、臭素原子又はヨウ素原子を表し、その他の記号は前記と同じ意味を表す。〕 Manufacturing method K
The compound represented by formula (A11) (hereinafter referred to as compound (A11)) is obtained by reacting compound (A8) with hydroxylamine in the presence of a base to obtain a compound represented by formula (B10) (hereinafter referred to as compound ( B10)) (hereinafter referred to as step (K-1)), and compound (B10) and the compound represented by formula (M10) (hereinafter referred to as compound (M10)) in the presence of a base It can be produced by the step of reacting below (hereinafter referred to as step (K-2)).
Figure JPOXMLDOC01-appb-C000016
 [In the formula, X 53 represents a chlorine atom, a bromine atom or an iodine atom, and other symbols have the same meanings as above. ]
　工程（Ｋ－１）は、化合物（Ａ９）に代えて化合物（Ａ８）を用い、メチルアミンに代えてヒドロキシルアミンを用い、製造法Ｊに準じて実施することができる。 Step (K-1) can be carried out according to production method J using compound (A8) instead of compound (A9) and hydroxylamine instead of methylamine.
　工程（Ｋ－２）は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類、水及びこれらの２つ以上の混合物が挙げられる。
　塩基としては例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、水素化ナトリウム及びリン酸三カリウムが挙げられる。
　反応には、化合物（Ｂ１０）１モルに対して、化合物（Ｍ１０）が通常１～１０モルの割合、塩基が通常１～１０モルの割合で用いられる。
　反応温度は通常－２０～１２０℃の範囲である。反応時間は通常０．１～４８時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ａ１１）を単離することができる。
　化合物（Ｍ１０）は、市販の化合物である。 Step (K-2) is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water and mixtures of two or more thereof.
Bases include, for example, organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
In the reaction, the compound (M10) is generally used in an amount of 1 to 10 mol, and the base is generally used in an amount of 1 to 10 mol, per 1 mol of the compound (B10).
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 48 hours.
After completion of the reaction, compound (A11) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
Compound (M10) is a commercially available compound.
製造法Ｌ
　式（Ａ１２）で示される化合物（以下、化合物（Ａ１２）と記す）は、式（Ｂ１１）で示される化合物（以下、化合物（Ｂ１１）と記す）と２－ヨード－３－メトキシアクリル酸メチルとを塩基及び金属触媒の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000017
 〔式中、記号は前記と同じ意味を表す。〕
　反応は、化合物（Ｂ２）に代えて化合物（Ｂ１１）を用い、化合物（Ｍ１）に代えて２－ヨード－３－メトキシアクリル酸メチルを用い、製造法Ｃに準じて実施することができる。
　化合物（Ｂ１１）及び２－ヨード－３－メトキシアクリル酸メチルは、公知の方法に準じて製造することができる。 Manufacturing method L
The compound represented by formula (A12) (hereinafter referred to as compound (A12)) is a compound represented by formula (B11) (hereinafter referred to as compound (B11)) and methyl 2-iodo-3-methoxyacrylate. can be prepared by reacting in the presence of a base and a metal catalyst.
Figure JPOXMLDOC01-appb-C000017
 [In the formula, symbols have the same meanings as described above. ]
The reaction can be carried out according to Production Method C using compound (B11) in place of compound (B2) and methyl 2-iodo-3-methoxyacrylate in place of compound (M1).
Compound (B11) and methyl 2-iodo-3-methoxyacrylate can be produced according to known methods.
製造法Ｍ
　式（Ｉ）で示される化合物のＮオキシドは、式（Ｉ）で示される化合物と酸化剤とを反応させることにより製造することができる。反応は、例えば米国特許出願公開第2018/0009778号明細書又は国際公開第2016/121970号に記載の方法に準じて実施することができる。 Manufacturing method M
The N-oxide of the compound of formula (I) can be prepared by reacting the compound of formula (I) with an oxidizing agent. The reaction can be carried out, for example, according to the method described in US Patent Application Publication No. 2018/0009778 or International Publication No. 2016/121970.
参考製造法ａ
　化合物（Ｂ１）は、化合物（Ａ２）と酸とを反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000018
 〔式中、記号は前記と同じ意味を表す。〕
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、アルコール類；炭化水素類；エーテル類；ハロゲン化炭化水素類；アミド類；エステル類；ニトリル類；水及びこれらの２つ以上の混合物が挙げられる。
　反応に用いられる酸としては例えば、酢酸、トリフルオロ酢酸、塩酸、硫酸、モントモリロナイトが挙げられる。
　反応には、化合物（Ａ２）１モルに対して、酸が通常０．１～５モルの割合で用いられる。
　反応温度は通常０～１５０℃の範囲である。反応時間は通常０．１～４８時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｂ１）を単離することができる。 Reference manufacturing method a
Compound (B1) can be produced by reacting compound (A2) with an acid.
Figure JPOXMLDOC01-appb-C000018
 [In the formula, symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, alcohols; hydrocarbons; ethers; halogenated hydrocarbons; amides;
Acids used in the reaction include, for example, acetic acid, trifluoroacetic acid, hydrochloric acid, sulfuric acid, and montmorillonite.
In the reaction, an acid is usually used in a proportion of 0.1 to 5 mol per 1 mol of compound (A2).
The reaction temperature is usually in the range of 0-150°C. The reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, the compound (B1) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
参考製造法ｂ
　式（Ｂ５１）で示される化合物（以下、化合物（Ｂ５１）と記す）は、化合物（Ｂ３）とビス（ピナコラト）ジボロンとを塩基及びパラジウム触媒の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000019
 〔式中、記号は前記と同じ意味を表す。〕
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類；エーテル類；ハロゲン化炭化水素類；アミド類；エステル類；ジメチルスルホキシド（以下、ＤＭＳＯと記す）等のスルホキシド（以下、スルホキシド類と記す）；ニトリル類及びこれらの２つ以上の混合物が挙げられる。
　反応に用いられる塩基としては例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類及びリン酸三カリウムが挙げられる。
　パラジウム触媒としては、例えば、［１，１’－ビス（ジフェニルホスフィノ）フェロセン］パラジウム（ＩＩ）ジクロリドが挙げられる。
　反応には、化合物（Ｂ３）１モルに対して、ビス（ピナコラト）ジボロンが通常１～５モルの割合、塩基が通常１～５モルの割合、パラジウム触媒が通常０．０１～０．５モルの割合で用いられる。
　反応温度は通常０～１５０℃の範囲である。反応時間は通常０．１～４８時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｂ５１）を単離することができる。 Reference manufacturing method b
The compound represented by formula (B51) (hereinafter referred to as compound (B51)) can be produced by reacting compound (B3) with bis(pinacolato)diboron in the presence of a base and a palladium catalyst.
Figure JPOXMLDOC01-appb-C000019
 [In the formula, the symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; Nitriles and mixtures of two or more thereof are included.
Examples of bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates and tripotassium phosphate.
Palladium catalysts include, for example, [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.
For the reaction, relative to 1 mol of compound (B3), bis(pinacolato)diboron is usually used at a ratio of 1 to 5 mol, a base is usually used at a ratio of 1 to 5 mol, and a palladium catalyst is usually used at a ratio of 0.01 to 0.5 mol. used at a rate of
The reaction temperature is usually in the range of 0-150°C. The reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, compound (B51) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
参考製造法ｃ
　式（Ｂ５２）で示される化合物（以下、化合物（Ｂ５２）と記す）は、化合物（Ｂ３）と式（Ｍ１１）で示される化合物（以下、化合物（Ｍ１１）と記す）とを反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000020
 〔式中、Ｒ５５はメチル基又はエチル基を表し、その他の記号は前記と同じ意味を表す。〕
　反応は、例えば国際公開第２０１６／１２３２５３号に記載の方法に準じて実施することができる。
　化合物（Ｍ１１）は、市販の化合物であるか、公知の方法に準じて製造することができる。 Reference manufacturing method c
A compound represented by formula (B52) (hereinafter referred to as compound (B52)) is produced by reacting compound (B3) with a compound represented by formula (M11) (hereinafter referred to as compound (M11)). can do.
Figure JPOXMLDOC01-appb-C000020
 [In the formula, R 55 represents a methyl group or an ethyl group, and other symbols have the same meanings as above. ]
The reaction can be carried out, for example, according to the method described in WO2016/123253.
Compound (M11) is a commercially available compound, or can be produced according to a known method.
参考製造法ｄ
　化合物（Ｂ５）は、化合物（Ｂ３）とＮ－ホルミルサッカリンとをパラジウム触媒、配位子、トリエチルシラン及び塩基の存在下で反応させて式（Ｂ５３）で示される化合物（以下、化合物（Ｂ５３）と記す）を得る工程（以下、工程（ｄ－１）と記す）、化合物（Ｂ５３）と水素化ホウ素ナトリウムとを反応させて式（Ｂ５４）で示される化合物（以下、化合物（Ｂ５４）と記す）を得る工程（以下、工程（ｄ－２）と記す）、及び化合物（Ｂ５４）と、四塩化炭素、四臭化炭素、又はヨウ素とをトリフェニルホスフィンの存在下で反応させる工程（以下、工程（ｄ－３）と記す）により製造することができる。
Figure JPOXMLDOC01-appb-C000021
 〔式中、記号は前記と同じ意味を表す。〕 Reference manufacturing method d
Compound (B5) is prepared by reacting compound (B3) with N-formylsaccharin in the presence of a palladium catalyst, a ligand, triethylsilane and a base to obtain a compound represented by formula (B53) (hereinafter referred to as compound (B53) (hereinafter referred to as step (d-1)), a compound represented by formula (B54) by reacting compound (B53) with sodium borohydride (hereinafter referred to as compound (B54) ) (hereinafter referred to as step (d-2)), and a step of reacting compound (B54) with carbon tetrachloride, carbon tetrabromide, or iodine in the presence of triphenylphosphine (hereinafter referred to as It can be produced by the step (d-3)).
Figure JPOXMLDOC01-appb-C000021
 [In the formula, symbols have the same meanings as described above. ]
　工程（ｄ－１）は、Ａｎｇｅｗ．Ｃｈｅｍ．Ｉｎｔ．Ｅｄ．，２０１３，５２，８６１１－８６１５等に記載の方法に準じて実施することができる。 In the step (d-1), Angew. Chem. Int. Ed. , 2013, 52, 8611-8615 and the like.
　工程（ｄ－２）は、Ｃｈｅｍｉｓｔｒｙ－Ａ　Ｅｕｒｏｐｅａｎ　Ｊｏｕｒｎａｌ，２０１９，２５（１５），３９５０－３９５６等に記載の方法に準じて実施することができる。 Step (d-2) can be carried out according to the method described in Chemistry-A European Journal, 2019, 25(15), 3950-3956 and the like.
　工程（ｄ－３）は、Ｊ．Ｏｒｇ．Ｓｙｎｔｈ．，１９７４，５４，６３等に記載の方法に準じて実施することができる。 In step (d-3), J. Org. Synth. , 1974, 54, 63 and the like.
参考製造法ｅ
　式（Ｂ５５）で示される化合物（以下、化合物（Ｂ５５）と記す）は、化合物（Ｂ２）と酸化剤とを反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000022
 〔式中、記号は前記と同じ意味を表す。〕
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類、アルコール類、水及びこれらの２つ以上の混合物が挙げられる。
　反応に用いられる酸化剤としては、例えば、メタクロロ過安息香酸及び過酸化水素水が挙げられる。
　酸化剤として過酸化水素水を用いる場合は、必要に応じて塩基を用いてもよい。
　反応に用いられる塩基としては、アルカリ金属水酸化物類が挙げられる。
　反応に塩基が用いられる場合、化合物（Ｂ２）１モルに対して、塩基は通常０．１～５モルの割合で用いられる。
　反応には、化合物（Ｂ２）１モルに対して、酸化剤が通常１～５モルの割合で用いられる。
　反応温度は通常－２０～１２０℃の範囲であり、反応時間は通常０．１～４８時間の範囲である。
　反応終了後は、反応混合物に水及びチオ硫酸ナトリウム等の還元剤を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｂ５５）を単離することができる。 Reference manufacturing method e
A compound represented by formula (B55) (hereinafter referred to as compound (B55)) can be produced by reacting compound (B2) with an oxidizing agent.
Figure JPOXMLDOC01-appb-C000022
 [In the formula, the symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water and mixtures of two or more thereof.
The oxidizing agent used in the reaction includes, for example, meta-chloroperbenzoic acid and hydrogen peroxide solution.
When using hydrogen peroxide water as the oxidizing agent, a base may be used as necessary.
Bases used in the reaction include alkali metal hydroxides.
When a base is used in the reaction, the base is usually used in a proportion of 0.1 to 5 mol per 1 mol of compound (B2).
In the reaction, the oxidizing agent is generally used in a proportion of 1 to 5 mol per 1 mol of compound (B2).
The reaction temperature is usually in the range of -20 to 120°C, and the reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, water and a reducing agent such as sodium thiosulfate are added to the reaction mixture, the mixture is extracted with an organic solvent, and the organic layer is dried and concentrated to isolate compound (B55). can do.
参考製造法ｆ
　式（Ｂ５６）で示される化合物（以下、化合物（Ｂ５６）と記す）は、式（Ｂ５７）で示される化合物（以下、化合物（Ｂ５７）と記す）とビス（ピナコラト）ジボロンとを塩基及びパラジウム触媒の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000023
 〔式中、記号は前記と同じ意味を表す。〕
　反応は、化合物（Ｂ３）に代えて化合物（Ｂ５７）を用い、参考製造法ｂに準じて実施することができる。
　化合物（Ｂ５７）は、公知の方法に準じて製造することができる。 Reference manufacturing method f
The compound represented by formula (B56) (hereinafter referred to as compound (B56)) is prepared by reacting the compound represented by formula (B57) (hereinafter referred to as compound (B57)) with bis(pinacolato)diboron as a base and a palladium catalyst. can be produced by reacting in the presence of
Figure JPOXMLDOC01-appb-C000023
 [In the formula, symbols have the same meanings as described above. ]
The reaction can be carried out according to Reference Production Method b using compound (B57) in place of compound (B3).
Compound (B57) can be produced according to known methods.
　本発明化合物は、下記群（ａ）、群（ｂ）、群（ｃ）、及び群（ｄ）からなる群より選ばれる１以上の成分（以下、本成分と記す）と混用又は併用することができる。
　前記混用又は併用とは、本発明化合物と本成分とを、同時に、別々に又は時間間隔をおいて使用することを意味する。
　本発明化合物と本成分とを同時に使用する場合、本発明化合物及び本成分が、それぞれ別個の製剤に含まれていてもよく、１つの製剤に含まれていてもよい。
　本発明の１つの側面は、群（ａ）、群（ｂ）、群（ｃ）、及び群（ｄ）からなる群より選ばれる１以上の成分（すなわち、本成分）、並びに本発明化合物を含有する組成物（以下、組成物Ａと記す）である。 The compound of the present invention can be mixed or used in combination with one or more components (hereinafter referred to as the present component) selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) below. can be done.
The mixed use or combined use means using the compound of the present invention and this component at the same time, separately or with a time interval.
When the compound of the present invention and the component of the present invention are used simultaneously, the compound of the present invention and the component of the present invention may be contained in separate formulations or may be contained in one formulation.
One aspect of the present invention is one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) (that is, the present component), and the compound of the present invention It is a composition containing (hereinafter referred to as composition A).
　群（ａ）は、アセチルコリンエステラーゼ阻害剤（例えばカーバメート系殺虫剤、有機リン系殺虫剤）、GABA作動性塩素イオンチャネルブロッカー（例えばフェニルピラゾール系殺虫剤）、ナトリウムチャネルモジュレーター（例えば、ピレスロイド系殺虫剤）、ニコチン性アセチルコリン受容体競合的モジュレーター（例えば、ネオニコチノイド系殺虫剤）、ニコチン性アセチルコリン受容体アロステリックモジュレーター、グルタミン酸作動性塩素イオンチャネルアロステリックモジュレーター（例えば、マクロライド系殺虫剤）、幼若ホルモンミミック、マルチサイト阻害剤、弦音器官TRPVチャネルモジュレーター、ダニ類生育阻害剤、微生物由来昆虫中腸内膜破壊剤、ミトコンドリアATP合成酵素阻害剤、酸化的リン酸化脱共役剤、ニコチン性アセチルコリン受容体チャネルブロッカー（例えば、ネライストキシン系殺虫剤）、キチン合成阻害剤、脱皮阻害剤、エクダイソン受容体アゴニスト、オクトパミン受容体アゴニスト、ミトコンドリア電子伝達系複合体I, II, III及びIVの阻害剤、電位依存性ナトリウムチャネルブロッカー、アセチルCoAカルボキシラーゼ阻害剤、リアノジン受容体モジュレーター（例えば、ジアミド系殺虫剤）、弦音器官モジュレーター、微生物殺虫剤、並びにその他の殺虫活性成分、殺ダニ活性成分及び殺線虫活性成分からなる群である。これらは、IRACの作用機構に基づく分類に記載されている。 Group (a) includes acetylcholinesterase inhibitors (e.g. carbamate insecticides, organophosphorus insecticides), GABAergic chloride ion channel blockers (e.g. phenylpyrazole insecticides), sodium channel modulators (e.g. pyrethroid insecticides). ), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamatergic chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormones mimic, multisite inhibitor, chordotonal TRPV channel modulator, mite growth inhibitor, microbial-derived insect midgut membrane disruptor, mitochondrial ATP synthase inhibitor, oxidative phosphorylation uncoupler, nicotinic acetylcholine receptor channel Blockers (e.g. nereistoxin insecticides), chitin synthesis inhibitors, moulting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, inhibitors of mitochondrial electron transport chain complexes I, II, III and IV, voltage dependent from sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal modulators, microbial insecticides, and other insecticidal, acaricidal and nematicidal active ingredients. It is a group of They are described in the IRAC mechanism-based classification.
　群（ｂ）は、核酸合成阻害剤（例えば、フェニルアミド系殺菌剤、アシルアミノ酸系殺菌剤）、細胞分裂及び細胞骨格阻害剤（例えば、MBC殺菌剤）、呼吸阻害剤（例えば、QoI殺菌剤、QiI殺菌剤）、アミノ酸合成及びタンパク質合成阻害剤（例えば、アニリノピリジン系殺菌剤）、シグナル伝達阻害剤、脂質合成及び膜合成阻害剤、ステロール生合成阻害剤（例えば、トリアゾール系などのDMI殺菌剤）、細胞壁合成阻害剤、メラニン合成阻害剤、植物防御誘導剤、多作用点接触活性殺菌剤、微生物殺菌剤、及びその他の殺菌活性成分からなる群である。これらは、FRACの作用機構に基づく分類に記載されている。 Group (b) includes nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeletal inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides). , QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyridine-based fungicides), signal transduction inhibitors, lipid and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMIs such as triazoles) fungicides), cell wall synthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-site contact active fungicides, microbial fungicides, and other fungicidal active ingredients. They are described in the FRAC mechanism-based classification.
　群（ｃ）は、植物成長調整成分（菌根菌及び根粒菌を含む）の群である。 Group (c) is a group of plant growth-regulating components (including mycorrhizal fungi and rhizobia).
　群（ｄ）は、忌避成分の群である。 Group (d) is a group of repellent ingredients.
　以下に、本成分と本発明化合物の組合せの例を記載する。例えば、アラニカルブ(alanycarb) + SXはアラニカルブ(alanycarb)とSXとの組合せを意味する。
　なお、SXの略号は、実施例に記載の化合物群SX1～SX90から選ばれるいずれか１つの本発明化合物を意味する。また、以下に記載する本成分はいずれも公知の成分であり、市販の製剤から得るか、公知の方法により製造することができる。本成分が微生物の場合は、菌寄託機関から入手することもできる。なお、括弧内の数字はCAS RN（登録商標）を表す。 Examples of combinations of this component and the compound of the present invention are described below. For example, alanycarb + SX means the combination of alanycarb and SX.
The abbreviation SX means any one compound of the present invention selected from the compound group SX1 to SX90 described in Examples. In addition, all of the components described below are known components and can be obtained from commercially available formulations or produced by known methods. If this component is a microorganism, it can also be obtained from a bacteria depository. The numbers in parentheses represent CAS RN (registered trademark).
　上記群（ａ）の本成分と本発明化合物との組合せ：
　アバメクチン(abamectin) + SX, アセフェート(acephate) + SX, アセキノシル(acequinocyl) + SX, アセタミプリド(acetamiprid) + SX, アセトプロール(acetoprole) + SX, アクリナトリン(acrinathrin) + SX, アシノナピル(acynonapyr) + SX, アフィドピロペン(afidopyropen) + SX, アフォキソラネル(afoxolaner) + SX, アラニカルブ(alanycarb) + SX, アルジカルブ(aldicarb) + SX, アレスリン(allethrin) + SX, アルファシペルメトリン(alpha-cypermethrin) + SX, アルファエンドスルファン(alpha-endosulfan) + SX, リン化アルミニウム(aluminium phosphide) + SX, アミトラズ(amitraz) + SX, アザジラクチン(azadirachtin) + SX, アザメチホス(azamethiphos) + SX, アジンホスエチル(azinphos-ethyl) + SX, アジンホスメチル(azinphos-methyl) + SX, アゾシクロチン(azocyclotin) + SX, Celastrus angulatus樹皮(bark of Celastrus angulatus) + SX, ベンダイオカルブ(bendiocarb) + SX, ベンフルトリン(benfluthrin) + SX, ベンフラカルブ(benfuracarb) + SX, ベンスルタップ(bensultap) + SX, ベンゾキシメート(benzoximate) + SX, ベンズピリモキサン(benzpyrimoxan) + SX, ベータシフルトリン(beta-cyfluthrin) + SX, べータシペルメトリン(beta-cypermethrin) + SX, ビフェナゼート(bifenazate) + SX, ビフェントリン(bifenthrin) + SX, ビオアレスリン(bioallethrin) + SX, ビオレスメトリン(bioresmethrin) + SX, ビストリフルロン(bistrifluron) + SX, ホウ砂(borax) + SX, ホウ酸(boric acid) + SX, ブロフラニリド(broflanilide) + SX, ブロモプロピレート(bromopropylate) + SX, ブプロフェジン(buprofezin) + SX, ブトカルボキシム(butocarboxim) + SX, ブトキシカルボキシム(butoxycarboxim) + SX, カズサホス(cadusafos) + SX, リン化カルシウム(calcium phosphide) + SX, カルバリル(carbaryl) + SX, カルボフラン(carbofuran) + SX, カルボスルファン(carbosulfan) + SX, カルタップ塩酸塩(cartap hydrochloride) + SX, カルタップ(cartap) + SX, キノメチオナート(chinomethionat) + SX, クロラントラニリプロール(chlorantraniliprole) + SX, クロルデン(chlordane) + SX, クロレトキシホス(chlorethoxyfos) + SX, クロルフェナピル(chlorfenapyr) + SX, クロルフェンビンホス(chlorfenvinphos) + SX, クロルフルアズロン(chlorfluazuron) + SX, クロルメホス(chlormephos) + SX, クロルピクリン(chloropicrin) + SX, クロルピリホス(chlorpyrifos) + SX, クロルピリホスメチル(chlorpyrifos-methyl) + SX, クロマフェノジド(chromafenozide) + SX, クロフェンテジン(clofentezine) + SX, クロチアニジン(clothianidin) + SX, コンカナマイシンＡ(concanamycin A) + SX, クマホス(coumaphos) + SX, クリオライト(cryolite) + SX, シアノホス(cyanophos) + SX, シアントラニリプロール(cyantraniliprole) + SX, シクラニリプロール(cyclaniliprole) + SX, シクロブトリフルラム(cyclobutrifluram) + SX, シクロプロトリン(cycloprothrin) + SX, シクロキサプリド(cycloxaprid) + SX, シエノピラフェン(cyenopyrafen) + SX, cyetpyrafen + SX, シフルメトフェン(cyflumetofen) + SX, シフルトリン(cyfluthrin) + SX, シハロジアミド(cyhalodiamide) + SX, シハロトリン(cyhalothrin) + SX, シヘキサチン(cyhexatin) + SX, シペルメトリン(cypermethrin) + SX, シフェノトリン(cyphenothrin) + SX, シプロフラニリド(cyproflanilide) + SX, シロマジン(cyromazine) + SX, ダゾメット(dazomet) + SX, デルタメトリン(deltamethrin) + SX, ジメトン－S－メチル(demeton-S-methyl) + SX, ジアフェンチウロン(diafenthiuron) + SX, ダイアジノン(diazinon) + SX, ジクロルボス(dichlorvos) + SX, ジクロロメゾチアズ(dicloromezotiaz) + SX, ジコホル(dicofol) + SX, ジクロトホス(dicrotophos) + SX, ジフロビダジン(diflovidazin) + SX, ジフルベンズロン(diflubenzuron) + SX, ジメフルトリン(dimefluthrin) + SX, ジメトエート(dimethoate) + SX, ジメチルビンホス(dimethylvinphos) + SX, ジンプロピリダズ(dimpropyridaz) + SX, ジノテフラン(dinotefuran) + SX, 八ホウ酸二ナトリウム(disodium octaborate) + SX, ジスルホトン(disulfoton) + SX, DNOC(2-methyl-4,6-dinitrophenol) + SX, ドラメクチン(doramectin) + SX, セイヨウオシダ乾燥葉(dried leaves of Dryopteris filix-mas) + SX, エマメクチン安息香酸塩(emamectin-benzoate) + SX, エンペントリン(empenthrin) + SX, エンドスルファン(endosulfan) + SX, EPN(O-ethyl O-(4-nitrophenyl) phenylphosphonothioate) + SX, イプシロンメトフルトリン(epsilon-metofluthrin) + SX, イプシロンモンフルオロトリン(epsilon-momfluorothrin) + SX, エスフェンバレレート(esfenvalerate) + SX, エチオフェンカルブ(ethiofencarb) + SX, エチオン(ethion) + SX, エチプロール(ethiprole) + SX, エトプロホス(ethoprophos) + SX, エトフェンプロックス(etofenprox) + SX, エトキサゾール(etoxazole) + SX, ニガヨモギ抽出物(extract of Artemisia absinthium) + SX, インドセンダン抽出物(extract of Azadirachta indica) + SX, Cassia nigricans抽出物(extract of Cassia nigricans) + SX, クリトリア・テルナテアの抽出物(extract of clitoria　ternatea) + SX, ヒレハリソウ抽出物(extract of Symphytum officinale) + SX, アリタソウ抽出物(extracts or simulated blend of Chenopodium ambrosioides) + SX, タンジー抽出物(extract of Tanacetum vulgare) + SX, セイヨウイラクサ抽出物(extract of Urtica dioica) + SX, ヤドリギ抽出物(extract of Viscum album) + SX, ファンフル(famphur) + SX, フェナミホス(fenamiphos) + SX, フェナザキン(fenazaquin) + SX, 酸化フェンブタスズ(fenbutatin oxide) + SX, フェニトロチオン(fenitrothion) + SX, フェンメゾジチアズ(fenmezoditiaz) + SX, フェノブカルブ(fenobucarb) + SX, フェノキシカルブ(fenoxycarb) + SX,
フェンプロパトリン(fenpropathrin) + SX, フェンピロキシメート(fenpyroximate) + SX, フェンチオン(fenthion) + SX, フェンバレレート(fenvalerate) + SX, フィプロニル(fipronil) + SX, フロメトキン(flometoquin) + SX, フロニカミド(flonicamid) + SX, フルアクリピリム(fluacrypyrim) + SX, フルアザインドリジン(fluazaindolizine) + SX, フルアズロン(fluazuron) + SX, フルベンジアミド(flubendiamide) + SX, フルクロルジニリプロール(fluchlordiniliprole) + SX, フルシクロクスロン(flucycloxuron) + SX, フルシトリネート(flucythrinate) + SX, フルエンスルホン(fluensulfone) + SX, フルフェンプロックス(flufenoprox) + SX, フルフェノクスロン(flufenoxuron) + SX, フルフィプロール(flufiprole) + SX, フルメトリン(flumethrin) + SX, フルペンチオフェノックス(flupentiofenox) + SX, フルピラジフロン(flupyradifurone) + SX, フルピリミン(flupyrimin) + SX, フルララネル(fluralaner) + SX, フルバリネート(fluvalinate) + SX, フルキサメタミド(fluxametamide) + SX, ホルメタネート(formetanate) + SX, ホスチアゼート(fosthiazate) + SX, フラメトリン(furamethrin) + SX, フラチオカルブ(furathiocarb) + SX, ガンマシハロトリン(gamma-cyhalothrin) + SX, GS-オメガ/カッパHXTX-Hv1aペプチド(GS-omega/kappa HXTX-Hv1a peptide) + SX, ハルフェンプロックス(halfenprox) + SX, ハロフェノジド(halofenozide) + SX, ヘプタフルトリン(heptafluthrin) + SX, ヘプテノホス(heptenophos) + SX, ヘキサフルムロン(hexaflumuron) + SX, ヘキシチアゾクス(hexythiazox) + SX, ホップベータ酸のカリウム塩(potassium salt of hop beta acid) + SX, ヒドラメチルノン(hydramethylnon) + SX, ヒドロプレン(hydroprene) + SX, イミシアホス(imicyafos) + SX, イミダクロプリド(imidacloprid) + SX, イミダクロチズ(imidaclothiz) + SX, イミプロトリン(imiprothrin) + SX, インダザピロキサメト(indazapyroxamet) + SX, インドキサカルブ(indoxacarb) + SX, イソシクロセラム(isocycloseram) + SX, イソフェンホス(isofenphos) + SX, イソプロカルブ(isoprocarb) + SX, イソプロピルＯ－(メトキシアミノチオホスホリル) サリチラート(isopropyl-O-(methoxyaminothiophosphoryl) salicylate) + SX, イソキサチオン(isoxathion) + SX, イベルメクチン(ivermectin) + SX, カデスリン(kadethrin) + SX, カッパテフルトリン(kappa-tefluthrin) + SX, カッパビフェントリン(kappa-bifenthrin) + SX, キノプレン(kinoprene) + SX, ラムダシハロトリン(lambda-cyhalothrin) + SX, レノレマイシン(lenoremycin) + SX, レピメクチン(lepimectin) + SX, 石灰硫黄合剤(lime sulfur) + SX, ロチラネル(lotilaner) + SX, ルフェヌロン(lufenuron) + SX, マシン油(machine oil) + SX, マラチオン(malathion) + SX, メカルバム(mecarbam) + SX, メペルフルトリン(meperfluthrin) + SX, メタフルミゾン(metaflumizone) + SX, メタム(metam) + SX, メタミドホス(methamidophos) + SX, メチダチオン(methidathion) + SX, メチオカルブ(methiocarb) + SX, メソミル(methomyl) + SX, メトプレン(methoprene) + SX, メトキシクロル(methoxychlor) + SX, メトキシフェノジド(methoxyfenozide) + SX, 臭化メチル(methyl bromide) + SX, メトフルトリン(metofluthrin) + SX, メトルカルブ(metolcarb) + SX, メトキサジアゾン(metoxadiazone) + SX, メビンホス(mevinphos) + SX, ミルベメクチン(milbemectin) + SX, ミルベマイシンオキシム(milbemycin oxime) + SX, モンフルオロトリン(momfluorothrin) + SX, モノクロトホス(monocrotophos) + SX, モキシデクチン(moxidectin) + SX, ナレッド(naled) + SX, ニコフルプロール(nicofluprole) + SX, ニコチン(nicotine) + SX, 硫酸ニコチン(nicotine-sulfate) + SX, ニテンピラム(nitenpyram) + SX, ノバルロン(novaluron) + SX, ノビフルムロン(noviflumuron) + SX, アメリカアリタソウ種子油(oil of the seeds of Chenopodium anthelminticum) + SX, オメトエート(omethoate) + SX, オキサミル(oxamyl) + SX, オキサゾスルフィル(oxazosulfyl) + SX, オキシジメトンメチル(oxydemeton-methyl) + SX, 
パラチオン(parathion) + SX, パラチオンメチル(parathion-methyl) + SX, ペルメトリン(permethrin) + SX, フェノトリン(phenothrin) + SX, フェントエート(phenthoate) + SX, ホレート(phorate) + SX, ホサロン(phosalone) + SX, ホスメット(phosmet) + SX, ホスファミドン(phosphamidon) + SX, ホスフィン(phosphine) + SX, ホキシム(phoxim) + SX, ピリミカーブ(pirimicarb) + SX, ピリミホスメチル(pirimiphos-methyl) + SX, プラレトリン(prallethrin) + SX, プロフェノホス(profenofos) + SX, プロフルトリン(profluthrin) + SX, プロパルギット(propargite) + SX, プロペタムホス(propetamphos) + SX, プロポキスル(propoxur) + SX, アルギニン酸プロピレングリコール(propylene glycol alginate) + SX, プロチオホス(prothiofos) + SX, ピフルブミド(pyflubumide) + SX, ピメトロジン(pymetrozine) + SX, ピラクロホス(pyraclofos) + SX, ピレトリン(pyrethrins) + SX, ピリダベン(pyridaben) + SX, ピリダリル(pyridalyl) + SX, ピリダフェンチオン(pyridaphenthion) + SX, ピリフルキナゾン(pyrifluquinazone) + SX, ピリミジフェン(pyrimidifen) + SX, ピリミノストロビン(pyriminostrobin) + SX, ピリプロール(pyriprole) + SX, ピリプロキシフェン(pyriproxyfen) + SX, キナルホス(quinalphos) + SX, レスメトリン(resmethrin) + SX, ロテノン(rotenone) + SX, リアノジン(ryanodine) + SX, サロラネル(sarolaner) + SX, セラメクチン(selamectin) + SX, シグマシペルメトリン(sigma-cypermethrin) + SX, シラフルオフェン(silafluofen) + SX, ホウ酸ナトリウム(sodium borate) + SX, メタホウ酸ナトリウム(sodium metaborate) + SX, スピドキサマト(spidoxamat) + SX, スピネトラム(spinetoram) + SX, スピノサド(spinosad) + SX, スピロジクロフェン(spirodiclofen) + SX, スピロメシフェン(spiromesifen) + SX, スピロピジオン(spiropidion) + SX, スピロテトラマト(spirotetramat) + SX, スルフルラミド(sulfluramid) + SX, スルホテップ(sulfotep) + SX, スルホキサフロル(sulfoxaflor) + SX, 硫黄(sulfur) + SX, フッ化スルフリル(sulfuryl fluoride) + SX, 吐酒石(tartar emetic) + SX, タウフルバリネート(tau-fluvalinate) + SX, テブフェノジド(tebufenozide) + SX, テブフェンピラド(tebufenpyrad) + SX, テブピリムホス(tebupirimfos) + SX, テフルベンズロン(teflubenzuron) + SX, テフルトリン(tefluthrin) + SX, テメホス(temephos) + SX, テルブホス(terbufos) + SX, アリタソウから抽出したテルペン成分(terpene constituents of the extract of chenopodium ambrosioides near ambrosioides) + SX, テトラクロラントラニリプロール(tetrachlorantraniliprole) + SX, テトラクロルビンホス(tetrachlorvinphos) + SX, テトラジホン(tetradifon) + SX, テトラメトリン(tetramethrin) + SX, テトラメチルフルトリン(tetramethylfluthrin) + SX, テトラニリプロール(tetraniliprole) + SX, シータシペルメトリン(theta-cypermethrin) + SX, チアクロプリド(thiacloprid) + SX, チアメトキサム(thiamethoxam) + SX, チオシクラム(thiocyclam) + SX, チオジカルブ(thiodicarb) + SX, チオファノックス(thiofanox) + SX, チオメトン(thiometon) + SX, チオスルタップ二ナトリウム塩(thiosultap-disodium) + SX, チオスルタップ一ナトリウム塩(thiosultap-monosodium) + SX, チオキサザフェン(tioxazafen) + SX, トルフェンピラド(tolfenpyrad) + SX, トラロメトリン(tralomethrin) + SX, トランスフルトリン(transfluthrin) + SX, トリアザメート(triazamate) + SX, トリアゾホス(triazophos) + SX, トリクロルホン(trichlorfon) + SX, トリフルエンフロネート(trifluenfuronate) + SX, トリフルメゾピリム(triflumezopyrim) + SX, トリフルムロン(triflumuron) + SX, トリメタカルブ(trimethacarb) + SX, チクロピラゾフロル(tyclopyrazoflor) + SX, バミドチオン(vamidothion) + SX, スリナムニガキ木材抽出物(wood extract of Quassia amara) + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, キシリルカルブ(xylylcarb) + SX, ゼータシペルメトリン(zeta-cypermethrin) + SX, リン化亜鉛(zinc phosphide) + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, 2-({2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (1445683-71-5) + SX, (2Z)-2-({2-fluoro-4-methyl-5-[(R)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (2377084-09-6) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX, 
BT作物のタンパク質Cry1Ab (BT crop protein Cry1Ab) + SX, BT作物のタンパク質Cry1Ac (BT crop protein Cry1Ac) + SX, BT作物のタンパク質Cry1Fa (BT crop protein Cry1Fa) + SX, BT作物のタンパク質Cry1A.105 (BT crop protein Cry1A.105) + SX, BT作物のタンパク質Cry2Ab (BT crop protein Cry2Ab) + SX, BT作物のタンパク質Vip3A (BT crop protein Vip3A) + SX, BT作物のタンパク質mCry3A (BT crop protein mCry3A) + SX, BT作物のタンパク質Cry3Ab (BT crop protein Cry3Ab) + SX, BT作物のタンパク質Cry3Bb (BT crop protein Cry3Bb) + SX, BT作物のタンパク質Cry34Ab1/Cry35Ab1 (BT crop protein Cry34Ab1/Cry35Ab1) + SX, アドクソフィエス・オラナ顆粒病ウイルスBV-0001株(Adoxophyes orana granulosis virus strain BV-0001) + SX, アンチカルシア・ゲマタリス核多角体病ウイルス(Anticarsia gemmatalis mNPV) + SX, オートグラファ・カリフォルニア核多角体病ウイルス(Autographa californica mNPV) + SX, シジア・ポモネラ顆粒病ウイルスV15株(Cydia pomonella GV strain V15) + SX, シジア・ポモネラ顆粒病ウイルスV22株(Cydia pomonella GV strain V22) + SX, クリプトフレビア・ロイコトレタ顆粒病ウイルス(Cryptophlebia leucotreta GV) + SX, デンドロリムス・プンクタタス細胞質多面体ウイルス(Dendrolimus punctatus cypovirus) + SX, ヘリコベルパ・アルミゲラ核多角体病ウイルスBV-0003株(Helicoverpa armigera NPV strain BV-0003) + SX, ヘリコベルパ・ゼア核多角体病ウイルス(Helicoverpa zea NPV) + SX, リュマントリア・ディスパル核多角体病ウイルス(Lymantria dispar NPV) + SX, マメストラ・ブラシカエ核多角体病ウイルス(Mamestra brassicae NPV) + SX, マメストラ・コンフィグラタ核多角体病ウイルス(Mamestra configurata NPV) + SX, ネオディプリオン・アビエンティス核多角体病ウイルス(Neodiprion abietis NPV) + SX, ネオディプリオン・レコンテイ核多角体病ウイルス(Neodiprion lecontei NPV) + SX, ネオディプリオン・セルティファー核多角体病ウイルス(Neodiprion sertifer NPV) + SX, ノゼマ・ロクスタエ(Nosema locustae) + SX, オルギイア・プソイドツガタ核多角体病ウイルス(Orgyia pseudotsugata NPV) + SX, ピエリス・ラパエ顆粒病ウイルス(Pieris rapae GV) + SX, プロジア・インテルプンクテラ顆粒病ウイルス(Plodia interpunctella GV) + SX, スポドプテラ・エクシグア核多角体病ウイルス(Spodoptera exigua mNPV) + SX, スポドプテラ・リットラリス核多角体病ウイルス(Spodoptera littoralis mNPV) + SX, スポドプテラ・リツラ核多角体病ウイルス(Spodoptera litura NPV) + SX, 
Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX, Bacillus thuringiensis subsp. Aizawai strain NB200 + SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306) + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp. morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. dendrolimus + SX, Bacillus thuringiensis var. galleriae + SX, Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype strain H-14 + SX, Bacillus thuringiensis var. japonensis strain buibui + SX, Bacillus thuringiensis var. san diego strain M-7 + SX, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var. T36 + SX, Beauveria bassiana strain ANT-03 + SX, Beauveria bassiana strain ATCC74040 + SX, Beauveria bassiana strain GHA + SX,
Beauveria brongniartii + SX, Burkholderia rinojensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dectylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX, Lecanicillium lecanii strain KV01 + SX, Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX, Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5/F52 + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX, Wolbachia pipientis + SX。 A combination of this component of group (a) above and a compound of the present invention:
abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acynonapyr + SX, aphidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha endosulfan -endosulfan + SX, aluminum phosphide + SX, amitraz + SX, azadirachtin + SX, azamethiphos + SX, azinphos-ethyl + SX, azinphos- methyl) + SX, azocyclotin + SX, bark of Celastrus angulatus + SX, bendiocarb + SX, benfluthrin + SX, benfuracarb + SX, bensultap ) + SX, benzoximate + SX, benzpyrimoxan + SX, beta-cyfluthrin + SX, beta-cypermethrin + SX, bifenazate + SX, bifenthrin + SX, bioallethrin + SX, bioresmethrin + SX, bistrifl uron + SX, borax + SX, boric acid + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarbboxim ) + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphide + SX, carbaryl + SX, carbofuran + SX, carbosulfan + SX, cartap hydrochloride + SX, cartap + SX, chinomethionat + SX, chlorantraniliprole + SX, chlordane + SX, chlorethoxyfos + SX, chlorfenapyr + SX, chlorfenvinphos + SX, chlorfluazuron + SX, chlormephos + SX, chloropicrin + SX, chlorpyrifos + SX, chlorpyrifos-methyl + SX, chromafenozide + SX, clofentezine + SX, clothianidin + SX, concanamycin A + SX, coumaphos + SX, cryolite + SX, cyanophos + SX, cyantraniliprole + SX, cyclaniliprole + SX, cyclobutriflurum butrifluram + SX, cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyetpyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, cyphenothrin + SX, cyproflanilide + SX, cyromazine + SX, dazomet ) + SX, deltamethrin + SX, demeton-S-methyl + SX, diafenthiuron + SX, diazinon + SX, dichlorvos + SX, dicloromezotiaz + SX, dicofol + SX, dicrotophos + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, dimethoate + SX, dimethylvinphos + SX, dimpropyridaz + SX, dinotefuran + SX, disodium octaborate + SX, disulfoton + SX, DNOC(2-methyl- 4,6-dinitrophenol + SX, doramectin + SX, dried leaves of Dryopteris filix-mas + SX, emamectin benzoin emamectin-benzoate + SX, empenthrin + SX, endosulfan + SX, EPN(O-ethyl O-(4-nitrophenyl) phenylphosphonothioate) + SX, epsilon-metofluthrin + SX, epsilon-momfluorothrin + SX, esfenvalerate + SX, ethiofencarb + SX, ethion + SX, ethiprole + SX, ethoprophos + SX, etofenprox + SX, etoxazole + SX, extract of Artemisia absinthium + SX, extract of Azadirachta indica + SX, extract of Cassia nigricans Cassia nigricans + SX, extract of clitoria ternatea + SX, extract of Symphytum officinale + SX, extracts or simulated blend of Chenopodium ambrosioides + SX, tansy extract extract of Tanacetum vulgare + SX, extract of Urtica dioica + SX, extract of Viscum album + SX, famphur + SX, fenamiphos + SX, fenazaquin + SX, fenbutatin oxide + SX, fenitrothion + SX, fenitrothion fenmezoditiaz + SX, fenobucarb + SX, fenoxycarb + SX,
fenpropathrin + SX, fenpyroximate + SX, fenthion + SX, fenvalerate + SX, fipronil + SX, flometoquin + SX, flonicamid + SX, fluacrypyrim + SX, fluazaindolizine + SX, fluazuron + SX, flubendiamide + SX, fluchlordiniliprole + SX, flucycloxuron flucycloxuron + SX, flucythrinate + SX, fluensulfone + SX, flufenoprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin (flumethrin) + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + SX, fluralaner + SX, fluvalinate + SX, fluxametamide + SX, formetanate + SX, fosthiazate + SX, furamethrin + SX, furathiocarb + SX, gamma-cyhalothrin + SX, GS-omega/kappa HXTX-Hv1a Peptide (GS-omega/kappa HXTX-Hv1a peptide) + SX, halfenprox + SX, halofenozide + SX, heptafluthrin (hepta fluthrin + SX, heptenophos + SX, hexaflumuron + SX, hexythiazox + SX, potassium salt of hop beta acid + SX, hydramethylnon ) + SX, hydroprene + SX, imicyafos + SX, imidacloprid + SX, imidaclothiz + SX, imiprothrin + SX, indazapyroxamet + SX, indoxacarb + SX, isocycloseram + SX, isofenphos + SX, isoprocarb + SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate salicylate + SX, isoxathion + SX, ivermectin + SX, kadethrin + SX, kappa-tefluthrin + SX, kappa-bifenthrin + SX, kinoprene ) + SX, lambda-cyhalothrin + SX, lenoremycin + SX, lepimectin + SX, lime sulfur + SX, lotilaner + SX, lufenuron ( lufenuron + SX, machine oil + SX, malathion + SX, mecarbam + SX, meperfluthrin + SX, metaflumizone + SX, metam + SX, methamidophos + SX, methidathion + SX, methiocarb + SX, methomyl + SX, methoprene + SX, methoxychlor + SX, methoxyfenozide + SX, methyl bromide + SX, metofluthrin + SX, metolcarb + SX, metoxadiazone + SX, mevinphos + SX, milbemectin ) + SX, milbemycin oxime + SX, momfluorothrin + SX, monocrotophos + SX, moxidectin + SX, naled + SX, nicofluprole + SX, nicotine + SX, nicotine-sulfate + SX, nitenpyram + SX, novaluron + SX, noviflumuron + SX, oil of the seeds of Chenopodium anthelminticum) + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX,
parathion + SX, parathion-methyl + SX, permethrin + SX, phenothrin + SX, phenthoate + SX, forate + SX, phosalone + SX, phosmet + SX, phosphamidon + SX, phosphine + SX, phoxim + SX, pirimicarb + SX, pirimiphos-methyl + SX, prallethrin + SX, profenofos + SX, profluthrin + SX, propargite + SX, propetamphos + SX, propoxur + SX, propylene glycol alginate + SX, prothiofos + SX, pyflubumide + SX, pymetrozine + SX, pyraclofos + SX, pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridafenthione (pyridaphenthion) + SX, pyrifluquinazone + SX, pyrimidifen + SX, pyriminostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, ryanodine + SX, sarolaner + SX, sera Mectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate + SX, sodium metaborate + SX, spidoxamat + SX, spinetoram + SX, spinosad + SX, spirodiclofen + SX, spiromesifen + SX, spiropidion + SX, spirotetramat + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride + SX, tartar emetic + SX, taufulvali tau-fluvalinate + SX, tebufenozide + SX, tebufenpyrad + SX, tebupirimfos + SX, teflubenzuron + SX, tefluthrin + SX, temephos + SX , terbufos + SX, terpene constituents of the extract of chenopodium ambrosioides near ambrosioides + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX , tetradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, tetra Niliprole + SX, theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiophanox thiofanox + SX, thiometon + SX, thiosultap-disodium + SX, thiosultap-monosodium + SX, tioxazafen + SX, tolfenpyrad + SX, tralomethrin + SX, transfluthrin + SX, triazamate + SX, triazophos + SX, trichlorfon + SX, trifluenfuronate + SX, triflumesopyrim (triflumezopyrim) + SX, triflumuron + SX, trimethacarb + SX, tyclopyrazoflor + SX, vamidothion + SX, wood extract of Quassia amara + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide + SX, 4-[5-( 3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20 -3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl )propanamide (1118626-57-5) + SX, 2-({2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2, 2-trifluoroethyl)-1,3-thiazolidin-4-one (1445683-71-5) + SX, (2Z)-2-({2-fluoro-4-methyl-5-[(R)-(2, 2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (2377084-09-6) + SX, N-{4-chloro -3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768- 21-9) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, 1 ,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2- fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropane ecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carbboxamide + SX, 7-fluoro- N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfonyl) -2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl) -2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b ][1,4]oxazepin-10-one (2607927-97-7) + SX,
BT crop protein Cry1Ab + SX, BT crop protein Cry1Ac + SX, BT crop protein Cry1Fa + SX, BT crop protein Cry1A.105 ( BT crop protein Cry1A.105) + SX, BT crop protein Cry2Ab (BT crop protein Cry2Ab) + SX, BT crop protein Vip3A (BT crop protein Vip3A) + SX, BT crop protein mCry3A (BT crop protein mCry3A) + SX, BT crop protein Cry3Ab (BT crop protein Cry3Ab) + SX, BT crop protein Cry3Bb (BT crop protein Cry3Bb) + SX, BT crop protein Cry34Ab1/Cry35Ab1 (BT crop protein Cry34Ab1/Cry35Ab1) + SX, Adxofies Adoxophyes orana granulosis virus strain BV-0001 + SX, Anticarsia gemmatalis mNPV + SX, Autographa californica mNPV) + SX, Cydia pomonella GV strain V15 + SX, Cydia pomonella GV strain V22 + SX, Cryptophlevia leukotreta granulosis virus ( Cryptophlebia leucotreta GV) + SX, Dendrolimus punctatus cypovirus + SX, Helicoverpa armigera nuclear polyhedrosis virus BV-0003 (Helicoverpa armigera NPV st rain BV-0003) + SX, Helicoverpa zea NPV + SX, Lymantria dispar NPV + SX, Mamestra brassicae nuclear polyhedrosis virus brassicae NPV) + SX, Mamestra configurata NPV + SX, Neodiprion abietis NPV + SX, Neodiprion recontei nuclear polyhedrosis Virus (Neodiprion lecontei NPV) + SX, Neodiprion sertifer NPV + SX, Nosema locustae + SX, Orgyia pseudotsugata NPV ) + SX, Pieris rapae GV + SX, Plodia interpunctella GV + SX, Spodoptera exigua mNPV + SX, Spodoptera littoralis nuclear polyhedrosis virus (Spodoptera littoralis mNPV) + SX, Spodoptera littoralis nuclear polyhedrosis virus (Spodoptera litura NPV) + SX,
Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX, Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306) + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype strain H-14 + SX, Bacillus thuringiensis var. japonensis strain buibui + SX, Bacillus thuringien sis var. san diego strain M-7 + SX, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var. SX, Beauveria bassiana strain GHA + SX,
Beauveria brongniartii + SX, Burkholderia rinojensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dectylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. var. anisopliae BIPESCO 5/F52 + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX, Wolbachia pipientis + SX.
　上記群（ｂ）の本成分と本発明化合物との組合せ：
　アシベンゾラルSメチル(acibenzolar-S-methyl) + SX, アルジモルフ(aldimorph) + SX, アメトクトラジン(ametoctradin) + SX, アミノピリフェン(aminopyrifen) + SX, アミスルブロム(amisulbrom) + SX, アニラジン(anilazine) + SX, アザコナゾール(azaconazole) + SX, アゾキシストロビン(azoxystrobin) + SX, 塩基性硫酸銅(basic copper sulfate) + SX, ベナラキシル(benalaxyl) + SX, ベナラキシルM(benalaxyl-M) + SX, ベノダニル(benodanil) + SX, ベノミル(benomyl) + SX, ベンチアバリカルブ(benthiavalicarb) + SX, ベンチアバリカルブイソプロピル(benthiavalicarb-isopropyl) + SX, ベンゾビンジフルピル(benzovindiflupyr) + SX, ビナパクリル(binapacryl) + SX, ビフェニル(biphenyl) + SX, ビテルタノール(bitertanol) + SX, ビキサフェン(bixafen) + SX, ブラストサイジンS(blasticidin-S) + SX, ボルドー液(Bordeaux mixture) + SX, ボスカリド(boscalid) + SX, ブロモタロニル(bromothalonil) + SX, ブロムコナゾール(bromuconazole) + SX, ブピリメート(bupirimate) + SX, キャプタホール(captafol) + SX, キャプタン(captan) + SX, カルベンダジム(carbendazim) + SX, カルボキシン(carboxin) + SX, カルプロパミド(carpropamid) + SX, キノメチオナート(chinomethionat) + SX, キチン(chitin) + SX, クロロインコナジド(chloroinconazide) + SX, クロロネブ(chloroneb) + SX, クロロタロニル(chlorothalonil) + SX, クロゾリネート(chlozolinate) + SX, コレトクロリンＢ(colletochlorin B) + SX, 酢酸銅(II) (copper(II) acetate) + SX, 水酸化銅(II) (copper(II) hydroxide) + SX, 塩基性塩化銅(copper oxychloride) + SX, 硫酸銅(II) (copper(II) sulfate) + SX, クモキシストロビン(coumoxystrobin) + SX, シアゾファミド(cyazofamid) + SX, シフルフェナミド(cyflufenamid) + SX, シモキサニル(cymoxanil) + SX, シプロコナゾール(cyproconazole) + SX, シプロジニル(cyprodinil) + SX, ジクロベンチアゾクス(dichlobentiazox) + SX, ジクロフルアニド(dichlofluanid) + SX, ジクロシメット(diclocymet) + SX, ジクロメジン(diclomezine) + SX, ジクロラン(dicloran) + SX, ジエトフェンカルブ(diethofencarb) + SX, ジフェノコナゾール(difenoconazole) + SX, ジフルメトリム(diflumetorim) + SX, ジメタクロン(dimethachlone) + SX, ジメチリモール(dimethirimol) + SX, ジメトモルフ(dimethomorph) + SX, ジモキシストロビン(dimoxystrobin) + SX, ジニコナゾール(diniconazole) + SX, ジニコナゾールM(diniconazole-M) + SX, ジノカップ(dinocap) + SX, 亜リン酸水素二カリウム(dipotassium hydrogenphosphite) + SX, ジピメチトロン(dipymetitrone) + SX, ジチアノン(dithianon) + SX, ドデシルベンゼンスルホン酸ビスエチレンジアミン銅(II)錯塩(dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt) + SX, ドデモルフ(dodemorph) + SX, ドジン(dodine) + SX, エジフェンホス(edifenphos) + SX, エノキサストロビン(enoxastrobin) + SX, エポキシコナゾール(epoxiconazole) + SX, エタコナゾール(etaconazole) + SX, エタボキサム(ethaboxam) + SX, エチリモール(ethirimol) + SX, エトリジアゾール(etridiazole) + SX, ティーツリー抽出物(extract of Melaleuca alternifolia) + SX, オオイタドリ抽出物(extract of Reynoutria sachalinensis) + SX, ハウチワマメ苗木の子葉の抽出物(extract of the cotyledons of lupine plantlets ("BLAD")) + SX, ニンニク抽出物(extract of Allium sativum) + SX, スギナ抽出物(extract of Equisetum arvense) + SX, キンレンカ抽出物(extract of Tropaeolum majus) + SX, ファモキサドン(famoxadone) + SX, フェンアミドン(fenamidone) + SX, フェナミンストロビン(fenaminstrobin) + SX, フェナリモル(fenarimol) + SX, フェンブコナゾール(fenbuconazole) + SX, フェンフラム(fenfuram) + SX, フェンヘキサミド(fenhexamid) + SX, フェノキサニル(fenoxanil) + SX, フェンピクロニル(fenpiclonil) + SX, フェンピコキサミド(fenpicoxamid) + SX, フェンプロピジン(fenpropidin) + SX, フェンプロピモルフ(fenpropimorph) + SX, フェンピラザミン(fenpyrazamine) + SX, 酢酸トリフェニル錫(fentin acetate) + SX, 塩化トリフェニル錫(fentin chloride) + SX, 水酸化トリフェニル錫(fentin hydroxide) + SX, フェルバム(ferbam) + SX, フェリムゾン(ferimzone) + SX, フロリルピコキサミド(florylpicoxamid) + SX, フルアジナム(fluazinam) + SX, フルベネテラム(flubeneteram) + SX, フルジオキソニル(fludioxonil) + SX, フルフェノキサジアザム(flufenoxadiazam) + SX, フルフェノキシストロビン(flufenoxystrobin) + SX, フルインダピル(fluindapyr) + SX, フルメチルスルホリム(flumetylsulforim) + SX, フルモルフ(flumorph) + SX, フルオピコリド(fluopicolide) + SX, フルオピラム(fluopyram) + SX, フルオピモミド(fluopimomide) + SX, フルオルイミド(fluoroimide) + SX, フルオキサピプロリン(fluoxapiprolin) +SX, フルオキサストロビン(fluoxastrobin) + SX, フルオキシチオコナゾール(fluoxytioconazole) + SX, フルキンコナゾール(fluquinconazole) + SX, フルシラゾール(flusilazole) + SX, フルスルファミド(flusulfamide) + SX, フルチアニル(flutianil) + SX, フルトラニル(flutolanil) + SX, フルトリアホール(flutriafol) + SX, フルキサピロキサド(fluxapyroxad) + SX, ホルペット(folpet) + SX, ホセチル(fosetyl) + SX, ホセチルアルミニウム(fosetyl-aluminium) + SX, フベリダゾール(fuberidazole) + SX, フララキシル(furalaxyl) + SX, フラメトピル(furametpyr) + SX, グアザチン(guazatine) + SX, ヘキサコナゾール(hexaconazole) + SX, ヒメキサゾール(hymexazole) + SX, イマザリル(imazalil) + SX,
イミベンコナゾール(imibenconazole) + SX, イミノクタジン(iminoctadine) + SX, イミノクタジン酢酸塩(iminoctadine triacetate) + SX, インピルフルキサム(inpyrfluxam) + SX, ヨードカルブ(iodocarb) + SX, イプコナゾール(ipconazole) + SX, イプフェントリフルコナゾール(ipfentrifluconazole) + SX, イプフルフェノキン(ipflufenoquin) + SX, イプロベンホス(iprobenfos) + SX, イプロジオン(iprodione) + SX, イプロバリカルブ(iprovalicarb) + SX, イソフェタミド(isofetamid) + SX, イソフルシプラム(isoflucypram) + SX, イソプロチオラン(isoprothiolane) + SX, イソピラザム(isopyrazam) + SX, イソチアニル(isotianil) + SX, カスガマイシン(kasugamycin) + SX, クレソキシムメチル(kresoxim-methyl) + SX, ラミナリン(laminarin) + SX, オークの葉及び樹皮(leaves and bark of Quercus) + SX, マンコゼブ(mancozeb) + SX, マンデストロビン(mandestrobin) + SX, マンジプロパミド(mandipropamid) + SX, マンネブ(maneb) + SX, メフェントリフルコナゾール(mefentrifluconazole) + SX, メパニピリム(mepanipyrim) + SX, メプロニル(mepronil) + SX, メプチルジノカップ(meptyldinocap) + SX, メタラキシル(metalaxyl) + SX, メタラキシルM(metalaxyl-M) + SX, メタリルピコキサミド(metarylpicoxamid) + SX, メトコナゾール(metconazole) + SX, メタスルホカルブ(methasulfocarb) + SX, メチラム(metiram) + SX, メトミノストロビン(metominostrobin) + SX, メトラフェノン(metrafenone) + SX, メチルテトラプロール(metyltetraprole) + SX, ミクロブタニル(myclobutanil) + SX, ナフチフィン(naftifine) + SX, ヌアリモール(nuarimol) + SX, オクチリノン(octhilinone) + SX, オフラセ(ofurace) + SX, オリサストロビン(orysastrobin) + SX, オキサジキシル(oxadixyl) + SX, オキサチアピプロリン(oxathiapiprolin) + SX, oxine-copper + SX, オキソリニック酸(oxolinic acid) + SX, オキスポコナゾール(oxpoconazole) + SX, オキスポコナゾールフマル酸塩(oxpoconazole fumarate) + SX, オキシカルボキシン(oxycarboxin) + SX, オキシテトラサイクリン(oxytetracycline) + SX, ペフラゾエート(pefurazoate) + SX, ペンコナゾール(penconazole) + SX, ペンシクロン(pencycuron) + SX, ペンフルフェン(penflufen) + SX, ペンチオピラド(penthiopyrad) + SX, フェナマクリル(phenamacril) + SX, 亜リン酸(phosphorous acid) + SX, フサライド(phthalide) + SX, ピカルブトラゾクス(picarbutrazox) + SX, ピコキシストロビン(picoxystrobin) + SX, ピペラリン(piperalin) + SX, ポリオキシン(polyoxins) + SX, 炭酸水素カリウム(potassium hydrogencarbonate) + SX, 亜リン酸二水素カリウム(potassium dihydrogenphosphite) + SX, プロベナゾール(probenazole) + SX, プロクロラズ(prochloraz) + SX, プロシミドン(procymidone) + SX, プロパミジン(propamidine) + SX, プロパモカルブ(propamocarb) + SX, プロピコナゾール(propiconazole) + SX, プロピネブ(propineb) + SX, プロキナジド(proquinazid) + SX, プロチオカルブ(prothiocarb) + SX, プロチオコナゾール(prothioconazole) + SX, ピジフルメトフェン(pydiflumetofen) + SX, ピラクロストロビン(pyraclostrobin) + SX, ピラメトストロビン(pyrametostrobin) + SX, ピラオキシストロビン(pyraoxystrobin) + SX, ピラプロポイン(pyrapropoyne) + SX, ピラジフルミド(pyraziflumid) + SX, ピラゾホス(pyrazophos) + SX, ピリベンカルブ(pyribencarb) + SX, ピリブチカルブ(pyributicarb) + SX, ピリダクロメチル(pyridachlometyl) + SX, ピリフェノックス(pyrifenox) + SX, ピリメタニル(pyrimethanil) + SX, ピリモルフ(pyrimorph) + SX, ピリオフェノン(pyriofenone) + SX, ピリソキサゾール(pyrisoxazole) + SX, ピロキロン(pyroquilon) + SX, キラヤ科植物抽出物(Quillaja extract) + SX, キンコナゾール(quinconazole) + SX, キノフメリン(quinofumelin) + SX, キノキシフェン(quinoxyfen) + SX, キントゼン(quintozene) + SX, キヌアのサポニン(Saponins of Chenopodium quinoa) + SX, セボクチラミン(seboctylamine) + SX, セダキサン(sedaxane) + SX, シルチオファム(silthiofam) + SX, シメコナゾール(simeconazole) + SX, 炭酸水素ナトリウム(sodium hydrogencarbonate) + SX, スピロキサミン(spiroxamine) + SX, ストレプトマイシン(streptomycin) + SX, 硫黄(sulfur) + SX, テブコナゾール(tebuconazole) + SX, テブフロキン(tebufloquin) + SX, テクロフタラム(teclofthalam) + SX, テクナゼン(tecnazene) + SX, テルビナフィン(terbinafine) + SX, テトラコナゾール(tetraconazole) + SX, チアベンダゾール(thiabendazole) + SX, チフルザミド(thifluzamide) + SX, チオファネート(thiophanate) + SX, チオファネートメチル(thiophanate-methyl) + SX, チウラム(thiram) + SX, チモール(thymol) + SX, チアジニル(tiadinil) + SX, トルクロホスメチル(tolclofos-methyl) + SX, トルフェンピラド(tolfenpyrad) + SX, トルプロカルブ(tolprocarb) + SX, トリルフルアニド(tolylfluanid) + SX, トリアジメホン(triadimefon) + SX, トリアジメノール(triadimenol) + SX, トリアゾキシド(triazoxide) + SX, トリクロピリカルブ(triclopyricarb) + SX, トリシクラゾール(tricyclazole) + SX, トリデモルフ(tridemorph) + SX, トリフロキシストロビン(trifloxystrobin) + SX, トリフルミゾール(triflumizole) + SX, トリホリン(triforine) + SX, トリチコナゾール(triticonazole) + SX, バリダマイシン(validamycin) + SX, バリフェナレート(valifenalate) + SX, ビンクロゾリン(vinclozolin) + SX, マスタードパウダー(yellow mustard powder) + SX, zinc thiazole + SX, ジネブ(zineb) + SX, ジラム(ziram) + SX, ゾキサミド(zoxamide) + SX,
N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S, 5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX,
(2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide(2043675-28-9) + SX, 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, 
N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylate + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methylpropanoyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 
Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo(商標) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB/BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002/AQ30002 + SX, Bacillus subtilis strain QST30004/AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON/M/91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SX, Pseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa strain PF-A22UL + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX。 Combination of this component of group (b) above with a compound of the present invention:
acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl-M + SX, benodanil + SX, benomyl + SX, benthiavalicarb + SX, benthiavalicarb-isopropyl + SX, benzovindiflupyr + SX, binapacryl + SX, biphenyl + SX, bitertanol + SX, bixafen + SX, blasticidin-S + SX, Bordeaux mixture + SX, boscalid + SX, bromothalonil ( bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionat + SX, chitin + SX, chloroinconazide + SX, chloroneb + SX, chlorothalonil + SX, clozolinate (chlozolinate) + SX, colletochlorin B + SX, copper(II) acetate + SX, copper(II) hydroxide + SX, basic copper chloride (copper oxychloride) + SX, copper(II) sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SX, cymoxanil + SX, cyproconazole + SX, cyprodinil + SX, dichlobentiazox + SX, dichlofluanid + SX, diclocymet + SX, diclomezine + SX, dichloran + SX, diethofencarb + SX, difenoconazole + SX, diflumetorim + SX, dimethachlone + SX, dimethirimol + SX, dimethomorph + SX , dimoxystrobin + SX, diniconazole + SX, diniconazole-M + SX, dinocap + SX, dipotassium hydrogenphosphite + SX, dipimethitron ( dipymetitrone + SX, dithianon + SX, dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt + SX, dodemor ph) + SX, dodine + SX, edifenphos + SX, enoxastrobin + SX, epoxiconazole + SX, etaconazole + SX, ethaboxam + SX , ethirimol + SX, etridiazole + SX, tea tree extract (extract of Melaleuca alternifolia) + SX, extract of Reynoutria sachalinensis + SX, extract of lupine seedling cotyledons (extract of the cotyledons of lupine plantlets ("BLAD")) + SX, garlic extract (extract of Allium sativum) + SX, horsetail extract (extract of Equisetum arvense) + SX, nasturtium extract (extract of Tropaeolum majus) + SX, famoxadone + SX, fenamidone + SX, fenaminstrobin + SX, fenarimol + SX, fenbuconazole + SX, fenfuram + SX, fenhexamide (fenhexamid) + SX, fenoxanil + SX, fenpiclonil + SX, fenpicoxamid + SX, fenpropidin + SX, fenpropimorph + SX, fenpyrazamine ( fenpyrazamine + SX, fentin acetate + SX, triphenyltin chloride + SX, fentin hydroxide + SX, ferb am) + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, flubeneteram + SX, fludioxonil + SX, flufenoxadiazam ) + SX, flufenoxystrobin + SX, fluindapyr + SX, flumethylsulforim + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiproline +SX, fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole (fluquinconazole) + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, fluxapyroxad + SX, folpet + SX, fosetyl + SX, fosetyl-aluminium + SX, fuberidazole + SX, furalaxyl + SX, furametpyr + SX, guazatine ( guazatine + SX, hexaconazole + SX, hymexazole + SX, imazalil + SX,
imibenconazole + SX, iminoctadine + SX, iminoctadine triacetate + SX, inpyrfluxam + SX, iodocarb + SX, ipconazole + SX, ipfentrifluconazole + SX, ipflufenoquin + SX, iprobenfos + SX, iprodione + SX, iprovalicarb + SX, isofetamide + SX, isoflur cypram + SX, isoprothiolane + SX, isopyrazam + SX, isotianil + SX, kasugamycin + SX, kresoxim-methyl + SX, laminarin + SX , oak leaves and bark of Quercus + SX, mancozeb + SX, mandestrobin + SX, mandipropamid + SX, maneb + SX, mefentrifluconazole (mefentrifluconazole) + SX, mepanipyrim + SX, mepronil + SX, meptyldinocap + SX, metalaxyl + SX, metalaxyl-M + SX, methallyl pico metarylpicoxamid + SX, metconazole + SX, metasulfocarb + SX, metiram + SX, metominostrob in) + SX, metrafenone + SX, methyltetraprole + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX, octhilinone + SX, ofrace (ofurace) + SX, orysastrobin + SX, oxadixyl + SX, oxathiapiprolin + SX, oxine-copper + SX, oxolinic acid + SX, oxpoconazole ( oxpoconazole + SX, oxpoconazole fumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefurazoate + SX, penconazole + SX, pencycuron + SX, penflufen + SX, penthiopyrad + SX, phenamacril + SX, phosphorous acid + SX, phthalide + SX, picalbutrazox picarbutrabox + SX, picoxystrobin + SX, piperalin + SX, polyoxins + SX, potassium hydrogencarbonate + SX, potassium dihydrogenphosphite + SX, probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb rb) + SX, propiconazole + SX, propineb + SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen ) + SX, pyraclostrobin + SX, pyrametostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridaclomethyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriophenone (pyriofenone) + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract + SX, quinconazole + SX, quinofumelin + SX, quinoxyfen ) + SX, quintozene + SX, Saponins of Chenopodium quinoa + SX, seboctylamine + SX, sedaxane + SX, silthiofam + SX, simeconazole + SX , sodium hydrogencarbonate + SX, spiroxamine + SX, streptomycin + SX, sulfur ) + SX, tebuconazole + SX, tebufloquin + SX, teclofthalam + SX, tecnazene + SX, terbinafine + SX, tetraconazole + SX, thiabendazole ( thiabendazole + SX, thifluzamide + SX, thiophanate + SX, thiophanate-methyl + SX, thiram + SX, thymol + SX, tiadinil + SX, tolclofos tolclofos-methyl + SX, tolfenpyrad + SX, tolprocarb + SX, tolylfluanid + SX, triadimefon + SX, triadimenol + SX, triazoxide ( triazoxide + SX, triclopyricarb + SX, tricyclazole + SX, tridemorph + SX, trifloxystrobin + SX, triflumizole + SX, triforine ) + SX, triticonazole + SX, validamycin + SX, valifenalate + SX, vinclozolin + SX, yellow mustard powder + SX, zinc thiazole + SX , zineb + SX, ziram + SX, zoxamide + SX,
N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781 -91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenoxy) -2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N- methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4 -(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX, N'-[5 -bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, 4-(2-bromo-4- fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4- methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N- [(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl) )-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4 -chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R , 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3 ) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6 ) + SX, (1R, 2S, 5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1 -ol (1801930-08-4) + SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol -1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-h ydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2- (1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2, 4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1 -chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-( trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy )-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2 -methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[ 1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (161 6239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carbboxamide (1847460- 02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carbboxamide (1847460-05- 2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide ( 1445331-27-0) + SX,
(2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54 -3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, N- (1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carbboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8 -fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl )isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl )isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl }methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy- N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({ 4-[5 -(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pheny l}methyl)urea + SX, N'-ethyl-N-methoxy-N-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-acetyl-2-(ethanesulfonyl)- N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide(2043675-28-9) + SX, 3-(4-bromo-7-fluoroindol-1-yl)butan- 2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromoindol-1-yl)butan-2-yl N-[(3- hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin -2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl] -L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)- 1-[1-(naphthalen-1-yl)cyclopropyl]e thyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3 -(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX,
N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl }methyl)propanamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N- ({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoromethyl) -4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2, 4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl] phenyl}methyl)urea + SX, N,N-diethyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N- methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phe nyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4 -[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 4-({4-[5-(trifluoromethyl)-1,2,4 -oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin- 3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2 -({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4 -[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl) -1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole -4-carboxylate + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl )-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole- 4-carboxamide + SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carbboxamide + SX, N, N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy -3-(1H-1,2,4-triazol-1-yl)propanoate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1 ,2,4-triazol-1-yl)propanoate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4- triazol-1-yl)propanoate + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-( difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihy droisoquinoline + SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]- 2-phenoxyacetamide + SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, ethyl 1-[(4 -{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2 -ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy )-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carbboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N- [2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carbboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2 -difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carbboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2 -dimethylcyclobutyl)-5-methylthiazole-4-carbboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spi ro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carbboxamide + SX, 2-[(2-methoxyacetyl)( 2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carbboxamide + SX, 2-[(2-methylpropanoyl)(2,6-difluoropyridin-4- yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[ 1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl )ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2 -amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX , 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl ) -1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4 -oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2 -yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5 -[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6 -methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2 -fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX,3-[3 -(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6- dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-meth ylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX,
Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo™ EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 , Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB/BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002/AQ30002 + SX, Bacillus subtilis strain QST30004/AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans s carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SX, Pseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomon SX syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa strain PF-A22UL + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium ol gandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichod erma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX.
　上記群（ｃ）の本成分と本発明化合物との組合せ：
　１－メチルシクロプロペン(1-methylcyclopropene) + SX, １，３－ジフェニルウレア(1,3-diphenylurea) + SX, ２，３，５－トリヨード安息香酸(2,3,5-triiodobenzoic acid) + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, ５－アミノレブリン酸塩酸塩(5-aminolevulinic acid hydrochloride) + SX, ６－ベンジルアミノプリン(6-benzylaminopurine) + SX, アブシシン酸(abscisic acid) + SX, AVG (aminoethoxyvinylglycine) + SX, アニシフルプリン(anisiflupurin) + SX, アンシミドール(ancymidol) + SX, ブトルアリン(butralin) + SX, 炭酸カルシウム(calcium carbonate) + SX, 塩化カルシウム(calcium chloride) + SX, ギ酸カルシウム(calcium formate) + SX, 過酸化カルシウム(calcium peroxide) + SX, 石灰硫黄(calcium polysulfide) + SX, 硫酸カルシウム(calcium sulfate) + SX, クロルメコートクロリド(chlormequat-chloride) + SX, クロロプロファム(chlorpropham) + SX, 塩化コリン(choline chloride) + SX, クロプロップ(cloprop) + SX, シアナミド(cyanamide) + SX, シクラニリド(cyclanilide) + SX, ダミノジッド(daminozide) + SX, デカン－１－オール(decan-1-ol) + SX, ジクロルプロップ(dichlorprop) + SX, ジケグラック(dikegulac) + SX, ジメチピン(dimethipin) + SX, ジクワット(diquat) + SX, エテホン(ethephon) + SX, エチクロゼート(ethychlozate) + SX, フルメトラリン(flumetralin) + SX, フルルプリミドール(flurprimidol) + SX, ホルクロルフェヌロン(forchlorfenuron) + SX, ホルモノネチン(formononetin) + SX, ジベレリンＡ(Gibberellin A) + SX, ジベレリンＡ３(Gibberellin A3) + SX, イナベンフィド(inabenfide) + SX, カイネチン(Kinetin) + SX, lipochitooligosaccharide SP104 + SX, マレイン酸ヒドラジド(maleic hydrazide) + SX, メフルイジド(mefluidide) + SX, メピコートクロリド(mepiquat-chloride) + SX, 酸化型グルタチオン(oxidized glutathione) + SX, パクロブトラゾール(paclobutrazol) + SX, ペンディメタリン(pendimethalin) + SX, プロヘキサジオンカルシウム(prohexadione-calcium) + SX, プロヒドロジャスモン(prohydrojasmon) + SX, ピラフルフェンエチル(pyraflufen-ethyl) + SX, シントフェン(sintofen) + SX, １－ナフタレン酢酸ナトリウム(sodium 1-naphthaleneacetate) + SX, シアン酸ナトリウム(sodium cyanate) + SX, チジアズロン(thidiazuron) + SX, トリアペンテノール(triapenthenol) + SX, トリブホス(tribufos) + SX, トリネキサパックエチル(trinexapac-ethyl) + SX, ウニコナゾールP (uniconazole-P) + SX, ２－（ナフタレン－１－イル）アセトアミド(2-(naphthalen-1-yl)acetamide) + SX, ［４－オキソ－４－（２－フェニルエチル）アミノ］酪酸 + SX, ５－（トリフルオロメチル）ベンゾ［b］チオフェン－２－カルボン酸メチル + SX, ３－［（６－クロロ－４－フェニルキナゾリン－２－イル）アミノ］プロパン－１－オール + SX, Claroideoglomus etunicatum + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 + SX, Rhizophagus irregularis DAOM 197198 + SX, Azorhizobium caulinodans + SX, Azospirillum amazonense + SX, 
Azospirillum brasilense XOH + SX, Azospirillum brasilense Ab-V5 + SX, Azospirillum brasilense Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 + SX, Bradyrhizobium elkanii SEMIA 5019 + SX, Bradyrhizobium japonicum TA-11 + SX, Bradyrhizobium japonicum USDA 110 + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Delftia acidovorans RAY209 + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + SX, Mesorhizobium loti + SX, Rhizobium etli + SX, Rhizobium galegae + SX, Rhizobium leguminosarum bv. Phaseoli + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium leguminosarum bv. Viciae + SX, Rhizobium trifolii + SX, Rhizobium tropici + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, Zucchini Yellow Mosaik Virus weak strain + SX。 Combination of this component of group (c) above with a compound of the present invention:
1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX , IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy) acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancimidol + SX, Butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat-chloride + SX, chlorpropham + SX, choline chloride + SX, cloprop + SX, cyanamide + SX, cyclanilide + SX, daminozide + SX, decan-1-ol ol) + SX, dichlorprop + SX, dikegulac + SX, dimethipin + SX, diquat + SX, ethephon + SX, ethychlozate + SX, flumetralin (flumetralin) + SX, flurprimidol + SX, forchlorfenuron + SX, formononetin + SX, Gibberellin A + SX, Gibberellin A3 + SX, Inabenfide (inabenfide) + SX, Kinetin + SX, lipochitooligosaccharide SP104 + SX, maleic hydrazide + SX, mefluidide + SX, mepiquat-chloride + SX, oxidized glutathione (oxidized glutathione) + SX, paclobutrazol + SX, pendimethalin + SX, prohexadione-calcium + SX, prohydrojasmon + SX, pyraflufen pyraflufen-ethyl + SX, sintofen + SX, sodium 1-naphthaleneacetate + SX, sodium cyanate + SX, thidiazuron + SX, tripentenol (triapenthenol) + SX, tribufos + SX, trinexapac-ethyl + SX, uniconazole-P + SX, 2-(naphthalen-1-yl)acetamide (2-(napht halen-1-yl)acetamide) + SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid + SX, methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate + SX , 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol + SX, Claroideoglomus etunicatum + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 + SX, Rhizophagus irregularis DAOM 197198 + SX, Azorhizobium caulinodans + SX, Azospirillum amazonense + SX,
Azospirillum brasilense XOH + SX, Azospirillum brasilense Ab-V5 + SX, Azospirillum brasilense Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 + SX, Bradyrhizobium SX elkanii SEMIA 5019 + SX, Bradyrhizobium japonicum TA-11 + SX, Bradyrhizobium japonicum USDA 110 + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Delftia acidovorans RAY209 + SX, Mesorhizobium ciceri + SX, Mesorhizobium ciceri + SX, Mesorhizobium lotizobium + SX SX, Rhizobium etli + SX, Rhizobium galegae + SX, Rhizobium leguminosarum bv. Phaseoli + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium leguminosarum bv. , Sinorhizobium meliloti + SX, Zucchini Yellow Mosaik Virus weak strain + SX.
　上記群（ｄ）の本成分と本発明化合物との組合せ：
　アントラキノン(anthraquinone) + SX, ディート(deet) + SX, イカリジン(icaridin) + SX。 Combination of this component of group (d) above with a compound of the present invention:
anthraquinone + SX, deet + SX, icaridin + SX.
　本発明化合物と本成分との比は、特に限定されるものではないが、重量比（本発明化合物：本成分）で１０００：１～１：１０００、５００：１～１：５００、１００：１～１：１００、５０：１、２０：１、１０：１、９：１、８：１、７：１、６：１、５：１、４：１、３：１、２：１、１：１、１：２、１：３、１：４、１：５、１：６、１：７、１：８、１：９、１：１０、１：２０、１：５０等が挙げられる。 The ratio of the compound of the present invention to the component is not particularly limited, but the weight ratio (compound of the present invention:the component) is 1000:1 to 1:1000, 500:1 to 1:500, 100:1. ~1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1 : 1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, etc. .
　本発明化合物は、有害生物に対して効力を有する。有害生物としては、例えば、植物病原性微生物、有害昆虫や有害ダニ類等の有害節足動物、有害線虫、及び有害軟体動物が挙げられる。 The compound of the present invention has efficacy against pests. Examples of pests include phytopathogenic microorganisms, harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks.
　本発明化合物は、真菌（fungi）、卵菌(Oomycete)、ネコブカビ(Phytomyxea) 、細菌(bacteria)等の植物病原性微生物が引き起こす植物病害を防除することが出来る。真菌（fungi）としては、例えば、子嚢菌門（Ascomycota）、担子菌門（Basidiomycota）、Blasocladiomycota、Chytridiomycota、Mucoromycota及びOlpidiomycotaが挙げられる。具体的には、例えば、以下のものが挙げられる。括弧内は、各病害を引き起こす植物病原性微生物の学名を示す。 The compound of the present invention can control plant diseases caused by phytopathogenic microorganisms such as fungi, Oomycete, Phytomyxea, and bacteria. Fungi include, for example, Ascomycota, Basidiomycota, Blasocladiomycota, Chytridiomycota, Mucoromycota and Olpidiomycota. Specifically, the following are mentioned, for example. Parentheses indicate the scientific name of the phytopathogenic microorganism that causes each disease.
　イネの病害：いもち病（Pyricularia oryzae）、ごま葉枯病（Cochliobolus miyabeanus）、紋枯病（Rhizoctonia solani）、馬鹿苗病（Gibberella fujikuroi）、黄化萎縮病（Sclerophthora macrospora）、にせいもち病及び穂枯病（Epicoccum nigrum）、苗立枯病（Trichoderma viride、Rhizopus oryzae）、疑似紋枯症（赤色菌核病菌（Waitea circinata）、褐色菌核病菌（Ceratobasidium setariae）、褐色紋枯病菌（Thanatephorus cucumeris））；
　コムギの病害：うどんこ病（Blumeria graminis）、赤かび病（Fusarium graminearum、Fusarium avenaceum、Fusarium culmorum、Microdochium nivale）、黄さび病（Puccinia striiformis）、黒さび病（Puccinia graminis）、赤さび病（Puccinia recondita）、紅色雪腐病（Microdochium nivale、Microdochium majus）、雪腐小粒菌核病（Typhula incarnata、Typhula ishikariensis）、裸黒穂病（Ustilago tritici）、なまぐさ黒穂病（Tilletia caries、Tilletia controversa）、眼紋病（Pseudocercosporella herpotrichoides）、葉枯病（Septoria tritici）、ふ枯病（Stagonospora nodorum）、黄斑病（Pyrenophora tritici-repentis）、リゾクトニア属菌による苗立枯れ病（Rhizoctonia solani）、立枯病（Gaeumannomyces graminis）、いもち病（Pyricularia graminis-tritici）；
　オオムギの病害：うどんこ病（Blumeria graminis）、赤かび病（Fusarium graminearum、Fusarium avenaceum、Fusarium culmorum、Microdochium nivale）、黄さび病（Puccinia striiformis）、黒さび病（Puccinia graminis）、小さび病（Puccinia hordei）、裸黒穂病（Ustilago nuda）、雲形病（Rhynchosporium secalis）、網斑病（Pyrenophora teres）、斑点病（Cochliobolus sativus）、斑葉病（Pyrenophora graminea）、ラムラリアリーフスポット病（Ramularia collo-cygni）、リゾクトニア属菌による苗立枯れ病（Rhizoctonia solani）；
　トウモロコシの病害：さび病（Puccinia sorghi）、南方さび病（Puccinia polysora）、すす紋病（Setosphaeria turcica）、熱帯性さび病（Physopella zeae）、ごま葉枯病（Cochliobolus heterostrophus）、炭疽病（Colletotrichum graminicola）、グレーリーフスポット病（Cercospora zeae-maydis）、褐斑病（Kabatiella zeae）、ファエオスファエリアリーフスポット病（Phaeosphaeria maydis）、Diplodia病（Stenocarpella maydis、Stenocarpella macrospora）、ストークロット病（Fusarium graminearum、Fusarium verticilioides、Colletotrichum graminicola）、黒穂病（Ustilago maydis）、フイソデルマ病（Physoderma maydis）、tar spot病(Phyllachora maydis)；
　ワタの病害：炭疽病（Colletotrichum gossypii）、白かび病（Ramularia areola）、黒斑病（Alternaria macrospora、Alternaria gossypii）、Black root rot病 (Thielaviopsis basicola）；
　コーヒーの病害：さび病（Hemileia vastatrix）、リーフスポット病（Cercospora coffeicola)；
　ナタネの病害：菌核病（Sclerotinia sclerotiorum）、黒斑病（Alternaria brassicae）、根朽病（Phoma lingam）、light leaf spot病（Pyrenopeziza brassicae）；
　サトウキビの病害：さび病（Puccinia melanocephela、Puccinia kuehnii）、黒穂病 (Ustilago scitaminea）；
　ヒマワリの病害：さび病（Puccinia helianthi）、べと病（Plasmopara halstedii）；
カンキツ類の病害：黒点病（Diaporthe citri）、そうか病（Elsinoe fawcetti）、緑かび病（Penicillium digitatum）、青かび病（Penicillium italicum）、疫病（Phytophthora parasitica、Phytophthora citrophthora）、こうじかび病（Aspergillus niger）；
　リンゴの病害：モニリア病（Monilinia mali）、腐らん病（Valsa ceratosperma）、うどんこ病（Podosphaera leucotricha）、斑点落葉病（Alternaria alternata apple pathotype）、黒星病（Venturia inaequalis）、炭疽病（Glomerella cingulata、Colletotrichum acutatum）、褐斑病（Diplocarpon mali）、輪紋病（Botryosphaeria berengeriana）、疫病（Phytophtora cactorum）、赤星病（Gymnosporangium juniperi-virginianae、Gymnosporangium yamadae）；
　ナシの病害：黒星病（Venturia nashicola、Venturia pirina）、黒斑病（Alternaria alternata Japanese pear pathotype）、赤星病（Gymnosporangium haraeanum）；
　モモの病害：灰星病（Monilinia fructicola）、黒星病（Cladosporium carpophilum）、ホモプシス腐敗病（Phomopsis sp.）、縮葉病（Taphrina deformans）；
　ブドウの病害：黒とう病（Elsinoe ampelina）、晩腐病（Glomerella cingulata、Colletotrichum acutatum）、うどんこ病（Uncinula necator）、さび病（Phakopsora ampelopsidis）、ブラックロット病（Guignardia bidwellii）、べと病（Plasmopara viticola）；
　カキの病害：炭疽病（Gloeosporium kaki、Colletotrichum acutatum）、落葉病（Cercospora kaki、Mycosphaerella nawae）；
　イチジクの病害：さび病（Phakopsora nishidana）；
　ウリ類の病害：炭疽病（Colletotrichum lagenarium）、うどんこ病（Sphaerotheca fuliginea）、つる枯病（Didymella bryoniae）、褐斑病（Corynespora cassiicola）、つる割病（Fusarium oxysporum）、べと病（Pseudoperonospora cubensis）、疫病（Phytophthora capsici）、苗立枯病（Pythium sp.）；
　トマトの病害：輪紋病（Alternaria solani）、葉かび病（Cladosporium fulvum）、すすかび病（Pseudocercospora fuligena）、疫病（Phytophthora infestans）、うどんこ病（Leveillula taurica）；
　ナスの病害：褐紋病（Phomopsis vexans）、うどんこ病（Erysiphe cichoracearum）；
　アブラナ科野菜の病害：黒斑病（Alternaria japonica）、白斑病（Cercosporella brassicae）、根こぶ病（Plasmodiophora brassicae）、べと病（Peronospora parasitica）、白さび病（Albugo candida）；
　ネギの病害：さび病（Puccinia allii）；
　ダイズの病害：紫斑病（Cercospora kikuchii）、黒とう病（Elsinoe glycines）、黒点病（Diaporthe phaseolorum var. sojae）、さび病（Phakopsora pachyrhizi)、褐色輪紋病（Corynespora cassiicola）、炭疽病（Colletotrichum glycines、Colletotrichum truncatum）、葉腐病（Rhizoctonia solani）、褐紋病（Septoria glycines）、斑点病（Cercospora sojina）、菌核病（Sclerotinia sclerotiorum）、うどんこ病（Microsphaera diffusa）、茎疫病（Phytophthora sojae）、べと病（Peronospora manshurica）、突然死病（Fusarium virguliforme）、黒根腐病（Calonectria ilicicola）、Diaporthe/Phomopsis complex（Diaporthe longicolla）；
　インゲンの病害：菌核病（Sclerotinia sclerotiorum）、さび病（Uromyces appendiculatus）、角斑病（Phaeoisariopsis griseola）、炭疽病（Colletotrichum lindemuthianum）、根腐病（Fusarium solani）；
　ラッカセイの病害：黒渋病（Cercospora personata）、褐斑病（Cercospora arachidicola）、白絹病（Sclerotium rolfsii）、黒根腐病（Calonectria ilicicola）；
　エンドウの病害：うどんこ病（Erysiphe pisi）、根腐病（Fusarium solani）；
　ジャガイモの病害：夏疫病（Alternaria solani）、疫病（Phytophthora infestans）、緋色腐敗病（Phytophthora erythroseptica）、粉状そうか病（Spongospora subterranea f. sp. subterranea）、半身萎凋病（Verticillium albo－atrum、Verticillium dahliae、Verticillium nigrescens）、乾腐病（Fusarium solani）、がん腫病（Synchytrium endobioticum）；
　イチゴの病害：うどんこ病（Sphaerotheca humuli）；
　チャの病害：網もち病（Exobasidium reticulatum）、白星病（Elsinoe leucospila）、輪斑病（Pestalotiopsis sp.）、炭疽病（Colletotrichum theae－sinensis）；
　タバコの病害：赤星病（Alternaria longipes）、炭疽病（Colletotrichum tabacum）、べと病（Peronospora tabacina）、疫病（Phytophthora nicotianae）；
　テンサイの病害：褐斑病（Cercospora beticola）、葉腐病（Thanatephorus cucumeris）、根腐病（Thanatephorus cucumeris）、黒根病（Aphanomyces cochlioides）、さび病（Uromyces betae）；
　バラの病害：黒星病（Diplocarpon rosae）、うどんこ病（Sphaerotheca pannosa）；
　キクの病害：褐斑病（Septoria chrysanthemi－indici）、白さび病（Puccinia horiana）；
　タマネギの病害：白斑葉枯病（Botrytis cinerea、Botrytis byssoidea、Botrytis squamosa)、灰色腐敗病（Botrytis allii）、小菌核性腐敗病（Botrytis squamosa）；
　種々の作物の病害：灰色かび病（Botrytis cinerea）、菌核病（Sclerotinia sclerotiorum）、黒腐菌核病(Sclerotium cepivorum)、苗立枯病（Pythium aphanidermatum、Pythium irregulare、Pythium ultimum）；
　ダイコンの病害：黒斑病（Alternaria brassicicola）；
　シバの病害：ダラースポット病（Sclerotinia homoeocarpa）、ブラウンパッチ病、ラージパッチ病（Rhizoctonia solani）、赤焼病（Pythium aphanidermatum）；
　バナナの病害：シガトカ病（Mycosphaerella fijiensis、Mycosphaerella musicola）;
　レンズマメの病害：Ascochyta病（Ascochyta lentis）;
　ヒヨコマメの病害：Ascochyta病（Ascochyta rabiei）;
　ピーマンの病害：炭疽病（Colletotrichum scovillei）；
　マンゴーの病害：炭疽病（Colletotrichum acutatum）；
　果樹の病害：白紋羽病（Rosellinia necatrix）、紫紋羽病（Helicobasidium mompa）；
　収穫後のリンゴ、ナシ等の果実の病害：ムコールロット病（Mucor piriformis）；
Aspergillus属、Penicillium属、Fusarium属、Gibberella属、Tricoderma属、Thielaviopsis属、Rhizopus属、Mucor属、Corticium属、Phoma属、Rhizoctonia属、Diplodia属等によって引き起こされる、種子病害又は生育初期の病害；
　ウイルス病：Olpidium brassicaeによって媒介されるレタスのビッグベイン病、Polymyxa属（例えば、Polymyxa betae及びPolymyxa graminis）によって媒介される各種作物のウイルス病；
　細菌(bacteria)が引き起こす病害：イネの苗立枯細菌病（Burkholderia plantarii）、イネの内穎褐変病（Pantoea ananatis）、イネの白葉枯病（Xanthomonas oryzae pv. oryzae.）、キュウリの斑点細菌病（Pseudomonas ｓyringae pv． lachrymans）、ナスの青枯病（Ralstonia solanacearum）、カンキツのかいよう病（Xanthomonas citri）、ハクサイの軟腐病（Erwinia carotovora）、ジャガイモのそうか病（Streptomyces scabiei）、トウモロコシのGoss's wilt病（Clavibacter michiganensis）、ブドウ、オリーブ、モモ等のピアス病（Xylella fastidiosa）、リンゴ、モモ、サクランボ等のバラ科植物の根頭がんしゅ病（Agrobacterium tumefaciens）。 Rice diseases: Pyricularia oryzae, Cochliobolus miyabeanus, Rhizoctonia solani, Gibberella fujikuroi, Sclerophthora macrospora, Sclerophthora macrospora, and Epicoccum nigrum, Trichoderma viride, Rhizopus oryzae, pseudocolonial blight (Waitea circinata, Ceratobasidium setariae, Thanatephorus cucumeris));
Wheat diseases: Powdery mildew (Blumeria graminis), Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale, Yellow rust (Puccinia striiformis), Black rust (Puccinia graminis), Red rust (Puccinia recondita) ), red snow rot (Microdochium nivale, Microdochium majus), snow rot (Typhula incarnata, Typhula ishikariensis), naked smut (Ustilago tritici), raw smut (Tilletia caries, Tilletia controversa), eye spot Pseudocercosporella herpotrichoides, Septoria tritici, Stagonospora nodorum, Pyrenophora tritici-repentis, Rhizoctonia solani, Gaeumannomyces graminis , rice blast (Pyricularia graminis-tritici);
Barley diseases: Powdery mildew (Blumeria graminis), Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale, Yellow rust (Puccinia striiformis), Black rust (Puccinia graminis), Small rot (Puccinia) hordei), Naked smut (Ustilago nuda), Rhynchosporium secalis, Pyrenophora teres, Cochliobolus sativus, Pyrenophora graminea, Ramularia collo-cygni ), seedling wilt caused by Rhizoctonia (Rhizoctonia solani);
Corn diseases: Puccinia sorghi, Puccinia polysora, Setosphaeria turcica, Physopella zeae, Cochliobolus heterostrophus, Colletotrichum graminicola ), gray leaf spot (Cercospora zeae-maydis), brown spot (Kabatiella zeae), Phaeosphaeria leaf spot (Phaeosphaeria maydis), Diplodia (Stenocarpella maydis, Stenocarpella macrospora), Stokerot disease (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis), Physoderma maydis, tar spot (Phyllachora maydis);
Cotton diseases: Colletotrichum gossypii, Ramularia areola, Alternaria macrospora, Alternaria gossypii, Black root rot (Thielaviopsis basicola);
Coffee diseases: rust (Hemileia vastatrix), leaf spot (Cercospora coffeicola);
Diseases of oilseed rape: Sclerotinia sclerotiorum, Alternaria brassicae, Phoma lingam, light leaf spot Pyrenopeziza brassicae;
Sugar cane diseases: rust (Puccinia melanocephela, Puccinia kuehnii), smut (Ustilago scitaminea);
sunflower diseases: rust (Puccinia helianthi), downy mildew (Plasmopara halstedii);
Citrus diseases: Diaporthe citri, Elsinoe fawcetti, Penicillium digitatum, Penicillium italicum, Phytophthora parasitica, Phytophthora citrophthora, Aspergillus niger ;
Apple diseases: Monilinia mali, rot (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), leaf spot (Alternaria alternata apple pathotype), scab (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum) acutatum), Diplocarpon mali, Botryosphaeria berengeriana, Phytophtora cactorum, Gymnosporangium juniperi-virginianae, Gymnosporangium yamadae;
pear diseases: Venturia nashicola, Venturia pirina, Alternaria alternata Japanese pear pathotype, Gymnosporangium haraeanum;
Peach diseases: Monilinia fructicola, Cladosporium carpophilum, Phomopsis sp., Taphrina deformans;
Grape diseases: black rot (Elsinoe ampelina), late rot (Glomerella cingulata, Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), blacklot (Guignardia bidwellii), downy mildew ( Plasmopara viticola);
Diseases of oysters: anthracnose (Gloeosporium kaki, Colletotrichum acutatum), defoliation (Cercospora kaki, Mycosphaerella nawae);
Fig diseases: Rust (Phakopsora nishidana);
Cucurbit diseases: Colletotrichum lagenarium, Sphaerotheca fuliginea, Didymella bryoniae, Corynespora cassiicola, Fusarium oxysporum, Pseudoperonospora cubensis ), late blight (Phytophthora capsici), seedling blight (Pythium sp.);
Tomato diseases: Alternaria solani, Cladosporium fulvum, Pseudocercospora fuligena, Phytophthora infestans, Leveillula taurica;
Eggplant diseases: Phomopsis vexans, powdery mildew (Erysiphe cichoracearum);
Diseases of cruciferous vegetables: black spot (Alternaria japonica), white spot (Cercosporella brassicae), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), white rust (Albugo candida);
Diseases of Allium: Rust (Puccinia allii);
Soybean diseases: purpura (Cercospora kikuchii), black spot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), brown spot (Corynespora cassiicola), anthracnose (Colletotrichum glycines) , Colletotrichum truncatum), leaf rot (Rhizoctonia solani), brown spot (Septoria glycines), leaf spot (Cercospora sojina), sclerotinia (Sclerotinia sclerotiorum), powdery mildew (Microsphaera diffusa), stem blight (Phytophthora sojae) , downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme), black root rot (Calonectria ilicicola), Diaporthe/Phomopsis complex (Diaporthe longicolla);
Common bean diseases: Sclerotinia sclerotiorum, Uromyces appendiculatus, Phaeoisariopsis griseola, Colletotrichum lindemuthianum, Fusarium solani;
Peanut diseases: black stain (Cercospora personata), brown spot (Cercospora arachidicola), white silk (Sclerotium rolfsii), black root rot (Calonectria ilicicola);
Pea diseases: powdery mildew (Erysiphe pisi), root rot (Fusarium solani);
Potato diseases: Alternaria solani, Phytophthora infestans, Phytophthora erythroseptica, Spongospora subterranea f. sp. subterranea, Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens), dry rot (Fusarium solani), carcinoma (Synchytrium endobioticum);
Diseases of strawberries: powdery mildew (Sphaerotheca humuli);
Tea diseases: Exobasidium reticulatum, Elsinoe leucospira, Pestalotiopsis sp., Colletotrichum theae-sinensis;
Tobacco diseases: Alternaria longipes, Colletotrichum tabacum, Downy mildew (Peronospora tabacina), Phytophthora nicotianae;
Sugar beet diseases: Cercospora beticola, Thanatephorus cucumeris, Thanatephorus cucumeris, Aphanomyces cochlioides, Uromyces betae;
diseases of roses: scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa);
Chrysanthemum diseases: brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana);
Onion diseases: white spot blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), sclerotium rot (Botrytis squamosa);
various crop diseases: Botrytis cinerea, Sclerotinia sclerotiorum, Sclerotium cepivorum, Pythium aphanidermatum, Pythium irregulare, Pythium ultimum;
Diseases of radish: Alternaria brassicicola;
Diseases of turfgrass: dollar spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), red scorch (Pythium aphanidermatum);
Banana diseases: sigatoka (Mycosphaerella fijiensis, Mycosphaerella musicola);
Diseases of lentils: Ascochyta disease (Ascochyta lentis);
Diseases of chickpeas: Ascochyta disease (Ascochyta rabiei);
Diseases of peppers: Colletotrichum scovillei;
mango diseases: Colletotrichum acutatum;
Fruit tree diseases: Roselinia necatrix, Helicobasidium mompa;
Post-harvest fruit diseases such as apples and pears: Mucor piriformis;
Seed diseases or early growth diseases caused by Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, Diplodia, etc.;
Viral diseases: Big Vein disease of lettuce mediated by Olpidium brassicae, viral diseases of various crops mediated by Polymyxa genera (e.g. Polymyxa betae and Polymyxa graminis);
Diseases caused by bacteria: Burkholderia plantarii in rice, Pantoea ananatis in rice, Xanthomonas oryzae pv. oryzae in rice, bacterial spot in cucumber (Pseudomonas syringae pv. lachrymans), eggplant wilt (Ralstonia solanacearum), citrus canker (Xanthomonas citri), Chinese cabbage soft rot (Erwinia carotovora), potato scab (Streptomyces scabiei), maize Goss's wilt Pierce disease (Xylella fastidiosa) of grapes, olives, peaches, etc., root canker disease of roses, such as apples, peaches, cherries (Agrobacterium tumefaciens).
　有害節足動物、有害線虫、及び有害軟体動物としては、例えば以下のものが挙げられる。 Examples of harmful arthropods, harmful nematodes, and harmful molluscs include the following.
　半翅目(Hemiptera)：ヒメトビウンカ(Laodelphax striatellus)、トビイロウンカ(Nilaparvata lugens)、セジロウンカ(Sogatella furcifera)、トウモロコシウンカ(Peregrinus maidis)、キタウンカ(Javesella pellucida)、クロフツノウンカ(Perkinsiella saccharicida)、Tagosodes orizicolus等のウンカ科(Delphacidae)；ツマグロヨコバイ(Nephotettix cincticeps)、タイワンツマグロヨコバイ(Nephotettix virescens)、クロスジツマグロヨコバイ(Nephotettix nigropictus)、イナズマヨコバイ(Recilia dorsalis)、チャノミドリヒメヨコバイ(Empoasca onukii)、ジャガイモヒメヨコバイ(Empoasca fabae)、コーンリーフホッパー(Dalbulus maidis)、シロオオヨコバイ(Cofana spectra)、Amrasca biguttula biguttula等のヨコバイ科(Cicadellidae)；ヨーロピアンスピトルバグ(Philaenus spumarius)等のアワフキムシ科(Aphrophoridae); Mahanarva posticata、Mahanarva fimbriolata等のコガシラアワフキムシ科(Cercopidae)；マメクロアブラムシ(Aphis fabae)、ダイズアブラムシ(Aphis glycines)、ワタアブラムシ(Aphis gossypii)、ヨーロッパリンゴアブラムシ(Aphis pomi)、ユキヤナギアブラムシ(Aphis spiraecola)、モモアカアブラムシ(Myzus persicae)、ムギワラギクオマルアブラムシ(Brachycaudus helichrysi)、ダイコンアブラムシ(Brevicoryne brassicae)、rosy apple aphid(Dysaphis plantaginea)、ニセダイコンアブラムシ(Lipaphis erysimi)、チューリップヒゲナガアブラムシ(Macrosiphum euphorbiae)、ジャガイモヒゲナガアブラムシ(Aulacorthum solani)、レタスヒゲナガアブラムシ(Nasonovia ribisnigri)、ムギクビレアブラムシ(Rhopalosiphum padi)、トウモロコシアブラムシ(Rhopalosiphum maidis)、ミカンクロアブラムシ(Toxoptera citricida)、モモコフキアブラムシ(Hyalopterus pruni)、ヒエノアブラムシ(Melanaphis sacchari)、オカボノクロアブラムシ(Tetraneura nigriabdominalis)、カンシャワタアブラムシ(Ceratovacuna lanigera)、リンゴワタムシ(Eriosoma lanigerum)、イングリッシュグレインエイフィッド（Sitobion avenae）等のアブラムシ科(Aphididae)；ブドウネアブラムシ(Daktulosphaira vitifoliae)、ピーカンフィロキセラ(Phylloxera devastatrix)、ピーカンリーフフィロキセラ (Phylloxera notabilis)、サウザンピーカンリーフフィロキセラ(Phylloxera russelae)等のネアブラムシ科(Phylloxeridae)；ツガカサアブラムシ(Adelges tsugae)、バルサムウーリーアフィッド(Adelges piceae)、ヒメカサアブラムシ(Aphrastasia pectinatae)等のカサアブラムシ科(Adelgidae)；イネクロカメムシ(Scotinophara lurida)、ブラックパディーバグ(Scotinophara coarctata)、アオクサカメムシ(Nezara antennata)、トゲシラホシカメムシ(Eysarcoris aeneus)、オオトゲシラホシカメムシ(Eysarcoris lewisi)、シラホシカメムシ(Eysarcoris ventralis)、ムラサキシラホシカメムシ(Eysarcoris annamita)、クサギカメムシ(Halyomorpha halys)、ミナミアオカメムシ(Nezara viridula)、ブラウンスティンクバグ(Euschistus heros)、レッドバンデッドスティンクバグ(Piezodorus guildinii)、Oebalus pugnax、Dichelops melacanthus等のカメムシ科(Pentatomidae)；Scaptocoris castanea等のツチカメムシ科(Cydnidae)；ホソヘリカメムシ(Riptortus clavatus)、クモヘリカメムシ(Leptocorisa chinensis)、ホソクモヘリカメムシ(Leptocorisa acuta)等のホソヘリカメムシ科(Alydidae)；ホソハリカメムシ(Cletus punctiger)、アシビロヘリカメムシ(Leptoglossus australis)等のヘリカメムシ科(Coreidae)；カンシャコバネナガカメムシ(Cavelerius saccharivorus)、コバネヒョウタンナガカメムシ(Togo hemipterus)、アメリカコバネナガカメムシ(Blissus leucopterus)等のナガカメムシ科(Lygaeidae)；アカヒゲホソミドリカスミカメ(Trigonotylus caelestialium)、アカスジカスミカメ(Stenotus rubrovittatus)、フタトゲムギカスミカメ(Stenodema calcarata)、サビイロカスミカメ(Lygus lineolaris)等のカスミカメムシ科(Miridae)；オンシツコナジラミ(Trialeurodes vaporariorum)、タバココナジラミ(Bemisia tabaci)、ミカンコナジラミ(Dialeurodes citri)、ミカントゲコナジラミ(Aleurocanthus spiniferus)、チャトゲコナジラミ(Aleurocanthus camelliae)、ヒサカキワタフキコナジラミ(Pealius euryae)等のコナジラミ科(Aleyrodidae)；シュロマルカイガラムシ(Abgrallaspis cyanophylli)、アカマルカイガラムシ(Aonidiella aurantii)、
ナシマルカイガラムシ(Diaspidiotus perniciosus)、クワシロカイガラムシ(Pseudaulacaspis pentagona)、ヤノネカイガラムシ(Unaspis yanonensis)、ニセヤノネカイガラムシ(Unaspis citri)等のマルカイガラムシ科(Diaspididae)；ルビーロウムシ(Ceroplastes rubens)等のカタカイガラムシ科(Coccidae)；イセリアカイガラムシ(Icerya purchasi)、キイロワタフキカイガラムシ(Icerya seychellarum)等のワタフキカイガラムシ科(Margarodidae)；ナスコナガイガラムシ(Phenacoccus solani)、クロテンコナカイガラムシ(Phenacoccus solenopsis)、フジコナカイガラムシ(Planococcus kraunhiae)、クワコナカイガラムシ(Pseudococcus comstocki)、ミカンコナカイガラムシ(Planococcus citri)、ガハニコナカイガラムシ(Pseudococcus calceolariae)、ナガオコナカイガラムシ(Pseudococcus longispinus)、タトルミーリーバグ(Brevennia rehi)等のコナカイガラムシ科(Pseudococcidae)；ミカンキジラミ(Diaphorina citri)、ミカントガリキジラミ(Trioza erytreae)、ナシキジラミ(Cacopsylla pyrisuga)、チュウゴクナシキジラミ(Cacopsylla chinensis)、ジャガイモトガリキジラミ(Bactericera cockerelli)、ピアプシラ(Cacopsylla pyricola)等のキジラミ科(Psyllidae)；プラタナスグンバイ(Corythucha ciliata)、アワダチソウグンバイ(Corythucha marmorata)、ナシグンバイ(Stephanitis nashi)、ツツジグンバイ(Stephanitis pyrioides)等のグンバイムシ科(Tingidae)；トコジラミ(Cimex lectularius)、ネッタイトコジラミ(Cimex hemipterus)等のトコジラミ科(Cimicidae)；Quesada gigas等のセミ科(Cicadidae)；ブラジルサシガメ(Triatoma infestans)、オオサシガメ（Triatoma rubrofasciata）、Triatoma dimidiata、ベネズエラサシガメ(Rhodonius prolixus)等のサシガメ科(Reduviidae)。 Hemiptera: Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodes orizicolus, etc. Delphacidae: Leafhopper (Nephotettix cincticeps), Leafhopper (Nephotettix virescens), Leafhopper (Nephotettix nigropictus), Leafhopper (Recilia dorsalis), Leafhopper (Empoasca onukii), Potato Leafhopper (Empoasca fabae) , Corn leaf hopper (Dalbulus maidis), White leafhopper (Cofana spectra), Amrasca biguttula biguttula, etc. Cicadellidae; European Spittle Bug (Philaenus spumarius), etc. Aphis fabae, Aphis glycines, Aphis gossypii, Aphis pomi, Aphis spiraecola, Green peach aphid ( Myzus persicae), Brachycaudus helichrysi, Brevicoryne brassicae, rosy apple aphid (Dysaphis plantaginea), Lipaphis erysimi, Macrosiphum euphorbiae, potato aphid Aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), wheat neck aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus aphid (Toxoptera citricida), peach aphid (Hyalopterus pruni), hienoaphis (Melanaphis) Aphididae such as sacchari, Tetraneura nigriabdominalis, Ceratovacuna lanigera, Eriosoma lanigerum, English grain aphid (Sitobion avenae); Daktulosphaira vitifoliae , Phylloxera devastatrix, Phylloxera notabilis, southern pecan leaf phylloxera (Phylloxera russelae); Adelgidae, such as Aphrastasia pectinatae; Scotinophara lurida, Scotinophara coarctata, Nezara antennata, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Eysarcoris annamita, Halyomorpha halys, Nezara viridula, brown stink bugs (Euschistus heroes), red bandeds Tinkbug (Piezodorus guildinii), O Pentatomidae, such as ebalus pugnax and Dichelops melacanthus; Cydnidae, such as Scaptocoris castanea; Riptortus clavatus, Leptocorisa chinensis, and Leptocorisa acuta Alydidae; Coreidae such as Cletus punctiger and Leptoglossus australis; Cavelerius saccharivorus, Togo hemipterus, Lygaeidae such as Blissus leucopterus; Trigonotylus caelestialium, Stenotus rubrovittatus, Stenodema calcarata, Lygus lineolaris, etc. Family: Miridae; Trialeurodes vaporariorum, Bemisia tabaci, Dialeurodes citri, Aleurocanthus spiniferus, Aleurocanthus camelliae, Peealius euryae ), etc.; Aleyrodidae; Abgrallaspis cyanophylli;
Diaspididae, such as Diaspidiotus perniciosus, Pseudaulacaspis pentagona, Unaspis yanonensis, and Unaspis citri; Family Coccidae; Margarodidae including Icerya purchasi and Icerya seychellarum Phenacoccus solani Phenacoccus solenopsis Planococcus kraunhiae, Pseudococcus comstocki, Planococcus citri, Pseudococcus calceolariae, Pseudococcus longispinus, and Brevennia rehi Pseudococcidae; Psyllidae such as Diaphorina citri, Trioza erytreae, Cacopsylla pyrisuga, Cacopsylla chinensis, Bactericera cockerelli, Cacopsylla pyricola ); Corythucha ciliata, Corythucha marmorata, Stephanitis nashi, Stephanitis pyrioides, and other Tingidae; Cimex lectularius, Cimex hemipterus, etc. of the bedbugs (Cimicidae) ); Cicadidae, such as Quesada gigas; Reduviidae, such as Triatoma infestans, Triatoma rubrofasciata, Triatoma dimidiata, and Rhodonius prolixus.
　鱗翅目(Lepidoptera)：ニカメイガ(Chilo suppressalis)、ダークヘディドステムボーラー(Chilo polychrysus)、ホワイトステムボーラー(Scirpophaga innotata)、イッテンオオメイガ(Scirpophaga incertulas)、Rupela albina、コブノメイガ(Cnaphalocrocis medinalis)、Marasmia patnalis、イネハカジノメイガ(Marasmia exigua)、ワタノメイガ(Notarcha derogata)、アワノメイガ(Ostrinia furnacalis)、ヨーロピアンコーンボーラー(Ostrinia nubilalis)、ハイマダラノメイガ(Hellula undalis)、モンキクロノメイガ(Herpetogramma luctuosale)、シバツトガ(Parapediasia teterrellus)、ライスケースワーム(Nymphula depunctalis)、シュガーケーンボーラー(Diatraea saccharalis)、エッグプラントフルーツボーラー（Leucinodes orbonalis）等のツトガ科(Crambidae)；モロコシマダラメイガ(Elasmopalpus lignosellus)、ノシメマダラメイガ(Plodia interpunctella)、フタモンマダラノメイガ(Euzophera batangensis)、スジマダラメイガ(Cadra cautella)等のメイガ科(Pyralidae)；ハスモンヨトウ(Spodoptera litura)、シロイチモジヨトウ(Spodoptera exigua)、アワヨトウ(Mythimna separata)、ヨトウガ(Mamestra brassicae)、イネヨトウ(Sesamia inferens)、シロナヨトウ(Spodoptera mauritia)、フタオビコヤガ(Naranga aenescens)、ツマジロクサヨトウ(Spodoptera frugiperda)、アフリカシロナヨトウ(Spodoptera exempta)、Spodoptera cosmioides、セミトロピカルアーミーワーム（Spodoptera eridania）、タマナヤガ(Agrotis ipsilon)、タマナギンウワバ(Autographa nigrisigna)、イネキンウワバ(Plusia festucae)、Soybean looper(Chrysodeixis includens)、トリコプルシア属(Trichoplusia spp.)、ニセアメリカタバコガ(Heliothis virescens)等のヘリオティス属(Heliothis spp.)、オオタバコガ(Helicoverpa armigera)、コーンイヤワーム(Helicoverpa zea)等のヘリコベルパ属(Helicoverpa spp.)、ベルベットビーンキャタピラー(Anticarsia gemmatalis)、コットンリーフワーム(Alabama argillacea)、ホップワインボーラー(Hydraecia immanis)等のヤガ科(Noctuidae)；モンシロチョウ(Pieris rapae)等のシロチョウ科(Pieridae)；ナシヒメシンクイ(Grapholita molesta)、スモモヒメシンクイ(Grapholita dimorpha)、マメシンクイガ(Leguminivora glycinivorella)、アズキサヤムシガ(Matsumuraeses azukivora)、リンゴコカクモンハマキ(Adoxophyes orana fasciata)、チャノコカクモンハマキ(Adoxophyes honmai)、チャハマキ(Homona magnanima)、ミダレカクモンハマキ(Archips fuscocupreanus)、コドリングモス(Cydia pomonella)、カンシャシンクイハマキ(Tetramoera schistaceana)、ビーンシュートボーラ(Epinotia aporema)、シトラスフルーツボーラー(Citripestis sagittiferella)、
ヨーロピアングレープワインモス（Lobesia botrana）等のハマキガ科(Tortricidae)；チャノホソガ(Caloptilia theivora)、キンモンホソガ(Phyllonorycter ringoniella)等のホソガ科(Gracillariidae)；モモシンクイガ(Carposina sasakii)等のシンクイガ科(Carposinidae)；コーヒーリーフマイナー(Leucoptera coffeella)、モモハモグリガ(Lyonetia clerkella)、ギンモンハモグリガ(Lyonetia prunifoliella)等のハモグリガ科(Lyonetiidae)；マイマイガ(Lymantria dispar)等のリマントリア属(Lymantria spp.)、チャドクガ(Euproctis pseudoconspersa)等のユープロクティス属(Euproctis spp.)等のドクガ科(Lymantriidae)；コナガ(Plutella xylostella)等のコナガ科(Plutellidae)；モモキバガ(Anarsia lineatella)、イモキバガ(Helcystogramma triannulella)、ワタアカミムシガ(Pectinophora gossypiella)、ジャガイモガ(Phthorimaea operculella)、Tuta absoluta等のキバガ科(Gelechiidae)；アメリカシロヒトリ(Hyphantria cunea)等のヒトリガ科(Arctiidae)；ジャイアントシュガーケーンボーラー(Telchin licus)等のカストニアガ科(Castniidae)；ヒメボクトウ（Cossus insularis）等のボクトウガ科（Cossidae）；ヨモギエダシャク(Ascotis selenaria)等のシャクガ科(Geometridae)；ヒロヘリアオイラガ(Parasa lepida)等のイラガ科(Limacodidae)；カキノヘタムシガ(Stathmopoda masinissa)等のニセマイコガ科(Stathmopodidae)；クロメンガタスズメ(Acherontia lachesis)等のスズメガ科(Sphingidae)；キクビスカシバ(Nokona feralis)、コスカシバ(Synanthedon hector)、ヒメコスカシバ(Synanthedon tenuis)等のスカシバガ科(Sesiidae)；イネツトムシ(Parnara guttata)等のセセリチョウ科(Hesperiidae)；イガ(Tinea translucens)、コイガ(Tineola bisselliella)等のヒロズコガ科(Tineidae)。 Lepidoptera: Chilo suppressalis, Chilo polychrysus, White stem borer (Scirpophaga innotata), Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis, Rice hare moth (Marasmia exigua), cotton moth (Notarcha derogata), corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), high spotted moth (Hellula undalis), monkey crocodile moth (Herpetogramma luctuosale), Shibatutoga (Parapediasia teterrellus) , Rice case worm (Nymphula depunctalis), Sugar cane borer (Diatraea saccharalis), Egg plant fruit borer (Leucinodes orbonalis), etc.; Pyralidae such as Euzophera batangensis, Cadra cautella; Spodoptera litura, Spodoptera exigua, Mythimna separata, Mamestra brassicae, Sesamia inferens), Spodoptera mauritia, Naranga aenescens, Spodoptera frugiperda, Spodoptera exempta, Spodoptera cosmioides, Semitropical armyworm (Spodoptera eridania), Spodoptera eridania (Agrotis ipsilon), Autographa nigrisigna, Plusia festucae, Soybean looper (Chrysodeixis includes), Trichoplusia spp., Heliothis spp. such as Heliothis virescens, Helicoverpa spp. such as Helicoverpa armigera and Helicoverpa zea, Velvet bean caterpillar (Anticarsia gemmatalis), Cotton leaf worm (Alabama argillacea), Hop wine borer (Hydraecia immanis) and other noctuids (Noctuidae); Pieridae such as Pieris rapae; orana fasciata), Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus, Cydia pomonella, Tetramoera schistaceana, Epinotia aporema , Citrus Fruit Borer (Citripestis sagittiferella),
Tortricidae, such as European grape wine moss (Lobesia botrana); Gracillariidae, such as Caloptilia theivora and Phyllonorycter ringoniella; Lyonetiidae, such as Leucoptera coffeella, Lyonetia clerkella, and Lyonetia prunifoliella; Lymantria spp., such as Lymantria dispar; Lymantriidae such as Euproctis spp.; Plutellidae such as Plutella xylostella; Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, potato moth ( Phthorimaea operculella, Tuta absoluta, etc.; Arctiidae, such as Hyphantria cunea; Geometridae, such as Ascotis selenaria; Limacodidae, such as Parasa lepida; Stathmopodidae, such as Stathmopoda masinissa; Sphingidae, such as Acherontia lachesis; lis), Synanthedon hector, Synanthedon tenuis, etc.; Sesiidae, such as; Parnara guttata, etc., Hesperiidae; Family (Tineidae).
　総翅目(Thysanoptera)：ミカンキイロアザミウマ(Frankliniella occidentalis)、ミナミキイロアザミウマ(Thrips palmi)、チャノキイロアザミウマ(Scirtothrips dorsalis)、ネギアザミウマ(Thrips tabaci)、ヒラズハナアザミウマ(Frankliniella intonsa)、イネアザミウマ(Stenchaetothrips biformis)、モトジロアザミウマ(Echinothrips americanus)、アボカドスリプス（Scirtothrips perseae）等のアザミウマ科(Thripidae)；イネクダアザミウマ(Haplothrips aculeatus)等のクダアザミウマ科(Phlaeothripidae)。 Thysanoptera: Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips , Echinothrips americanus, Scirtothrips perseae, etc.; Phlaeothripidae, such as Haplothrips aculeatus.
　双翅目(Diptera)：タネバエ(Delia platura)、タマネギバエ(Delia antiqua)、テンサイモグリハナバエ(Pegomya cunicularia)等のハナバエ科(Anthomyiidae)；シュガービートルートマゴット(Tetanops myopaeformis)等のハネフリバエ科(Ulidiidae)；イネハモグリバエ(Agromyza oryzae)、トマトハモグリバエ(Liriomyza sativae)、マメハモグリバエ(Liriomyza trifolii)、ナモグリバエ(Chromatomyia horticola)等のハモグリバエ科(Agromyzidae)；イネキモグリバエ(Chlorops oryzae)等のキモグリバエ科(Chloropidae)；ウリミバエ(Bactrocera cucurbitae)、ミカンコミバエ(Bactrocera dorsalis)、ナスミバエ(Bactrocera latifrons)、オリーブミバエ(Bactrocera oleae)、クインスランドミバエ(Bactrocera tryoni)、チチュウカイミバエ(Ceratitis capitata)、アップルマゴット(Rhagoletis pomonella)、オウトウハマダラミバエ(Rhacochlaena japonica)等のミバエ科(Tephritidae)；イネヒメハモグリバエ(Hydrellia griseola)、トウヨウイネクキミギワバエ(Hydrellia philippina)、イネクキミギワバエ(Hydrellia sasakii)等のミギワバエ科(Ephydridae)；オウトウショウジョウバエ(Drosophila suzukii)、キイロショウジョウバエ（Drosophila melanogaster）等のショウジョウバエ科(Drosophilidae)；オオキモンノミバエ(Megaselia spiracularis)等のノミバエ科(Phoridae)；オオチョウバエ(Clogmia albipunctata)等のチョウバエ科(Psychodidae)；チビクロバネキノコバエ(Bradysia difformis)等のクロバネキノコバエ科(Sciaridae)；ヘシアンバエ(Mayetiola destructor)、イネノシントメタマバエ(Orseolia oryzae)等のタマバエ科(Cecidomyiidae)；Diopsis macrophthalma等のシュモクバエ科(Diopsidae)；Glossina palpalis、Glossina morsitans等のツェツェバエ科(Glossinidae)；アシマダラブユ（Simulium japonicum）、Simulium damnosum等のブユ科(Simuliidae)；サシチョウバエ亜科(Phlebotominae)；キリウジガガンボ(Tipula aino)、コモンクレーンフライ(Tipula oleracea)、ヨーロピアンクレーンフライ(Tipula paludosa)等のガガンボ科(Tipulidae)；アカイエカ(Culex pipiens pallens)、コガタアカイエカ(Culex tritaeniorhynchus)、チカイエカ(Culex pipiens f. molestus)、ネッタイイエカ(Culex quinquefasciatus)、トビイロイエカ(Culex pipiens pipiens)、ニセシロハシイエカ(Culex vishnui)、ヒトスジシマカ(Aedes albopictus)、ネッタイシマカ(Aedes aegypti)、シナハマダラカ(Anopheles sinensis)、ガンビエハマダラカ(Anopheles gambiae)、ステフェンスハマダラカ(Anopheles stephensi)、Anopheles coluzzii、Anopheles albimanus、Anopheles sundaicus、Anopheles arabiensis、Anopheles funestus、Anopheles darlingi、Anopheles farauti、Anopheles minimus等のカ科(Culicidae)；キアシオオブユ(Prosimulium yezoensis)、ツメ卜ゲブユ(Simulium ornatum)等のブユ科(Simulidae)；ウシアブ(Tabanus trigonus)等のアブ科(Tabanidae)；イエバエ(Musca domestica)、オオイエバエ(Muscina stabulans)、サシバエ(Stomoxys calcitrans)、ノサシバエ(Haematobia irritans)等のイエバエ科(Muscidae)；クロバエ科(Calliphoridae)；ニクバエ科(Sarcophagidae)；オオユスリカ(Chironomus plumosus)、セスジユスリカ(Chironomus yoshimatsui)、ハイイロユスリカ(Glyptotendipes tokunagai)等のユスリカ科(Chironomidae)；ヒメイエバエ科(Fannidae)。 Diptera: Anthomyiidae, such as Delia platura, Delia antiqua, and Pegomya cunicularia; Ulidiidae, such as Tetanops myopaeformis Agromyzidae, such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, and Chromatomyia horticola; Chloropidae, such as Chlorops oryzae; Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, Ceratitis capitata, Rhagoletis pomonella, Rjapachla fruit fly ), etc.; Drosophilidae, such as Drosophila melanogaster; Phoridae, such as Megaselia spiracularis; Psychodidae, such as Clogmia albipunctata; Bradysia difformis Sciaridae, such as; Mayetiola dest Cecidomyiidae, such as Orseolia oryzae; Diopsidae, such as Diopsis macrophthalma; Glossinidae, such as Glossina palpalis and Glossina morsitans; Simulium japonicum, Simulium damnosum Blackfly family (Simuliidae) such as Blackfly (Simuliidae); Sandfly subfamily (Phlebotominae); pipiens pallens, Culex tritaeniorhynchus, Culex pipiens f. molestus, Culex quinquefasciatus, Culex pipiens pipiens, Culex vishnui, Aedes albopictus aegypti), Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles sundaicus, Anopheles arabiensis, Anopheles funestus, Anopheles minidarlingi, Anopheles farauti, Anopheles, etc. Culicidae; Simulidae such as Prosimulium yezoensis and Simulium ornatum; Tabanidae such as Tabanus trigonus; Musca domestica and Muscinasta bulans ), marbling Muscidae such as Stomoxys calcitrans and Haematobia irritans; Calliphoridae; Sarcophagidae; Chironomus plumosus, Chironomus yoshimatsui, Glyptotendipes tokunagai of Chironomidae (Chironomidae);
　鞘翅目(Coleoptera)：ダイアブロティカ属(Diabrotica spp.、例えば、ウエスタンコーンルートワーム(Diabrotica virgifera virgifera)、サザンコーンルートワーム(Diabrotica undecimpunctata howardi)、ノーザンコーンルートワーム(Diabrotica barberi)、メキシカンコーンルートワーム(Diabrotica virgifera zeae)）、バンデッドキューカンバービートル(Diabrotica balteata)、キューカビットビートル(Diabrotica speciosa)等のビーンリーフビートル(Cerotoma trifurcata)、クビアカクビホソハムシ(Oulema melanopus)、ウリハムシ(Aulacophora femoralis)、キスジノミハムシ(Phyllotreta striolata)、キャベッジフリービートル(Phyllotreta cruciferae)、ウエスタンブラックフリービートル(Phyllotreta pusilla)、キャベッジステムフリービートル(Psylliodes chrysocephala)、ホップフリービートル(Psylliodes punctulata)、コロラドハムシ(Leptinotarsa decemlineata)、イネドロオイムシ(Oulema oryzae)、グレープコラスピス(Colaspis brunnea)、コーンフリービートル(Chaetocnema pulicaria)、サツマイモヒサゴトビハムシ(Chaetocnema confinis)、ポテトフリービートル(Epitrix cucumeris)、イネトゲハムシ(Dicladispa armigera)、サザンコーンリーフビートル(Myochrous denticollis)、ヨツモンカメノコハムシ(Laccoptera quadrimaculata)、タバコノミハムシ(Epitrix hirtipennis)等のハムシ科(Chrysomelidae)；シードコーンビートル(Stenolophus lecontei)、スレンダーシードコーンビートル(Clivina impressifrons)等のオサムシ科(Carabidae)；ドウガネブイブイ(Anomala cuprea)、ヒメコガネ(Anomala rufocuprea)、アオドウガネ(Anomala albopilosa)、マメコガネ(Popillia japonica)、ナガチャコガネ(Heptophylla picea)、ヨーロピアンチェーファー(Rhizotrogus majalis)、クロマルコガネ(Tomarus gibbosus)、クロコガネ属(Holotrichia spp.)、ジューン・ビートル(Phyllophaga crinita)等のフィロファガ属(Phyllophaga spp.)、Diloboderus abderus等のディロボデルス属(Diloboderus spp.)等のコガネムシ科(Scarabaeidae)；ワタミヒゲナガゾウムシ(Araecerus coffeae)等のヒゲナガゾウムシ科（Anthriibidae);アリモドキゾウムシ(Cylas formicarius)等のホソクチゾウムシ科(Aponidae)；ブラジルマメゾウムシ(Zabrotes subfasciatus)等のマメゾウムシ科(Bruchidae)；マツノキクイムシ(Tomicus piniperda)、コーヒーベリーボーラー(Hypothenemus hampei)等のキクイムシ科(Scolytidae)；イモゾウムシ(Euscepes postfasciatus)、アルファルファタコゾウムシ(Ｈypera postica)、コクゾウムシ(Sitophilus zeamais)、ココクゾウムシ(Sitophilus oryzae)、グラナリアコクゾウムシ(Sitophilus granarius)、イネゾウムシ(Echinocnemus squameus)、イネミズゾウムシ(Lissorhoptrus oryzophilus)、シロスジオサゾウムシ(Rhabdoscelus lineaticollis)、ワタミハナゾウムシ(Anthonomus grandis)、シバオサゾウムシ(Sphenophorus venatus)、サザンコーンビルバグ(Sphenophorus callosus)、ソイビーンストークウィービル(Sternechus subsignatus)、シュガーケーンウィービル(Sphenophorus levis)、サビヒョウタンゾウムシ(Scepticus griseus)、トビイロヒョウタンゾウムシ(Scepticus uniformis)、Aracanthus mourei等のAracanthus属(Aracanthus spp.)、コットンルートボーラー (Eutinobothrus brasiliensis)等のゾウムシ科(Curculionidae)；コクヌストモドキ(Tribolium castaneum)、ヒラタコクヌストモドキ(Tribolium confusum)、ガイマイゴミムシダマシ(Alphitobius diaperinus)等のゴミムシダマシ科(Tenebrionidae)；ニジュウヤホシテントウ(Epilachna vigintioctopunctata)等のテントウムシ科(Coccinellidae)；ヒラタキクイムシ(Lyctus brunneus)、コナナガシンクイ(Rhizopertha dominica)等のナガシンクイムシ科(Bostrychidae)；
ヒョウホンムシ科(Ptinidae)；ゴマダラカミキリ(Anoplophora malasiaca)、Migdolus fryanus、クビアカツヤカミキリ（Aromia bungii）等のカミキリムシ科(Cerambycidae)；オキナワカンシャクシコメツキ(Melanotus okinawensis)、トビイロムナボソコメツキ(Agriotes fuscicollis)、クシコメツキ(Melanotus legatus)、アシブトコメツキ属(Anchastus spp.)、コノデルス属(Conoderus spp.)、クテニセラ属(Ctenicera spp.)、リモニウス属(Limonius spp.)、アエオルス属(Aeolus spp.)等のコメツキムシ科(Elateridae)；アオバアリガタハネカクシ(Paederus fuscipes)等のハネカクシ科(Staphylinidae)；ヒメマルカツオブシムシ(Anthrenus verbasci)、ハラジロカツオブシムシ(Dermestes maculates)、ヒメアカカツオブシムシ(Trogoderma granarium)等のカツオブシムシ科(Dermestidae)；タバコシバンムシ(Lasioderma serricorne)、ジンサンシバンムシ(Stegobium paniceum)等のシバンムシ科(Anobiidae)；アカチビヒラタムシ(Cryptolestes ferrugineus)等のチビヒラタムシ科(Laemophloeidae)；ノコギリヒラタムシ(Oryzaephilus surinamensis)等のホソヒラタムシ科(Silvanidae)、ブロッサムビートル（Brassicogethes aeneus）等のケシキスイムシ科（Nitidulidae）。 Coleoptera: Diabrotica spp., e.g. Western Corn Rootworm (Diabrotica virgifera virgifera), Southern Corn Rootworm (Diabrotica undecimpunctata howardi), Northern Corn Rootworm (Diabrotica barberi), Mexican Corn Rootworm (Diabrotica virgifera zeae)), banded cucumber beetle (Diabrotica balteata), cucumber beetle (Diabrotica speciosa) and other bean leaf beetles (Cerotoma trifurcata), neck beetle (Oulema melanopus), cucumber beetle (Aulacophora femoralis), cucumber beetle (Phyllotreta striolata), cabbage-free beetle (Phyllotreta cruciferae), western black-free beetle (Phyllotreta pusilla), cabbage stem-free beetle (Psylliodes chrysocephala), hop-free beetle (Psylliodes punctulata), Colorado potato beetle (Leptinotarsa decemlineata), rice beetle (Oulema oryzae) ), Grape colaspis (Colaspis brunnea), Corn-free beetle (Chaetocnema pulicaria), Sweet potato beetle (Chaetocnema confinis), Potato-free beetle (Epitrix cucumeris), Rice beetle (Dicladispa armigera), Southern corn leaf beetle (Myochrous denticollis), Chrysomelidae, such as Laccoptera quadrimaculata and Epitrix hirtipennis; Carabidae, such as Stenolophus lecontei and Clivina impressifrons; Anomala cuprea, Anomala rufocuprea, Anomala albopilosa, Popillia japonica, Heptophylla picea, Rhizotrogus majalis, Tomarus gibbosus, Holotrichia spp ), Phyllophaga spp. such as June Beetle (Phyllophaga crinita), Scarabaeidae such as Diloboderus spp. such as Diloboderus abderus; Anthriibidae; Aponidae, such as Cylas formicarius; Bruchidae, such as Zabrotes subfasciatus; Tomicus piniperda, Hypothenemus hampei Scolytidae such as; Euscepes postfasciatus, Hypera postica, Sitophilus zeamais, Sitophilus oryzae, Sitophilus granarius, Echinocnemus squameus, rice weevil (Lissorhoptrus oryzophilus), Rhabdoscelus lineaticollis, Boll weevil (Anthonomus grandis), Sphenophorus venatus, Southern cornbill bug (Sphenophorus callosus), Soybean stalk weevil (Sternechus subsignatus), Sugarcane wee Bill (Sphenophorus levi s), Scepticus griseus, Scepticus uniformis, Aracanthus spp. Tribolium castaneum), Tribolium confusum, Tenebrionidae such as Alphitobius diaperinus; Coccinellidae such as Epilachna vigintioctopunctata; Lyctus brunneus, Bostrychidae, such as Rhizopertha dominica;
Ptinidae; Cerambycidae such as Anoplophora malasiaca, Migdolus fryanus, Aromia bungii; Melanotus okinawensis, Agriotes fuscicollis, Click beetles such as Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., Limonius spp., Aeolus spp. Family (Elateridae); Staphylinidae such as Paederus fuscipes; Dermestidae such as Anthrenus verbasci, Dermestes maculates, and Trogoderma granarium; Anobiidae such as Lasioderma serricorne and Stegobium paniceum; Laemophloeidae such as Cryptolestes ferrugineus; Silvanidae such as Oryzaephilus surinamensis ), Blossom Beetle (Brassicogethes aeneus), etc. Nitidulidae.
　直翅目(Orthoptera)：トノサマバッタ(Locusta migratoria)、モロッコトビバッタ(Dociostaurus maroccanus)、オーストラリアトビバッタ(Chortoicetes terminifera)、アカトビバッタ(Nomadacris septemfasciata)、ブラウンローカスト(Locustana pardalina)、ツリーローカスト(Anacridium melanorhodon)、イタリアンローカスト(Calliptamus italicus)、ディファレンシャルグラスホッパー(Melanoplus differentialis)、ツーストライプドグラスホッパー(Melanoplus bivittatus)、マイグレトリーグラスホッパー(Melanoplus sanguinipes)、レッドレッグドグラスホッパー(Melanoplus femurrubrum)、クリアウィングドグラスホッパー(Camnula pellucida)、サバクワタリバッタ(Schistocerca gregaria)、イエローウィングドローカスト(Gastrimargus musicus)、スパースローテッドローカスト(Austracris guttulosa)、コバネイナゴ(Oxya yezoensis)、ハネナガイナゴ(Oxya japonica)、タイワンツチイナゴ(Patanga succincta)等のバッタ科(Acrididae)；ケラ(Gryllotalpa orientalis)等のケラ科(Gryllotalpidae)；ヨーロッパイエコオロギ(Acheta domestica)、エンマコオロギ(Teleogryllus emma)等のコオロギ科(Gryllidae)；モルモンクリケット(Anabrus simplex)等のキリギリス科(Tettigoniidae)。 Orthoptera: Migratory Locust (Locusta migratoria), Moroccan Locust (Dociostaurus maroccanus), Australian Locust (Chortoicetes terminifera), Red Locust (Nomadacris septemfasciata), Brown Locust (Locustana pardalina), Tree Locust (Anacridium melanorhodon), Italian Locust (Calliptamus italicus), differential grasshopper (Melanoplus differentialis), two-striped grasshopper (Melanoplus bivittatus), migratory grasshopper (Melanoplus sanguinipes), red legged grasshopper (Melanoplus femurrubrum), clear winged grasshopper (Camnula pellucida), Grasshoppers (Schistocerca gregaria), yellow-winged locust (Gastrimargus musicus), sparse locust (Austracris guttulosa), Oxya yezoensis, Oxya japonica, Patanga succincta, etc. ); Gryllotalpidae, such as the cricket (Gryllotalpa orientalis); Gryllidae, such as the European domestic cricket (Acheta domestica) and Teleogryllus emma;
　膜翅目(Hymenoptera)：カブラハバチ(Athalia rosae)、ニホンカブラバチ(Athalia japonica)等のハバチ科(Tenthredinidae)；ヒアリ(Solenopsis invicta)、アカカミアリ(Solenopsis geminata)等のトフシアリ属(Solenopsis spp.)、ブラウンリーフカッティングアント(Atta capiguara)等のハキリアリ属(Atta spp.)、ヒメハキリアリ属(Acromyrmex spp.)、サシハリアリ(Paraponera clavata)、ルリアリ(Ochetellus glaber)、イエヒメアリ(Monomorium pharaonis)、アルゼンチンアリ(Linepithema humile)、クロヤマアリ(Formica  japonica)、アミメアリ(Pristomyrmex punctutus)、オオズアリ(Pheidole noda)、ツヤオオズアリ(Pheidole megacephala)、クロオオアリ(Camponotus japonicus)、ムネアカオオアリ(Camponotus obscuripes)等のオオアリ属(Camponotus spp.)、オキシデンタリスシュウカクアリ(Pogonomyrmex occidentalis)等のシュウカクアリ属(Pogonomyrmex spp.)、コカミアリ(Wasmania auropunctata)等のコカミアリ属(Wasmania spp.)、アシナガキアリ(Anoplolepis gracilipes)等のアリ科(Formicidae)；オオスズメバチ(Vespa mandarinia)、ケブカスズメバチ(Vespa simillima)、コガタスズメバチ(Vespa analis)、ツマアカスズメバチ(Vespa velutina)、セグロアシナガバチ(Polistes jokahamae)等のスズメバチ科(Vespidae)；モミノオオキバチ(Urocerus gigas)等のキバチ科(Siricidae)；アリガタバチ科(Bethylidae)。 Hymenoptera: Tenthredinidae, such as Athalia rosae and Athalia japonica; Solenopsis spp., such as Solenopsis invicta and Solenopsis geminata, brown leaf-cutting ants (Atta capiguara), Acromyrmex spp., Paraponera clavata, Ochetellus glaver, Monomorium pharaonis, Linepithema humile , Formica japonica, Pristomyrmex punctutus, Pheidole noda, Pheidole megacephala, Camponotus japonicus, Camponotus obscuripes, etc., Camponotus spp. Pogonomyrmex spp. such as Pogonomyrmex occidentalis, Wasmania spp. such as Wasmania auropunctata, Formicidae such as Anoplolepis gracilipes; Vespa mandarinia ), Vespa simillima, Vespa analis, Vespa velutina, Polistes jokahamae, etc.; Siricidae, such as Urocerus gigas ; Bethylidae.
　ゴキブリ目(Blattodea)：チャバネゴキブリ(Blattella germanica)等のチャバネゴキブリ科(Ectobiidae)；クロゴキブリ(Periplaneta fuliginosa)、ワモンゴキブリ(Periplaneta americana)、コワモンゴキブリ（Periplaneta australasiae）、トビイロゴキブリ(Periplaneta brunnea)、トウヨウゴキブリ(Blatta orientalis)等のゴキブリ科(Blattidae)；ヤマトシロアリ(Reticulitermes speratus)、イエシロアリ(Coptotermes formosanus)、アメリカカンザイシロアリ(Incisitermes minor)、ダイコクシロアリ(Cryptotermes domesticus)、タイワンシロアリ(Odontotermes formosanus)、コウシュンシロアリ(Neotermes koshunensis)、サツマシロアリ(Glyptotermes satsumensis)、ナカジマシロアリ(Glyptotermes nakajimai)、カタンシロアリ(Glyptotermes fuscus)、オオシロアリ(Hodotermopsis sjostedti)、コウシュウイエシロアリ(Coptotermes guangzhouensis)、アマミシロアリ(Reticulitermes amamianus)、ミヤタケシロアリ(Reticulitermes miyatakei)、カンモンシロアリ(Reticulitermes kanmonensis)、タカサゴシロアリ(Nasutitermes takasagoensis)、ニトベシロアリ(Pericapritermes nitobei)、ムシャシロアリ(Sinocapritermes mushae)、Cornitermes cumulans等のシロアリ科(Termitidae)。 Blattodea: Ectobiidae, such as Blattella germanica; Blatta orientalis); Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis, Reticulitermes amamianus, Reticutermes miyatakei), Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, and Cornitermes cumulans.
　ノミ目(Siphonaptera): ヒトノミ(Pulex irritans)、ネコノミ(Ctenocephalides felis)、イヌノミ(Ctenocephalides canis)、ケオプスネズミノミ(Xenopsylla cheopis) 、ニワトリノミ(Echidnophaga gallinacea)等のヒトノミ科（Pulicidae）；スナノミ(Tunga penetrans)等のスナノミ科（Hectopsyllidae）；ヨーロッパネズミノミ(Nosopsyllus fasciatus)等のナガノミ科（Ceratophyllidae）。 Siphonaptera: Pulicidae, such as Pulex irritans, Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, and Echidnophaga gallinacea; Hectopsyllidae, such as penetrans; Ceratophyllidae, such as the European rat flea (Nosopsyllus fasciatus).
　咀顎目(Psocodae)：アタマジラミ(Pediculus humanus capitis)等のヒトジラミ科（Pediculidae）；ケジラミ(Pthirus pubis)等のケジラミ科（Pthiridae）；ウシジラミ(Haematopinus eurysternus)、ブタジラミ(Haematopinus suis)等のケモノジラミ科（Haematopinidae）；ウシホソジラミ(Linognathus vituli)、ヒツジ体幹寄生ホソジラミ(Linognathus ovillus)、ケブカウシジラミ(Solenopotes capillatus)等のケモノホソジラミ科（Linognathidae）；ウシハジラミ(Bovicola bovis)、ヒツジジラミ(Bovicola ovis)、Bovicola breviceps、Damalinia forficula、ウェルネッキエラ属(Werneckiella spp.)等のボビコラ科（Bovicoliidae）；イヌハジラミ(Trichodectes canis)、ネコハジラミ(Felicola subrostratus)等のケモノハジラミ科（Trichodectidae）；ニワトリハジラミ(Menopon gallinae)、ニワトリオオハジラミ(Menacanthus stramineus)、トリノトン属(Trinoton spp.)等のタンカクハジラミ科（Menoponidae）；クミングシア属(Cummingsia spp.)等のケモノタンカクハジラミ科（Trimenoponidae）；コナチャタテ(Trogium pulsatorium)等のコチャタテ科(Trogiidae)；ウスグロチャタテ(Liposcelis corrodens)、ヒラタチャタテ(Liposcelis bostrychophila)、ソウメンチャタテ(Liposcelis pearmani)、カツブシチャタテ(Liposcelis entomophila)等のコナチャタテ科(Liposcelidae又はLiposcelididae)。 Psocodae: Pediculidae, such as head lice (Pediculus humanus capitis); Pthiridae, such as pubic lice (Pthirus pubis); Haematopinidae); Linognathidae, such as Linognathus vituli, Linognathus ovillus, Solenopotes capillatus; Bovicola bovis, Bovicola forvis, Bovicola breviceps, Damalin Bovicoliidae, such as Werneckiella spp.; Trichodectidae, such as Trichodectes canis and Felicola subrostratus; Menopon gallinae, Menacanthus stramineus ), Menoponidae such as Trinoton spp.; Trimenoponidae such as Cummingsia spp.; Trogiidae such as Trogium pulsatorium; Liposcelidae or Liposcelididae, such as Liposcelis corrodens, Liposcelis bostrychophila, Liposcelis pearmani, and Liposcelis entomophila.
　シミ目(Thysanura):ヤマトシミ(Ctenolepisma villosa)、セイヨウシミ(Lepisma saccharina)等のシミ科(Lepismatidae)。 Thysanura: Lepismatidae, such as Ctenolepisma villosa and Lepisma saccharina.
　ダニ目(Acari)：ナミハダニ(Tetranychus urticae)、カンザワハダニ(Tetranychus kanzawai)、ミツユビナミハダニ(Tetranychus evansi)、ミカンハダニ(Panonychus citri)、リンゴハダニ(Panonychus ulmi)、オリゴニカス属(Oligonychus spp.)等のハダニ科(Tetranychidae)；ミカンサビダニ(Aculops pelekassi)、リュウキュウミカンサビダニ(Phyllocoptruta citri)、トマトサビダニ(Aculops lycopersici)、チャノサビダニ(Calacarus carinatus)、チャノナガサビダニ(Acaphylla theavagrans)、ニセナシサビダニ(Eriophyes chibaensis)、リンゴサビダニ(Aculus schlechtendali)、カキサビダニ(Aceria diospyri)、Aceria tosichella、シソサビダニ(Shevtchenkella sp.)等のフシダニ科(Eriophyidae)；チャノホコリダニ(Polyphagotarsonemus latus)等のホコリダニ科(Tarsonemidae)；ミナミヒメハダニ(Brevipalpus phoenicis)等のヒメハダニ科(Tenuipalpidae)；ケナガハダニ科(Tuckerellidae)；フタトゲチマダニ(Haemaphysalis longicornis)、キチマダニ(Haemaphysalis flava)、ヤマトマダニ(Haemaphysalis japonica)、ツリガネチマダニ(Haemaphysalis campanulata)、アメリカイヌカクマダニ(Dermacentor variabilis)、タイワンカクマダニ(Dermacentor taiwanensis)、ロッキーマウンテンウッドチック(Dermacentor andersoni)、アミメカクマダニ（Dermacentor reticulatus）、ヤマトマダニ(Ixodes ovatus)、シュルツマダニ(Ixodes persulcatus)、ブラックレッグドチック(Ixodes scapularis)、西部クロアシマダニ(Ixodes pacificus)、Ixodes holocyclus、Ixodes ricinus、ローンスターチック(Amblyomma americanum)、ガルフコーストチック(Amblyomma maculatum)、オウシマダニ(Rhipicephalus　microplus)、キャトルチック(Rhipicephalus annulatus)、クリイロコイタマダニ(Rhipicephalus sanguineus)、Rhipicephalus appendiculatus、Rhipicephalus decoloratus等のマダニ科（Ixodidae）；ナガヒメダニ(Argas persicus)、Ornithodoros hermsi、Ornithodoros turicata等のヒメダニ科(Argasidae)、ケナガコナダニ(Tyrophagus putrescentiae)、ホウレンソウケナガコナダニ(Tyrophagus similis)等のコナダニ科(Acaridae)；コナヒョウヒダニ(Dermatophagoides farinae)、ヤケヒョウヒダニ(Dermatophagoides pteronyssinus)等のチリダニ科(Pyroglyphidae)；ホソツメダニ(Cheyletus eruditus)、クワガタツメダニ(Cheyletus malaccensis)、ミナミツメダニ(Chelacaropsis moorei)、イヌツメダニ(Cheyletiella yasguri)等のツメダニ科(Cheyletidae)；ヒツジキュウセンヒゼンダニ(Psoroptes ovis)、ウマキュウセンヒゼンダニ(Psoroptes equi)、Knemidocoptes mutans、ミミヒゼンダニ(Otodectes cynotis)、ショクヒヒゼンダニ属(Chorioptes spp.)等のキュウセン科(Psoroptidae)；ネコショウセンコウヒゼンダニ(Notoedres cati)、ネズミショウセンコウヒゼンダニ(Notoedres muris)、センコウヒゼンダニ(Sarcoptes scabiei)等のヒゼンダニ科(Sarcoptidae)；ウサギズツキダニ(Listrophorus gibbus)等のズツキダニ科(Listrophoridae)；ワクモ(Dermanyssus gallinae)等のサシダニ科(Dermanyssidae)；トリサシダニ(Ornithonyssus sylviarum)、イエダニ(Ornithonyssus bacoti)等のオオサシダニ科(Macronyssidae)、ミツバチヘギイタダニ(Varroa jacobsoni)等のヘギイタダニ科(Varroidae)、イヌニキビダニ(Demodex canis)、ネコニキビダニ(Demodex cati)等のニキビダニ科(Demodicidae)、アカツツガムシ(Leptotrombidium akamushi)、フトゲツツガムシ(Leptotrombidium pallidum)、タテツツガムシ(Leptotrombidium scutellare)等のツツガムシ科(Trombiculidae)。 Acari: Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oligonychus spp. ); Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Apple rust mite ( Aculus schlechtendali), Aceria diospyri, Aceria tosichella, Shevtchenkella sp., and other Eriophyidae; Polyphagotarsonemus latus, and other Tarsonemidae; Brevipalpus phoenicis, etc. Family (Tenuipalpidae); Tuckerellidae; Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis Dermacentor taiwanensis), Rocky Mountain wood tick (Dermacentor andersoni), Black-legged tick (Dermacentor reticulatus), Yamato tick (Ixodes ovatus), Schulz tick (Ixodes persulcatus), Black-legged tick (Ixodes scapularis), Western black-legged tick (Ixodes scapularis) (Ixodes pacificus), Ixodes holocyclus, Ixodes ricinus, Lone Star Tick (Amblyomma americanum), Gulf Coast Tick (Amblyomma maculatum), Rhipicephalus microplus, Cattle Tick (Rhipicephalus annulatus), Rhipicephalus sanguineus, Rhipicephalus Ixodidae, such as appendiculatus and Rhipicephalus decoloratus; Argasidae, such as Argas persicus, Ornithodoros hermsi, and Ornithodoros turicata; Pyroglyphidae such as Dermatophagoides farinae and Dermatophagoides pteronyssinus; Cheyletidae); Psoroptidae such as Psoroptes ovis, Psoroptes equi, Knemidocoptes mutans, Otodectes cynotis, Chorioptes spp.; Sarcoptidae, such as Notoedres cati, Notoedres muris, Sarcoptes scabiei; Listrophorus gibbus, etc. (Listrophoridae); Dermanyssidae, such as red mites (Dermanyssus gallinae); Macronyssidae, such as Ornithonyssus sylviarum and Ornithonyssus bacoti; ), Demodicidae such as Demodex canis and Demodex cati; ).
　クモ目(Araneae)：カバキコマチグモ(Cheiracanthium japonicum)等のコマチグモ科(Eutichuridae)；セアカゴケグモ(Latrodectus hasseltii)等のヒメグモ科(Theridiidae)。
　オビヤスデ目(Polydesmida)：ヤケヤスデ(Oxidus gracilis)、アカヤスデ(Nedyopus tambanus)等のヤケヤスデ科(Paradoxosomatidae)。
　等脚目(Isopoda)：オカダンゴムシ(Armadillidium vulgare)等のオカダンゴムシ科(Armadillidiidae)。
　唇脚綱(Chilopoda)：ゲジ(Thereuonema hilgendorfi)等のゲジ科(Scutigeridae)；トビズムカデ(Scolopendra subspinipes)等のオオムカデ科(Scolopendridae)；イッスンムカデ(Bothropolys rugosus)等のイッスンムカデ科(Ethopolyidae)。
　腹足綱(Gastropoda)：チャコウラナメクジ(Limax marginatus)、キイロコウラナメクジ(Limax flavus)等のコウラナメクジ科(Limacidae)；ナメクジ(Meghimatium bilineatum)等のナメクジ科(Philomycidae)；スクミリンゴガイ(Pomacea canaliculata)等のリンゴガイ科(Ampullariidae)；ヒメモノアラガイ(Austropeplea ollula)等のモノアラガイ科(Lymnaeidae)。 Araneae: Eutichuridae, such as Cheiracanthium japonicum; Theridiidae, such as Latrodectus hasseltii.
Polydesmida: Paradoxosomatidae, such as Oxidus gracilis and Nedyopus tambanus.
Isopoda: Armadillidiidae, such as Armadillidium vulgare.
Chilopoda: Scutigeridae, such as Thereuonema hilgendorfi; Scolopendridae, such as Scolopendra subspinipes; Ethopolyidae, such as Bothropolys rugosus.
Gastropoda: Limacidae, such as Limax marginatus and Limax flavus; Philomycidae, such as Meghimatium bilineatum; Pomacea canaliculata, etc. Lymnaeidae, such as Austropeplea ollula.
　線虫類(Nematoda)：イネシンガレセンチュウ(Aphelenchoides besseyi)等のアフェレンコイデス科(Aphelenchoididae)；ミナミネグサレセンチュウ(Pratylenchus coffeae)、Pratylenchus brachyurus、ムギネグサレセンチュウ(Pratylenchus neglectus)、Radopholus similis等のプラティレンクス科(Pratylenchidae)；ジャワネコブセンチュウ(Meloidogyne javanica)、サツマイモネコブセンチュウ(Meloidogyne incognita)、guava root-knot nematodes (Meloidogyne enterolobii)、キタネコブセンチュウ(Meloidogyne hapla)、ダイズシストセンチュウ(Heterodera glycines)、ジャガイモシストセンチュウ(Globodera rostochiensis)、ジャガイモシロシストセンチュウ(Globodera pallida)等のヘテロデラ科(Heteroderidae)；Rotylenchulus reniformis等のホプロライムス科(Hoplolaimidae)；イチゴメセンチュウ(Nothotylenchus acris)、ナミクキセンチュウ(Ditylenchus dipsaci)等のアングイナ科(Anguinidae)；ミカンネセンチュウ(Tylenchulus semipenetrans)等のティレンクルス科(Tylenchulidae)；ブドウオオハリセン(Xiphinema index)等のロンギドルス科(Longidoridae)；トリコドルス科(Trichodoridae)；マツノザイセンチュウ(Bursaphelenchus xylophilus)等のパラシタアフェレンクス科(Parasitaphelenchidae)。 Nematoda: Aphelenchoididae such as Aphelenchoides besseyi; Pratylenchidae; Meloidogyne javanica, Meloidogyne incognita, guava root-knot nematodes (Meloidogyne enterolobii), Meloidogyne hapla, Heterodera glycines, potato cyst nematode ( Heteroderidae such as Globodera rostochiensis and Globodera pallida; Hoplolimidae such as Rotylenchus reniformis; Anguinidae); Tylenchulidae, such as citrus nematode (Tylenchulus semipenetrans); Longidoridae, such as Xiphinema index; Trichodoridae; Aphelenx family (Parasitaphelenchidae).
　有害昆虫、有害ダニ類等の有害節足動物、有害軟体動物及び有害線虫は、殺虫剤、殺ダニ剤、殺軟体動物剤及び殺線虫剤に薬剤感受性の低下した、又は薬剤抵抗性の発達した有害昆虫、有害ダニ類等の有害節足動物、有害軟体動物及び有害線虫であってもよい。 Harmful insects, harmful arthropods such as harmful mites, harmful molluscs and harmful nematodes have reduced drug sensitivity or drug resistance to insecticides, acaricides, molluscicides and nematicides. It may be developed harmful insects, harmful arthropods such as harmful mites, harmful mollusks, and harmful nematodes.
　本発明の有害生物防除方法としては、本発明化合物又は組成物Ａの有効量を、有害生物に直接、及び／又は、有害生物の生息場所（植物、土壌、家屋内、動物等）に施用することにより行われる。本発明の有害生物の防除方法としては、例えば、茎葉処理、土壌処理、根部処理、シャワー処理、燻煙処理、水面処理及び種子処理が挙げられる。 As the method for controlling pests of the present invention, an effective amount of the compound of the present invention or composition A is applied directly to pests and/or to habitats of pests (plants, soil, indoors, animals, etc.). It is done by Examples of the pest control method of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, smoking treatment, water surface treatment and seed treatment.
　本発明化合物又は組成物Ａは、通常、固体担体、液体担体、ガス状担体等の不活性担体と界面活性剤等を混合し、必要に応じて結合剤、分散剤、安定剤等の製剤用補助剤を添加して、水性懸濁製剤、油性懸濁製剤、油剤、乳剤、エマルション製剤、マイクロエマルション製剤、マイクロカプセル製剤、水和剤、顆粒水和剤、粉剤、粒剤、錠剤、エアゾール剤、樹脂製剤等に製剤化して用いる。これらの製剤に限らず、Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271～276, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517に記載の剤型に製剤化して用いることができる。
　これらの製剤には本発明化合物又は組成物Ａが重量比で通常０．０００１～９９％含有される。 The compound or composition A of the present invention is usually prepared by mixing an inert carrier such as a solid carrier, a liquid carrier, or a gaseous carrier with a surfactant or the like, and optionally adding a binder, a dispersant, a stabilizer, or the like for formulation. Aqueous suspension formulations, oily suspension formulations, oil solutions, emulsion formulations, emulsion formulations, microemulsion formulations, microcapsule formulations, wettable powders, wettable granules, powders, granules, tablets, aerosols by adding auxiliary agents , formulated into resin formulations, etc., for use. Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271-276, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517 It can be formulated and used in the dosage form described in .
These preparations usually contain 0.0001 to 99% by weight of the compound of the present invention or Composition A.
　固体担体としては、例えば、クレー（パイロフィライトクレー、カオリンクレー等）、タルク、炭酸カルシウム、珪藻土、ゼオライト、ベントナイト、酸性白土、アタパルジャイト、ホワイトカーボン、硫酸アンモニウム、バーミキュライト、パーライト、軽石、硅砂、化学肥料（硫安、燐安、硝安、尿素、塩安等）の微粉末及び粒状物、並びに樹脂（ポリエチレン、ポリプロピレン、ポリエステル、ポリウレタン、ポリアミド、ポリ塩化ビニル等）が挙げられる。 Examples of solid carriers include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice stone, silica sand, chemical fertilizers. fine powders and granules of (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.) and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).
　液体担体としては、例えば、水、アルコール類（エタノール、シクロヘキサノール、ベンジルアルコール、プロピレングリコール、ポリエチレングリコール等）、ケトン類（アセトン、シクロヘキサノン等）、芳香族炭化水素（キシレン、フェニルキシリルエタン、メチルナフタレン等）、脂肪族炭化水素類（ヘキサン、シクロヘキサン等）、エステル類（酢酸エチル、オレイン酸メチル、炭酸プロピレン等）、ニトリル類（アセトニトリル等）、エーテル類（エチレングリコールジメチルエーテル等）、アミド類（Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルオクタンアミド等）、スルホキシド類（ジメチルスルホキシド等）、ラクタム類（Ｎ－メチルピロリドン、Ｎ－オクチルピロリドン等）、脂肪酸類（オレイン酸等）、植物油（大豆油等）が挙げられる。 Examples of liquid carriers include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylylethane, methyl naphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides ( N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethylsulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), vegetable oils ( soybean oil, etc.).
　ガス状担体としては、例えば、フルオロカーボン、ブタンガス、ＬＰＧ（液化石油ガス）、ジメチルエーテル、窒素、及び炭酸ガスが挙げられる。 Examples of gaseous carriers include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.
　界面活性剤としては、例えば、非イオン界面活性剤（ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリエチレングリコール脂肪酸エステル等）及び陰イオン界面活性剤（アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アルキル硫酸塩等）が挙げられる。 Examples of surfactants include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkylsulfonates, alkylarylsulfonates , alkyl sulfates, etc.).
　その他の製剤用補助剤としては、結合剤、分散剤、着色剤及び安定剤等が挙げられ、具体的には例えば、多糖類（デンプン、アラビアガム、セルロース誘導体、アルギン酸等）、リグニン誘導体、合成水溶性高分子（ポリビニルアルコール、ポリビニルピロリドン、ポリアクリル酸類等）、酸性リン酸イソプロピル、及びジブチルヒドロキシトルエンが挙げられる。 Other formulation adjuvants include binders, dispersants, colorants, stabilizers, etc. Specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, Examples include water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acidic isopropyl phosphate, and dibutylhydroxytoluene.
　また、本発明化合物の持つ効力を高めたり補助したりする成分としてアジュバントを用いることができる。具体的には、Nimbus（登録商標）、Assist（登録商標）、Aureo（登録商標）、Iharol（登録商標）、Silwet L-77（登録商標）、BreakThru（登録商標）、SundanceII（登録商標）、Induce（登録商標）、Penetrator（登録商標）、AgriDex（登録商標）、Lutensol A8（登録商標）、NP-7（登録商標）、Triton（登録商標）、Nufilm（登録商標）、Emulgator NP7（登録商標）、Emulad（登録商標）、TRITON X 45（登録商標）、AGRAL 90（登録商標）、AGROTIN（登録商標）、ARPON（登録商標）、EnSpray N（登録商標）、及びBANOLE（登録商標）等が挙げられる。 In addition, an adjuvant can be used as a component that enhances or assists the efficacy of the compound of the present invention. Specifically, Nimbus®, Assist®, Aureo®, Iharol®, Silwet L-77®, BreakThru®, Sundance II®, Induce®, Penetrator®, AgriDex®, Lutensol A8®, NP-7®, Triton®, Nufilm®, Emulgator NP7® ), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark) mentioned.
　本発明において、植物としては、植物全体、茎葉、花、穂、果実、樹幹、枝、樹冠、種子、栄養生殖器官及び苗が挙げられる。 In the present invention, plants include whole plants, foliage, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs and seedlings.
　栄養生殖器官とは、植物の根、茎、葉等のうち、その部位を本体から切り離して土壌に設置した場合に、成長する能力を持つものを意味する。栄養生殖器官としては、例えば、塊根（tuberous root）、横走根（creeping root）、鱗茎（bulb）、球茎（corm又はsolid bulb）、塊茎（tuber）、根茎（rhizome）、匍匐枝（stolon）、担根体（rhizophore）、茎断片（cane cuttings）、むかご（propagule）及びつる（vine cutting）が挙げられる。なお、匍匐枝は、ランナー（runner）と呼ばれることもあり、むかごは、珠芽とも呼ばれ、肉芽（broad bud）、鱗芽（bulbil）に分けられる。つるとは、サツマイモやヤマノイモ等の苗条（葉及び茎の総称、shoot）を意味する。鱗茎、球茎、塊茎、根茎、茎断片、担根体又は塊根を総称して、球根とも呼ばれている。イモの栽培は塊茎を土壌に植え付けることで始めるが、用いられる塊茎は一般に種芋と呼ばれる。 The vegetative reproductive organ means the plant's roots, stems, leaves, etc. that have the ability to grow when the part is separated from the main body and placed in the soil. Vegetative reproductive organs include, for example, tuberous root, creeping root, bulb, corm or solid bulb, tuber, rhizome, stolon , rhizophore, cane cuttings, propagule and vine cuttings. The stolons are sometimes called runners, and the mukago is also called buds, which are divided into broad buds and bulbils. A vine means a shoot (collective term for leaves and stems, shoot) of sweet potato, yamanoimo, and the like. Bulbs, corms, tubers, rhizomes, stem fragments, rhizophores or tuberous roots are collectively called bulbs. Cultivation of potatoes begins by planting tubers in the soil, and the tubers used are generally called seed potatoes.
　本発明化合物又は組成物Ａの有効量を土壌に施用して有害生物を防除する方法としては、例えば、植物を植えつける前又は植えつけた後の土壌に本発明化合物又は組成物Ａの有効量を施用する方法が挙げられる。より具体的には、例えば、植穴処理（植穴散布、植穴処理土壌混和）、株元処理（株元散布、株元土壌混和、株元灌注、育苗期後半株元処理）、植溝処理（植溝散布、植溝土壌混和）、作条処理（作条散布、作条土壌混和、生育期作条散布）、播種時作条処理（播種時作条散布、播種時作条土壌混和）、全面処理（全面土壌散布、全面土壌混和）、側条処理、水面処理（水面施用、湛水後水面施用）、その他土壌散布処理（生育期粒剤葉面散布、樹冠下または主幹周辺散布、土壌表面散布、土壌表面混和、播穴散布、畦部地表面散布、株間散布）、その他灌注処理（土壌灌注、育苗期灌注、薬液注入処理、地際部灌注、薬液ドリップイリゲーション、ケミゲーション）、育苗箱処理（育苗箱散布、育苗箱灌注、育苗箱薬液湛水）、育苗トレイ処理（育苗トレイ散布、育苗トレイ灌注、育苗トレイ薬液湛水）、苗床処理（苗床散布、苗床灌注、水苗代苗床散布、苗浸漬）、床土混和処理（床土混和、播種前床土混和、播種時覆土前散布、播種時覆土後散布、覆土混和）、及びその他処理（培土混和、鋤き込み、表土混和、雨落ち部土壌混和、植位置処理、粒剤花房散布、ペースト肥料混和）が挙げられる。 As a method for controlling pests by applying an effective amount of the compound of the present invention or composition A to soil, for example, an effective amount of the compound of the present invention or composition A is applied to soil before or after planting plants. and the method of applying. More specifically, for example, planting hole treatment (planting hole spraying, planting hole treatment soil mixing), stock base treatment (stock base spraying, stock base soil mixing, stock irrigation, late seedling period stock base treatment), planting groove Treatment (ditch spraying, ditch soil mixing), cropping treatment (cropping spraying, cropping soil mixing, growing season cropping), cropping treatment at the time of sowing (crop spraying at the time of sowing, cropping soil mixing at the time of sowing) ), full surface treatment (overall soil spraying, full soil mixing), side row treatment, water surface treatment (water surface application, water surface application after flooding), other soil spraying treatments (granule spraying during the growing season, foliar spraying, under the canopy or around the trunk) , soil surface spraying, soil surface mixing, sowing hole spraying, furrow ground surface spraying, interplant spraying), other irrigation treatments (soil irrigation, seedling irrigation, chemical injection treatment, ground irrigation, chemical drip irrigation, chemigation) , Raising seedling box treatment (Raising seedling box spraying, Raising seedling box irrigation, Raising seedling box chemical flooding), Raising seedling tray treatment (Raising seedling tray scattering, Raising seedling tray irrigation, Raising seedling tray chemical flooding), Nursery bed treatment (Raising seedling bed, Nursery bed irrigation, Water nursery Seedling spraying, seedling soaking), bed soil mixing treatment (bed soil mixing, bed soil mixing before sowing, spreading before covering soil at seeding, spraying after covering soil at seeding, mixing soil covering), and other treatments (mixing soil, plowing, topsoil) mixing, rainfall soil mixing, planting position treatment, granule spraying, paste fertilizer mixing).
　種子処理としては、例えば、種子又は栄養生殖器官への本発明化合物又は組成物Ａの処理が挙げられ、詳しくは、例えば、本発明化合物又は組成物Ａの懸濁液を霧状にして種子表面又は栄養生殖器官表面に吹きつける吹きつけ処理、本発明化合物又は組成物Ａを種子又は栄養生殖器官に塗布する塗沫処理、本発明化合物又は組成物Ａの薬液に一定時間種子を浸漬する浸漬処理、本発明化合物又は組成物Ａを含有する担体で種子又は栄養生殖器官をコートする方法（フィルムコート処理、ペレットコート処理等）が挙げられる。上記の栄養生殖器官としては、特に種芋が挙げられる。
　組成物Ａを種子又は栄養生殖器官に処理する場合、組成物Ａを１つの製剤として種子又は栄養生殖器官に処理することもできるし、組成物Ａを異なる複数の製剤として複数回に分けて種子又は栄養生殖器官に処理することもできる。組成物Ａを異なる複数の製剤として複数回に分けて処理する方法としては、例えば、有効成分として本発明化合物のみを含む製剤を処理し、種子又は栄養生殖器官を風乾させた後、本成分を含む製剤を処理する方法；及び、有効成分として本発明化合物及び本成分を含む製剤を処理し、種子又は栄養生殖器官を風乾させた後、処理済みの本成分以外の本成分を含む製剤を処理する方法、が挙げられる。
　本発明における本発明化合物又は組成物Ａを保持している種子又は栄養生殖器官とは、種子又は栄養生殖器官の表面に、本発明化合物又は組成物Ａが付着している状態のものを意味する。上記の本発明化合物又は組成物Ａを保持している種子又は栄養生殖器官は、種子又は栄養生殖器官へ本発明化合物又は組成物Ａが付着される前後に、本発明化合物又は組成物Ａ以外の資材が付着されていてもよい。
　また、組成物Ａが種子又は栄養生殖器官の表面に層となって付着している場合、該層は、１つの層又は複数の層からなる。また、複数の層からなる場合、各々の層は、１以上の有効成分を含んでいる層であるか、又は、１以上の有効成分を含んでいる層と有効成分を含んでいない層とからなる。
　本発明化合物又は組成物Ａを保持している種子又は栄養生殖器官は、例えば、本発明化合物又は組成物Ａ含む製剤を前記の種子処理の方法により、種子又は栄養生殖器官に施用することによって得ることができる。 Seed treatment includes, for example, the treatment of seeds or vegetative reproductive organs with the compound of the present invention or composition A. Specifically, for example, a suspension of the compound of the present invention or composition A is atomized and applied to the seed surface. Alternatively, a spraying treatment in which the surface of the vegetative reproductive organs is sprayed, a smearing treatment in which the compound of the present invention or composition A is applied to seeds or vegetative reproductive organs, and an immersion treatment in which seeds are immersed in a chemical solution of the compound of the present invention or composition A for a certain period of time. , a method of coating seeds or vegetative reproductive organs with a carrier containing the compound of the present invention or composition A (film coating, pellet coating, etc.). The vegetative and reproductive organs mentioned above include, in particular, seed potatoes.
When the composition A is applied to the seed or the vegetative reproductive organ, the seed or the vegetative reproductive organ can be treated with the composition A as a single formulation, or the composition A can be divided into a plurality of different formulations and applied to the seeds. Alternatively, it can be processed into vegetative and reproductive organs. As a method of treating composition A in a plurality of times as different formulations, for example, a formulation containing only the compound of the present invention as an active ingredient is treated, seeds or vegetative reproductive organs are air-dried, and then this component is added. and treating a formulation containing the compound of the present invention and the present ingredient as active ingredients, air-drying the seeds or vegetative reproductive organs, and then treating the formulation containing the present ingredient other than the treated present ingredient and a method for doing so.
The seed or vegetative reproductive organ retaining the compound of the present invention or composition A in the present invention means a state in which the compound of the present invention or composition A is attached to the surface of the seed or vegetative reproductive organ. . The seed or vegetative reproductive organ holding the compound of the present invention or composition A described above is treated with a compound other than the compound of the present invention or composition A before or after the compound of the present invention or composition A is attached to the seed or vegetative reproductive organ. Materials may be attached.
In addition, when the composition A adheres to the surface of a seed or vegetative reproductive organ in a layer, the layer consists of one layer or multiple layers. Also, when it consists of a plurality of layers, each layer is a layer containing one or more active ingredients, or a layer containing one or more active ingredients and a layer not containing an active ingredient. Become.
Seeds or vegetative reproductive organs retaining the compound of the present invention or composition A are obtained, for example, by applying a formulation containing the compound of the present invention or composition A to seeds or vegetative reproductive organs by the method of seed treatment described above. be able to.
　本発明化合物又は組成物Ａを農業分野の有害生物防除に用いる場合、その施用量は、１０,０００ｍ2あたりの本発明化合物の量で通常１～１０,０００ｇである。種子又は栄養生殖器官に処理する場合は、種子又は栄養生殖器官１Ｋｇに対して、本発明化合物の量が、通常０．００１～１００ｇの範囲で施用される。本発明化合物又は組成物Ａが乳剤、水和剤、フロアブル剤等に製剤化されている場合は、通常、有効成分濃度が０．０１～１０,０００ｐｐｍとなるように水で希釈して施用し、粒剤、粉剤等は、通常、そのまま施用する。 When the compound of the invention or composition A is used for controlling pests in the agricultural field, the application rate is usually 1 to 10,000 g of the compound of the invention per 10,000 m 2 . When seeds or vegetative reproductive organs are treated, the amount of the compound of the present invention is usually applied in the range of 0.001 to 100 g per 1 kg of seeds or vegetative reproductive organs. When the compound of the present invention or composition A is formulated as an emulsion, wettable powder, flowable powder, etc., it is usually applied after being diluted with water so that the concentration of the active ingredient is 0.01 to 10,000 ppm. , granules, powders and the like are usually applied as they are.
　また、シート状やひも状に加工した樹脂製剤を作物に巻き付ける、作物近傍に張り渡す、株元土壌に敷く等の方法により処理することもできる。 It can also be treated by wrapping a sheet-shaped or string-shaped resin formulation around crops, spreading it around crops, or laying it on the soil at the base of the plant.
　本発明化合物又は組成物Ａを家屋内に生息する有害節足動物の防除に用いる場合、その施用量は、面上に処理する場合は処理面積１ｍ2あたりの本発明化合物の量で、通常、０．０１～１,０００ｍｇであり、空間に処理する場合は処理空間１ｍ３あたりの本発明化合物の量で、通常、０．０１～５００ｍｇである。本発明化合物又は組成物Ａが乳剤、水和剤、フロアブル剤等に製剤化されている場合は、通常、有効成分濃度が０．１～１０,０００ｐｐｍとなるように水で希釈して施用し、油剤、エアゾール剤、燻煙剤、毒餌剤等はそのまま施用する。 When the compound of the present invention or composition A is used for controlling harmful arthropods living in houses, the amount of application is the amount of the compound of the present invention per 1 m 2 of the treated area when the surface is treated. The amount is 0.01 to 1,000 mg, and when the space is treated, the amount of the compound of the present invention per 1 m 3 of space to be treated is usually 0.01 to 500 mg. When the compound of the present invention or composition A is formulated as an emulsion, wettable powder, flowable powder, etc., it is usually applied after being diluted with water so that the concentration of the active ingredient is 0.1 to 10,000 ppm. , oils, aerosols, smoke agents, poison baits, etc., are applied as they are.
　本発明化合物又は組成物Ａをウシ、ウマ、ブタ、ヒツジ、ヤギ、ニワトリ等の家畜、イヌ、ネコ、ラット、マウス等の小動物の外部寄生虫防除に用いる場合は、獣医学的に公知の方法で動物に使用することができる。具体的な使用方法としては、全身抑制を目的にする場合には、例えば錠剤、飼料混入、坐薬、注射（筋肉内、皮下、静脈内、腹腔内等）により投与され、非全身的抑制を目的とする場合には、例えば油剤若しくは水性液剤を噴霧する、ポアオン処理若しくはスポットオン処理を行う、シャンプー製剤で動物を洗う又は樹脂製剤を首輪や耳札にして動物に付ける等の方法により用いられる。動物に投与する場合の本発明化合物又は組成物Ａの量は、通常、動物の体重１ｋｇに対して、０．１～１,０００ｍｇの範囲である。 When the compound of the present invention or composition A is used for controlling ectoparasites of domestic animals such as cattle, horses, pigs, sheep, goats, chickens, etc., and small animals such as dogs, cats, rats, mice, etc., veterinary known methods are used. Can be used on animals with As a specific method of use, for the purpose of systemic suppression, for example, it is administered by tablet, feed, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), and non-systemic suppression is intended. In the case of, for example, spraying an oily or aqueous solution, performing pour-on treatment or spot-on treatment, washing the animal with a shampoo formulation, or attaching a resin formulation to the animal as a collar or ear tag, etc. It is used. The amount of the compound of the present invention or composition A when administered to an animal is generally in the range of 0.1 to 1,000 mg per kg body weight of the animal.
　本発明化合物又は組成物Ａは、畑、水田、芝生、果樹園等の農耕地における有害生物の防除剤として使用することができる。植物としては、例えば以下のものが挙げられる。 The compound or composition A of the present invention can be used as a pest control agent in agricultural lands such as fields, paddy fields, lawns, and orchards. Examples of plants include the following.
　トウモロコシ（馬歯種、硬粒種、軟粒種、爆裂種、糯種、甘味種、フィールドコーン）、イネ（長粒種、短粒種、中粒種、ジャポニカ種、熱帯ジャポニカ種、インディカ種、ジャワニカ種、水稲、陸稲、浮稲、直播、移植、糯米）、コムギ（パンコムギ（硬質、軟質、中質、赤コムギ、白コムギ）、デュラムコムギ、スペルトコムギ、クラブコムギ、それぞれの冬コムギ型、春コムギ型）、オオムギ（二条オオムギ（＝ビールムギ）、六条オオムギ、ハダカムギ、もち麦、それぞれの冬オオムギ型、春オオムギ型）、ライムギ（冬ライムギ型、春ライムギ型）、トリティカーレ（冬トリティカーレ型、春トリティカーレ型）、エンバク（冬エンバク型、春エンバク型）、ソルガム、ワタ（アップランド種、ピマ種）、ダイズ（完熟種子収穫品種、枝豆品種、青刈り品種、それぞれの無限伸育型、有限伸育型、半有限伸育型）、ピーナッツ、ソバ、テンサイ（製糖用、飼料用、根菜、葉菜、燃料）、ナタネ（冬ナタネ型、春ナタネ型）、カノーラ（冬カノーラ型、春カノーラ型）、ヒマワリ（搾油用、食用、観賞用）、サトウキビ、タバコ、チャノキ、クワ、ナス科野菜（ナス、トマト、ピーマン、トウガラシ、ジャガイモ等）、ウリ科野菜（キュウリ、カボチャ、ズッキーニ、スイカ、メロン等）、アブラナ科野菜（ダイコン、カブ、セイヨウワサビ、コールラビ、ハクサイ、キャベツ、カラシナ、ブロッコリー、カリフラワー等）、キク科野菜（ゴボウ、シュンギク、アーティチョーク、レタス等）、ユリ科野菜（ネギ、タマネギ、ニンニク、アスパラガス等）、セリ科野菜（ニンジン、パセリ、セロリ、アメリカボウフウ等）、アカザ科野菜（ホウレンソウ、フダンソウ等）、シソ科野菜（シソ、ミント、バジル等）、イチゴ、サツマイモ、ヤマノイモ、サトイモ、仁果類（リンゴ、セイヨウナシ、ニホンナシ、チュウゴクナシ、カリン、マルメロ等）、核果類（モモ、スモモ、ネクタリン、ウメ、オウトウ、アンズ、プルーン等）、カンキツ類（ウンシュウミカン、オレンジ、レモン、ライム、グレープフルーツ等）、堅果類（クリ、クルミ、ハシバミ、アーモンド、ピスタチオ、カシューナッツ、マカダミアナッツ等）、液果類（ブルーベリー、クランベリー、ブラックベリー、ラズベリー等）、ブドウ、カキ、イチジク、オリーブ、ビワ、バナナ、コーヒー、ナツメヤシ、ココヤシ、観賞植物、森林植物、シバ類、牧草類。 Maize (horse tooth, hard grain, soft grain, explosive, glutinous, sweet, field corn), rice (long grain, short grain, medium grain, japonica, tropical japonica, indica, Javanica, paddy rice, upland rice, floating rice, direct seeding, transplantation, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, winter wheat type, spring wheat type, respectively) ), barley (two-rowed barley (= beer barley), six-rowed barley, naked barley, glutinous barley, winter barley type, spring barley type, respectively), rye (winter rye type, spring rye type), triticare (winter triticale type, spring triticale type) ), oats (winter oat type, spring oat type), sorghum, cotton (upland, pima), soybean (ripe seed harvest varieties, edamame varieties, green crop varieties, infinite growth type, limited growth type of each) , semi-limited growing type), peanuts, buckwheat, sugar beet (for sugar manufacturing, feed, root vegetables, leafy vegetables, fuel), rapeseed (winter rape type, spring rape type), canola (winter canola type, spring canola type), Sunflower (for oil extraction, food, ornamental use), sugarcane, tobacco, tea tree, mulberry, solanaceous vegetables (eggplant, tomato, green pepper, hot pepper, potato, etc.), cucurbitaceous vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.) , Cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), Asteraceous vegetables (burdock, chrysanthemum, artichoke, lettuce, etc.), liliaceous vegetables (green onions, onions, garlic, Asparagus, etc.), Umbelliferous vegetables (carrots, parsley, celery, American bowhu, etc.), Chenopodiaceous vegetables (spinach, chard, etc.), Labiatae vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yamanoimo, taro, Pome fruits (apples, pears, Japanese pears, Chinese pears, Chinese quince, quince, etc.), stone fruits (peaches, plums, nectarines, plums, cherry blossoms, apricots, prunes, etc.), citrus fruits (unshu mandarin oranges, oranges, lemons, limes, grapefruit, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas , coffee, dates, coconut palms, ornamental plants, forest plants, moss species, pastures.
　上記植物は、一般的に栽培される品種であれば特に限定はない。上記植物には、自然交配で作出しうる植物、突然変異により発生しうる植物、F1ハイブリッド植物、及び遺伝子組換え作物も含まれる。遺伝子組換え作物としては、例えばイソキサフルトール等のHPPD（４－ヒドロキシフェニルピルビン酸ジオキシゲナーゼ酵素）阻害剤、イマゼタピル、チフェンスルフロンメチル等のALS（アセト乳酸合成酵素）阻害剤、EPSP（５－エノールピルビルシキミ酸－３－リン酸合成酵素）阻害剤、グルタミン合成酵素阻害剤、PPO（プロトポルフィリノーゲン酸化酵素）阻害剤、ブロモキシニル、又はジカンバ等の除草剤に対する耐性が付与された植物；バチルス・チューリンゲンシス（Bacillus thuringiensis）などのバチルス属で知られている選択的毒素等を合成することが可能となった植物；有害昆虫由来の内在性遺伝子に部分的に一致する遺伝子断片等を合成し、標的有害昆虫体内でジーンサイレンシング（RNAi；RNA interference）を誘導することにより特異的な殺虫活性を付与することができる植物が挙げられる。 The above plants are not particularly limited as long as they are commonly cultivated varieties. The above plants also include plants that can be produced by natural crossing, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include HPPD (4-hydroxyphenylpyruvate dioxygenase) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron-methyl, and EPSP (5 - enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or plants tolerant to herbicides such as dicamba ;Plants capable of synthesizing selective toxins, etc. known in the genus Bacillus, such as Bacillus thuringiensis; Gene fragments, etc. that partially match endogenous genes derived from harmful insects Plants capable of synthesizing and conferring specific insecticidal activity by inducing gene silencing (RNAi; RNA interference) in target pests.
　以下に製造例、参考製造例、製剤例及び試験例を示して、本発明をより具体的に説明するが、本発明はこれらの例に限定されない。 The following Production Examples, Reference Production Examples, Formulation Examples and Test Examples are shown to more specifically explain the present invention, but the present invention is not limited to these examples.
　本明細書中、Meはメチル基を表し、Etはエチル基を表し、Prはプロピル基を表し、i-Prはイソプロピル基を表し、i-Buはイソブチル基を表し、t-Buはｔｅｒｔ－ブチル基を表し、c-Prはシクロプロピル基を表し、c-Buはシクロブチル基を表し、c-Penはシクロペンチル基を表し、c-Hexはシクロヘキシル基を表し、Phはフェニル基を表し、2-Pyは２－ピリジル基を表し、3-Pyは３－ピリジル基を表し、4-Pyは４－ピリジル基を表す。フェニル基、ピリジル基、2-pyrimidinyl、4-pyrimidinyl、3-pyridazinyl、1-pyrazolyl、3-pyrazolyl、4-pyrazolyl、5-pyrazolyl、5-oxazolyl、5-thiazolyl、1-imidazolyl、2-oxadiazolyl、2-benzoxazolyl、又は2-benzoimidazolylが置換基を有する場合は、置換基を記号の前に置換位置とともに記す。例えば、2-F-Phは２－フルオロフェニルを表し、2-OCF3-Phは２－（トリフルオロメトキシ）フェニル基を表し、2-Ph-Phは２－フェニルフェニル基、3-Cl-2-Pyは３－クロロ－２－ピリジル基を表す。また、CH(CH3)c-Prは１－シクロプロピルエチル基を表し、CH2(2-F-3-F-Ph)は（２，３－ジフルオロフェニル）メチル基を表し、O(3-CF3-5-CF3-Ph)は［３，５－ビス（トリフルオロメチル）フェニル］オキシ基を表し、OCH2(2-OPh-Ph)は（２－フェノキシフェニル）メトキシ基を表し、Oi-Prはイソプロピルオキシ基を表す。 In the present specification, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, i-Pr represents an isopropyl group, i-Bu represents an isobutyl group, t-Bu represents tert- represents a butyl group, c-Pr represents a cyclopropyl group, c-Bu represents a cyclobutyl group, c-Pen represents a cyclopentyl group, c-Hex represents a cyclohexyl group, Ph represents a phenyl group, 2 -Py represents a 2-pyridyl group, 3-Py represents a 3-pyridyl group, and 4-Py represents a 4-pyridyl group. Phenyl group, pyridyl group, 2-pyrimidinyl, 4-pyrimidinyl, 3-pyridazinyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 5-oxazolyl, 5-thiazolyl, 1-imidazolyl, 2-oxadiazolyl, When 2-benzoxazolyl or 2-benzoimidazolyl has a substituent, the substituent is described together with the substitution position before the symbol. For example, 2-F-Ph represents 2-fluorophenyl, 2-OCF 3 -Ph represents a 2-(trifluoromethoxy)phenyl group, 2-Ph-Ph represents a 2-phenylphenyl group, 3-Cl- 2-Py represents a 3-chloro-2-pyridyl group. Further, CH(CH 3 )c-Pr represents a 1-cyclopropylethyl group, CH 2 (2-F-3-F-Ph) represents a (2,3-difluorophenyl)methyl group, and O(3 -CF 3 -5-CF 3 -Ph) represents a [3,5-bis(trifluoromethyl)phenyl]oxy group, and OCH 2 (2-OPh-Ph) represents a (2-phenoxyphenyl)methoxy group. , Oi-Pr represents an isopropyloxy group.
　まず、本発明化合物の製造例を示す。 First, a production example of the compound of the present invention is shown.
　化合物の物性値を液体クロマトグラフィー／質量分析（以下、ＬＣＭＳと記す）で測定した場合には、測定された分子イオン値［Ｍ＋Ｈ］+又は［Ｍ－Ｈ］-及び保持時間（以下、ＲＴと記す）を記す。液体クロマトグラフィー（以下、ＬＣと記す）及び質量分析（以下、ＭＳと記す）の条件は以下の通りである。 When the physical properties of a compound are measured by liquid chromatography/mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M+H] + or [M−H] − and retention time (hereinafter referred to as RT write). Conditions for liquid chromatography (hereinafter referred to as LC) and mass spectrometry (hereinafter referred to as MS) are as follows.
［ＬＣ条件］
カラム：L-column2 ODS、内径４．６ｍｍ、長さ３０ｍｍ、粒子径３μｍ（一般財団法人化学物質評価研究機構）
ＵＶ測定波長：２５４ｎｍ
移動相：Ａ液：０．１％ギ酸水溶液、Ｂ液：０．１％ギ酸アセトニトリル
流速：２．０ｍＬ／分
ポンプ：ＬＣ－２０ＡＤ（島津製作所製）２台（高圧グラジエント）
グラジエント条件：［表ＬＣ１］に記載の濃度勾配で送液する。 [LC conditions]
Column: L-column2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (Chemicals Evaluation and Research Organization)
UV measurement wavelength: 254 nm
Mobile phase: A solution: 0.1% formic acid aqueous solution, B solution: 0.1% formic acid acetonitrile Flow rate: 2.0 mL / min Pump: LC-20AD (manufactured by Shimadzu Corporation) 2 units (high pressure gradient)
Gradient conditions: The concentration gradient described in [Table LC1] is applied.
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000024
［ＭＳ条件］
検出器：ＬＣＭＳ－２０２０（島津製作所製）
イオン化法：ＤＵＩＳ [MS conditions]
Detector: LCMS-2020 (manufactured by Shimadzu Corporation)
Ionization method: DUIS
参考製造例１
　アルゴン雰囲気下、１－（ｔｅｒｔ－ブトキシカルボニル）－６－ブロモインドール７．４９ｇ、［１，１’－ビス（ジフェニルホスフィノ）フェロセン］パラジウム（ＩＩ）ジクロリド０．５５ｇ、ビス（ピナコラト）ジボロン７．６２ｇ、酢酸カリウム７．３６ｇ、及びＤＭＳＯ５０ｍＬの混合物を、９０℃で８時間撹拌した。得られた混合物を室温に冷却後、水を加え、ろ過した。得られたろ液にＭＴＢＥを加え、水及び飽和食塩水で順次洗浄した。得られた有機層を無水硫酸ナトリウムで乾燥し、減圧下で濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体１を７．７４ｇ得た。
Figure JPOXMLDOC01-appb-C000025
 中間体１：1H-NMR (CDCl3) δ: 8.66 (1H, s), 7.66 (1H, d), 7.63 (1H, d), 7.56 (1H, d), 6.56 (1H, d), 1.68 (9H, s), 1.35 (12H, s). Reference Production Example 1
Under an argon atmosphere, 7.49 g of 1-(tert-butoxycarbonyl)-6-bromoindole, 0.55 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, and 7 bis(pinacolato)diboron A mixture of .62 g, 7.36 g potassium acetate, and 50 mL DMSO was stirred at 90° C. for 8 hours. After cooling the resulting mixture to room temperature, water was added and filtered. MTBE was added to the resulting filtrate, and the mixture was washed with water and saturated brine in that order. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography to obtain 7.74 g of Intermediate 1 represented by the following formula.
Figure JPOXMLDOC01-appb-C000025
 Intermediate 1: 1 H-NMR (CDCl 3 ) δ: 8.66 (1H, s), 7.66 (1H, d), 7.63 (1H, d), 7.56 (1H, d), 6.56 (1H, d), 1.68 (9H, s), 1.35 (12H, s).
参考製造例１－１
　参考製造例１に準じて製造した化合物及びその物性値を以下に示す。
Figure JPOXMLDOC01-appb-C000026
 中間体３：1H-NMR (CDCl3) δ: 8.55 (1H, s), 7.60 (1H, d), 7.33 (1H, s), 6.48 (1H, d), 2.60 (3H, s), 1.68 (9H, s), 1.35 (12H, s). Reference Production Example 1-1
The compounds produced according to Reference Production Example 1 and their physical properties are shown below.
Figure JPOXMLDOC01-appb-C000026
 Intermediate 3: 1 H-NMR (CDCl 3 ) δ: 8.55 (1H, s), 7.60 (1H, d), 7.33 (1H, s), 6.48 (1H, d), 2.60 (3H, s), 1.68. (9H, s), 1.35 (12H, s).
Figure JPOXMLDOC01-appb-C000027
 中間体５：1H-NMR (CDCl3) δ: 8.43 (1H, s), 7.91-7.82 (3H, m), 7.58-7.50 (5H, m), 7.46 (1H, dd), 7.41 (1H, dd), 1.33 (12H, s).
Figure JPOXMLDOC01-appb-C000027
 Intermediate 5: 1 H-NMR (CDCl 3 ) δ: 8.43 (1H, s), 7.91-7.82 (3H, m), 7.58-7.50 (5H, m), 7.46 (1H, dd), 7.41 (1H, dd), 1.33 (12H, s).
製造例１
　３．４３ｇの中間体１、トリス（ジベンジリデンアセトン）ジパラジウム（０）０．９２ｇ、２－ヨード－３－メトキシアクリル酸メチル２．６６ｇ、ＳＰｈｏｓ０．８２ｇ、リン酸三カリウム８．５ｇ、トルエン２５ｍＬ、及び水０．１ｍＬの混合物を、還流下で１４時間撹拌した。得られた混合物を室温に冷却後、水を加え、ろ過した。得られたろ液に酢酸エチルを加え、水及び飽和食塩水で順次洗浄した。得られた有機層を無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（酢酸エチル：ヘキサン＝１：４）に付し、次式で示される本発明化合物１－１を１．４５ｇ得た。
Figure JPOXMLDOC01-appb-C000028
 本発明化合物１－１：1H-NMR (CDCl3) δ: 8.14 (1H, s), 7.60 (1H, s), 7.58 (1H, d), 7.53 (1H, d), 7.17 (1H, dd), 6.54 (1H, dd), 3.86 (3H, s), 3.74 (3H, s), 1.65 (9H, s). Production example 1
3.43 g of intermediate 1, 0.92 g of tris(dibenzylideneacetone)dipalladium(0), 2.66 g of methyl 2-iodo-3-methoxyacrylate, 0.82 g of SPhos, 8.5 g of tripotassium phosphate, toluene A mixture of 25 mL and 0.1 mL of water was stirred under reflux for 14 hours. After cooling the resulting mixture to room temperature, water was added and filtered. Ethyl acetate was added to the obtained filtrate, and the mixture was washed with water and saturated brine in that order. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 1.45 g of the present compound 1-1 represented by the following formula.
Figure JPOXMLDOC01-appb-C000028
 Compound 1-1 of the present invention: 1 H-NMR (CDCl 3 ) δ: 8.14 (1H, s), 7.60 (1H, s), 7.58 (1H, d), 7.53 (1H, d), 7.17 (1H, dd ), 6.54 (1H, dd), 3.86 (3H, s), 3.74 (3H, s), 1.65 (9H, s).
製造例１－１
　製造例１に準じて製造した化合物及びその物性値を以下に示す。
Figure JPOXMLDOC01-appb-C000029
 　本発明化合物２－１：ＬＣＭＳ：３１９［Ｍ＋Ｈ］＋，ＲＴ＝２．２２分 Production Example 1-1
The compounds produced according to Production Example 1 and their physical properties are shown below.
Figure JPOXMLDOC01-appb-C000029
 Compound 2-1 of the present invention: LCMS: 319 [M+H] + , RT=2.22 min
参考製造例２
　０．３３ｇの本発明化合物１－１、モンモリロナイト０．６６ｇ、及びトルエン３ｍＬの混合物を、還流下で１０時間撹拌した。得られた混合物を室温に冷却後、ろ過した。得られたろ液を減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体２を０．１５ｇ得た。
Figure JPOXMLDOC01-appb-C000030
 中間体２：1H-NMR (CDCl3) δ: 8.12 (1H, s), 7.61 (1H, d), 7.59 (1H, s), 7.38 (1H, s), 7.20 (1H, dd), 7.07 (1H, dd), 6.53 (1H, dd), 3.85 (3H, s), 3.74 (3H, s). Reference Production Example 2
A mixture of 0.33 g of the present compound 1-1, 0.66 g of montmorillonite, and 3 mL of toluene was stirred under reflux for 10 hours. The resulting mixture was cooled to room temperature and then filtered. The resulting filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.15 g of Intermediate 2 represented by the following formula.
Figure JPOXMLDOC01-appb-C000030
 Intermediate 2: 1 H-NMR (CDCl 3 ) δ: 8.12 (1H, s), 7.61 (1H, d), 7.59 (1H, s), 7.38 (1H, s), 7.20 (1H, dd), 7.07. (1H, dd), 6.53 (1H, dd), 3.85 (3H, s), 3.74 (3H, s).
参考製造例２－１
　参考製造例２に準じて製造した化合物及びその物性値を以下に示す。
Figure JPOXMLDOC01-appb-C000031
 中間体４：1H-NMR (CDCl3) δ: 8.02 (1H, s), 7.61 (1H, s), 7.48 (1H, s), 7.17-7.13 (2H, m), 6.47-6.44 (1H, m), 3.82 (3H, s), 3.70 (3H, s), 2.26 (3H, s). Reference Production Example 2-1
The compounds produced according to Reference Production Example 2 and their physical properties are shown below.
Figure JPOXMLDOC01-appb-C000031
 Intermediate 4: 1 H-NMR (CDCl 3 ) δ: 8.02 (1H, s), 7.61 (1H, s), 7.48 (1H, s), 7.17-7.13 (2H, m), 6.47-6.44 (1H, m), 3.82 (3H, s), 3.70 (3H, s), 2.26 (3H, s).
製造例２
　０．１０ｇの中間体２、ヨウ化メチル０．１２ｇ、炭酸セシウム０．２０ｇ、及びＮＭＰ３ｍＬの混合物を、６０℃で４時間撹拌した。得られた混合物を室温に冷却後、飽和食塩水を加え、ＭＴＢＥで抽出した。得られた有機層を無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（酢酸エチル：ヘキサン＝１：２）に付し、次式で示される本発明化合物１－２を０．１０ｇ得た。
Figure JPOXMLDOC01-appb-C000032
 本発明化合物１－２：1H-NMR (CDCl3) δ: 7.62-7.56 (2H, m), 7.28 (1H, s), 7.06-7.01 (2H, m), 6.45 (1H, d), 3.85 (3H, s), 3.77 (3H, s), 3.74 (3H, s). Production example 2
A mixture of 0.10 g of intermediate 2, 0.12 g of methyl iodide, 0.20 g of cesium carbonate and 3 mL of NMP was stirred at 60° C. for 4 hours. After cooling the resulting mixture to room temperature, saturated brine was added and the mixture was extracted with MTBE. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 0.10 g of the present compound 1-2 represented by the following formula.
Figure JPOXMLDOC01-appb-C000032
 Compound 1-2 of the present invention: 1 H-NMR (CDCl 3 ) δ: 7.62-7.56 (2H, m), 7.28 (1H, s), 7.06-7.01 (2H, m), 6.45 (1H, d), 3.85 (3H, s), 3.77 (3H, s), 3.74 (3H, s).
製造例２－１
　製造例２に準じて製造した化合物及びその物性値を以下に示す。
　式（Ａ－１）
Figure JPOXMLDOC01-appb-C000033
 で示される化合物において、Ｒ2及びＥが［表Ａ－１］に記載のいずれかの組合せである化合物。 Production example 2-1
The compounds produced according to Production Example 2 and their physical properties are shown below.
Formula (A-1)
Figure JPOXMLDOC01-appb-C000033
 wherein R 2 and E are any combination described in [Table A-1].
Figure JPOXMLDOC01-appb-T000034
 　本発明化合物１－３：1H-NMR (CDCl3) δ: 7.62-7.57 (2H, m), 7.32 (1H, s), 7.10 (1H, dd), 7.04 (1H, d), 6.45 (1H, d), 4.16 (2H, q), 3.85 (3H, s), 3.75 (3H, s), 1.45 (3H, t).
　本発明化合物１－４：1H-NMR (CDCl3) δ: 7.61-7.57 (2H, m), 7.31 (1H, s), 7.08 (1H, d), 7.04 (1H, dd), 6.44 (1H, dd), 4.06 (2H, t), 3.85 (3H, s), 3.74 (3H, s), 1.86 (2H, dt), 0.93 (3H, t).
　本発明化合物１－５：1H-NMR (CDCl3) δ: 7.62-7.57 (2H, m), 7.29 (1H, s), 7.09-7.01 (2H, m), 6.44 (1H, d), 3.89 (2H, d), 3.85 (3H, s), 3.74 (3H, s), 2.23-2.14 (1H, m), 0.92 (6H, d).
　本発明化合物１－６：1H-NMR (CDCl3) δ: 7.65 (1H, d), 7.57 (1H, s), 7.53-7.49 (5H, m), 7.36-7.31 (2H, m), 7.11 (1H, dd), 6.65 (1H, dd), 3.83 (3H, s), 3.72 (3H, s).
　本発明化合物１－７：ＬＣＭＳ：３２２［Ｍ＋Ｈ］+，ＲＴ＝２．０２分
　本発明化合物１－８：ＬＣＭＳ：３３６［Ｍ＋Ｈ］+，ＲＴ＝２．１０分
　本発明化合物１－９：1H-NMR (CDCl3) δ: 7.93 (1H, s), 7.60 (1H, s), 7.51 (1H, d), 7.40 (1H, s), 6.48 (1H, d), 3.83 (3H, s), 3.70 (3H, s), 2.25 (3H, s), 1.64 (9H, s).
　本発明化合物１－１０：1H-NMR (CDCl3) δ: 7.61 (1H, s), 7.45 (1H, s), 7.06 (1H, s), 7.00 (1H, d), 6.37 (1H, d), 3.85 (2H, d), 3.81 (3H, s), 3.70 (3H, s), 2.25 (3H, s), 2.16 (1H, td), 0.91 (6H, d).
Figure JPOXMLDOC01-appb-T000034
 Compound 1-3 of the present invention: 1 H-NMR (CDCl 3 ) δ: 7.62-7.57 (2H, m), 7.32 (1H, s), 7.10 (1H, dd), 7.04 (1H, d), 6.45 (1H , d), 4.16 (2H, q), 3.85 (3H, s), 3.75 (3H, s), 1.45 (3H, t).
Compound 1-4 of the present invention: 1 H-NMR (CDCl 3 ) δ: 7.61-7.57 (2H, m), 7.31 (1H, s), 7.08 (1H, d), 7.04 (1H, dd), 6.44 (1H , dd), 4.06 (2H, t), 3.85 (3H, s), 3.74 (3H, s), 1.86 (2H, dt), 0.93 (3H, t).
Invention compound 1-5: 1 H-NMR (CDCl 3 ) δ: 7.62-7.57 (2H, m), 7.29 (1H, s), 7.09-7.01 (2H, m), 6.44 (1H, d), 3.89 (2H, d), 3.85 (3H, s), 3.74 (3H, s), 2.23-2.14 (1H, m), 0.92 (6H, d).
Invention compound 1-6: 1 H-NMR (CDCl 3 ) δ: 7.65 (1H, d), 7.57 (1H, s), 7.53-7.49 (5H, m), 7.36-7.31 (2H, m), 7.11 (1H, dd), 6.65 (1H, dd), 3.83 (3H, s), 3.72 (3H, s).
Invention compound 1-7: LCMS: 322 [M+H] + , RT=2.02 minutes Invention compound 1-8: LCMS: 336 [M+H] + , RT=2.10 minutes Invention compound 1-9: 1 H-NMR ( CDCl3 ) δ: 7.93 (1H, s), 7.60 (1H, s), 7.51 (1H, d), 7.40 (1H, s), 6.48 (1H, d), 3.83 (3H, s) , 3.70 (3H, s), 2.25 (3H, s), 1.64 (9H, s).
Compound 1-10 of the present invention: 1 H-NMR (CDCl 3 ) δ: 7.61 (1H, s), 7.45 (1H, s), 7.06 (1H, s), 7.00 (1H, d), 6.37 (1H, d ), 3.85 (2H, d), 3.81 (3H, s), 3.70 (3H, s), 2.25 (3H, s), 2.16 (1H, td), 0.91 (6H, d).
Figure JPOXMLDOC01-appb-C000035
 本発明化合物１－１３：1H-NMR (CDCl3) δ: 7.80 (2H, d), 7.73 (1H, dd), 7.70 (1H, s), 7.63 (2H, d), 7.42 (1H, d), 7.24 (1H, dd), 6.75 (1H, dd), 4.06 (3H, s), 3.90 (3H, s).
Figure JPOXMLDOC01-appb-C000035
 Compounds of the present invention 1-13: 1 H-NMR (CDCl 3 ) δ: 7.80 (2H, d), 7.73 (1H, dd), 7.70 (1H, s), 7.63 (2H, d), 7.42 (1H, d ), 7.24 (1H, dd), 6.75 (1H, dd), 4.06 (3H, s), 3.90 (3H, s).
Figure JPOXMLDOC01-appb-C000036
 本発明化合物１－１６：1H-NMR (CDCl3) δ: 7.64 (1H, d), 7.56 (1H, s), 7.49-7.26 (9H, m), 7.10-7.08 (3H, m), 6.62 (1H, dd), 5.13 (2H, s), 3.82 (3H, s), 3.72 (3H, s).
Figure JPOXMLDOC01-appb-C000036
 Invention compound 1-16: 1 H-NMR (CDCl 3 ) δ: 7.64 (1H, d), 7.56 (1H, s), 7.49-7.26 (9H, m), 7.10-7.08 (3H, m), 6.62 (1H, dd), 5.13 (2H, s), 3.82 (3H, s), 3.72 (3H, s).
Figure JPOXMLDOC01-appb-C000037
 本発明化合物１－１７：1H-NMR (CDCl3) δ: 7.64 (1H, dd), 7.57 (1H, s), 7.53 (1H, dd), 7.47-7.33 (6H, m), 7.31 (1H, d), 7.15 (1H, t), 7.13-7.09 (2H, m), 6.95 (1H, dd), 6.64 (1H, dd), 5.12 (2H, s), 3.82 (3H, s), 3.72 (3H, s).
Figure JPOXMLDOC01-appb-C000037
 Compound 1-17 of the present invention: 1 H-NMR (CDCl 3 ) δ: 7.64 (1H, dd), 7.57 (1H, s), 7.53 (1H, dd), 7.47-7.33 (6H, m), 7.31 (1H , d), 7.15 (1H, t), 7.13-7.09 (2H, m), 6.95 (1H, dd), 6.64 (1H, dd), 5.12 (2H, s), 3.82 (3H, s), 3.72 ( 3H, s).
参考製造例３－１
　アルゴン雰囲気下、１－（ｔｅｒｔ－ブトキシカルボニル）－６－ブロモインドール１２．０ｇ、アセト酢酸メチル７．０６ｇ、酢酸パラジウム（ＩＩ）０．９２ｇ、２－ジ－ｔｅｒｔ－ブチルホスフィノ－２’，４’，６’－トリイソプロピルビフェニル１．７４ｇ、リン酸三カリウム２５．９ｇ、及びトルエン１２０ｍＬの混合物を還流下で５時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣にメタノール８０ｍＬを加え、この混合物に２８％ナトリウムメトキシドメタノール溶液１６．２ｍＬを加え、４０℃で７時間撹拌した。得られた混合物に飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（酢酸エチル：ヘキサン＝１：２）に付し、次式で示される中間体６を５．１３ｇ得た。
Figure JPOXMLDOC01-appb-C000038
 中間体６：1H-NMR (CDCl3) δ: 8.12 (1H, br s), 7.59 (1H, d), 7.34 (1H, s), 7.20 (1H, dd), 7.04 (1H, dd), 6.54-6.52 (1H, m), 3.73 (2H, s), 3.69 (3H, s). Reference Production Example 3-1
Under an argon atmosphere, 1-(tert-butoxycarbonyl)-6-bromoindole 12.0 g, methyl acetoacetate 7.06 g, palladium(II) acetate 0.92 g, 2-di-tert-butylphosphino-2', A mixture of 1.74 g of 4′,6′-triisopropylbiphenyl, 25.9 g of tripotassium phosphate and 120 mL of toluene was stirred under reflux for 5 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. 80 mL of methanol was added to the obtained residue, 16.2 mL of 28% sodium methoxide methanol solution was added to the mixture, and the mixture was stirred at 40° C. for 7 hours. A saturated aqueous ammonium chloride solution was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 5.13 g of intermediate 6 represented by the following formula.
Figure JPOXMLDOC01-appb-C000038
 Intermediate 6: 1 H-NMR (CDCl 3 ) δ: 8.12 (1H, br s), 7.59 (1H, d), 7.34 (1H, s), 7.20 (1H, dd), 7.04 (1H, dd), 6.54-6.52 (1H, m), 3.73 (2H, s), 3.69 (3H, s).
参考製造例３－２
　５．３ｇの中間体６、二炭酸ジ－ｔｅｒｔ－ブチル６．１４ｇ、及びＴＨＦ１００ｍＬの混合物に、４－ジメチルアミノピリジン０．１７ｇを加え、室温で３時間撹拌した。得られた混合物を減圧下で濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィー（酢酸エチル：ヘキサン＝１：４）に付し、次式で示される中間体７を７．２１ｇ得た。
Figure JPOXMLDOC01-appb-C000039
 中間体７：1H-NMR (CDCl3) δ: 8.12 (1H, s), 7.56 (1H, d), 7.51 (1H, d), 7.16 (1H, dd), 6.54 (1H, dd), 3.75 (2H, s), 3.70 (3H, s), 1.67 (9H, s). Reference Production Example 3-2
To a mixture of 5.3 g of intermediate 6, 6.14 g of di-tert-butyl dicarbonate and 100 mL of THF, 0.17 g of 4-dimethylaminopyridine was added and stirred at room temperature for 3 hours. The resulting mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 7.21 g of intermediate 7 represented by the following formula.
Figure JPOXMLDOC01-appb-C000039
 Intermediate 7: 1 H-NMR (CDCl 3 ) δ: 8.12 (1H, s), 7.56 (1H, d), 7.51 (1H, d), 7.16 (1H, dd), 6.54 (1H, dd), 3.75. (2H, s), 3.70 (3H, s), 1.67 (9H, s).
製造例３
　２．８９ｇの中間体７、カリウムｔ－ブトキシド１．３５ｇ、ＴＨＦ３０ｍＬ及びｔ－ブタノール１０ｍＬの混合物に、氷冷下で亜硝酸イソアミル１．５５ｇを滴下ロートで加え、室温で６時間撹拌した。得られた混合物に１Ｎ塩酸を加え、酢酸エチルで抽出した。得られた有機層を水及び飽和食塩水で順次洗浄し、硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣に炭酸カリウム１．６６ｇ、及びＤＭＦ４０ｍＬを加え、この混合物にヨウ化メチル１．７１ｇを加え、室温で１日間撹拌した。得られた混合物に塩化アンモニウム水溶液を加え、ＭＴＢＥで抽出した。得られた有機層を水、飽和食塩水で順次洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（酢酸エチル：ヘキサン＝１：４）に付し、次式で示される本発明化合物１－１１を０．２７ｇ、本発明化合物１－１２を０．０８ｇ、中間体８を０．２２ｇ、中間体９を０．０８ｇ得た。
Figure JPOXMLDOC01-appb-C000040
 本発明化合物１－１１：1H-NMR (CDCl3) δ: 8.29 (1H, s), 7.68-7.65 (1H, m), 7.61-7.58 (1H, m), 7.29-7.26 (1H, m), 6.59-6.57 (1H, m), 4.08 (3H, s), 3.91 (3H, s), 1.66 (9H, s). Production example 3
To a mixture of 2.89 g of intermediate 7, 1.35 g of potassium t-butoxide, 30 mL of THF and 10 mL of t-butanol, 1.55 g of isoamyl nitrite was added with a dropping funnel under ice cooling, and the mixture was stirred at room temperature for 6 hours. 1N Hydrochloric acid was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. 1.66 g of potassium carbonate and 40 mL of DMF were added to the resulting residue, 1.71 g of methyl iodide was added to the mixture, and the mixture was stirred at room temperature for 1 day. Aqueous ammonium chloride solution was added to the resulting mixture, and the mixture was extracted with MTBE. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 0.27 g of the present compound 1-11 represented by the following formula, 0.08 g of the present compound 1-12, 0.22 g of intermediate 8 and 0.08 g of intermediate 9 were obtained.
Figure JPOXMLDOC01-appb-C000040
 Invention compound 1-11: 1 H-NMR (CDCl 3 ) δ: 8.29 (1H, s), 7.68-7.65 (1H, m), 7.61-7.58 (1H, m), 7.29-7.26 (1H, m) , 6.59-6.57 (1H, m), 4.08 (3H, s), 3.91 (3H, s), 1.66 (9H, s).
Figure JPOXMLDOC01-appb-C000041
 本発明化合物１－１２：1H-NMR (CDCl3) δ: 8.66 (1H, s), 7.68 (1H, d), 7.59 (1H, d), 7.46 (1H, dd), 6.58 (1H, d), 4.16 (3H, s), 3.88 (3H, s), 1.67 (9H, s).
Figure JPOXMLDOC01-appb-C000041
 Compound 1-12 of the present invention: 1 H-NMR (CDCl 3 ) δ: 8.66 (1H, s), 7.68 (1H, d), 7.59 (1H, d), 7.46 (1H, dd), 6.58 (1H, d ), 4.16 (3H, s), 3.88 (3H, s), 1.67 (9H, s).
Figure JPOXMLDOC01-appb-C000042
 中間体８：1H-NMR (CDCl3) δ: 8.26 (1H, s), 7.67 (1H, d), 7.59 (1H, s), 7.29 (1H, dd), 7.18 (1H, dd), 6.58-6.56 (1H, m), 4.07 (3H, s), 3.91 (3H, s).
Figure JPOXMLDOC01-appb-C000042
 Intermediate 8: 1 H-NMR (CDCl 3 ) δ: 8.26 (1H, s), 7.67 (1H, d), 7.59 (1H, s), 7.29 (1H, dd), 7.18 (1H, dd), 6.58. -6.56 (1H, m), 4.07 (3H, s), 3.91 (3H, s).
Figure JPOXMLDOC01-appb-C000043
 中間体９：1H-NMR (CDCl3) δ: 8.26 (1H, s), 7.64 (1H, d), 7.58 (1H, s), 7.38 (1H, dd), 7.29 (1H, dd), 6.58-6.55 (1H, m), 4.03 (3H, s), 3.97 (3H, s).
Figure JPOXMLDOC01-appb-C000043
 Intermediate 9: 1 H-NMR (CDCl 3 ) δ: 8.26 (1H, s), 7.64 (1H, d), 7.58 (1H, s), 7.38 (1H, dd), 7.29 (1H, dd), 6.58. -6.55 (1H, m), 4.03 (3H, s), 3.97 (3H, s).
製造例４
　０．０８ｇの本発明化合物１－１１及びＴＨＦ３ｍＬの混合物に、メチルアミン（９．８Ｍメタノール溶液）１ｍＬを加え、室温で６時間撹拌した。得られた混合物を減圧下で濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィー（酢酸エチル：ヘキサン＝１：１）に付し、次式で示される本発明化合物１－１４を０．０２ｇ得た。
Figure JPOXMLDOC01-appb-C000044
 本発明化合物１－１４：1H-NMR (CDCl3) δ: 8.31 (1H, br s), 7.64 (1H, d), 7.58 (1H, d), 7.31 (1H, dd), 6.81 (1H, s), 6.57 (1H, d), 3.99 (3H, s), 2.96 (3H, d), 1.66 (9H, s). Production example 4
1 mL of methylamine (9.8 M methanol solution) was added to a mixture of 0.08 g of the present compound 1-11 and 3 mL of THF, and the mixture was stirred at room temperature for 6 hours. The resulting mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain 0.02 g of the present compound 1-14 represented by the following formula. rice field.
Figure JPOXMLDOC01-appb-C000044
 Invention compound 1-14: 1 H-NMR (CDCl 3 ) δ: 8.31 (1H, br s), 7.64 (1H, d), 7.58 (1H, d), 7.31 (1H, dd), 6.81 (1H, s), 6.57 (1H, d), 3.99 (3H, s), 2.96 (3H, d), 1.66 (9H, s).
製造例４－１
　製造例４に準じて製造した化合物及びその物性値を以下に示す。
Figure JPOXMLDOC01-appb-C000045
 本発明化合物１－１５：1H-NMR (CDCl3) δ: 7.78 (2H, d), 7.73 (1H, s), 7.71 (1H, d), 7.63 (2H, d), 7.40 (1H, d), 7.28 (1H, dd), 6.87 (1H, br s), 6.73 (1H, dd), 3.98 (3H, s), 2.95 (3H, d). Production Example 4-1
The compounds produced according to Production Example 4 and their physical properties are shown below.
Figure JPOXMLDOC01-appb-C000045
 Compound 1-15 of the present invention: 1 H-NMR (CDCl 3 ) δ: 7.78 (2H, d), 7.73 (1H, s), 7.71 (1H, d), 7.63 (2H, d), 7.40 (1H, d ), 7.28 (1H, dd), 6.87 (1H, br s), 6.73 (1H, dd), 3.98 (3H, s), 2.95 (3H, d).
Figure JPOXMLDOC01-appb-C000046
 本発明化合物２－２：1H-NMR (CDCl3) δ: 8.15 (1H, br s), 7.81 (2H, d), 7.71 (1H, dd), 7.54-7.36 (8H, m), 6.79 (1H, d), 3.70 (3H, s), 3.02 (3H, d).
Figure JPOXMLDOC01-appb-C000046
 Compound 2-2 of the present invention: 1 H-NMR (CDCl 3 ) δ: 8.15 (1H, br s), 7.81 (2H, d), 7.71 (1H, dd), 7.54-7.36 (8H, m), 6.79 ( 1H, d), 3.70 (3H, s), 3.02 (3H, d).
　次に、実施例に記載された製造例及び本明細書に記載された製造法のいずれかに準じて製造される本発明化合物の例を以下に示す。 Examples of the compounds of the present invention produced according to any of the production examples described in the examples and the production methods described in this specification are shown below.
　式（１Ａ）：
Figure JPOXMLDOC01-appb-C000047
 で示される化合物（以下、化合物（１Ａ）と記す）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX1と記す）。 Formula (1A):
Figure JPOXMLDOC01-appb-C000047
 In the compound represented by (hereinafter referred to as compound (1A)), X 1 is CH, X 2 is C(O)OCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, and X Compounds in which 3 and X4 are CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX1).
群Ｘ：Me,Et,Pr,i-Pr,c-Pr,c-Bu,c-Pen,c-Hex,(CH2)3CH3,CH2CH(CH3)2,
CH(CH3)CH2CH3,t-Bu,CH2c-Pr,(CH2)4CH3,(CH2)2CH(CH3)2,CH(CH3)(CH2)2CH3,
CH(CH2CH3)CH2CH3,CH2CH(CH3)CH2CH3,C(CH3)2CH2CH3,CH2t-Bu,CH2c-Bu,CH2Py,
(CH2)2c-Pr,CH2(1-methylcyclopropyl),CH2(2-methylcyclopropyl),CH(CH3)c-Pr,(CH2)3c-Pr,(CH2)5CH3,(CH2)3CH(CH3)2,(CH2)2CH(CH3)CH2CH3,
CH2CH(CH3)(CH2)2CH3,CH(CH3)(CH2)3CH3,CH2CH(CH2CH3)2,CH2Cl,CH2Br,CH2OCH3,CH2OCH2CH3,CH2O(CH2)2CH3,CHF2,CF3,CH2CF3,CH2CHF2,CH2CH2CHF2,CH2CH2CF3,CH2CF2CF3,(CH2)2CF2CF3,CH2(CF2)2CF3,(CH2)2CF(CF3)2,(CH2)2(CF2)5CF3,CH2CFHCF3,CF2CHF(CF3),CF2CHF(OCF3),CH2CF2CF2H,CH2CH=CH2,CH2CH=CHCH3,CH2CH=C(CH3)2,CH2CH=CF2,CH2CH=CCl2,CH2CH=CHCH2CH3,CH2CH=CH(CH2)2CH3,CH2C(CH3)=CH2,CH2C(CH3)=CHCH3,CH2C(CH3)=C(CH3)2,CH2C(CH3)=CHCH2CH3,CH2CF=CH2,CH2CF=CHCH3,CH2CF=C(CH3)2,CH2CF=CF2,CH2CF=CHCH2CH3,CH2CF=CH(CH2)2CH3,CH2CCl=CH2,CH2CCl=CHCH3,CH2CCl=C(CH3)2,CH2CCl=CCl2,CH2CCl=CHCH2CH3,CH2CCl=CH(CH2)2CH3,(CH2)2CH=CH2,(CH2)2CH=CHCH3,(CH2)2CH=CHCH2CH3,(CH2)2CH=C(CH3)2,(CH2)2C(CH3)=CH2,(CH2)2C(CH3)=CHCH3,(CH2)3CH=CH2,(CH2)3C(CH3)=CH2,(CH2)4CH=CH2,CH2C≡CH,CH2C≡CCH3,CH2C≡CCH2CH3,CH2C≡C(c-Pr),(CH2)2C≡CH,(CH2)2C≡CCH3,(CH2)2C≡CCH2CH3,(CH2)3C≡CH,(CH2)3C≡CCH3,2-oxiranyl,2-tetrahydrofuranyl,2-tetrahydropyranyl,CH2(2-oxiranyl),CH2(2-tetrahydrofuranyl),CH2(2-tetrahydropyranyl),Ph,2-F-Ph,3-F-Ph,4-F-Ph,2-Cl-Ph,3-Cl-Ph,4-Cl-Ph,2-Br-Ph,3-Br-Ph,4-Br-Ph,2-I-Ph,3-I-Ph,4-I-Ph,2-Me-Ph,3-Me-Ph,4-Me-Ph,2-CF3-Ph,3-CF3-Ph,4-CF3-Ph,2-OMe-Ph,3-OMe-Ph,4-OMe-Ph,2-OCF3-Ph,3-OCF3-Ph,4-OCF3-Ph,2-Ph-Ph,3-Ph-Ph,4-Ph-Ph,2-OPh-Ph,3-OPh-Ph,4-OPh-Ph,2-F-3-F-Ph,2-F-4-F-Ph,2-F-5-F-Ph,2-F-6-F-Ph,3-F-4-F-Ph,3-F-5-F-Ph,2-Cl-3-Cl-Ph,2-Cl-4-Cl-Ph,2-Cl-5-Cl-Ph,2-Cl-6-Cl-Ph,3-Cl-4-Cl-Ph,3-Cl-5-Cl-Ph,3-CF3-5-CF3-Ph,CH2Ph,CH2(2-F-Ph),CH2(3-F-Ph),CH2(4-F-Ph),CH2(2-Cl-Ph),CH2(3-Cl-Ph),CH2(4-Cl-Ph),CH2(2-Br-Ph),CH2(3-Br-Ph),CH2(4-Br-Ph),CH2(2-I-Ph),CH2(3-I-Ph),CH2(4-I-Ph),CH2(2-Me-Ph),CH2(3-Me-Ph),CH2(4-Me-Ph),CH2(2-CF3-Ph),CH2(3-CF3-Ph),CH2(4-CF3-Ph),CH2(2-OMe-Ph),CH2(3-OMe-Ph),CH2(4-OMe-Ph),CH2(2-OCF3-Ph),CH2(3-OCF3-Ph),CH2(4-OCF3-Ph),CH2(2-Ph-Ph),CH2(3-Ph-Ph),CH2(4-Ph-Ph),CH2(2-OPh-Ph),CH2(3-OPh-Ph),CH2(4-OPh-Ph),CH2(2-F-3-F-Ph),CH2(2-F-4-F-Ph),CH2(2-F-5-F-Ph),CH2(2-F-6-F-Ph),CH2(3-F-4-F-Ph),CH2(3-F-5-F-Ph),CH2(2-Cl-3-Cl-Ph),CH2(2-Cl-4-Cl-Ph),CH2(2-Cl-5-Cl-Ph),CH2(2-Cl-6-Cl-Ph),CH2(3-Cl-4-Cl-Ph),CH2(3-Cl-5-Cl-Ph),CH2(3-CF3-5-CF3-Ph),2-Py,3-Cl-2-Py,5-Cl-2-Py,5-CF3-2-Py,3-Cl-5-CF3-2-Py,3-Py,6-Cl-3-Py,4-Py,2-Cl-6-Cl-4-Py,3-Cl-5-Cl-4-Py,2-thienyl,3-thienyl,2-pyrimidinyl,4-Cl-6-Cl-2-pyrimidinyl,4-CF3-6-CF3-2-pyrimidinyl,4-OMe-6-OMe-2-pyrimidinyl,4-pyrimidinyl,6-CF3-4-pyrimidinyl,5-pyrimidinyl,3-pyridazinyl,6-CF3-3-pyridazinyl,4-pyridazinyl,1-pyrazolyl,3-CF3-1-pyrazolyl,4-CF3-1-pyrazolyl,1-Me-3-pyrazolyl,1-Ph-3-pyrazolyl,1-Me-5-Me-3-pyrazolyl,1-Me-4-pyrazolyl,1-Me-3-CF3-4-pyrazolyl,1-Me-3-CF2H-4-pyrazolyl,1-Me-3-CF3-5-pyrazolyl,2-furanyl,3-furanyl,3-isoxazolyl,4-isoxazolyl,5-isoxazolyl,2-oxazolyl,5-oxazolyl,2-CF3-5-oxazolyl,2-thienyl,3-thienyl,2-thiazolyl,5-thiazolyl,2-CF3-5-thiazolyl,2-Cl-5-thiazolyl,1-imidazolyl,4-CF3-1-imidazolyl,1-triazolyl,5-CF3-2-oxadiazolyl,5-CF3-2-oxathiazolyl,2-benzoxazolyl,5-CF3-2-benzoxazolyl,1-Me-2-benzoimidazolyl,5-CF3-1-Me-2-benzoimidazolylからなる群。
群Ｙ：C(O)OMe,C(O)OEt,C(O)OPr,C(O)O(t-Bu),C(O)Me,C(O)Et,C(O)NMe2,C(O)NEt2からなる群。 Group X: Me, Et, Pr, i-Pr, c-Pr, c-Bu, c-Pen, c-Hex, ( CH2 ) 3CH3 , CH2CH ( CH3 ) 2 ,
CH( CH3 ) CH2CH3 , t-Bu,CH2c-Pr,( CH2 ) 4CH3 ,( CH2 ) 2CH ( CH3 ) 2 ,CH ( CH3 ) ( CH2 ) 2 CH3 ,
CH ( CH2CH3 ) CH2CH3 , CH2CH ( CH3 ) CH2CH3 , C ( CH3 ) 2CH2CH3 , CH2t -Bu,CH2c - Bu, CH2Py ,
( CH2 )2c-Pr, CH2 (1-methylcyclopropyl), CH2 ( 2 -methylcyclopropyl),CH( CH3 )c-Pr,( CH2 ) 3c - Pr,( CH2 ) 5CH3 ,( CH2 )3CH( CH3 ) 2 , ( CH2 )2CH ( CH3 ) CH2CH3 ,
CH2CH( CH3 )( CH2 ) 2CH3 ,CH ( CH3 ) ( CH2 ) 3CH3 , CH2CH ( CH2CH3 ) 2 , CH2Cl , CH2Br , CH2OCH 3 , CH2OCH2CH3 , CH2O ( CH2 ) 2CH3 , CHF2 , CF3 , CH2CF3 , CH2CHF2 , CH2CH2CHF2 , CH2CH2CF3 , CH2CF2CF3 ,( CH2 ) 2CF2CF3 , CH2 ( CF2 ) 2CF3 , ( CH2 ) 2CF ( CF3 ) 2 , ( CH2 ) 2 ( CF2 ) 5CF 3 , CH2CFHCF3 , CF2CHF ( CF3 ), CF2CHF ( OCF3 ), CH2CF2CF2H , CH2CH = CH2 , CH2CH = CHCH3 , CH2CH=C ( CH3 ) 2 , CH2CH =CF2, CH2CH=CCl2, CH2CH = CHCH2CH3 , CH2CH = CH ( CH2 ) 2CH3 , CH2C ( CH3 ) = CH2 , CH2C( CH3 )= CHCH3, CH2C(CH3)=C(CH3)2 , CH2C ( CH3 ) = CHCH2CH3 , CH2CF = CH2 , CH 2CF =CHCH3, CH2CF =C( CH3 ) 2 , CH2CF = CF2,CH2CF= CHCH2CH3 , CH2CF = CH ( CH2 ) 2CH3 , CH2CCl = CH2 , CH2CCl= CHCH3, CH2CCl=C(CH3)2 , CH2CCl = CCl2 , CH2CCl = CHCH2CH3 , CH2CCl = CH ( CH2 ) 2CH3 , ( CH2 )2CH= CH2 ,( CH2 )2CH= CHCH3 ,( CH2 )2CH= CHCH2CH3 ,( CH2 ) 2CH = C ( CH3 ) 2 , ( CH2 ) 2C ( CH3 )= CH2 ,( CH2 ) 2C ( CH3 )= CHCH3 ,( CH2 )3CH= CH2 , ( CH 2 ) 3C ( CH3 )= CH2 , ( CH2 )4CH= CH2 , CH2C = CH,CH2C = CCH3 ,CH2C = CCH2CH3 ,CH2C = C( c-Pr),( CH2 )2C≡CH,( CH2 ) 2C≡CCH3 ,( CH2 ) 2C≡CCH2CH3 , ( CH2 ) 3C≡CH , ( CH2 ) 3 C≡CCH3,2 - oxiranyl,2-tetrahydrofuranyl,2-tetrahydropyranyl, CH2 (2-oxiranyl), CH2 (2-tetrahydrofuranyl), CH2 (2-tetrahydropyranyl),Ph,2-F-Ph,3 -F-Ph,4-F-Ph,2-Cl-Ph,3-Cl-Ph,4-Cl-Ph,2-Br-Ph,3-Br-Ph,4-Br-Ph,2-I -Ph, 3 -I-Ph,4-I-Ph,2-Me-Ph,3-Me-Ph,4-Me-Ph,2- CF3 -Ph,3-CF3-Ph,4-CF 3 -Ph,2-OMe-Ph,3-OMe-Ph,4-OMe-Ph,2-OCF3-Ph, 3 -OCF3 - Ph,4-OCF3-Ph,2-Ph-Ph, 3 -Ph-Ph,4-Ph-Ph,2-OPh-Ph,3-OPh-Ph,4-OPh-Ph,2-F-3-F-Ph,2-F-4-F-Ph,2 -F-5-F-Ph,2-F-6-F-Ph,3-F-4-F-Ph,3-F-5-F-Ph,2-Cl-3-Cl-Ph,2 -Cl-4-Cl-Ph,2-Cl-5-Cl-Ph,2-Cl-6-Cl-Ph,3-Cl-4-Cl-Ph,3-Cl-5-Cl-Ph,3 -CF3-5- CF3 - Ph,CH2Ph, CH2 ( 2 -F-Ph), CH2 (3-F-Ph), CH2 (4-F-Ph), CH2 (2- Cl-Ph), CH2 (3-Cl-Ph), CH2 (4-Cl-Ph), CH2 (2-Br-Ph), CH2 (3-Br-Ph), CH2 (4- Br-Ph), CH2 (2-I-Ph), CH2 (3-I-Ph), CH2 (4-I-Ph), CH2 (2-Me-Ph), CH2 (3- Me-Ph), CH2 (4-Me-Ph), CH2 (2- CF3 -Ph), CH2 ( 3 -CF3- Ph), CH2 (4- CF3 -Ph), CH2 (2-OMe-Ph), CH2 (3-OMe-Ph), CH2 (4-OMe-Ph), CH2 (2-OCF 3 -Ph), CH2 ( 3 -OCF3-Ph), CH2 (4- OCF3 -Ph), CH2 (2-Ph-Ph), CH2 (3-Ph-Ph), CH2 ( 4-Ph-Ph), CH2 (2-OPh-Ph), CH2 (3-OPh-Ph), CH2 (4-OPh-Ph), CH2 (2-F-3-F-Ph) , CH2 (2-F-4-F-Ph), CH2 (2-F-5-F-Ph), CH2 (2-F-6-F-Ph), CH2 (3-F- 4-F-Ph), CH2 (3-F-5-F-Ph), CH2 (2-Cl-3-Cl-Ph), CH2 (2-Cl-4-Cl-Ph),CH 2 (2-Cl-5-Cl-Ph), CH2 (2-Cl-6-Cl-Ph), CH2 (3-Cl-4-Cl-Ph), CH2 (3-Cl-5- Cl-Ph), CH2 ( 3 -CF3-5- CF3 -Ph),2-Py,3-Cl-2-Py,5-Cl-2-Py,5- CF3-2 -Py, 3-Cl-5-CF3-2-Py, 3 -Py,6-Cl-3-Py,4-Py,2-Cl-6-Cl-4-Py,3-Cl-5-Cl-4 -Py,2-thienyl,3-thienyl,2-pyrimidinyl,4-Cl-6-Cl-2-pyrimidinyl,4-CF3-6 - CF3-2 -pyrimidinyl,4-OMe-6-OMe-2 -pyrimidinyl,4-pyrimidinyl,6-CF3-4-pyrimidinyl,5-pyrimidinyl, 3 -pyridazinyl,6-CF3-3-pyridazinyl,4-pyridazinyl,1-pyrazolyl, 3 -CF3-1 - pyrazolyl, 4-CF3-1-pyrazolyl,1-Me- 3 -pyrazolyl,1-Ph-3-pyrazolyl,1-Me-5-Me-3-pyrazolyl,1-Me-4-pyrazolyl,1-Me-3 -CF3-4-pyrazolyl,1-Me- 3 - CF2H -4-pyrazolyl,1-Me- 3 -CF3-5-pyrazolyl,2-fur anyl,3-furanyl,3-isoxazolyl,4-isoxazolyl,5-isoxazolyl,2-oxazolyl,5-oxazolyl,2-CF3-5-oxazolyl,2-thienyl, 3 -thienyl,2-thiazolyl,5-thiazolyl ,2-CF3-5 - thiazolyl,2-Cl-5-thiazolyl,1-imidazolyl,4- CF3-1 -imidazolyl,1-triazolyl,5-CF3-2 - oxadiazolyl,5 - CF3-2 the group consisting of -oxathiazolyl, 2-benzoxazolyl, 5-CF 3 -2-benzoxazolyl, 1-Me-2-benzoimidazolyl, 5-CF 3 -1-Me-2-benzoimidazolyl;
Group Y: C(O)OMe, C(O)OEt, C(O)OPr, C(O)O(t-Bu), C(O)Me, C(O)Et, C(O)NMe 2 , C(O) NEt2 .
　化合物（１Ａ）において、Ｘ１がＣＨであり、Ｘ２がＣ（Ｏ）ＮＨＣＨ３であり、Ｒ１、Ｒ２及びＲ３が水素原子であり、Ｘ３及びＸ４がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX2と記す）。
　化合物（１Ａ）において、Ｘ１がＣＨであり、Ｘ２が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ１、Ｒ２及びＲ３が水素原子であり、Ｘ３及びＸ４がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX3と記す）。
　化合物（１Ａ）において、Ｘ１が窒素原子であり、Ｘ２がＣ（Ｏ）ＯＣＨ３であり、Ｒ１、Ｒ２及びＲ３が水素原子であり、Ｘ３及びＸ４がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX4と記す）。
　化合物（１Ａ）において、Ｘ１が窒素原子であり、Ｘ２がＣ（Ｏ）ＮＨＣＨ３であり、Ｒ１、Ｒ２及びＲ３が水素原子であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX5と記す）。
　化合物（１Ａ）において、Ｘ１が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX6と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX7と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX8と記す）。
 　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX9と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX10と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX11と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX12と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX13と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX14と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX15と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX16と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX17と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3及びＸ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX18と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX19と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX20と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX21と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX22と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX23と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX24と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX25と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX26と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX27と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX28と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX29と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX30と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX31と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX32と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX33と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX34と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX35と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3が窒素原子であり、Ｘ4がＣＨであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX36と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX37と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX38と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX39と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX40と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX41と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX42と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX43と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX44と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX45と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX46と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX47と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX48と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX49と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX50と記す）。
　化合物（１Ａ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX51と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX52と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX53と記す）。
　化合物（１Ａ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ3がＣＨであり、Ｘ4がＣＣｌであり、Ｅが群Ｘ及び群Ｙに記載のいずれかの置換基である化合物（以下、化合物群SX54と記す）。 In compound (1A), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 3 and X 4 are CH, E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX2).
In compound (1A), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 , R 2 and R 3 are hydrogen atoms , X 3 and X 4 are CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX3).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 3 and X 4 are CH, Compounds in which E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX4).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 3 and X 4 are CH, Compounds in which E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX5).
In compound (1A), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 , R 2 and R 3 are hydrogen atoms; and X 3 and X 4 are CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX6).
In compound (1A), X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 and X 4 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX7);
In compound (1A), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 and X 4 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX8);
In compound (1A), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, X 3 and X 4 are CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX9).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, X 3 and X 4 is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX10).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, X 3 and X 4 is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX11).
In compound (1A), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R compounds in which 2 is a methyl group, X 3 and X 4 are CH, and E is any one of substituents described in groups X and Y (hereinafter referred to as compound group SX12);
In compound (1A), X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is chlorine atom, and X 3 and X 4 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX13);
In compound (1A), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is chlorine atom, and X 3 and X 4 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX14);
In compound (1A), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom, X 3 and X 4 are CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX15).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom, X 3 and X 4 is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX16).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom, X 3 and X 4 is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX17).
In compound (1A), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R compounds in which 2 is a chlorine atom, X 3 and X 4 are CH, and E is any one of the substituents described in groups X and Y (hereinafter referred to as compound group SX18);
In compound (1A), X 1 is CH, X 2 is C(O)OCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 3 is nitrogen atom, and X 4 is a compound in which CH is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX19);
In compound (1A), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 3 is nitrogen atom, and X 4 is a compound in which CH is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX20);
In compound (1A), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 , R 2 and R 3 are hydrogen atoms , X 3 is a nitrogen atom, X 4 is CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX21).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 3 is a nitrogen atom, and X 4 is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX22).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 3 is a nitrogen atom, and X 4 is CH and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX23).
In compound (1A), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 , R 2 and R 3 are hydrogen atoms; is, X 3 is a nitrogen atom, X 4 is CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX24).
In compound (1A), X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 is a nitrogen atom. and X 4 is CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX25).
In compound (1A), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 is a nitrogen atom. and X 4 is CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX26).
In compound (1A), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, R 2 is a methyl group , X3 is a nitrogen atom, X4 is CH, and E is any one of the substituents described in Groups X and Y (hereinafter referred to as Compound Group SX27).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 is a nitrogen atom and X 4 is CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX28).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 is a nitrogen atom and X 4 is CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX29).
In compound (1A), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R compounds in which 2 is a methyl group, X 3 is a nitrogen atom, X 4 is CH, and E is any one of the substituents described in groups X and Y (hereinafter referred to as compound group SX30);
In compound (1A), X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is chlorine atom, and X 3 is nitrogen atom and X 4 is CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX31).
In compound (1A), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is chlorine atom, X 3 is nitrogen atom and X 4 is CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX32).
In compound (1A), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom , X3 is a nitrogen atom, X4 is CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX33).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom, and X 3 is a nitrogen atom and X 4 is CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX34).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom, and X 3 is a nitrogen atom and X 4 is CH, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX35).
In compound (1A), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R compounds in which 2 is a chlorine atom, X 3 is a nitrogen atom, X 4 is CH, and E is any one of the substituents described in groups X and Y (hereinafter referred to as compound group SX36);
In compound (1A), X 1 is CH, X 2 is C(O)OCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 3 is CH, X 4 is CCl and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX37).
In compound (1A), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 3 is CH, X 4 is CCl and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX38).
In compound (1A), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 , R 2 and R 3 are hydrogen atoms , X 3 is CH, X 4 is CCl, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX39).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 3 is CH, and X 4 is CCl and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX40).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 3 is CH, and X 4 is CCl and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX41).
In compound (1A), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 , R 2 and R 3 are hydrogen atoms; and X 3 is CH, X 4 is CCl, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX42).
In compound (1A), X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 is CH , X 4 is CCl, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX43).
In compound (1A), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 is CH , X 4 is CCl, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX44).
In compound (1A), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, X 3 is CH, X 4 is CCl, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX45).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 is CH. and X 4 is CCl, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX46).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 3 is CH. and X 4 is CCl, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX47).
In compound (1A), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R compounds in which 2 is a methyl group, X 3 is CH, X 4 is CCl, and E is any one of the substituents described in groups X and Y (hereinafter referred to as compound group SX48);
In compound (1A), X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is chlorine atom, and X 3 is CH , X 4 is CCl, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX49).
In compound (1A), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is chlorine atom, and X 3 is CH , X 4 is CCl, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX50).
In compound (1A), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom, X 3 is CH, X 4 is CCl, and E is any one of the substituents described in Groups X and Y (hereinafter referred to as Compound Group SX51).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom, and X 3 is CH. and X 4 is CCl, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX52).
In compound (1A), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom, and X 3 is CH. and X 4 is CCl, and E is any one of the substituents described in Group X and Group Y (hereinafter referred to as Compound Group SX53).
In compound (1A), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R compounds in which 2 is a chlorine atom, X 3 is CH, X 4 is CCl, and E is any one of the substituents described in groups X and Y (hereinafter referred to as compound group SX54);
　式（１Ｂ）：
Figure JPOXMLDOC01-appb-C000048
 で示される化合物（以下、化合物（１Ｂ）と記す）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX55と記す）。 Formula (1B):
Figure JPOXMLDOC01-appb-C000048
 In the compound represented by (hereinafter referred to as compound (1B)), X 1 is CH, X 2 is C(O)OCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, and X Compounds in which 5 and X6 are CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX55).
群Ｚ：
CH2OPh,CH2O(2-F-Ph),CH2O(3-F-Ph),CH2O(4-F-Ph),CH2O(2-Cl-Ph),CH2O(3-Cl-Ph),CH2O(4-Cl-Ph),CH2O(2-Br-Ph),CH2O(3-Br-Ph),CH2O(4-Br-Ph),CH2O(2-I-Ph),CH2O(3-I-Ph),CH2O(4-I-Ph),CH2O(2-Me-Ph),CH2O(3-Me-Ph),CH2O(4-Me-Ph),CH2O(2-CF3-Ph),CH2O(3-CF3-Ph),CH2O(4-CF3-Ph),CH2O(2-OMe-Ph),CH2O(3-OMe-Ph),CH2O(4-OMe-Ph),CH2O(2-OCF3-Ph),CH2O(3-OCF3-Ph),CH2O(4-OCF3-Ph),CH2O(2-Ph-Ph),CH2O(3-Ph-Ph),CH2O(4-Ph-Ph),
CH2O(2-OPh-Ph),CH2O(3-OPh-Ph),CH2O(4-OPh-Ph),CH2O(2-F-3-F-Ph),CH2O(2-F-4-F-Ph),CH2O(2-F-5-F-Ph),CH2O(2-F-6-F-Ph),CH2O(3-F-4-F-Ph),CH2O(3-F-5-F-Ph),CH2O(2-Cl-3-Cl-Ph),CH2O(2-Cl-4-Cl-Ph),CH2O(2-Cl-5-Cl-Ph),CH2O(2-Cl-6-Cl-Ph),CH2O(3-Cl-4-Cl-Ph),CH2O(3-Cl-5-Cl-Ph),CH2O(3-CF3-5-CF3-Ph),OPh,O(2-F-Ph), O(3-F-Ph), O(4-F-Ph),
O(2-Cl-Ph),O(3-Cl-Ph),O(4-Cl-Ph),O(2-Br-Ph),O(3-Br-Ph),O(4-Br-Ph),O(2-I-Ph),O(3-I-Ph),O(4-I-Ph),O(2-Me-Ph),O(3-Me-Ph),O(4-Me-Ph),O(2-CF3-Ph),O(3-CF3-Ph),O(4-CF3-Ph),
O(2-OMe-Ph),O(3-OMe-Ph),O(4-OMe-Ph),O(2-OCF3-Ph), O(3-OCF3-Ph), O(4-OCF3-Ph),
O(2-Ph-Ph),O(3-Ph-Ph),O(4-Ph-Ph),O(2-OPh-Ph),O(3-OPh-Ph),O(4-OPh-Ph),O(2-F-3-F-Ph),O(2-F-4-F-Ph),O(2-F-5-F-Ph),O(2-F-6-F-Ph),O(3-F-4-F-Ph),O(3-F-5-F-Ph),O(2-Cl-3-Cl-Ph),O(2-Cl-4-Cl-Ph),O(2-Cl-5-Cl-Ph),O(2-Cl-6-Cl-Ph),O(3-Cl-4-Cl-Ph),O(3-Cl-5-Cl-Ph),O(3-CF3-5-CF3-Ph),OCH2Ph,OCH2(2-F-Ph),OCH2(3-F-Ph),OCH2(4-F-Ph),OCH2(2-Cl-Ph),OCH2(3-Cl-Ph),OCH2(4-Cl-Ph),OCH2(2-Br-Ph),OCH2(3-Br-Ph),OCH2(4-Br-Ph),OCH2(2-I-Ph),OCH2(3-I-Ph),OCH2(4-I-Ph),OCH2(2-Me-Ph),OCH2(3-Me-Ph),OCH2(4-Me-Ph),OCH2(2-CF3-Ph),OCH2(3-CF3-Ph),OCH2(4-CF3-Ph),OCH2(2-OMe-Ph),OCH2(3-OMe-Ph),OCH2(4-OMe-Ph),OCH2(2-OCF3-Ph),OCH2(3-OCF3-Ph),OCH2(4-OCF3-Ph),OCH2(2-Ph-Ph),OCH2(3-Ph-Ph),OCH2(4-Ph-Ph),OCH2(2-OPh-Ph),OCH2(3-OPh-Ph),OCH2(4-OPh-Ph),OCH2(2-F-3-F-Ph),OCH2(2-F-4-F-Ph),OCH2(2-F-5-F-Ph),OCH2(2-F-6-F-Ph),OCH2(3-F-4-F-Ph),OCH2(3-F-5-F-Ph),OCH2(2-Cl-3-Cl-Ph),OCH2(2-Cl-4-Cl-Ph),OCH2(2-Cl-5-Cl-Ph),OCH2(2-Cl-6-Cl-Ph),OCH2(3-Cl-4-Cl-Ph),OCH2(3-Cl-5-Cl-Ph),OCH2(3-CF3-5-CF3-Ph),
CH2ON=C(Me)Ph,CH2ON=C(Me)(3-Cl-Ph),CH2ON=C(Me)(4-Cl-Ph),CH2ON=C(Me)(3-CF3-Ph),CH2ON=C(Me)(4-CF3-Ph),C(Me)=NOMe,C(Me)=NOEt,C(Me)=NOPh,C(Me)=NO(3-Cl-Ph),C(Me)=NO(4-Cl-Ph),C(Me)=NO(3-CF3-Ph),C(Me)=NO(4-CF3-Ph),CH=NOMe,CH=NOEt,CH=NOPh,CH=NO(3-Cl-Ph),CH=NO(4-Cl-Ph),CH=NO(3-CF3-Ph),CH=NO(4-CF3-Ph),C(Me)=N-N=CMe2,C(Me)=N-N=CEt2,C(Me)=N-N=C(Me)Ph,C(Me)=N-NC(Me)(3-Cl-Ph),C(Me)=N-NC(Me)(4-Cl-Ph),C(Me)=N-NC(Me)(3-CF3-Ph),C(Me)=N-NC(Me)(4-CF3-Ph),CH=N-N=CMe2,CH=N-N=CEt2,CH=N-N=C(Me)Ph,CH=N-NC(Me)(3-Cl-Ph),CH=N-NC(Me)(4-Cl-Ph),CH=N-NC(Me)(3-CF3-Ph),CH=N-NC(Me)(4-CF3-Ph),C(Me)=N-NMe2,C(Me)=N-NEt2,C(Me)=N-N(Me)Ph,C(Me)=N-N(Me)(3-Cl-Ph),C(Me)=N-N(Me)(4-Cl-Ph),C(Me)=N-N(Me)(3-CF3-Ph),C(Me)=N-N(Me)(4-CF3-Ph),CH=N-NMe2,CH=N-NEt2,CH=N-N(Me)Ph,CH=N-N(Me)(3-Cl-Ph),CH=N-N(Me)(4-Cl-Ph),CH=N-N(Me)(3-CF3-Ph),CH=N-N(Me)(4-CF3-Ph),OMe,OEt,OPr,Oi-Pr,Oc-Pr,Oc-Bu,Oc-Pen,Oc-Hex,O(CH2)3CH3,OCH2CH(CH3)2,OCH(CH3)CH2CH3,Ot-Bu,OCH2c-Pr,O(CH2)4CH3,O(CH2)2CH(CH3)2,OCH(CH3)(CH2)2CH3,OCH(CH2CH3)CH2CH3,OCH2CH(CH3)CH2CH3,OC(CH3)2CH2CH3,OCH2t-Bu,OCH2c-Bu,OCH2c-Pen,O(CH2)2c-Pr,OCH2(1-methylcyclopropyl),OCH2(2-methylcyclopropyl),OCH(CH3)c-Pr,O(CH2)3c-Pr,O(CH2)5CH3,O(CH2)3CH(CH3)2,O(CH2)2CH(CH3)CH2CH3,OCH2CH(CH3)(CH2)2CH3,OCH(CH3)(CH2)3CH3,OCH2CH(CH2CH3)2,OCH2OCH3,OCH2OCH2CH3,OCF3,OCH2CF3,OCH2CHF2,OCH2CH2CHF2,OCH2CH2CF3,OCH2CF2CF3,O(CH2)2CF2CF3,OCH2(CF2)2CF3,O(CH2)2CF(CF3)2,O(CH2)2(CF2)5CF3,OCH2CF2CF2H,OCH2CFHCF3,OCH2CH=CH2,OCH2CH=CHCH3,OCH2CH=C(CH3)2,OCH2CH=CF2,OCH2CH=CCl2,OCH2CH=CHCH2CH3,OCH2CH=CH(CH2)2CH3,OCH2C(CH3)=CH2,OCH2C(CH3)=CHCH3,OCH2C(CH3)=C(CH3)2,OCH2C(CH3)=CHCH2CH3,OCH2CF=CH2,OCH2CF=CHCH3,OCH2CF=C(CH3)2,OCH2CF=CF2,OCH2CF=CHCH2CH3,OCH2CF=CH(CH2)2CH3,OCH2CCl=CH2,OCH2CCl=CHCH3,OCH2CCl=C(CH3)2,OCH2CCl=CCl2,OCH2CCl=CHCH2CH3,OCH2CCl=CH(CH2)2CH3,O(CH2)2CH=CH2,O(CH2)2CH=CHCH3,O(CH2)2CH=CHCH2CH3,O(CH2)2CH=C(CH3)2,O(CH2)2C(CH3)=CH2,O(CH2)2C(CH3)=CHCH3,O(CH2)3CH=CH2,O(CH2)3C(CH3)=CH2,O(CH2)4CH=CH2,OCH2C≡CH,OCH2C≡CCH3,OCH2C≡CCH2CH3,OCH2C≡Cc-Pr,O(CH2)2C≡CH,O(CH2)2C≡CCH3,O(CH2)2C≡CCH2CH3,O(CH2)3C≡CH,O(CH2)3C≡CCH3,O(2-Py),O(3-Py),O(4-Py),CN,NO2,F,Cl,Br,Iからなる群。 Group Z:
CH2OPh, CH2O ( 2 -F-Ph), CH2O (3-F-Ph), CH2O (4-F-Ph), CH2O (2-Cl-Ph), CH2 O(3-Cl-Ph), CH2O (4-Cl-Ph), CH2O (2-Br-Ph), CH2O (3-Br-Ph), CH2O (4-Br- Ph), CH2O (2-I-Ph), CH2O (3-I-Ph), CH2O (4-I-Ph), CH2O (2-Me-Ph), CH2O (3-Me-Ph), CH2O (4-Me-Ph), CH2O (2- CF3 -Ph), CH2O (3- CF3 -Ph), CH2O (4-CF 3 -Ph), CH2O (2-OMe-Ph), CH2O (3-OMe-Ph), CH2O (4-OMe-Ph), CH2O (2- OCF3 -Ph), CH2O ( 3 -OCF3-Ph), CH2O (4- OCF3 -Ph), CH2O (2-Ph-Ph), CH2O (3-Ph-Ph), CH2O ( 4-Ph-Ph),
CH2O (2-OPh-Ph), CH2O (3-OPh-Ph), CH2O (4-OPh-Ph), CH2O (2-F-3-F-Ph), CH2 O(2-F-4-F-Ph), CH2O (2-F-5-F-Ph), CH2O (2-F-6-F-Ph), CH2O (3-F-Ph) -4-F-Ph), CH2O (3-F-5-F-Ph), CH2O (2-Cl-3-Cl-Ph), CH2O (2-Cl-4-Cl- Ph), CH2O (2-Cl-5-Cl-Ph), CH2O (2-Cl-6-Cl-Ph), CH2O (3-Cl-4-Cl-Ph), CH2 O(3-Cl-5-Cl-Ph), CH2O ( 3 -CF3-5- CF3 -Ph), OPh, O(2-F-Ph), O(3-F-Ph), O(4-F-Ph),
O(2-Cl-Ph), O(3-Cl-Ph), O(4-Cl-Ph), O(2-Br-Ph), O(3-Br-Ph), O(4-Br -Ph), O(2-I-Ph), O(3-I-Ph), O(4-I-Ph), O(2-Me-Ph), O(3-Me-Ph), O (4-Me-Ph), O(2- CF3 -Ph), O(3- CF3 -Ph), O(4- CF3 -Ph),
O(2-OMe-Ph), O(3-OMe-Ph), O(4-OMe-Ph), O(2-OCF3-Ph), O( 3 - OCF3 -Ph), O(4 -OCF3 -Ph),
O(2-Ph-Ph), O(3-Ph-Ph), O(4-Ph-Ph), O(2-OPh-Ph), O(3-OPh-Ph), O(4-OPh) -Ph), O(2-F-3-F-Ph), O(2-F-4-F-Ph), O(2-F-5-F-Ph), O(2-F-6 -F-Ph), O(3-F-4-F-Ph), O(3-F-5-F-Ph), O(2-Cl-3-Cl-Ph), O(2-Cl -4-Cl-Ph), O(2-Cl-5-Cl-Ph), O(2-Cl-6-Cl-Ph), O(3-Cl-4-Cl-Ph), O(3 -Cl-5-Cl-Ph),O( 3 -CF3-5- CF3 -Ph),OCH2Ph,OCH2( 2 -F-Ph), OCH2 (3-F - Ph),OCH 2 (4-F-Ph),OCH2( 2 -Cl-Ph), OCH2 (3-Cl-Ph),OCH2(4-Cl-Ph), OCH2 ( 2 -Br-Ph),OCH 2 (3-Br-Ph), OCH2 (4-Br-Ph),OCH2( 2 -I-Ph), OCH2 (3-I-Ph), OCH2 (4-I-Ph),OCH 2 (2-Me-Ph), OCH2 (3-Me-Ph), OCH2 (4-Me-Ph),OCH2( 2 - CF3 -Ph), OCH2 ( 3 -CF3-Ph) , OCH2 (4- CF3 -Ph),OCH2( 2 -OMe-Ph), OCH2 (3-OMe-Ph), OCH2 (4-OMe-Ph),OCH2( 2 - OCF3- Ph), OCH2 ( 3 -OCF3-Ph), OCH2 (4-OCF3-Ph),OCH2( 2 -Ph-Ph), OCH2 ( 3 -Ph-Ph), OCH2 (4- Ph-Ph),OCH2( 2 -OPh-Ph), OCH2 (3-OPh-Ph), OCH2 (4-OPh-Ph),OCH2( 2 -F-3-F-Ph),OCH 2 (2-F-4-F-Ph), OCH2 ( 2 -F-5-F-Ph), OCH2 ( 2 -F-6-F-Ph), OCH2 (3-F-4- F-Ph), OCH 2 (3-F-5-F-Ph), OCH 2 (2-Cl-3-Cl-Ph), OCH 2 (2-Cl-4-Cl-Ph), OCH 2 ( 2-Cl-5-Cl-Ph),OCH2( 2 -Cl-6-Cl-Ph), OCH2 (3-Cl-4-Cl-Ph), OCH2 (3-Cl-5-Cl-Ph), OCH2 ( 3 -CF3-5- CF3 -Ph),
CH2ON =C(Me)Ph, CH2ON =C(Me)(3-Cl-Ph), CH2ON =C(Me)(4-Cl-Ph), CH2ON =C(Me) (3- CF3 -Ph), CH2ON =C(Me)(4- CF3 -Ph),C(Me)=NOMe,C(Me)=NOEt,C(Me)=NOPh,C(Me )=NO(3-Cl-Ph), C(Me)=NO(4-Cl-Ph), C(Me)=NO(3- CF3 -Ph), C(Me)=NO(4-CF 3 -Ph),CH=NOMe,CH=NOEt,CH=NOPh,CH=NO(3-Cl-Ph),CH=NO(4-Cl-Ph),CH=NO(3- CF3 -Ph) ,CH=NO(4- CF3 -Ph),C(Me)=NN= CMe2 ,C(Me)=NN= CEt2 ,C(Me)=NN=C(Me)Ph,C(Me) =N-NC(Me)(3-Cl-Ph), C(Me)=N-NC(Me)(4-Cl-Ph), C(Me)=N-NC(Me)(3- CF3 -Ph),C(Me)=N-NC(Me)(4- CF3 -Ph),CH=NN= CMe2 ,CH=NN= CEt2 ,CH=NN=C(Me)Ph,CH= N-NC(Me)(3-Cl-Ph),CH=N-NC(Me)(4-Cl-Ph),CH=N-NC(Me)(3- CF3 -Ph),CH=N -NC(Me)(4- CF3 -Ph), C(Me)=N- NMe2 , C(Me)=N- NEt2 , C(Me)=NN(Me)Ph, C(Me)= NN(Me)(3-Cl-Ph),C(Me)=NN(Me)(4-Cl-Ph),C(Me)=NN(Me)(3- CF3 -Ph),C(Me )=NN(Me)(4- CF3 -Ph),CH=N- NMe2 ,CH=N- NEt2 ,CH=NN(Me)Ph,CH=NN(Me)(3-Cl-Ph) ,CH=NN(Me)(4-Cl-Ph),CH=NN(Me)(3- CF3 -Ph),CH=NN(Me)(4- CF3 -Ph),OMe,OEt,OPr ,Oi-Pr,Oc-Pr,Oc-Bu,Oc-Pen,Oc-Hex,O( CH2 ) 3CH3,OCH2CH(CH3)2 , OCH ( CH3 ) CH2CH3 , Ot -Bu,OCH2c-Pr,O( CH2 ) 4CH3 , O ( CH2 ) 2C H( CH3 ) 2 ,OCH( CH3 )( CH2 ) 2CH3 ,OCH ( CH2CH3 ) CH2CH3 , OCH2CH ( CH3 ) CH2CH3 , OC ( CH3 ) 2 CH2CH3 , OCH2t - Bu,OCH2c - Bu,OCH2c-Pen,O( CH2 )2c - Pr, OCH2 (1-methylcyclopropyl), OCH2 ( 2 -methylcyclopropyl),OCH ( CH3 )c-Pr,O( CH2 ) 3c -Pr,O( CH2 ) 5CH3 ,O( CH2)3CH(CH3)2 , O ( CH2 ) 2CH ( CH3 ) ) CH2CH3 , OCH2CH ( CH3 ) ( CH2 ) 2CH3 , OCH ( CH3 ) ( CH2 ) 3CH3 , OCH2CH ( CH2CH3 ) 2 , OCH2OCH3 , OCH2OCH2CH3 , OCF3 , OCH2CF3 , OCH2CHF2 , OCH2CH2CHF2 , OCH2CH2CF3 , OCH2CF2CF3 , O ( CH2 ) 2CF2CF _ 3 , OCH2 ( CF2) 2CF3,O(CH2)2CF(CF3)2 , O ( CH2 ) 2 ( CF2 ) 5CF3 , OCH2CF2CF2H , OCH2CFHCF 3 , OCH2CH = CH2 , OCH2CH = CHCH3,OCH2CH=C(CH3)2 , OCH2CH = CF2 , OCH2CH = CCl2 ,OCH2CH= CHCH2CH3 , OCH2CH=CH( CH2 )2CH3,OCH2C( CH3 )= CH2 , OCH2C ( CH3 )= CHCH3 , OCH2C ( CH3 ) = C ( CH3 ) 2 , OCH2C( CH3 )=CHCH2CH3,OCH2CF= CH2 ,OCH2CF = CHCH3 , OCH2CF = C ( CH3 ) 2 , OCH2CF = CF2 , OCH2CF = CHCH 2CH3 , OCH2CF = CH ( CH2 ) 2CH3 , OCH2 CCl= CH2 , OCH2 CCl=CHCH3, OCH2 CCl=C( CH3 ) 2 , OCH2 CCl = CCl2 , OCH2 CCl= CHCH2CH3 , OCH2 CCl = CH ( CH2 ) 2CH 3 ,O( CH2 )2CH = CH2 ,O( CH2 )2CH = CHCH3 ,O( CH2 )2CH= CHCH2CH3 ,O ( CH2 ) 2CH =C ( CH3 ) 2 ,O( CH2 ) 2C ( CH3 )= CH2 ,O( CH2 ) 2C ( CH3 )= CHCH3 ,O( CH2 ) 3CH = CH2 ,O( CH2 ) 3C ( CH3 )= CH2 ,O ( CH2 )4CH = CH2 , OCH2C≡CH , OCH2C≡CCH3 , OCH2C≡CCH2CH3 , OCH2C≡Cc - Pr,O ( CH2 ) 2C =CH,O( CH2 ) 2C = CCH3 ,O( CH2 ) 2C = CCH2CH3 ,O( CH2 ) 3C = CH,O( CH2 ) 3C The group consisting of ≡CCH3 , O(2-Py), O(3-Py), O(4 - Py), CN, NO2, F, Cl, Br, and I;
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX56と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX57と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX58と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX59と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX60と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX61と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX62と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX63と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX64と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX65と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX66と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX67と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX68と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX69と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX70と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX71と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ5及びＸ6がＣＨであり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX72と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX73と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX74と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX75と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX76と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX77と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1、Ｒ2及びＲ3が水素原子であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX78と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX79と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX80と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX81と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX82と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX83と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2がメチル基であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX84と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX85と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX86と記す）。
　化合物（１Ｂ）において、Ｘ1がＣＨであり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX87と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＯＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX88と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2がＣ（Ｏ）ＮＨＣＨ3であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX89と記す）。
　化合物（１Ｂ）において、Ｘ1が窒素原子であり、Ｘ2が５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基であり、Ｒ1及びＲ3が水素原子であり、Ｒ2が塩素原子であり、Ｘ5がＣＨであり、Ｘ6が窒素原子であり、Ｅが群Ｘ及び群Ｚに記載のいずれかの置換基である化合物（以下、化合物群SX90と記す）。 In compound (1B), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 5 and X 6 are CH, E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX56).
In compound (1B), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, and R 1 , R 2 and R 3 are hydrogen atoms; , X 5 and X 6 are CH, and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX57).
In compound (1B), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 5 and X 6 are CH, Compounds in which E is any one of the substituents described in Groups X and Z (hereinafter referred to as Compound Group SX58).
In compound (1B), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 5 and X 6 are CH, Compounds in which E is any one of the substituents described in Groups X and Z (hereinafter referred to as Compound Group SX59).
In compound (1B), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 , R 2 and R 3 are hydrogen atoms; and X 5 and X 6 are CH, and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX60).
In compound (1B), X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 5 and X 6 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX61);
In compound (1B), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 5 and X 6 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX62);
In compound (1B), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R 2 is a methyl group, X 5 and X 6 are CH, and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX63).
In compound (1B), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, X 5 and X 6 is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX64).
In compound (1B), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, X 5 and X 6 is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX65).
In compound (1B), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R compounds in which 2 is a methyl group, X 5 and X 6 are CH, and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX66);
In compound (1B), X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is chlorine atom, and X 5 and X 6 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX67);
In compound (1B), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is chlorine atom, and X 5 and X 6 are a compound in which CH is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX68);
In compound (1B), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R 2 is a chlorine atom, X 5 and X 6 are CH, and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX69).
In compound (1B), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom, and X 5 and X 6 is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX70).
In compound (1B), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom, X 5 and X 6 is CH and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX71).
In compound (1B), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R compounds in which 2 is a chlorine atom, X 5 and X 6 are CH, and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX72);
In compound (1B), X 1 is CH, X 2 is C(O)OCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 5 is CH, and X 6 is nitrogen A compound in which E is any one of the substituents described in Groups X and Z (hereinafter referred to as Compound Group SX73).
In compound (1B), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 5 is CH, and X 6 is nitrogen A compound in which E is any one of the substituents described in Groups X and Z (hereinafter referred to as Compound Group SX74).
In compound (1B), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, and R 1 , R 2 and R 3 are hydrogen atoms; , X 5 is CH, X 6 is a nitrogen atom, and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX75).
In compound (1B), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 5 is CH, and X 6 is a compound which is a nitrogen atom and in which E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX76);
In compound (1B), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 , R 2 and R 3 are hydrogen atoms, X 5 is CH, and X 6 is a compound which is a nitrogen atom and in which E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX77);
In compound (1B), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 , R 2 and R 3 are hydrogen atoms; and X 5 is CH, X 6 is a nitrogen atom, and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX78).
In compound (1B), X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 5 is CH , X 6 is a nitrogen atom, and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX79).
In compound (1B), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 5 is CH , X 6 is a nitrogen atom, and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX80).
In compound (1B), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R 2 is a methyl group, X 5 is CH, X 6 is a nitrogen atom, and E is any one of the substituents described in Groups X and Z (hereinafter referred to as Compound Group SX81).
In compound (1B), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 5 is CH. and X 6 is a nitrogen atom, and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX82).
In compound (1B), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a methyl group, and X 5 is CH. and X6 is a nitrogen atom, and E is any one of the substituents described in Group X and Group Z (hereinafter referred to as Compound Group SX83).
In compound (1B), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R compounds in which 2 is a methyl group, X 5 is CH, X 6 is a nitrogen atom, and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX84);
In compound (1B), X 1 is CH, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is chlorine atom, and X 5 is CH , X 6 is a nitrogen atom, and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX85).
In compound (1B), X 1 is CH, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is chlorine atom, and X 5 is CH , X 6 is a nitrogen atom, and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX86).
In compound (1B), X 1 is CH, X 2 is 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R 2 is a chlorine atom, X5 is CH, X6 is a nitrogen atom, and E is any one of the substituents described in Groups X and Z (hereinafter referred to as Compound Group SX87 ).
In compound (1B), X 1 is a nitrogen atom, X 2 is C(O)OCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom, and X 5 is CH. wherein X6 is a nitrogen atom and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX88 ).
In compound (1B), X 1 is a nitrogen atom, X 2 is C(O)NHCH 3 , R 1 and R 3 are hydrogen atoms, R 2 is a chlorine atom, and X 5 is CH. and X 6 is a nitrogen atom, and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX89).
In compound (1B), X 1 is a nitrogen atom, X 2 is a 5,6-dihydro-1,4,2-dioxazin-3-yl group, R 1 and R 3 are hydrogen atoms, and R compounds in which 2 is a chlorine atom, X 5 is CH, X 6 is a nitrogen atom, and E is any one of the substituents described in groups X and Z (hereinafter referred to as compound group SX90);
　次に本発明化合物の製剤例を示す。なお、部は重量部を表す。また、本発明化合物Ｓは、化合物群SX1～SX90に記載の化合物を表す。 Next, formulation examples of the compound of the present invention are shown. In addition, a part represents a weight part. In addition, the compound S of the present invention represents compounds described in the compound groups SX1 to SX90.
製剤例１
　ポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩及びシリカの混合物（重量比１：１）３５部と、本発明化合物Ｓのいずれか１種１０部と、水５５部とを混合し、湿式粉砕法で微粉砕することにより、製剤を得る。 Formulation example 1
35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and silica (weight ratio 1:1), 10 parts of any one of the compounds S of the present invention, and 55 parts of water are mixed and finely pulverized by a wet pulverization method. By doing so, a formulation is obtained.
製剤例２
　本発明化合物Ｓのいずれか１種５０部、リグニンスルホン酸カルシウム３部、ラウリル硫酸ナトリウム２部、及びシリカ４５部を粉砕混合することにより、製剤を得る。 Formulation example 2
A preparation is obtained by pulverizing and mixing 50 parts of any one compound S of the present invention, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of silica.
製剤例３
　本発明化合物Ｓのいずれか１種５部、ポリオキシエチレンスチリルフェニルエーテル９部、ポリオキシエチレンデシルエーテル（エチレンオキシド付加数：５）５部、ドデシルベンゼンスルホン酸カルシウム６部、及びキシレン７５部を混合することにより、製剤を得る。 Formulation example 3
5 parts of any one of the compounds S of the present invention, 9 parts of polyoxyethylene styryl phenyl ether, 5 parts of polyoxyethylene decyl ether (number of ethylene oxide additions: 5), 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene are mixed. By doing so, a formulation is obtained.
製剤例４
　本発明化合物Ｓのいずれか１種２部、シリカ１部、リグニンスルホン酸カルシウム２部、ベントナイト３０部、及びカオリンクレー６５部を粉砕混合し、適当量の水を加えて混練し、造粒機で造粒した後、乾燥することにより、製剤を得る。 Formulation example 4
2 parts of any one of the compound S of the present invention, 1 part of silica, 2 parts of calcium ligninsulfonate, 30 parts of bentonite, and 65 parts of kaolin clay are pulverized and mixed, kneaded with an appropriate amount of water, and granulated. After granulating with, the formulation is obtained by drying.
製剤例５
　本発明化合物Ｓのいずれか１種１０部を、ベンジルアルコール１８部とDMSO９部との混合物に混合し、そこに６．３部のGERONOL（登録商標） TE250、 Ethylan（登録商標） NS-500LQ ２．７部、及びソルベントナフサ ５４部を加え、混合して製剤を得る。 Formulation example 5
10 parts of any one of the compounds S of the present invention are mixed with a mixture of 18 parts of benzyl alcohol and 9 parts of DMSO, to which 6.3 parts of GERONOL® TE250, Ethylan® NS-500LQ2 are added. Add .7 parts and 54 parts solvent naphtha and mix to obtain a formulation.
製剤例６
　本発明化合物Ｓのいずれか１種０．１部及びケロシン３９．９部を混合溶解し、エアゾール容器に入れ、液化石油ガス（プロパン、ブタン及びイソブタンの混合物；飽和蒸気圧：０．４７ＭＰａ（２５℃））６０部を充填することにより製剤を得る。 Formulation example 6
0.1 part of any one of the compound S of the present invention and 39.9 parts of kerosene are mixed and dissolved, placed in an aerosol container, and liquefied petroleum gas (propane, butane and isobutane mixture; saturated vapor pressure: 0.47 MPa (25 C))) to obtain a formulation by filling 60 parts.
製剤例７
　本発明化合物Ｓのいずれか１種０．２部、除虫菊抽出粕粉５０部、タブ粉３０部及び木粉１９．８部を混合し、適量の水を加えて混練後、押出機にかけて板状シートとし、打抜機で渦巻状とすることにより製剤を得る。 Formulation example 7
0.2 parts of any one of the compounds S of the present invention, 50 parts of pyrethrum extract lees powder, 30 parts of tab powder and 19.8 parts of wood powder are mixed, kneaded by adding an appropriate amount of water, and extruded into a plate shape. The formulation is obtained by sheeting and coiling with a punch.
　次に、試験例を示す。
　試験例１～試験例７における無処理区とは、本発明化合物を含有するＤＭＳＯ希釈液の代わりにＤＭＳＯを分注する以外は各々の試験例に記載されたのと同じ条件で行った試験区を表す。また、試験例８～試験例１４における無処理とは、本発明化合物を含む製剤の水希釈液の散布を行わなかったことを意味する。 Next, test examples are shown.
The untreated section in Test Examples 1 to 7 is a test section performed under the same conditions as described in each Test Example except that DMSO is dispensed instead of the DMSO diluted solution containing the compound of the present invention. represents Further, "no treatment" in Test Examples 8 to 14 means that the water-diluted formulation containing the compound of the present invention was not sprayed.
試験例１　コムギ葉枯病菌（Septoria tritici）に対する防除試験
　本発明化合物１－４、１－５、１－６、１－７、１－１０、１－１７、又は２－１を１５０ｐｐｍ含有するようにＤＭＳＯで希釈し、タイタープレート（９６ウェル）に１μＬ分注した後、あらかじめコムギ葉枯病菌の胞子を接種したＹＢＧ培地を１５０μＬ分注した。このプレートを３日間、１８℃で培養しコムギ葉枯病菌を増殖させたのち、タイタープレートの各ウェルの５５０ｎｍの吸光度を測定し、その値をコムギ葉枯病菌の生育度とした。その結果、各々の本発明化合物を処理した区における生育度はいずれも、無処理区における生育度の５０％以下であった。 Test Example 1 Control test against wheat leaf blight fungus (Septoria tritici) 1 μL of the medium was added to a titer plate (96 wells), and then 150 μL of YBG medium previously inoculated with spores of the wheat leaf blight fungus was added. After culturing this plate at 18° C. for 3 days to grow the wheat leaf blight fungus, the absorbance at 550 nm of each well of the titer plate was measured, and the value was defined as the growth rate of the wheat leaf blight fungus. As a result, the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
試験例２　トウモロコシ黒穂病菌（Ustilago ｍaydis）に対する防除試験
　本発明化合物１－６、１－７、１－９、１－１０、又は２－１を１５０ｐｐｍ含有するようにＤＭＳＯで希釈し、タイタープレート（９６ウェル）に１μＬ分注した後、あらかじめトウモロコシ黒穂病菌の胞子を接種したジャガイモ煎汁液体培地（ＰＤＢ培地）を１５０μＬ分注した。このプレートを４日間、１８℃で培養しトウモロコシ黒穂病菌を増殖させたのち、タイタープレートの各ウェルの５５０ｎｍの吸光度を測定し、その値をトウモロコシ黒穂病菌の生育度とした。その結果、各々の本発明化合物を処理した区における生育度はいずれも、無処理区における生育度の５０％以下であった。 Test Example 2 Control test against corn smut (Ustilago maydis) Compound 1-6, 1-7, 1-9, 1-10, or 2-1 of the present invention was diluted with DMSO to contain 150 ppm, and a titer plate ( 96 wells), and then 150 μL of a potato decoction liquid medium (PDB medium) previously inoculated with corn smut spores was dispensed. This plate was cultured at 18° C. for 4 days to grow the corn smut fungus, and then the absorbance at 550 nm of each well of the titer plate was measured to determine the growth rate of the corn smut fungus. As a result, the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
試験例３　オオムギ雲形病菌（Rhynchosporium secalis）に対する防除試験
　本発明化合物１－１、１－４、１－５、１－６、１－７、１－８、１－９、１－１０、１－１３、１－１５、１－１７、２－１、又は２－２を１５０ｐｐｍ含有するようにＤＭＳＯで希釈し、タイタープレート（９６ウェル）に１μＬ分注した後、あらかじめオオムギ雲形病菌の胞子を接種したジャガイモ煎汁液体培地（ＰＤＢ培地）を１５０μＬ分注した。このプレートを７日間、１８℃で培養しオオムギ雲形病菌を増殖させたのち、タイタープレートの各ウェルの５５０ｎｍの吸光度を測定し、その値をオオムギ雲形病菌の生育度とした。その結果、各々の本発明化合物を処理した区における生育度はいずれも、無処理区における生育度の５０％以下であった。 Test Example 3 Control test against Rhynchosporium secalis Compounds of the present invention 1-1, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1- Dilute with DMSO to contain 13, 1-15, 1-17, 2-1, or 2-2 at 150 ppm, dispense 1 μL into a titer plate (96 wells), and inoculate in advance with spores of barley 150 μL of a potato decoction liquid medium (PDB medium) was dispensed. After culturing this plate at 18° C. for 7 days to proliferate the barley cloud, the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of the barley cloud. As a result, the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
試験例４　キュウリ灰色かび病菌（Botrytis cinerea）に対する防除試験
　本発明化合物１－４、１－５、１－６、１－７、１－８、１－９、１－１０、１－１５、又は１－１７を１５０ｐｐｍ含有するようにＤＭＳＯで希釈し、タイタープレート（９６ウェル）に１μＬ分注した後、あらかじめキュウリ灰色かび病菌の胞子を接種した完全培地を１５０μＬ分注した。このプレートを４日間、１８℃で培養しキュウリ灰色かび病菌を増殖させたのち、タイタープレートの各ウェルの５５０ｎｍの吸光度を測定し、その値をキュウリ灰色かび病菌の生育度とした。その結果、各々の本発明化合物を処理した区における生育度はいずれも、無処理区における生育度の５０％以下であった。 Test Example 4 Control test against cucumber gray mold (Botrytis cinerea) Compounds 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-15, or 1-17 was diluted with DMSO so as to contain 150 ppm, 1 μL was dispensed into a titer plate (96 wells), and then 150 μL of complete medium previously inoculated with spores of Botrytis cucumber was dispensed. After culturing this plate at 18° C. for 4 days to grow the cucumber botrytis, the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of the cucumber botrytis. As a result, the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
試験例５　モモ黒星病菌（Cladosporium carpophilum）に対する防除試験
　本発明化合物１－１、１－４、１－５、１－６、１－７、１－８、１－９、１－１０、１－１３、１－１５、１－１６、１－１７、又は２－１を１５０ｐｐｍ含有するようにＤＭＳＯで希釈し、タイタープレート（９６ウェル）に１μＬ分注した後、あらかじめモモ黒星病菌の胞子を接種したジャガイモ煎汁液体培地（ＰＤＢ培地）を１５０μＬ分注した。このプレートを５日間、１８℃で培養しモモ黒星病菌を増殖させたのち、タイタープレートの各ウェルの５５０ｎｍの吸光度を測定し、その値をモモ黒星病菌の生育度とした。その結果、各々の本発明化合物を処理した区における生育度はいずれも、無処理区における生育度の５０％以下であった。 Test Example 5 Control test against peach scab (Cladosporium carpophilum) Compounds of the present invention 1-1, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1- Dilute with DMSO to contain 13, 1-15, 1-16, 1-17, or 2-1 at 150 ppm, dispense 1 μL into a titer plate (96 well), and inoculate peach scab spores in advance. 150 μL of a potato decoction liquid medium (PDB medium) was dispensed. This plate was cultured at 18° C. for 5 days to grow the peach scab, and then the absorbance at 550 nm of each well of the titer plate was measured to determine the growth rate of the peach scab. As a result, the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
試験例６　イネごま葉枯病菌（Cochliobolus miyabeanus）に対する防除試験
　本発明化合物１－１、１－２、１－３、１－４、１－５、１－６、１－７、１－８、１－９、１－１０、１－１１、１－１３、１－１５、１－１６、１－１７、又は２－１を１５０ｐｐｍ含有するようにＤＭＳＯで希釈し、タイタープレート（９６ウェル）に１μＬ分注した後、あらかじめイネごま葉枯病菌の胞子を接種したＹＢ液体培地を１５０μＬ分注した。このプレートを３日間、２３℃で培養しイネごま葉枯病菌を増殖させたのち、タイタープレートの各ウェルの５５０ｎｍの吸光度を測定し、その値をイネごま葉枯病菌の生育度とした。その結果、各々の本発明化合物を処理した区における生育度はいずれも、無処理区における生育度の５０％以下であった。 Test Example 6 Control test against rice sesame leaf blight fungus (Cochliobolus miyabeanus) Compounds of the present invention 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-13, 1-15, 1-16, 1-17, or 2-1 diluted with DMSO to contain 150 ppm, titer plate (96 well) After 1 μL was dispensed, 150 μL of YB liquid medium previously inoculated with spores of the rice sesame leaf blight fungus was dispensed. After culturing this plate at 23° C. for 3 days to grow the rice and sesame leaf blight fungus, the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of the rice and sesame leaf blight fungus. As a result, the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
試験例７　ダイズさび病（Phakopsora pachyrhizi）に対する防除試験
　ダイズ（品種：黒千石）の本葉を直径１ｃｍに切り抜きリーフディスクを作製した。２４ウェルマイクロプレートの各ウェルに寒天培地（寒天濃度１．２％）を１ｍＬずつ分注した後、各ウェルの寒天培地の上に、当該リーフディスクを１枚ずつ置いた。０．５μＬのソルポール（登録商標）１２００ＫＸ、ＤＭＳＯ ４．５μＬ及びキシレン５μＬの混合物に、供試化合物を１００００ｐｐｍ含有するＤＭＳＯ溶液２０μＬを加えて混合した。得られた混合物をイオン交換水で希釈して供試化合物を所定濃度含有する混合物を調製した。得られた混合物を、リーフディスク１枚につき１０μＬ散布した。１日後に、ミトコンドリアチトクロームｂタンパク質にＦ１２９Ｌのアミノ酸置換を有するダイズさび病菌（Phakopsora pachyrhizi）の胞子の水懸濁液 (１．０×１０5/ｍＬ)を、リーフディスク上に噴霧接種した。接種後、人工気象器内(６時間点灯、１８時間消灯、温度２３℃、湿度６０％)に置いた。１日後、リーフディスクの表面の水滴が無くなるまで風乾させ、再び人工気象器内に１２日間置いた。その後、ダイズさび病の病斑面積を調査した。その結果、所定濃度を５０ｐｐｍとし、供試化合物として本発明化合物１－１、１－２、１－３、１－４、１－６、１－７、１－８、１－９、１－１０、１－１２、１－１３、１－１４、又は１－１５のいずれか１つを処理したリーフディスクの病斑面積は、いずれも無処理のリーフディスクの病斑面積の３０％以下であった。 Test Example 7 Prevention test against soybean rust (Phakopsora pachyrhizi) A leaf disc having a diameter of 1 cm was cut out from a true leaf of soybean (variety: Kurosengoku). After 1 mL of agar medium (agar concentration: 1.2%) was dispensed into each well of a 24-well microplate, one leaf disk was placed on each well of the agar medium. To a mixture of 0.5 μL of Sorpol® 1200KX, 4.5 μL of DMSO and 5 μL of xylene, 20 μL of DMSO solution containing 10000 ppm of the test compound was added and mixed. The obtained mixture was diluted with ion-exchanged water to prepare a mixture containing the test compound at a predetermined concentration. 10 μL of the resulting mixture was spread on each leaf disc. One day later, an aqueous spore suspension (1.0×10 5 /mL) of Phakopsora pachyrhizi having an amino acid substitution of F129L in the mitochondrial cytochrome b protein was spray-inoculated onto the leaf discs. After inoculation, the plants were placed in an artificial climate chamber (6 hours light, 18 hours light off, temperature 23°C, humidity 60%). After one day, the leaf disc was air-dried until no water droplets were left on the surface, and placed again in the climate chamber for 12 days. After that, the lesion area of soybean rust was investigated. As a result, the predetermined concentration was set to 50 ppm, and the present invention compounds 1-1, 1-2, 1-3, 1-4, 1-6, 1-7, 1-8, 1-9, 1- The lesion area of leaf discs treated with any one of 10, 1-12, 1-13, 1-14, or 1-15 is 30% or less of the lesion area of untreated leaf discs. there were.
試験例８　オオムギ網斑病（Pyrenophora teres）に対する防除試験
　プラスチックポットに土壌を詰め、そこにオオムギ（品種；ニシノホシ）を播種し、温室で７日間栽培した。製剤例１に記載の方法に準じて製剤化された本発明化合物１－４、１－６、１－７、１－１０、１－１５、又は２－１を、濃度が２００ｐｐｍとなるように水と混合した。得られた混合物を、上記オオムギの葉面に充分付着するように茎葉散布した。散布後オオムギを風乾し、１日後にオオムギ網斑病菌胞子の水懸濁液を噴霧接種した。接種後オオムギを昼間２３℃、夜間２０℃の温室内で多湿下に３日間置き、次に温室内で７日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したオオムギにおける病斑面積はいずれも、無処理のオオムギにおける病斑面積の３０％以下であった。 Test Example 8 Pyrenophora teres Control Test A plastic pot was filled with soil, and barley (cultivar: Nishinohoshi) was seeded therein and cultivated in a greenhouse for 7 days. Compound 1-4, 1-6, 1-7, 1-10, 1-15, or 2-1 of the present invention formulated according to the method described in Formulation Example 1, so that the concentration is 200 ppm Mixed with water. The resulting mixture was foliarly sprayed so as to sufficiently adhere to the foliage of the barley. After spraying, the barley was air-dried, and one day later, an aqueous suspension of spores of barley net spot fungus was inoculated by spraying. After inoculation, the barley was placed in a greenhouse at 23° C. during the day and 20° C. at night under high humidity for 3 days, then cultivated in the greenhouse for 7 days, and then the lesion area was examined. As a result, the lesion area in barley treated with each compound of the present invention was 30% or less of the lesion area in untreated barley.
試験例９　コムギさび病（Puccinia recondita）に対する防除試験
　プラスチックポットに土壌を詰め、そこにコムギ（品種；シロガネ）を播種し、温室内で９日間栽培した。製剤例１に記載の方法に準じて製剤化された本発明化合物１－６、１－７、１－９、１－１３、１－１５、１－１６、又は２－１を濃度が２００ｐｐｍとなるように水と混合し、得られた混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、２０℃、照明下で５～７日間栽培した後、コムギさび病菌の胞子をふりかけ接種した。接種後コムギを２３℃、暗黒多湿下に１日間置いた後、２０℃、照明下で８日間栽培し、病斑面積を調査した。その結果、各々の本発明化合物を処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の３０％以下であった。 Test Example 9 Control Test Against Wheat Rust (Puccinia recondita) A plastic pot was filled with soil, wheat (cultivar: Shirogane) was sown therein, and cultivated in a greenhouse for 9 days. Compound 1-6, 1-7, 1-9, 1-13, 1-15, 1-16, or 2-1 of the present invention formulated according to the method described in Formulation Example 1 at a concentration of 200 ppm The resulting mixture was foliarly sprayed so that it adhered sufficiently to the leaves of the above wheat. After spraying, the wheat was air-dried, cultivated under lighting at 20° C. for 5 to 7 days, and then inoculated with spores of wheat rust. After the inoculation, the wheat was placed under darkness and high humidity at 23°C for 1 day, then cultivated under illumination at 20°C for 8 days, and the lesion area was investigated. As a result, the lesion area in the wheat treated with each compound of the present invention was 30% or less of the lesion area in the untreated wheat.
試験例１０　コムギ葉枯病（Septoria tritici）に対する防除試験
　プラスチックポットに土壌を詰め、そこにコムギ（品種；アポジー）を播種し、温室内で１０日間栽培した。製剤例１に記載の方法に準じて製剤化された本発明化合物１－１、１－２、１－３、１－６、１－８、１－９、１－１１、１－１２、１－１４、又は１－１５を濃度が２００ｐｐｍとなるように水と混合し、得られた混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、４日後にコムギ葉枯病菌の胞子を含む水懸濁液を噴霧接種した。接種後コムギを１８℃多湿下に３日間置き、次に照明下で１４日から１８日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の３０％以下であった。 Test Example 10 Control Test Against Wheat Leaf Blight (Septoria tritici) Plastic pots were filled with soil, wheat (cultivar: Apogee) was sown therein, and cultivated in a greenhouse for 10 days. Compounds 1-1, 1-2, 1-3, 1-6, 1-8, 1-9, 1-11, 1-12 and 1 of the present invention formulated according to the method described in Formulation Example 1 -14 or 1-15 was mixed with water to a concentration of 200 ppm, and the resulting mixture was foliarly sprayed so that it adhered sufficiently to the leaves of the above wheat. After spraying, the wheat was air-dried, and four days later, an aqueous suspension containing spores of the wheat leaf blight fungus was inoculated by spraying. After inoculation, the wheat was placed under high humidity at 18°C for 3 days, then cultivated under lighting for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the wheat treated with each compound of the present invention was 30% or less of the lesion area in the untreated wheat.
試験例１１　ダイズさび病（Phakopsora pachyrhizi）に対する防除試験
　プラスチックポットに土壌を詰め、そこにダイズ（品種；黒千石）を播種し、温室内で１０～１４日間生育させた。製剤例１に記載の方法に準じて製剤化された本発明化合物１－６、１－９、又は１－１７を濃度が２００ｐｐｍとなるように水と混合し、得られた混合物を、上記ダイズの葉面に充分付着するように茎葉散布した。散布後ダイズを風乾し、２～５日後にダイズさび病菌胞子の水懸濁液を噴霧接種した。接種後ダイズを昼間２３℃、夜間２０℃の温室内で多湿下に１～２日間置き、次に温室内で１２日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したダイズにおける病斑面積はいずれも、無処理のダイズにおける病斑面積の３０％以下であった。 Test Example 11 Prevention test against soybean rust (Phakopsora pachyrhizi) Plastic pots were filled with soil, soybeans (cultivar: Kurosengoku) were seeded therein, and grown in a greenhouse for 10 to 14 days. Compound 1-6, 1-9, or 1-17 of the present invention formulated according to the method described in Formulation Example 1 was mixed with water to a concentration of 200 ppm, and the resulting mixture was added to the soybean. It was sprayed on the foliage so that it would adhere sufficiently to the leaf surfaces of . After spraying, the soybeans were air-dried, and 2 to 5 days later, an aqueous suspension of soybean rust spores was inoculated by spraying. After inoculation, the soybeans were placed in a greenhouse at 23° C. during the day and 20° C. at night under high humidity for 1 to 2 days, then cultivated in the greenhouse for 12 days, and then the lesion area was examined. As a result, the lesion area in the soybeans treated with each compound of the present invention was 30% or less of the lesion area in the untreated soybeans.
試験例１２　ダイズさび病（Phakopsora pachyrhizi）に対する防除試験
　プラスチックポットに土壌を詰め、そこにダイズ（品種；黒千石）を播種し、温室内で１０日間生育させ、ダイズさび病菌の胞子を含む水懸濁液を噴霧接種した。接種後ダイズを昼間２３℃、夜間２０℃の温室内で多湿下に１日間置き、次に温室で２日間栽培した後、製剤例１に記載の方法に準じて製剤化された本発明化合物１－４、１－５、１－６、１－１０、又は２－１を濃度が２００ｐｐｍとなるように水と混合し、得られた混合物を、上記ダイズの葉面に充分付着するように茎葉散布した。散布後ダイズを風乾し、温室内で８日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したダイズにおける病斑面積はいずれも、無処理のダイズにおける病斑面積の３０％以下であった。 Test Example 12 Control test against soybean rust (Phakopsora pachyrhizi) A plastic pot was filled with soil, soybeans (cultivar: Kurosengoku) were sown there, grown in a greenhouse for 10 days, and water suspension containing spores of soybean rust fungus. The suspension was spray inoculated. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under high humidity for 1 day, and then cultivated in the greenhouse for 2 days. -4, 1-5, 1-6, 1-10, or 2-1 is mixed with water so that the concentration is 200 ppm, and the resulting mixture is attached to the foliage of the soybean. disseminated. After spraying, the soybeans were air-dried, cultivated in a greenhouse for 8 days, and then the lesion area was investigated. As a result, the lesion area in the soybeans treated with each compound of the present invention was 30% or less of the lesion area in the untreated soybeans.
試験例１３　ダイズ斑点病（Cercospora sojina）に対する防除試験
　プラスチックポットに土壌を詰め、そこにダイズ（品種；タチナガハ）を播種し、温室内で１３日間生育させた。製剤例１に記載の方法に準じて製剤化された本発明化合物１－１、１－６、１－７、１－９、又は１－１０を濃度が２００ｐｐｍとなるように水と混合し、得られた混合物を、上記ダイズの葉面に充分付着するように茎葉散布した。散布後ダイズを風乾し、１日後にダイズ斑点病菌胞子の水懸濁液を噴霧接種した。接種後ダイズを昼間２３℃、夜間２０℃の温室内で多湿下に３日間置き、次に温室内で１６日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したダイズにおける病斑面積はいずれも、無処理のダイズにおける病斑面積の３０％以下であった。 Test Example 13 Control test against soybean spot (Cercospora sojina) Plastic pots were filled with soil, soybeans (cultivar: Tachinagaha) were sown there, and grown in a greenhouse for 13 days. Compound 1-1, 1-6, 1-7, 1-9, or 1-10 of the present invention formulated according to the method described in Formulation Example 1 is mixed with water to a concentration of 200 ppm, The resulting mixture was foliarly sprayed so that it adhered sufficiently to the foliage of the soybean. After spraying, the soybeans were air-dried, and one day later, they were inoculated by spraying an aqueous suspension of spores of the soybean leaf spot fungus. After inoculation, the soybeans were placed in a greenhouse at 23° C. during the day and 20° C. at night under high humidity for 3 days, then cultivated in the greenhouse for 16 days, and then the lesion area was examined. As a result, the lesion area in the soybeans treated with each compound of the present invention was 30% or less of the lesion area in the untreated soybeans.
試験例１４　トマト輪紋病（Alternaria solani）に対する防除試験
　プラスチックポットに土壌を詰め、そこにトマト（品種；パティオ）を播種し、温室内で２０日間生育させた。製剤例１に記載の方法に準じて製剤化された本発明化合物１－１、１－２、１－３、１－４、１－５、１－６、１－７、１－８、１－９、１－１１、１－１３、１－１４、１－１５、１－１６、１－１７、２－１、又は２－２を濃度が２００ｐｐｍとなるように水と混合し、得られた混合物を、上記トマトの葉面に充分付着するように茎葉散布した。散布後トマトを風乾し、１日後にトマト輪紋病菌胞子の水懸濁液を噴霧接種した。接種後トマトを１８℃、多湿下に６日間置いた後、病斑面積を調査した。その結果、各々の本発明化合物を処理したトマトにおける病斑面積はいずれも、無処理のトマトにおける病斑面積の３０％以下であった。 Test Example 14 Control test against tomato ring spot (Alternaria solani) Plastic pots were filled with soil, tomatoes (cultivar: patio) were seeded therein, and grown in a greenhouse for 20 days. Compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8 and 1 of the present invention formulated according to the method described in Formulation Example 1 -9, 1-11, 1-13, 1-14, 1-15, 1-16, 1-17, 2-1, or 2-2 is mixed with water so that the concentration is 200 ppm, and the resulting The resulting mixture was foliarly sprayed so as to sufficiently adhere to the leaf surface of the tomato. After spraying, the tomatoes were air-dried, and one day later, they were inoculated by spraying an aqueous suspension of spores of tomato ring-blight fungus. After the inoculation, the tomato was placed at 18° C. and high humidity for 6 days, and then the lesion area was examined. As a result, the lesion area on tomatoes treated with the compounds of the present invention was 30% or less of the lesion area on untreated tomatoes.
試験法１５
　供試化合物が２００ｐｐｍとなるように調製したアセトン溶液を内容量２０ｍＬの容器に注ぎ、供試化合物が１０ｍｇ／ｍ2となるように容器の内面に均一にコーティングし、その後乾燥させる。
　該容器にアカイエカ雌成虫５頭を入れ、蓋を閉める。所定時間経過後にアカイエカの状態を調査し死虫率を求める。死虫率は下式により計算する。
　　　死虫率（％）＝（死虫数／供試虫数）×１００ Test method 15
An acetone solution containing 200 ppm of the test compound is poured into a 20 mL container, and the inner surface of the container is uniformly coated with 10 mg/m 2 of the test compound, followed by drying.
Five Culex pipiens female adults are placed in the container and the lid is closed. After a predetermined period of time has passed, the state of Culex pipiens is investigated and the mortality rate is obtained. The mortality rate is calculated using the following formula.
Dead insect rate (%) = (number of dead insects/number of test insects) x 100
試験例１５
　試験法１５に従って実施した試験の結果を以下に示す。所定時間を１日とし、供試化合物として下記の本発明化合物を用いた結果、いずれも死虫率７０％以上を示した。
本発明化合物： １－１、１－６、及び２－１ Test example 15
The results of tests performed according to test method 15 are shown below. As a result of using the following compounds of the present invention as test compounds with a predetermined period of one day, all showed a mortality rate of 70% or more.
Compounds of the Invention: 1-1, 1-6, and 2-1
試験法１６
　供試化合物が８００ｐｐｍとなるように調製したアセトン溶液を内容量２０ｍＬの容器に注ぎ、供試化合物が４０ｍｇ／ｍ2となるように容器の内面に均一にコーティングし、その後乾燥させる。
　該容器にイエバエ雌成虫５頭を入れ、蓋を閉める。所定時間経過後にイエバエの状態を調査し死虫率を求める。死虫率は下式により計算する。
　　　死虫率（％）＝（死虫数／供試虫数）×１００ Test method 16
An acetone solution prepared to contain 800 ppm of the test compound is poured into a 20 mL container, and the inner surface of the container is evenly coated with 40 mg/m 2 of the test compound, followed by drying.
Five female adult house flies are placed in the container and the lid is closed. After a predetermined period of time has elapsed, the state of the housefly is investigated and the mortality rate is determined. The mortality rate is calculated using the following formula.
Dead insect rate (%) = (number of dead insects/number of test insects) x 100
試験例１６
　試験法１６に従って実施した試験の結果を以下に示す。所定時間を１日とし、供試化合物として下記の本発明化合物を用いた結果、死虫率７０％を示した。
本発明化合物： １－７ Test example 16
The results of tests performed according to test method 16 are shown below. As a result of using the following compound of the present invention as a test compound with a predetermined time of 1 day, the mortality rate was 70%.
Compounds of the present invention: 1-7
試験法１７
　供試化合物が２０００ｐｐｍとなるように調整したアセトン溶液を内容量２０ｍＬの容器に注ぎ、供試化合物が１００ｍｇ／ｍ2となるように容器の内面に均一にコーティングし、その後乾燥させる。
　該容器にフタトゲチマダニ若虫５頭を入れ、蓋を閉める。所定時間経過後にフタトゲチマダニの状態を調査し死虫率を求める。死虫率は下式により計算する。
　　　死虫率（％）＝（死虫数／供試虫数）×１００ Test method 17
An acetone solution containing 2000 ppm of the test compound is poured into a 20 mL container, and the inner surface of the container is uniformly coated with 100 mg/m 2 of the test compound, followed by drying.
Put 5 nymphs of Haemophilus longus in the container and close the lid. After a predetermined period of time has elapsed, the state of the tropic tick is investigated and the mortality rate is obtained. The mortality rate is calculated using the following formula.
Dead insect rate (%) = (number of dead insects/number of test insects) x 100
試験例１７
　試験法１７に従って実施した試験の結果を以下に示す。所定時間を２日とし、供試化合物として下記の本発明化合物を用いた結果、死虫率１００％を示した。
本発明化合物： ２－１ Test example 17
The results of tests performed according to test method 17 are shown below. Using the following compound of the present invention as a test compound with a predetermined time of 2 days, the mortality rate was 100%.
Compound of the present invention: 2-1
　本発明化合物は、有害生物に対して防除効力を有し、有害生物防除に用いることができる。 The compound of the present invention has a controlling effect on pests and can be used for controlling pests.

Claims (11)

  1. 　式（Ｉ）：
    Figure JPOXMLDOC01-appb-C000001
     〔式中、
    　Ｘ１は、ＣＨ又は窒素原子を表し、
    　Ｘ２は、Ｃ（Ｏ）ＯＣＨ３、Ｃ（Ｏ）ＮＨＣＨ３、又は５，６－ジヒドロ－１，４，２－ジオキサジン－３－イル基を表し、
    　Ｒ１、Ｒ２、及びＲ３は、同一又は相異なり、Ｃ１－Ｃ６アルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルコキシカルボニル基｛該Ｃ１－Ｃ６アルキル基、該Ｃ１－Ｃ６アルコキシ基、該Ｃ３－Ｃ６シクロアルキル基、及び該Ｃ２－Ｃ６アルコキシカルボニル基は、１以上のハロゲン原子で置換されていてもよい｝、シアノ基、ニトロ基、ハロゲン原子、又は水素原子を表し、
    　Ｊ及びＥの組合せは、
    　　Ｊが、Ｊ１で示される基であり、
    　　Ｅが、群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、Ｃ３－Ｃ１０脂環式炭化水素基、３－１０員非芳香族複素環基、Ｃ６－Ｃ１０アリール基、５－１０員芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基、該３－１０員非芳香族複素環基、該Ｃ６－Ｃ１０アリール基及び該５－１０員芳香族複素環基は、群Ｄより選ばれる１以上の置換基で置換されていてもよい｝、Ｃ（Ｏ）ＯＲ２５、Ｃ（Ｏ）Ｒ２６、又はＣ（Ｏ）ＮＲ２７Ｒ２８である組合せ；又は、
    　　Ｊが、Ｊ２で示される基であり、
    　　Ｅが、群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、Ｃ３－Ｃ１０脂環式炭化水素基、３－１０員非芳香族複素環基、Ｃ６－Ｃ１０アリール基、５－１０員芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基、該３－１０員非芳香族複素環基、該Ｃ６－Ｃ１０アリール基及び該５－１０員芳香族複素環基は、群Ｄより選ばれる１以上の置換基で置換されていてもよい｝、ＣＨ２－Ｌ１－Ｒ１２、ＣＨ２－Ｏ－Ｎ＝ＣＲ１３Ｒ１４、Ｃ（Ｒ１６）＝Ｎ－Ｏ－Ｒ１５、Ｃ（Ｒ１９）＝Ｎ－Ｎ＝ＣＲ１７Ｒ１８、Ｃ（Ｒ２２）＝Ｎ－ＮＲ２０Ｒ２１、Ｌ２Ｒ２３、シアノ基、ニトロ基、又はハロゲン原子である組合せを表し、
    　Ｊ１で示される基、及びＪ２で示される基は、下式で示される基であり、
    Figure JPOXMLDOC01-appb-C000002
     　＃は、Ｅとの結合位置を表し、
    　Ｘ3は、ＣＲ４又は窒素原子を表し、
    　Ｘ4は、ＣＲ５又は窒素原子を表し、
    　Ｘ5は、ＣＲ６又は窒素原子を表し、
    　Ｘ6は、酸素原子、硫黄原子、Ｎ（Ｒ７）、＊－Ｃ（Ｒ８）＝Ｃ（Ｒ９）－、＊－Ｃ（Ｒ１０）＝Ｎ－、又は＊－Ｎ＝Ｃ（Ｒ１１）－を表し、
    　＊は、Ｘ５との結合位置を表し、
    　Ｒ４、Ｒ５、Ｒ６、Ｒ８、Ｒ９、Ｒ１０、及びＲ１１は、同一又は相異なり、Ｃ１－Ｃ６アルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルコキシカルボニル基｛該Ｃ１－Ｃ６アルキル基、該Ｃ１－Ｃ６アルコキシ基、該Ｃ３－Ｃ６シクロアルキル基、及び該Ｃ２－Ｃ６アルコキシカルボニル基は、１以上のハロゲン原子で置換されていてもよい｝、シアノ基、ニトロ基、ハロゲン原子、又は水素原子を表し、
    　Ｒ７は、Ｃ１－Ｃ６アルキル基、Ｃ３－Ｃ６シクロアルキル基｛該Ｃ１－Ｃ６アルキル基及び該Ｃ３－Ｃ６シクロアルキル基は、１以上のハロゲン原子で置換されていてもよい｝、又は水素原子を表し、
    　Ｌ１及びＬ２は、同一又は相異なり、酸素原子又はＳ（Ｏ）ｎを表し、
    　ｎは、０、１、又は２を表し、
    　Ｒ１２、Ｒ１３、Ｒ１５、Ｒ１７、Ｒ２０、Ｒ２３、Ｒ２５、Ｒ２６、及びＲ２７は、同一又は相異なり、群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、Ｃ３－Ｃ１０脂環式炭化水素基、３－１０員非芳香族複素環基、Ｃ６－Ｃ１０アリール基、又は５－１０員芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基、該３－１０員非芳香族複素環基、該Ｃ６－Ｃ１０アリール基、及び該５－１０員芳香族複素環基は、群Ｄより選ばれる１以上の置換基で置換されていてもよい｝を表し、
    　Ｒ１４、Ｒ１６、Ｒ１８、Ｒ１９、Ｒ２１、Ｒ２２、及びＲ２８は、同一又は相異なり、Ｃ１－Ｃ６鎖式炭化水素基、Ｃ３－Ｃ１０脂環式炭化水素基｛該Ｃ１－Ｃ６鎖式炭化水素基及び該Ｃ３－Ｃ１０脂環式炭化水素基は、１以上のハロゲン原子で置換されていてもよい｝、又は水素原子を表し、
    　Ｒ１３及びＲ１４は、それらが結合する炭素原子と一緒になって、Ｃ３－Ｃ１０脂環式炭化水素基又は３－１０員非芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基及び該３－１０員非芳香族複素環基は、群Ｄより選ばれる１以上の置換基で置換されていてもよい｝を形成していてもよく、
    　Ｒ１７及びＲ１８は、それらが結合する炭素原子と一緒になって、Ｃ３－Ｃ１０脂環式炭化水素基又は３－１０員非芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基及び該３－１０員非芳香族複素環基は、群Ｄより選ばれる１以上の置換基で置換されていてもよい｝を形成していてもよい。
    　群Ａ：Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６アルキルチオ基｛該Ｃ１－Ｃ６アルコキシ基及び該Ｃ１－Ｃ６アルキルチオ基は、群Ｆより選ばれる１以上の置換基で置換されていてもよい｝、Ｃ３－Ｃ１０脂環式炭化水素基、３－１０員非芳香族複素環基、Ｃ６－Ｃ１０アリール基、５－１０員芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基、該３－１０員非芳香族複素環基、該Ｃ６－Ｃ１０アリール基、及び該５－１０員芳香族複素環基は、群Ｄより選ばれる１以上の置換基で置換されていてもよい｝、シアノ基、ニトロ基、ヒドロキシ基、ハロゲン原子、オキソ基、及びチオキソ基からなる群。
    　群Ｂ：オキソ基、チオキソ基、Ｃ１－Ｃ６鎖式炭化水素基、Ｃ１－Ｃ６アルコキシ基｛該Ｃ１－Ｃ６鎖式炭化水素基及び該Ｃ１－Ｃ６アルコキシ基は、１以上のハロゲン原子で置換されていてもよい｝、ハロゲン原子、及びシアノ基からなる群。
    　群Ｃ：Ｃ１－Ｃ６鎖式炭化水素基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６アルキルチオ基｛該Ｃ１－Ｃ６鎖式炭化水素基、該Ｃ１－Ｃ６アルコキシ基、及び該Ｃ１－Ｃ６アルキルチオ基は、群Ｆより選ばれる１以上の置換基で置換されていてもよい｝、群Ｂより選ばれる１以上の置換基で置換されていてもよいＣ３－Ｃ６シクロアルキル基、シアノ基、ニトロ基、ハロゲン原子、及びヒドロキシ基からなる群。
    　群Ｄ：Ｃ１－Ｃ６鎖式炭化水素基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ２－Ｃ６アルコキシカルボニル基、｛該Ｃ１－Ｃ６鎖式炭化水素基、該Ｃ１－Ｃ６アルコキシ基、該Ｃ１－Ｃ６アルキルチオ基、及び該Ｃ２－Ｃ６アルコキシカルボニル基は、群Ｇより選ばれる１以上の置換基で置換されていてもよい｝、Ｃ３－Ｃ１０脂環式炭化水素基、３－１０員非芳香族複素環基｛該Ｃ３－Ｃ１０脂環式炭化水素基及び該３－１０員非芳香族複素環基は、群Ｂより選ばれる１以上の置換基で置換されていてもよい｝、Ｃ６－Ｃ１０アリール基、５－１０員芳香族複素環基｛該Ｃ６－Ｃ１０アリール基及び該５－１０員芳香族複素環基は、群Ｃより選ばれる１以上の置換基で置換されていてもよい｝、Ｌ３Ｒ２４、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、及びアミノ基からなる群。
    　Ｌ３は、酸素原子又はＳ（Ｏ）ｍを表し、
    　ｍは、０、１、又は２を表し、
    　Ｒ２４は、Ｃ６－Ｃ１０アリール基又は５－１０員芳香族複素環基｛該Ｃ６－Ｃ１０アリール基及び該５－１０員芳香族複素環基は、群Ｃより選ばれる１以上の置換基で置換されていてもよい｝を表す。
    　群Ｆ：Ｃ１－Ｃ６アルコキシ基、Ｃ３－Ｃ６シクロアルキル基｛該Ｃ１－Ｃ６アルコキシ基及び該Ｃ３－Ｃ６シクロアルキル基は、１以上のハロゲン原子で置換されていてもよい｝、及びハロゲン原子からなる群。
    　群Ｇ：Ｃ１－Ｃ６アルコキシ基、Ｃ３－Ｃ６シクロアルキル基｛該Ｃ１－Ｃ６アルコキシ基及び該Ｃ３－Ｃ６シクロアルキル基は、１以上のハロゲン原子で置換されていてもよい｝、Ｃ６－Ｃ１０アリール基、５－１０員芳香族複素環基｛該Ｃ６－Ｃ１０アリール基及び該５－１０員芳香族複素環基は、群Ｃより選ばれる１以上の置換基で置換されていてもよい｝、及びハロゲン原子からなる群。〕
    で示される化合物、若しくはそのＮオキシド又はそれらの塩。     Formula (I):
    Figure JPOXMLDOC01-appb-C000001
     [In the formula,
    X 1 represents CH or a nitrogen atom,
    X 2 represents a C(O)OCH 3 , C(O)NHCH 3 , or 5,6-dihydro-1,4,2-dioxazin-3-yl group;
    R 1 , R 2 , and R 3 are the same or different and are a C1-C6 alkyl group, a C1-C6 alkoxy group, a C3-C6 cycloalkyl group, a C2-C6 alkoxycarbonyl group {the C1-C6 alkyl group, the The C1-C6 alkoxy group, the C3-C6 cycloalkyl group, and the C2-C6 alkoxycarbonyl group may be substituted with one or more halogen atoms}, a cyano group, a nitro group, a halogen atom, or a hydrogen atom represents
    The combination of J and E is
    J is a group represented by J1,
    E is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C10 alicyclic hydrocarbon group, a 3-10 membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10 membered aromatic heterocyclic group {the C3-C10 alicyclic hydrocarbon group, the 3-10 membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10 The membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group D}, C(O)OR 25 , C(O)R 26 , or C(O)NR 27 R 28 or
    J is a group represented by J2,
    E is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C10 alicyclic hydrocarbon group, a 3-10 membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10 membered aromatic heterocyclic group {the C3-C10 alicyclic hydrocarbon group, the 3-10 membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10 The membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D}, CH 2 —L 1 —R 12 , CH 2 —O—N=CR 13 R 14 , C( R 16 )=NO-R 15 , C(R 19 )=NN=CR 17 R 18 , C(R 22 )=N-NR 20 R 21 , L 2 R 23 , cyano group, nitro group, or represents a combination that is a halogen atom,
    The group represented by J1 and the group represented by J2 are groups represented by the following formulae,
    Figure JPOXMLDOC01-appb-C000002
     # represents the bonding position with E,
    X3 represents CR4 or a nitrogen atom ,
    X4 represents CR5 or a nitrogen atom;
    X5 represents CR6 or a nitrogen atom,
    X 6 is an oxygen atom, a sulfur atom, N(R 7 ), *-C(R 8 )=C(R 9 )-, *-C(R 10 )=N-, or *-N=C(R 11 ) represents -,
    * represents the binding position with X5 ,
    R 4 , R 5 , R 6 , R 8 , R 9 , R 10 and R 11 are the same or different, C1-C6 alkyl group, C1-C6 alkoxy group, C3-C6 cycloalkyl group, C2-C6 an alkoxycarbonyl group {the C1-C6 alkyl group, the C1-C6 alkoxy group, the C3-C6 cycloalkyl group, and the C2-C6 alkoxycarbonyl group may be substituted with one or more halogen atoms}; represents a cyano group, a nitro group, a halogen atom, or a hydrogen atom,
    R 7 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group {the C1-C6 alkyl group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, or a hydrogen atom represents
    L 1 and L 2 are the same or different and represent an oxygen atom or S(O) n ,
    n represents 0, 1, or 2;
    R 12 , R 13 , R 15 , R 17 , R 20 , R 23 , R 25 , R 26 and R 27 are the same or different and may be substituted with one or more substituents selected from group A A good C1-C6 chain hydrocarbon group, C3-C10 alicyclic hydrocarbon group, 3-10 membered non-aromatic heterocyclic group, C6-C10 aryl group, or 5-10 membered aromatic heterocyclic group {the C3 -C10 alicyclic hydrocarbon group, said 3-10 membered non-aromatic heterocyclic group, said C6-C10 aryl group, and said 5-10 membered aromatic heterocyclic group are substituted with one or more selected from group D may be substituted with a group],
    R 14 , R 16 , R 18 , R 19 , R 21 , R 22 and R 28 are the same or different and are C1-C6 chain hydrocarbon groups, C3-C10 alicyclic hydrocarbon groups {the C1- The C6 chain hydrocarbon group and the C3-C10 alicyclic hydrocarbon group may be substituted with one or more halogen atoms}, or represent a hydrogen atom,
    R 13 and R 14 together with the carbon atom to which they are attached are a C3-C10 alicyclic hydrocarbon group or a 3-10 membered non-aromatic heterocyclic group {the C3-C10 alicyclic hydrocarbon group and the 3- to 10-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from group D} may be formed,
    R 17 and R 18 together with the carbon atom to which they are attached are a C3-C10 alicyclic hydrocarbon group or a 3-10 membered non-aromatic heterocyclic group {the C3-C10 alicyclic hydrocarbon group and said 3- to 10-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from Group D}.
    Group A: C1-C6 alkoxy group, C1-C6 alkylthio group {the C1-C6 alkoxy group and the C1-C6 alkylthio group may be substituted with one or more substituents selected from group F}, C3 -C10 alicyclic hydrocarbon group, 3-10 membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10 membered aromatic heterocyclic group {the C3-C10 alicyclic hydrocarbon group, the 3- The 10-membered non-aromatic heterocyclic group, the C6-C10 aryl group, and the 5-10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group D}, cyano group , a nitro group, a hydroxy group, a halogen atom, an oxo group, and a thioxo group.
    Group B: an oxo group, a thioxo group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group and the C1-C6 alkoxy group are substituted with one or more halogen atoms; optionally], a halogen atom, and a cyano group.
    Group C: a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylthio group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, and the C1-C6 alkylthio group are optionally substituted with one or more substituents selected from group F}, optionally substituted with one or more substituents selected from group B C3-C6 cycloalkyl group, cyano group, nitro group, halogen A group consisting of an atom and a hydroxy group.
    Group D: C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylthio group, C2-C6 alkoxycarbonyl group, {said C1-C6 chain hydrocarbon group, said C1-C6 alkoxy group, said C1-C6 alkylthio group and said C2-C6 alkoxycarbonyl group optionally substituted with one or more substituents selected from group G}, C3-C10 alicyclic hydrocarbon group, 3-10 membered non- aromatic heterocyclic group {the C3-C10 alicyclic hydrocarbon group and the 3-10-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B}, C6 -C10 aryl group, 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C good}, the group consisting of L 3 R 24 , a halogen atom, a cyano group, a nitro group, a hydroxy group, and an amino group.
    L3 represents an oxygen atom or S ( O) m ,
    m represents 0, 1, or 2;
    R 24 is a C6-C10 aryl group or a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group are one or more substituents selected from Group C; may be substituted}.
    Group F: from a C1-C6 alkoxy group, a C3-C6 cycloalkyl group {the C1-C6 alkoxy group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, and a halogen atom the group.
    Group G: C1-C6 alkoxy group, C3-C6 cycloalkyl group {the C1-C6 alkoxy group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C}, and a group consisting of halogen atoms. ]
    A compound represented by or its N oxide or a salt thereof.
  2. 　Ｘ１がＣＨであり、Ｒ１、Ｒ２、及びＲ３が、同一又は相異なり、Ｃ１－Ｃ６アルキル基、ハロゲン原子、又は水素原子である、請求項１に記載の化合物、若しくはそのＮオキシド又はそれらの塩。 The compound according to claim 1, wherein X 1 is CH and R 1 , R 2 and R 3 are the same or different and are a C1-C6 alkyl group, a halogen atom or a hydrogen atom, or an N-oxide thereof or their salts.
  3. 　Ｘ１が窒素原子であり、Ｒ１、Ｒ２、及びＲ３が、同一又は相異なり、Ｃ１－Ｃ６アルキル基、ハロゲン原子、又は水素原子である、請求項１に記載の化合物、若しくはそのＮオキシド又はそれらの塩。 2. The compound according to claim 1 , or its N oxides or salts thereof;
  4. 　ＪがＪ１で示される基であり、Ｅが群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、群Ｄより選ばれる１以上の置換基で置換されていてもよいＣ６－Ｃ１０アリール基、群Ｄより選ばれる１以上の置換基で置換されていてもよい５－１０員芳香族複素環基、又はＣ（Ｏ）ＯＲ２５である、請求項１～３のいずれかに記載の化合物、若しくはそのＮオキシド又はそれらの塩。 J is a group represented by J1, E is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, substituted with one or more substituents selected from group D C6-C10 aryl group optionally substituted, 5-10 membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group D, or C(O)OR 25 4. The compound according to any one of 1 to 3, or its N-oxide or salt thereof.
  5. 　ＪがＪ２で示される基であり、Ｅが群Ａより選ばれる１以上の置換基で置換されていてもよいＣ１－Ｃ６鎖式炭化水素基、群Ｄより選ばれる１以上の置換基で置換されていてもよいＣ６－Ｃ１０アリール基、群Ｄより選ばれる１以上の置換基で置換されていてもよい５－１０員芳香族複素環基、ＣＨ２－Ｌ１－Ｒ１２、ＣＨ２－Ｏ－Ｎ＝ＣＲ１３Ｒ１４、Ｃ（Ｒ１６）＝Ｎ－Ｏ－Ｒ１５、Ｃ（Ｒ１９）＝Ｎ－Ｎ＝ＣＲ１７Ｒ１８、Ｃ（Ｒ２２）＝Ｎ－ＮＲ２０Ｒ２１、Ｌ２Ｒ２３、又はハロゲン原子である、請求項１～３のいずれかに記載の化合物、若しくはそのＮオキシド又はそれらの塩。 J is a group represented by J2, E is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, substituted with one or more substituents selected from group D a C6-C10 aryl group which may be substituted, a 5-10 membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D, CH 2 —L 1 —R 12 , CH 2 — ON=CR 13 R 14 , C(R 16 )=NO-R 15 , C(R 19 )=NN=CR 17 R 18 , C(R 22 )=N-NR 20 R 21 , L 2 R 23 , or the compound according to any one of claims 1 to 3, or its N-oxide or salt thereof, which is a halogen atom.
  6. 　請求項１～５のいずれかに記載の化合物、若しくはそのＮオキシド又はそれらの塩と不活性担体とを含有する農薬組成物。 An agricultural chemical composition containing the compound according to any one of claims 1 to 5, or its N oxide or salt thereof, and an inert carrier.
  7. 　群（ａ）、群（ｂ）、群（ｃ）及び群（ｄ）からなる群より選ばれる１以上の成分、並びに、請求項１～５のいずれかに記載の化合物、若しくはそのＮオキシド又はそれらの塩を含有する組成物：
    　　群（ａ）：殺虫活性成分、殺ダニ活性成分及び殺線虫活性成分からなる群；
    　　群（ｂ）：殺菌活性成分；
    　　群（ｃ）：植物成長調整成分；
    　　群（ｄ）：忌避成分。     One or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound according to any one of claims 1 to 5, or its N oxide, or Compositions containing those salts:
    Group (a): a group consisting of an insecticidal active ingredient, an acaricidal active ingredient and a nematicidal active ingredient;
    Group (b): fungicidal active ingredient;
    Group (c): plant growth regulating ingredients;
    Group (d): repellent ingredients.
  8. 　請求項１～５のいずれかに記載の化合物、若しくはそのＮオキシド若しくはそれらの塩の有効量又は請求項７に記載の組成物の有効量を植物又は土壌に処理することによる有害生物防除方法。 A method for controlling pests by applying an effective amount of the compound according to any one of claims 1 to 5, or its N oxide or salt thereof, or an effective amount of the composition according to claim 7 to plants or soil.
  9. 　請求項１～５のいずれかに記載の化合物、若しくはそのＮオキシド若しくはそれらの塩の有効量又は請求項７に記載の組成物の有効量をダイズ又はダイズを生育する土壌に施用することによる、ミトコンドリアチトクロームｂタンパク質にＦ１２９Ｌのアミノ酸置換を有するダイズさび病菌の防除方法。 by applying an effective amount of a compound according to any one of claims 1 to 5, or an N-oxide thereof or a salt thereof, or an effective amount of a composition according to claim 7 to soybeans or soil in which soybeans are grown, A method for controlling soybean rust having an F129L amino acid substitution in the mitochondrial cytochrome b protein.
  10. 　有害生物を防除するための、請求項１～５のいずれかに記載の化合物、若しくはそのＮオキシド若しくはそれらの塩又は請求項７に記載の組成物の使用。 Use of the compound according to any one of claims 1 to 5, or its N-oxide or salt thereof, or the composition according to claim 7 for controlling pests.
  11. 　請求項１～５のいずれかに記載の化合物、若しくはそのＮオキシド若しくはそれらの塩の有効量又は請求項７に記載の組成物の有効量を保持している種子又は栄養生殖器官。 A seed or vegetative reproductive organ retaining an effective amount of the compound according to any one of claims 1 to 5, or its N-oxide or salt thereof, or an effective amount of the composition according to claim 7.
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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61106538A (en) * 1984-10-19 1986-05-24 ゼネカ・リミテッド Acrylic acid derivative, manufacture and fungicidal composition
JPH04288069A (en) * 1990-10-02 1992-10-13 Roussel Uclaf Novel benzofuran derivative, process for producing same, novel intermediate obtained and use thereof as preventive for deleterious organism
JPH0827133A (en) * 1994-07-08 1996-01-30 Sumitomo Chem Co Ltd Bicyclic compound, its use and intermediate for producing the same
JPH11503114A (en) * 1995-03-21 1999-03-23 アグレボ・ユー・ケイ・リミテツド Fungicidal compounds
WO2021219778A1 (en) * 2020-04-30 2021-11-04 Syngenta Crop Protection Ag Microbiocidal compounds
WO2021219775A1 (en) * 2020-04-30 2021-11-04 Syngenta Crop Protection Ag Microbiocidal compounds
WO2021219780A1 (en) * 2020-05-01 2021-11-04 Syngenta Crop Protection Ag Microbiocidal compounds
WO2021224102A1 (en) * 2020-05-05 2021-11-11 Syngenta Crop Protection Ag Microbiocidal compounds

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61106538A (en) * 1984-10-19 1986-05-24 ゼネカ・リミテッド Acrylic acid derivative, manufacture and fungicidal composition
JPH04288069A (en) * 1990-10-02 1992-10-13 Roussel Uclaf Novel benzofuran derivative, process for producing same, novel intermediate obtained and use thereof as preventive for deleterious organism
JPH0827133A (en) * 1994-07-08 1996-01-30 Sumitomo Chem Co Ltd Bicyclic compound, its use and intermediate for producing the same
JPH11503114A (en) * 1995-03-21 1999-03-23 アグレボ・ユー・ケイ・リミテツド Fungicidal compounds
WO2021219778A1 (en) * 2020-04-30 2021-11-04 Syngenta Crop Protection Ag Microbiocidal compounds
WO2021219775A1 (en) * 2020-04-30 2021-11-04 Syngenta Crop Protection Ag Microbiocidal compounds
WO2021219780A1 (en) * 2020-05-01 2021-11-04 Syngenta Crop Protection Ag Microbiocidal compounds
WO2021224102A1 (en) * 2020-05-05 2021-11-11 Syngenta Crop Protection Ag Microbiocidal compounds

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ANA C KLOSOWSKI, LOUISE L MAY DE MIO, SIMONE MIESSNER, RONALDO RODRIGUES, GERD STAMMLER: "Detection of the F129L mutation in the cytochrome b gene in Phakopsora pachyrhizi : F129L mutation in the CYTB gene in P. pachyrhizi", PEST MANAGEMENT SCIENCE, vol. 72, no. 6, 1 June 2016 (2016-06-01), pages 1211 - 1215, XP055720325, ISSN: 1526-498X, DOI: 10.1002/ps.4099 *
HIDEO ISHI: "Current Status of QoI Fungicide Resistance", PLANT PROTECTION, vol. 69, no. 8, 1 January 2015 (2015-01-01), JP , pages 469 - 474, XP009521535, ISSN: 0037-4091 *

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