WO2022186377A1 - Composé à cycles condensés et son utilisation - Google Patents

Composé à cycles condensés et son utilisation 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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English (en)
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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    • 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

La présente invention concerne un composé, ou un sel de celui-ci, qui présente un excellent effet de lutte contre les organismes nuisibles et qui est représenté par la formule (I) [dans la formule, une combinaison de J et E est telle que J est un groupe représenté par J1 et E est un groupe hydrocarboné de type à chaîne en C1-C6 ou analogue qui peut être substitué par un ou plusieurs groupes substituants choisis parmi le groupe A, X1 représente CH ou un atome d'azote, X2 représente C(O)OCH3 ou analogue, R1, R2 et R3 peuvent être identiques les uns aux autres, ou différents les uns des autres, et représentent chacun un groupe alkyle en C1-C6, un groupe représenté par J1 est un groupe représenté par la formule ci-dessous, X3 représente CR4 ou un atome d'azote, X4 représente CR5 ou un atome d'azote, # désigne un site de liaison à E, R4 et R5 peuvent être identiques l'un à l'autre, ou différents l'un de l'autre, et représentent chacun un groupe alkyle en C1-C6 ou analogue] ; ou un N-oxyde associé.
PCT/JP2022/009401 2021-03-05 2022-03-04 Composé à cycles condensés et son utilisation WO2022186377A1 (fr)

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JPH04288069A (ja) * 1990-10-02 1992-10-13 Roussel Uclaf 新規なベンゾフラン誘導体、その製造法、得られる新規な中間体及びその有害生物防除剤としての用途
JPH0827133A (ja) * 1994-07-08 1996-01-30 Sumitomo Chem Co Ltd 双環式化合物、その用途およびその製造中間体
JPH11503114A (ja) * 1995-03-21 1999-03-23 アグレボ・ユー・ケイ・リミテツド 殺菌性化合物
WO2021219775A1 (fr) * 2020-04-30 2021-11-04 Syngenta Crop Protection Ag Composés microbiocides
WO2021219778A1 (fr) * 2020-04-30 2021-11-04 Syngenta Crop Protection Ag Composés microbiocides
WO2021219780A1 (fr) * 2020-05-01 2021-11-04 Syngenta Crop Protection Ag Composés microbiocides
WO2021224102A1 (fr) * 2020-05-05 2021-11-11 Syngenta Crop Protection Ag Composés microbiocides

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JPS61106538A (ja) * 1984-10-19 1986-05-24 ゼネカ・リミテッド アクリル酸誘導体、その製造法及びそれを含有する殺カビ組成物
JPH04288069A (ja) * 1990-10-02 1992-10-13 Roussel Uclaf 新規なベンゾフラン誘導体、その製造法、得られる新規な中間体及びその有害生物防除剤としての用途
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WO2021219775A1 (fr) * 2020-04-30 2021-11-04 Syngenta Crop Protection Ag Composés microbiocides
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