WO2015129773A1 - Dérivé d'isoxazole, et agent de lutte contre les maladies de plantes agricoles/horticoles - Google Patents

Dérivé d'isoxazole, et agent de lutte contre les maladies de plantes agricoles/horticoles Download PDF

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WO2015129773A1
WO2015129773A1 PCT/JP2015/055487 JP2015055487W WO2015129773A1 WO 2015129773 A1 WO2015129773 A1 WO 2015129773A1 JP 2015055487 W JP2015055487 W JP 2015055487W WO 2015129773 A1 WO2015129773 A1 WO 2015129773A1
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group
alkyl
substituents selected
optionally substituted
alkoxy
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PCT/JP2015/055487
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阿部　哲也
啓 川本
佐々木　隆行
富明 寺山
明弘 森脇
裕樹 林
山本　秀彦
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クミアイ化学工業株式会社
イハラケミカル工業株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—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
    • A01N47/12—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, neither directly attached to a ring nor the nitrogen atom being a member 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
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/48—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —S—C≡N groups
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • the present invention relates to a novel isoxazole derivative or a pesticide-acceptable salt thereof, an agricultural and horticultural plant disease control agent containing the derivative or a salt thereof as an active ingredient, and a production intermediate thereof.
  • Patent Document 1 describes an isoxazole derivative having a plant disease control effect
  • Patent Document 2 has a plant growth regulating action.
  • aromatic substituents at the 3-position of the isoxazole ring phenyl group, thienyl group, benzothienyl It is limited to a monocyclic or condensed structure such as a group, furyl group or pyridyl group, and does not describe a compound having a biaryl structure in which two aromatic rings are linked by a single bond.
  • Patent Document 3 describes a similar isoxazole derivative having a plant disease control effect, but does not describe a compound having a biaryl group as a 3-position substituent of the isoxazole ring.
  • control agents are used against crop diseases.
  • conventional control agents may have insufficient control efficacy, may be restricted in their use due to the emergence of drug-resistant pathogens, and may cause phytotoxicity or contamination of plants, Or, from the viewpoint of toxicity to human livestock and the effect on the environment, there are many things that are not necessarily satisfactory control agents. Therefore, there is a strong demand for the development of a control agent that has few such disadvantages and can be used safely.
  • X is a hydrogen atom; C 1 ⁇ C 6 alkyl group; C 1 ⁇ C 6 haloalkyl group; C 1 ⁇ C 6 optionally C 3 substituted by an alkyl group ⁇ C 6 cycloalkyl group; C 3 ⁇ C 6 halo cycloalkyl group; C 1 ⁇ C 6 optionally C 3 substituted by an alkyl group ⁇ C 6 cycloalkyl C 1 ⁇ C 6 alkyl group; C 3 ⁇ C 6 halocycloalkyl C 1 ⁇ C 6 alkyl group; C 1 -C 6 alkoxy C 1 -C 6 alkyl group; di (C 1 -C 6 alkoxy) C 1 -C 6 alkyl group; C 1 -C 6 haloalkoxy C 1 -C 6 alkyl group; C 3 -C 6 cyclo An alkoxy C 1 -C 6 alkyl group; a C 3 -C 6 halocycloalkoxy C 1
  • a group, a C 1 -C 6 alkylsulfonyl group or an OZ group, Z represents a C 2 -C 6 alkenyl group; a C 2 -C 6 alkynyl group; a C 1 -C 6 acyl group; a tri (C 1 -C 6 alkyl) silyl group; a C 1 -C 6 alkoxycarbonyl group; a carbamoyl group A C 1 -C 6 alkylaminocarbonyl group; a di (C 1 -C 6 alkyl) aminocarbonyl group; a (1-imidazolyl) carbonyl group; a C 1 -C 6 alkylsulfonyl group; a C 1 -C 6 haloalkylsulfonyl group; Dihydroxyphosphoryl group; or di (C 1 -C 6 alkoxy) phosphoryl group, Y 2 represents a hydrogen atom or a C 1 -C 6 alkyl group,
  • Q 2 in the general formula [I] may be substituted with one or more substituents selected from T; thiophene optionally substituted with one or more substituents selected from T; T A thiazole optionally substituted by one or more substituents selected from: isoxazole optionally substituted by one or more substituents selected from T; may be substituted by one or more substituents selected from T A good pyrazole; a pyridine optionally substituted by one or more substituents selected from T; a pyrimidine optionally substituted by one or more substituents selected from T; and one or more substituents selected from T
  • W 1 in the general formula [I] is a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group or a C 1 -C 6 haloalkoxy group.
  • the isoxazole derivative or the agrochemically acceptable salt thereof according to any one of (1) to (8).
  • An agricultural and horticultural fungicide comprising the isoxazole derivative according to any one of (1) to (9) or an agriculturally acceptable salt thereof as an active ingredient.
  • a plant disease control agent for agricultural and horticultural use comprising the isoxazole derivative according to any one of (1) to (9) above or an agriculturally acceptable salt thereof as an active ingredient.
  • the agent according to (10) or (11), wherein the disease-causing fungi are basidiomycetes, ascomycetes, imperfect fungi, oomycetes, and / or zygomycetes.
  • An agricultural and horticultural composition comprising the isoxazole derivative according to any one of (1) to (9) or a pesticide acceptable salt thereof, and a pesticide acceptable carrier.
  • An effective amount of the isoxazole derivative or the agricultural chemical acceptable salt thereof according to any one of (1) to (9) above is used as a useful plant, a part of the useful plant, or the useful plant grows.
  • a method of sterilizing the useful plant, comprising spraying to a place where the plant is located.
  • X is a hydrogen atom; C 1 ⁇ C 6 alkyl group; C 1 ⁇ C 6 haloalkyl group; C 1 ⁇ C 6 optionally C 3 substituted by an alkyl group ⁇ C 6 cycloalkyl group; C 3 ⁇ C 6 halo cycloalkyl group; C 1 ⁇ C 6 optionally C 3 substituted by an alkyl group ⁇ C 6 cycloalkyl C 1 ⁇ C 6 alkyl group; C 3 ⁇ C 6 halocycloalkyl C 1 ⁇ C 6 alkyl group; C 1 -C 6 alkoxy C 1 -C 6 alkyl group; di (C 1 -C 6 alkoxy) C 1 -C 6 alkyl group; C 1 -C 6 haloalkoxy C 1 -C 6 alkyl group; C 3 -C 6 cyclo An alkoxy C 1 -C 6 alkyl group; a C 3 -C 6 halocycloalkoxy C 1
  • Q 2 in the general formula [II] may be substituted with one or more substituents selected from T; thiophene optionally substituted with one or more substituents selected from T; T A thiazole optionally substituted by one or more substituents selected from: isoxazole optionally substituted by one or more substituents selected from T; may be substituted by one or more substituents selected from T A good pyrazole; a pyridine optionally substituted by one or more substituents selected from T; a pyrimidine optionally substituted by one or more substituents selected from T; and one or more substituents selected from T
  • the compound and the salt thereof according to any one of (22) to (25), which is a divalent group derived from a compound selected from the group consisting of pyrazines optionally substituted by .
  • W 2 in the general formula [II] is a halogen atom, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 1 to C 6 alkoxy group, or a C 1 to C 6 haloalkoxy group.
  • W 2 in the general formula [II] is a halogen atom, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 1 to C 6 alkoxy group, or a C 1 to C 6 haloalkoxy group.
  • X is a hydrogen atom; C 1 ⁇ C 6 alkyl group; C 1 ⁇ C 6 haloalkyl group; C 1 ⁇ C 6 optionally C 3 substituted by an alkyl group ⁇ C 6 cycloalkyl group; C 3 ⁇ C 6 halo Cycloalkyl group; C 1 -C 6 alkoxy C 1 -C 6 alkyl group; di (C 1 -C 6 alkoxy) C 1 -C 6 alkyl group; halogen atom; C 1 -C 6 alkoxy group; C 1 -C 6 haloalkoxy group; C 3 -C 6 cycloalkoxy group; C 3 -C 6 halocycloalkoxy group; cyano group; C 1 -C 6 alkylthio group; thiocyanato group; substituted by one or more substituents selected from T A pyridyl group which may be substituted; a furanyl group which may be substituted with one or more substituents
  • X in the general formula [III] is a hydrogen atom; a C 1 -C 6 alkyl group; a C 1 -C 6 haloalkyl group; a C 3 -C 6 cyclo group optionally substituted by a C 1 -C 6 alkyl group
  • the compound of the present invention is useful as an active ingredient of agricultural chemicals such as a plant disease control agent for agriculture and horticulture.
  • the plant disease control agent for agricultural and horticultural use containing the compound of the present invention exhibits an excellent control effect against a wide range of plant diseases caused by basidiomycetes, ascomycetes, imperfect fungi, oomycetes, zygomycetes, etc. Fungi that have acquired drug resistance can also be controlled.
  • the plant and disease control agent for agricultural and horticultural use containing the compound of the present invention is effective against cucumber gray mold, wheat rust, wheat leaf blight, and also against those fungi that have acquired drug resistance. It shows a sufficient control effect.
  • the halogen atom means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the notation such as C 1 to C 6 indicates that the number of carbon atoms of the subsequent substituent is 1 to 6 in this case.
  • the C 1 -C 6 alkyl group means a straight-chain or branched alkyl group having 1 to 6 carbon atoms unless otherwise specified, and includes, for example, methyl, ethyl, n-propyl, isopropyl, n -Butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3 -Dimethylbutyl, 2,2-dimethylbutyl, 2,
  • a C 1 -C 6 alkoxy group means a (C 1 -C 6 alkyl) -O— group in which the alkyl moiety has the above-mentioned meaning unless otherwise limited, and includes, for example, methoxy, ethoxy, n-propoxy , Isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1 , 2-dimethylpropoxy or n-hexyloxy.
  • the C 1 -C 6 haloalkyl group is a linear or branched haloalkyl group having 1 to 6 carbon atoms, which is substituted with 1 to 13 halogen atoms which are the same or different unless otherwise specified.
  • a C 1 -C 6 alkoxy C 1 -C 6 alkyl group means a (C 1 -C 6 alkoxy)-(C 1 -C 6 alkyl) -group in which the alkoxy part and the alkyl part have the above-mentioned meanings.
  • the di (C 1 -C 6 alkoxy) C 1 -C 6 alkyl group means that the alkoxy part and the alkyl part are as defined above (C 1 -C 6 alkoxy) 2- (C 1 -C 6 Alkyl)-group, and the two alkoxy groups are the same or different, and examples thereof include groups such as dimethoxymethyl, diethoxymethyl, ethoxy (methoxy) methyl, or 1,1-dimethoxyethyl.
  • the three or more C 1 ⁇ C 6 C 1 ⁇ C 6 alkyl group substituted with an alkoxy group a tri (C 1 ⁇ C 6 alkoxy) C 1 ⁇ C 6 alkyl group, tetra (C 1 ⁇ C 6 alkoxy) C 1 -C 6 alkyl group, penta (C 1 -C 6 alkoxy) C 1 -C 6 alkyl group and the like.
  • the C 3 -C 6 cycloalkyl group means a cycloalkyl group having 3 to 6 carbon atoms unless otherwise specified, and examples thereof include groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. .
  • the C 3 -C 6 halocycloalkyl group means a cycloalkyl group having 3 to 6 carbon atoms substituted with the same or different 1 to 11 halogen atoms unless otherwise limited, 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2,2-dichloro Cyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-diiodocyclopropyl, 1-fluorocyclobutyl, 2-fluorocyclobutyl, 3-fluorocyclobutyl 3,3-difluorocyclobutyl, heptafluorocyclobutyl, 2-chlorocyclobutyl, 3 Chloro
  • a C 3 -C 6 cycloalkyl C 1 -C 6 alkyl group means a cycloalkyl and an alkyl moiety as defined above (C 3 -C 6 cycloalkyl)-(C 1 -C 6 alkyl)
  • a group such as cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl, 1-cyclopropylpropyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, cyclobutylmethyl, 1-cyclobutylethyl, Mention may be made of groups such as cyclopentylmethyl or cyclohexylmethyl.
  • a C 3 -C 6 halocycloalkyl C 1 -C 6 alkyl group means that the halocycloalkyl and alkyl moieties are as defined above (C 3 -C 6 halocycloalkyl)-(C 1 -C 6 alkyl) - group, for example, 1-fluoro-cyclopropylmethyl, 2-fluoro cyclopropylmethyl, 2,2-difluoro cyclopropylmethyl, 1-chloro-cyclopropylmethyl, 2-chloro-cyclopropylmethyl, 2,2 Dichlorocyclopropylmethyl, 2,2-dibromocyclopropylmethyl, 2,2-diiodocyclopropylmethyl, 1- (1-fluorocyclopropyl) ethyl, 1- (1-chlorocyclopropyl) ethyl, 1- (2 , 2-Difluorocyclopropyl) ethyl, 2- (1-fluoro
  • a C 1 -C 6 haloalkoxy group means a (C 1 -C 6 haloalkyl) -O— group in which the haloalkyl moiety has the above-mentioned meaning, unless otherwise limited, for example, difluoromethoxy, trifluoromethoxy , Trichloromethoxy, tribromomethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 3,3,3-trifluoropropoxy, heptafluoro-2-propoxy, tri ( Mention may be made of groups such as (trifluoromethyl) methoxy, 3,3,3-trichloropropoxy or heptafluoropropoxy.
  • a C 1 -C 6 haloalkoxy C 1 -C 6 alkyl group means that the haloalkoxy and alkyl moieties are as defined above (C 1 -C 6 haloalkoxy)-(C 1 -C 6 alkyl).
  • the C 3 -C 6 cycloalkoxy group means a (C 3 -C 6 cycloalkyl) -O— group in which the cycloalkyl part has the above-mentioned meaning, for example, cyclopropoxy, cyclobutoxy, cyclopentyloxy or Mention may be made of groups such as cyclohexyloxy.
  • the C 3 -C 6 halocycloalkoxy group means a (C 3 -C 6 halocycloalkyl) -O— group in which the halocycloalkyl moiety has the above-mentioned meaning, for example, 2,2-difluorocyclo Propoxy, 2,2-dichlorocyclopropoxy, 3,3-difluorocyclobutoxy, 3,3-dichlorocyclobutoxy, 3-fluorocyclopentyloxy, 3,3-difluorocyclopentyloxy, nonafluorocyclopentyloxy, 3,3-dichloro Mention may be made of groups such as cyclopentyloxy, 4,4-difluorocyclohexyloxy or 4,4-dichlorocyclohexyloxy.
  • the C 3 -C 6 cycloalkoxy C 1 -C 6 alkyl group means (C 3 -C 6 cycloalkoxy)-(C 1 -C 6 alkyl) in which the cycloalkoxy part and the alkyl part have the above-mentioned meanings. ) — Group, for example, a group such as cyclopropoxymethyl, cyclobutoxymethyl, 1-cyclopropoxyethyl, 1-cyclobutoxyethyl or 1-cyclopropoxypropyl.
  • the C 3 -C 6 halocycloalkoxy C 1 -C 6 alkyl group means that the halocycloalkoxy moiety and the alkyl moiety have the above meaning (C 3 -C 6 halocycloalkoxy)-(C 1- C 6 alkyl) -group, for example 2,2-difluorocyclopropoxymethyl, 2,2-dichlorocyclopropoxymethyl, 3,3-difluorocyclobutoxymethyl, 3,3-dichlorocyclobutoxymethyl, 1- (2 , 2-difluorocyclopropoxy) ethyl or 1- (2,2-difluorocyclopropoxy) propyl.
  • the C 3 -C 6 cycloalkyl C 1 -C 6 alkoxy C 1 -C 6 alkyl group means that the cycloalkyl part, the alkoxy part and the alkyl part are as defined above (C 3 -C 6 cycloalkyl).
  • )-(C 1 -C 6 alkoxy)-(C 1 -C 6 alkyl) groups such as cyclopropylmethoxymethyl, cyclobutylmethoxymethyl, 2- (cyclopropylmethoxy) ethyl, 2- (cyclobutylmethoxy) Mention may be made of groups such as ethyl, 1- (cyclopropylmethoxy) ethyl or 1- (cyclobutylmethoxy) ethyl.
  • the C 3 -C 6 halocycloalkyl C 1 -C 6 alkoxy C 1 -C 6 alkyl group means that the halocycloalkyl part, alkoxy part and alkyl part have the above-mentioned meanings (C 3 -C 6 Halocycloalkyl)-(C 1 -C 6 alkoxy)-(C 1 -C 6 alkyl) groups such as 2,2-difluorocyclopropylmethoxymethyl, 2,2-dichlorocyclopropylmethoxymethyl, 3,3 -Groups such as difluorocyclobutylmethoxymethyl, 3,3-dichlorocyclobutylmethoxymethyl, 1- (2,2-difluorocyclopropylmethoxy) ethyl or 1- (3,3-difluorocyclobutylmethoxy) ethyl Can do.
  • the C 1 -C 6 alkoxy C 1 -C 6 alkoxy C 1 -C 6 alkyl group means that the alkoxy part and the alkyl part are as defined above (C 1 -C 6 alkoxy)-(C 1- C 6 alkoxy)-(C 1 -C 6 alkyl) groups such as (2-methoxyethoxy) methyl, (2-ethoxyethoxy) methyl, 2- (2-methoxyethoxy) ethyl, 1- (2-methoxy) Mention may be made of groups such as ethoxy) ethyl or 1- (2-methoxyethoxy) propyl.
  • the C 2 -C 6 alkenyl group means a straight or branched alkenyl group having 2 to 6 carbon atoms unless otherwise specified, and examples thereof include vinyl, 1-propenyl, isopropenyl, 2- Propenyl, 1-butenyl, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl, 3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1,3- Butadienyl, 1-pentenyl, 1-ethyl-2-propenyl, 2-pentenyl, 1-methyl-1-butenyl, 3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1-methyl-3-butenyl, 3-methyl-1-butenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2-but Nyl, 1,2-dimethyl-1-propen
  • the C 2 -C 6 alkynyl group means a straight-chain or branched alkynyl group having 2 to 6 carbon atoms unless otherwise specified, and includes, for example, ethynyl, 1-propynyl, 2-propynyl, -Butynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-ethyl-2-propynyl, 2-pentynyl, 3-pentynyl, 1-methyl-2-butynyl, 4-pentynyl 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-hexynyl, 1- (n-propyl) -2-propynyl, 2-hexynyl, 1-ethyl-2-butynyl, 3-hexynyl, -Methyl-2-pentynyl, 1-methyl-3-p
  • the C 2 -C 6 alkenyloxy C 1 -C 6 alkyl group means (C 2 -C 6 alkenyl) -O— (C 1 -C 6 alkyl) in which the alkenyl moiety and the alkyl moiety have the above-mentioned meanings.
  • ) -Group and examples thereof include 2-propenyloxymethyl, 3-butenyloxymethyl, 1- (2-propenyloxy) ethyl and 1- (2-propenyloxy) propyl.
  • the C 2 -C 6 alkynyloxy C 1 -C 6 alkyl group means (C 2 -C 6 alkynyl) -O— (C 1 -C 6 alkyl) in which the alkynyl moiety and the alkyl moiety are as defined above. ) -Group, such as 2-propynyloxymethyl, 3-butynyloxymethyl, 1- (2-propynyloxy) ethyl or 1- (2-propynyloxy) propyl.
  • a hydroxy C 1 -C 6 alkyl group means a HO— (C 1 -C 6 alkyl) -group in which the alkyl portion has the above meaning, such as hydroxymethyl, 1-hydroxyethyl, 2-hydroxy Mention may be made of groups such as ethyl, 1-hydroxypropyl, 1-hydroxybutyl or 2-hydroxypropan-2-yl.
  • a tri (C 1 -C 6 alkyl) silyl group means a (C 1 -C 6 alkyl) 3 —Si— group in which the alkyl portion has the above meaning, and the three alkyl groups are the same Or, differently, for example, groups such as trimethylsilyl, triethylsilyl, triisopropylsilyl, dimethylisopropylsilyl or tert-butyldimethylsilyl can be mentioned.
  • tri (C 1 ⁇ C 6 alkyl) silyloxy The C 1 ⁇ C 6 alkyl group, a tri (C 1 ⁇ C 6 alkyl) silyl moiety and the alkyl moiety is tri (C 1 ⁇ C the meaning of the 6 alkyl) silyl-O— (C 1 -C 6 alkyl) group, for example trimethylsilyloxymethyl, tert-butyldimethylsilyloxymethyl, triisopropylsilyloxymethyl, 1- (trimethylsilyloxy) -ethyl or 1- ( Mention may be made of groups such as tert-butyldimethylsilyloxy) -ethyl.
  • the 1,2,4-triazolyl C 1 -C 6 alkyl group means a 1,2,4-triazolyl- (C 1 -C 6 alkyl) group in which the alkyl portion has the above meaning, 1,2,4-triazol-1-yl) methyl group, 2- (1,2,4-triazol-1-yl) ethyl group, 1- (1,2,4-triazol-1-yl) ethyl, etc. Can be mentioned.
  • a C 2 -C 6 haloalkenyl group means a straight or branched alkenyl having 2 to 6 carbon atoms, which is substituted with the same or different 1 to 11 halogen atoms, unless otherwise specified.
  • a C 2 -C 6 haloalkynyl group is a linear or branched alkynyl group having 2 to 6 carbon atoms, which is substituted with the same or different 1 to 9 halogen atoms, unless otherwise specified.
  • a C 1 -C 6 alkoxycarbonyl group means a (C 1 -C 6 alkoxy) -C ( ⁇ O) — group in which the alkoxy moiety has the above meaning, such as methoxycarbonyl, ethoxycarbonyl, n There may be mentioned groups such as -propoxycarbonyl, isopropoxycarbonyl or tert-butoxycarbonyl.
  • the C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl group means that the alkoxycarbonyl moiety and the alkyl moiety have the above meanings (C 1 -C 6 alkoxycarbonyl)-(C 1 -C 6 alkyl). ) -Groups such as methoxycarbonylmethyl, 1- (methoxycarbonyl) ethyl or 2- (methoxycarbonyl) propan-2-yl.
  • a C 1 -C 6 alkylaminocarbonyl group means a (C 1 -C 6 alkyl) -NH—C ( ⁇ O) — group in which the alkyl portion has the above meaning, such as methylaminocarbonyl, Mention may be made of groups such as ethylaminocarbonyl, n-propylaminocarbonyl or isopropylaminocarbonyl.
  • the di (C 1 -C 6 alkyl) aminocarbonyl group means (C 1 -C 6 alkyl)- ⁇ (C 1 -C 6 alkyl)- ⁇ N—C in which the alkyl portion has the above-mentioned meaning.
  • ( ⁇ O) — group the two alkyl groups being the same or different, for example a group such as dimethylaminocarbonyl, diethylaminocarbonyl, di (n-propyl) aminocarbonyl or N-ethyl-N-methylaminocarbonyl Can be mentioned.
  • the C 1 -C 6 acyl group is a straight chain having 1 to 6 carbon atoms derived from formic acid or a linear or branched alkanecarboxylic acid having 1 to 5 carbon atoms.
  • it represents a branched acyl group, and examples include groups such as formyl, acetyl, propionyl, isobutyryl, and pivaloyl.
  • a C 1 -C 6 alkoxyimino group means a (C 1 -C 6 alkoxy) -N ⁇ CH— group (the rightmost CH— is attached for the purpose of explanation) where the alkoxy moiety has the above-mentioned meaning .). If this is shown in more detail by the chemical structural formula, it becomes an R 2 O—N ⁇ C (R 1 ) — group.
  • R 1 and R 2 are the same or different and each represents a hydrogen atom or a C 1 -C 6 alkyl group. Examples of these groups include groups such as methoxyimino, ethoxyimino, n-propoxyimino, and isopropoxyimino.
  • the C 1 -C 6 alkylamino group means a (C 1 -C 6 alkyl) -NH- group in which the alkyl portion has the above meaning, such as methylamino, ethylamino or n-propylamino.
  • the group can be mentioned.
  • the di (C 1 -C 6 alkyl) amino group means a (C 1 -C 6 alkyl)- ⁇ (C 1 -C 6 alkyl)- ⁇ N- group in which the alkyl portion has the above-mentioned meaning.
  • the two alkyl groups are the same or different and can include groups such as dimethylamino, diethylamino, di (n-propyl) amino or N-ethyl-N-methylamino.
  • an amino C 1 -C 6 alkyl group means an H 2 N— (C 1 -C 6 alkyl) -group in which the alkyl portion has the above meaning, such as aminomethyl, 1-aminoethyl, 2 Examples include groups such as -aminoethyl, 1-aminopropyl, 1-aminobutyl or 2-aminopropan-2-yl.
  • a C 1 -C 6 acylamino group means a (C 1 -C 6 acyl) -NH— group in which the acyl moiety has the above meaning, for example, formylamino, acetylamino, propionylamino, butyrylamino or iso Examples include groups such as butyrylamino.
  • the di (C 1 -C 6 acyl) amino group is a (C 1 -C 6 acyl)- ⁇ (C 1 -C 6 acyl)- ⁇ N- group wherein the acyl moiety has the above-mentioned meaning.
  • the two acyl groups are the same or different and can include groups such as diformylamino, diacetylamino, dipropionylamino, or N-acetyl-N-propionylamino.
  • the C 1 -C 6 acylamino C 1 -C 6 alkyl group means a (C 1 -C 6 acylamino)-(C 1 -C 6 alkyl) -group in which the acylamino moiety and the alkyl moiety are as defined above.
  • examples include groups such as 1- (formylamino) ethyl, 1- (acetylamino) ethyl, 1- (propionylamino) ethyl, 1- (butyrylamino) ethyl, 1- (isobutyrylamino) ethyl, and the like. Can do.
  • the C 1 -C 6 haloalkylcarbonylamino C 1 -C 6 alkyl group means that the haloalkyl part and the alkyl part are as defined above (C 1 -C 6 haloalkyl) -C ( ⁇ O) —NH—.
  • (C 1 -C 6 alkyl) -group such as 1- (trifluoroacetylamino) ethyl, 1- (chlorodifluoroacetylamino) ethyl or 1- (pentafluoropropionylamino) ethyl. it can.
  • a C 1 -C 6 alkylsulfonylamino group means a (C 1 -C 6 alkyl) -SO 2 —NH— group in which the alkyl portion has the above meaning, for example, methylsulfonylamino, ethylsulfonylamino , N-propylsulfonylamino, isopropylsulfonylamino, tert-butylsulfonylamino and the like.
  • the C 1 -C 6 haloalkylsulfonylamino group means a (C 1 -C 6 haloalkyl) -SO 2 —NH— group in which the haloalkyl moiety has the above meaning, such as fluoromethylsulfonylamino, difluoromethyl Sulfonylamino, trifluoromethylsulfonylamino, chloromethylsulfonylamino, trichloromethylsulfonylamino, 2,2,2-trifluoroethylsulfonylamino, 2,2-difluoroethylsulfonylamino or 3,3,3-trifluoropropylsulfonyl Mention may be made of groups such as amino.
  • a cyano C 1 -C 6 alkyl group means an NC- (C 1 -C 6 alkyl)-group in which the alkyl portion has the above-mentioned meaning, for example, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1 Mention may be made of groups such as -cyanopropyl, 1-cyanobutyl or 2-cyanopropan-2-yl.
  • the C 1 -C 6 alkylthio group means a (C 1 -C 6 alkyl) -S— group in which the alkyl portion has the above meaning, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n Mention may be made of groups such as -butylthio, isobutylthio, sec-butylthio or tert-butylthio.
  • a C 1 -C 6 alkylsulfinyl group means a (C 1 -C 6 alkyl) -SO— group in which the alkyl portion has the above-mentioned meaning, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, Mention may be made of groups such as isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl or tert-butylsulfinyl.
  • the C 1 -C 6 alkylsulfonyl group means a (C 1 -C 6 alkyl) -SO 2 -group in which the alkyl portion has the above meaning, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl. , Isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl and the like.
  • the C 1 -C 6 haloalkylthio group means a (C 1 -C 6 haloalkyl) -S— group in which the haloalkyl moiety has the above-mentioned meaning, for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, trichloro Methylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, 2,2,2-trichloroethylthio, 3,3,3-trifluoropropylthio, heptafluoropropylthio, 1,1,1, Mention may be made of groups such as 3,3,3-hexafluoropropan-2-ylthio, heptafluoropropan-2-ylthio or 4,4,4-trifluorobutylthio.
  • a C 1 -C 6 haloalkylsulfinyl group means a (C 1 -C 6 haloalkyl) -SO— group in which the haloalkyl moiety has the above meaning, such as difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethyl Mention may be made of groups such as sulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, pentafluoroethylsulfinyl, heptafluoropropylsulfinyl or heptafluoropropan-2-ylsulfinyl.
  • a C 1 -C 6 haloalkylsulfonyl group means a (C 1 -C 6 haloalkyl) -SO 2 — group in which the haloalkyl moiety has the above-mentioned meaning, such as difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloro And groups such as methylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, 3,3,3-trifluoropropylsulfonyl or heptafluoropropan-2-ylsulfonyl it can.
  • a C 1 -C 6 alkylsulfonyloxy group means a (C 1 -C 6 alkyl) -SO 2 —O— group in which the alkyl portion has the above-mentioned meaning, such as methylsulfonyloxy, ethylsulfonyloxy , N-propylsulfonyloxy, isopropylsulfonyloxy, n-butylsulfonyloxy, isobutylsulfonyloxy, sec-butylsulfonyloxy, tert-butylsulfonyloxy and the like.
  • the C 1 -C 6 haloalkylsulfonyloxy group means a (C 1 -C 6 haloalkyl) -SO 2 —O— group in which the haloalkyl moiety has the above meaning, such as difluoromethylsulfonyloxy, trifluoro Methylsulfonyloxy, trichloromethylsulfonyloxy, 2,2,2-trifluoroethylsulfonyloxy, 2,2,2-trichloroethylsulfonyloxy, 3,3,3-trifluoropropylsulfonyloxy or heptafluoropropane-2- Examples include ylsulfonyloxy groups.
  • the di (C 1 -C 6 alkoxy) phosphoryl group means (C 1 -C 6 alkoxy)- ⁇ (C 1 -C 6 alkoxy)- ⁇ P ( ⁇ O
  • the two alkoxy groups are the same or different and include, for example, groups such as dimethoxyphosphoryl, diethoxyphosphoryl, di (n-propyl) phosphoryl or P-methoxy-P-ethoxyphosphoryl. .
  • a divalent group derived from a compound such as benzene or thiophene is a divalent group formed by removing two hydrogen atoms bonded to a ring in a compound such as benzene or thiophene.
  • the divalent group derived from benzene may be any of an o-phenylene group, an m-phenylene group, and a p-phenylene group.
  • thiophene and other heterocyclic compounds there can be mentioned a divalent group formed by removing two hydrogen atoms bonded to the heterocyclic ring.
  • the position of the two hydrogen atoms to be removed may be any position on the heterocyclic ring.
  • a hydrogen atom bonded to a hetero atom such as imidazole or 1,2,4-triazole
  • one of the two hydrogen atoms removed is bonded to the hetero atom. It may be a hydrogen atom.
  • a phenyl group, benzene, and a heterocyclic compound or a group derived therefrom are named according to a common nomenclature in the field of organic chemistry. These phenyl groups, benzene, and heterocyclic compounds or groups derived therefrom may be substituted with various substituents. Examples of the substituent in the present invention include a group selected from the following substituent group.
  • Substituent group W 1 includes halogen atom, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 -C 6 alkylthio Group, C 1 -C 6 alkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylthio group, C 1 -C 6 haloalkylsulfinyl group, C 1 -C 6 haloalkylsulfonyl group, cyano group, Examples thereof include a substituent selected from the group consisting of a nitro group and a di (C 1 -C 6 alkyl) amino group.
  • Substituent group W 2 includes halogen atom, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 -C 6 alkylthio Group, C 1 -C 6 alkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylthio group, C 1 -C 6 haloalkylsulfinyl group, C 1 -C 6 haloalkylsulfonyl group, cyano group, And a substituent selected from the group consisting of nitro groups.
  • Substituent group W 3 is selected from the group consisting of halogen atoms, C 1 -C 6 alkyl groups, C 1 -C 6 haloalkyl groups, C 1 -C 6 alkoxy groups, and C 1 -C 6 haloalkoxy groups.
  • a substituent is mentioned.
  • Examples of the substituent group T include a substituent selected from the group consisting of a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, and a C 1 -C 6 alkoxy group.
  • Substituent group U is selected from the group consisting of halogen atoms, C 1 -C 6 alkyl groups, C 1 -C 6 haloalkyl groups, C 1 -C 6 alkoxy groups, mercapto groups, and C 1 -C 6 alkylthio groups.
  • the substituent which can be mentioned is mentioned. These substituents have been described above. These substituents may be one, or may be two or more substituents which are the same or different.
  • a preferred substituent group W 1 includes a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, and a C 1 -C 6 haloalkoxy group.
  • a halogen atom is more preferable.
  • the preferred substituent group W 2 includes a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, and a C 1 -C 6 haloalkoxy group.
  • a halogen atom is more preferable.
  • the preferred substituent group W 3 includes a substituent selected from the group consisting of a halogen atom, a C 1 -C 6 alkyl group, and a C 1 -C 6 haloalkyl group, and more preferably a halogen atom. Can be mentioned.
  • preferable T includes a halogen atom, a C 1 -C 6 alkyl group, and a C 1 -C 6 haloalkyl group, more preferably a halogen atom.
  • preferred X is a C 1 -C 6 alkyl group; a C 1 -C 6 haloalkyl group; and a C 1 -C 6 alkyl group which may be substituted.
  • More preferable X includes a group selected from the group consisting of a C 1 -C 6 alkyl group; a C 1 -C 6 haloalkyl group; and a C 1 -C 6 alkoxy C 1 -C 6 alkyl group.
  • Preferred X in the general formula [III] is a hydrogen atom; a C 1 -C 6 alkyl group; a C 1 -C 6 haloalkyl group; a C 3 -C 6 cyclo group optionally substituted by a C 1 -C 6 alkyl group.
  • More preferable X includes a group selected from the group consisting of a C 1 -C 6 alkyl group; a C 1 -C 6 haloalkyl group; and a C 1 -C 6 alkoxy C 1 -C 6 alkyl group.
  • Preferable Q 1 in the general formula [I] of the present invention includes a phenyl group which may be substituted with W 1 ; or a pyrazolyl group which may be substituted with one or more substituents selected from T.
  • Preferable Q 1 in the general formula [II] of the present invention includes a phenyl group which may be substituted with W 2 ; or a pyrazolyl group which may be substituted with one or more substituents selected from T.
  • Q 2 is benzene optionally substituted by one or more substituents selected from T; one or more substituents selected from T A thiazole optionally substituted by one or more substituents selected from T; an isoxazole optionally substituted by one or more substituents selected from T; one selected from T Pyrazole optionally substituted with one or more substituents; Pyridine optionally substituted with one or more substituents selected from T; Pyrimidine optionally substituted with one or more substituents selected from T; and T And a divalent group derived from a compound selected from the group consisting of pyrazine which may be substituted with one or more substituents selected from the above.
  • Q 2 is benzene optionally substituted by one or more substituents selected from T; thiazole optionally substituted by one or more substituents selected from T; one or more selected from T A group of pyridine which may be substituted by one or more substituents; a pyrimidine which may be substituted by one or more substituents selected from T; and a pyrazine which may be substituted by one or more substituents selected from T And a divalent group derived from a compound selected from:
  • Preferable Q 3 in the general formula [I] of the present invention is a pyridyl group optionally substituted by one or more substituents selected from U; or substituted by one or more substituents selected from U.
  • a good pyrimidinyl group may be mentioned.
  • Preferred Q 3 in the general formula [II] of the present invention is a pyridyl group which may be substituted with one or more substituents selected from U; or substituted with one or more substituents selected from U.
  • a good pyrimidinyl group may be mentioned.
  • More preferable Q 3 includes a 3-pyridyl group; or a 5-pyrimidinyl group.
  • Y 1 in the general formula [I] of the present invention includes a hydroxyl group or a C 1 -C 6 alkoxy group.
  • Y 1 and Y 2 may form C ⁇ C (R 3 ) R 4 together with the carbon atom to which they are bonded, where R 3 and R 2 4 are the same or different and each represents a hydrogen atom or a C 1 -C 5 alkyl group.
  • the total number of carbon atoms of R 3 and R 4 is preferably 5 or less.
  • Examples of C ⁇ C (R 3 ) R 4 groups include C ⁇ CH 2 , C ⁇ CH—CH 3 and the like.
  • the pesticidally acceptable salt and salt are a nitrogen-containing heterocyclic group, a hydroxyl group, a carboxyl in the compound of the present invention represented by the general formula [I], general formula [II] and general formula [III].
  • a group or amino group or the like is a salt of these with a metal or an organic base, or a salt of a mineral acid or an organic acid
  • the metal is an alkali metal such as sodium or potassium, or magnesium or calcium Alkaline earth metals such as triethylamine or diisopropylamine as organic bases, hydrochloric acid, hydrobromic acid or sulfuric acid as mineral acids, and organic acids
  • alkali metal such as sodium or potassium
  • triethylamine or diisopropylamine such as triethylamine or diisopropylamine as organic bases, hydrochloric acid, hydrobromic acid or sulfuric acid as mineral acids, and organic acids
  • the compounds included in the isoxazole derivative of the present invention may have geometrical isomers of E-form and Z-form depending on the type of substituent, but the present invention includes these E-form, Z-form, Or a mixture containing E-form and Z-form in any ratio.
  • the compounds included in the present invention may have optical isomers resulting from the presence of one or more asymmetric carbon atoms and asymmetric sulfur atoms. Body, racemate or diastereomer.
  • the compound of the present invention represented by the general formula [I] can be produced according to the production methods shown below, but is not limited to these methods.
  • a compound represented by the general formula [I-1] and “compound [I-1]” are agreed.
  • the compound represented by the general formula [I-1] can be produced, for example, using the compound represented by the general formula [II] according to the method consisting of the reaction formulas exemplified below.
  • the compound represented by the general formula [I-1] can be produced by reacting the compound represented by the general formula [II] with an appropriate reducing agent in an appropriate solvent.
  • the amount of the reducing agent used in this reaction may be appropriately selected from the range of usually 0.25 to 5 mol, preferably 0.25 to 2.0 mol, per 1 mol of compound [II].
  • Examples of reducing agents that can be used in this reaction include alkali metal salts of borohydride compounds such as sodium borohydride, lithium borohydride, lithium triethylborohydride; borane-tert-butylamine complex, borane-dimethylsulfide complex, etc.
  • organic Lewis bases such as lithium aluminum hydride, alkali metal hydride compounds such as sodium bis (2-methoxyethoxy) aluminum hydride, or organic aluminum hydride compounds such as diisobutylaluminum hydride. it can.
  • solvents such as diethyl ether, tetrahydrofuran, and 1,4-dioxane
  • aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene
  • Halogenated hydrocarbons alcohols such as methanol, ethanol and 2-propanol
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane
  • water or a mixed solvent thereof water or a mixed solvent thereof.
  • the solvent is used in an amount of 0.1 to 100 liters, preferably 0.3 to 20 liters, per 1 mol of compound [II].
  • the reaction temperature of this reaction may be selected from the range of any temperature from ⁇ 70 ° C. to the reflux temperature in the reaction system, preferably in the range of 0 ° C. to 60 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 10 minutes to 20 hours.
  • the compound [I-1] can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating. Further, after completion of the reaction, compound [I-1] may be isolated by performing an operation such as adding acetone to decompose excess reducing agent and then washing the mixture obtained by concentration. it can. The isolated compound [I-1] can be further purified by column chromatography, recrystallization or the like, if necessary.
  • the compound represented by the general formula [I-2] can be produced, for example, using the compound represented by the general formula [IV] according to the method consisting of the reaction formulas exemplified below.
  • the compound represented by the general formula [I-2] is produced by reacting the compound [IV] with a metal or organometallic compound in an appropriate solvent and then reacting with the compound [V].
  • Compound [IV] is a method described in J. Fluorine. Chem., Vol. 127, p. 880 (2006) and Russ. Chem. Bull., Vol. 51, p. 1270 (2002) or a method thereof. It can be manufactured according to. Examples of the metal that can be used in this reaction include alkali metals such as lithium, sodium, and potassium; alkaline earth metals such as magnesium.
  • organometallic compound examples include alkyllithiums such as n-butyllithium; Grignard reagents such as isopropylmagnesium bromide.
  • the amount of the metal or organometallic compound used in this reaction may be appropriately selected from the range of 1 to 3 mol, preferably 1.0 to 1.5 mol, relative to 1 mol of compound [IV]. is there.
  • the amount of [V] used in this reaction may be appropriately selected from the range of 1 to 5 mol, preferably 1.0 to 2.0 mol, per 1 mol of compound [IV].
  • the solvent that can be used in this reaction include ethers such as diethyl ether, tetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; and aliphatic carbonization such as pentane, hexane, cyclohexane, and heptane. Hydrogen, these mixed solvents, etc. can be mentioned.
  • the solvent is used in an amount of 0.1 to 100 liters, preferably 0.3 to 10 liters, per 1 mol of compound [IV].
  • the reaction temperature for this reaction may be selected usually from an arbitrary temperature range from ⁇ 70 ° C. to the reflux temperature in the reaction system, preferably in the range of ⁇ 70 ° C. to 50 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 6 hours.
  • compound [I-2] can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating.
  • the isolated compound [I-2] can be further purified by column chromatography, recrystallization or the like, if necessary.
  • the compound represented by the general formula [I-2] can also be produced according to the method consisting of the reaction formula illustrated below using, for example, the compound represented by the general formula [II].
  • M 1 represents an alkali metal or an alkaline earth metal, lithium as a preferable alkali metal, and magnesium as a preferable alkaline earth metal.
  • X, Y 2 , Q 1 , Q 2 and Q 3 has the same meaning as described above.
  • the compound represented by the general formula [I-2] is produced by reacting the compound [II] and the compound [VI] in an appropriate solvent in the presence or absence of an appropriate lanthanoid salt. can do.
  • the amount of [VI] used in this reaction may be appropriately selected from the range of 1 to 5 mol, preferably 1.0 to 3.0 mol, per 1 mol of compound [II].
  • the solvent that can be used in this reaction include those similar to those in Production Method 2.
  • the solvent is used in an amount of 0.1 to 100 liters, preferably 0.3 to 10 liters, per 1 mol of compound [II].
  • lanthanoid salts that can be used in this reaction include cerium salts such as cerium chloride.
  • the amount of the lanthanoid salt used is 1 to 5 mol, preferably 1.0 to 2.0 mol, per 1 mol of compound [II].
  • the reaction temperature of this reaction may be usually selected from an arbitrary temperature range from ⁇ 70 ° C. to the reflux temperature in the reaction system, and preferably from ⁇ 70 ° C. to room temperature.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 6 hours.
  • compound [I-2] can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating.
  • the isolated compound [I-2] can be further purified by column chromatography, recrystallization or the like, if necessary.
  • the compound represented by the general formula [I-3] can be produced, for example, using the compound represented by the general formula [I-2] according to the method consisting of the reaction formulas exemplified below. it can.
  • L 1 is a halogen atom, a C 1 -C 6 alkylsulfonyloxy group, a C 1 -C 6 haloalkylsulfonyloxy group, a phenylsulfonyloxy group, a p-toluenesulfonyloxy group, a cyano group or a 1-imidazolyl group.
  • X, Y 2 , Q 1 , Q 2 , Q 3 and Z have the same meaning as described above.) That is, the compound represented by the general formula [I-3] is obtained by reacting the compound [I-2] and the compound [VII] in an appropriate solvent in the presence or absence of an appropriate base. Can be manufactured.
  • the amount of compound [VII] used in this reaction may be appropriately selected from the range of usually 1 to 10 mol, preferably 1 to 3 mol, relative to 1 mol of compound [I-2].
  • the solvent that can be used in this reaction include ethers such as diethyl ether, tetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; dichloromethane, chloroform, 1,2-dichloroethane, and the like.
  • Halogenated hydrocarbons such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; nitriles such as acetonitrile and propionitrile And aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine and picoline; water or a mixed solvent thereof.
  • the amount of the solvent to be used is 0.1 to 100 liters, preferably 0.5 to 20 liters, per 1 mol of compound [I-2].
  • Examples of the base that can be used in this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide, sodium carbonate, potassium carbonate and the like.
  • Inorganic bases such as alkali metal carbonates, alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxide, sodium ethoxide, Metal salts of alcohols such as potassium tert-butoxide or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene, etc.
  • Organic bases etc. can be mentioned.
  • the amount of the base used may be appropriately selected from the range of 1 to 10 mol, preferably 1 to 3 mol, relative to 1 mol of compound [I-2].
  • the reaction temperature of this reaction may be selected from the range of any temperature from 0 ° C. to the reflux temperature in the reaction system, preferably 0 ° C. to 100 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 12 hours.
  • the compound [I-3] can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating.
  • the isolated compound [I-3] can be further purified by column chromatography, recrystallization or the like, if necessary.
  • Manufacturing method 5> the compound represented by the general formula [I-4] can be produced, for example, using the compound represented by the general formula [I-1] according to the method consisting of the reaction formulas exemplified below. it can.
  • the compound represented by the general formula [I-4] is obtained by reacting the compound [I-1] with an appropriate halogenating agent in an appropriate solvent in the presence or absence of an appropriate base.
  • the amount of the halogenating agent used in this reaction may be appropriately selected from the range of usually 1 to 20 mol, preferably 1 to 10 mol, relative to 1 mol of compound [I-1].
  • Examples of the halogenating agent that can be used in this reaction include thionyl chloride, phosphorus pentachloride, thionyl bromide, phosphorus tribromide, and the like.
  • a sulfonylating agent such as methanesulfonyl chloride can also be used in this reaction.
  • the solvent that can be used in this reaction include ethers such as diethyl ether, tetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; dichloromethane, chloroform, 1,2-dichloroethane, and the like.
  • Halogenated hydrocarbons such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; nitriles such as acetonitrile and propionitrile And aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane, or a mixed solvent thereof.
  • the amount of the solvent to be used is 0.1 to 100 liters, preferably 0.5 to 10 liters, per 1 mol of compound [I-1].
  • Examples of the base that can be used in this reaction include organic compounds such as triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, and 1,8-diazabicyclo [5.4.0] -7-undecene.
  • Examples include bases.
  • the amount of the base used may be appropriately selected from the range of 0 to 20 mol, preferably 0 to 5 mol, relative to 1 mol of compound [I-1].
  • the reaction temperature of this reaction may be usually selected from an arbitrary temperature range from 0 ° C. to the reflux temperature in the reaction system, preferably in the range of room temperature to 150 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 30 minutes to 24 hours.
  • the compound [I-4] can be isolated by pouring the reaction mixture into water, extracting the mixture with an organic solvent, and concentrating the mixture. The isolated compound [I-4] can be further purified by column chromatography, recrystallization or the like, if necessary.
  • Manufacturing method 6> the compound represented by the general formula [I-5] can be produced, for example, using the compound represented by the general formula [I-4] according to the method consisting of the reaction formulas exemplified below. it can.
  • the compound represented by the general formula [I-5] can be produced by reacting the compound [I-4] and the compound [VIII] in an appropriate solvent.
  • the amount of compound [VIII] used in this reaction may be appropriately selected from the range of usually 1 to 50 mol, preferably 1 to 20 mol, per 1 mol of compound [I-4].
  • Examples of the solvent that can be used in this reaction include aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; pentane, hexane, cyclohexane, heptane, and the like. Aliphatic hydrocarbons, or a mixed solvent thereof.
  • the amount of the solvent to be used is 0.1 to 100 liters, preferably 0.5 to 20 liters, per 1 mol of compound [I-4].
  • the reaction temperature of this reaction may be usually selected from the range of any temperature from room temperature to the reflux temperature in the reaction system, preferably in the range of room temperature to 150 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 1 to 24 hours.
  • compound [I-5] can be isolated by carefully pouring water into the reaction mixture, extracting with an organic solvent, and then concentrating.
  • sodium sulfate decahydrate is added to decompose excess [VIII], and then the organic layer obtained by separating the precipitated metal salt is concentrated. To isolate compound [I-5].
  • the isolated compound [I-5] can be further purified by column chromatography, recrystallization or the like, if necessary.
  • Manufacturing method 7> Among the compounds of the present invention, the compound represented by the general formula [I-6] can be produced, for example, using the compound represented by the general formula [I-7] according to the method consisting of the reaction formulas exemplified below. it can.
  • the compound represented by the general formula [I-6] is an appropriate combination of the compound [I-7] and the compound [IX] or a mineral acid salt of the compound [IX] such as hydrochloric acid or an organic acid salt such as acetic acid.
  • a suitable solvent in the presence or absence of a suitable acid.
  • the amount of compound [IX] used in this reaction may be appropriately selected from the range of usually 1 to 10 mol, preferably 1 to 3 mol, relative to 1 mol of compound [I-7].
  • solvents such as diethyl ether, tetrahydrofuran and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; N, N-dimethylformamide, Aprotic polar solvents such as N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide and sulfolane; Nitriles such as acetonitrile and propionitrile; Methanol, ethanol and 2-propanol Alcohols such as dichloromethane; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine and picoline; water, Alternatively, a mixed solvent thereof or the like can
  • the solvent is used in an amount of 0.1 to 100 liters, preferably 0.3 to 10 liters, per 1 mol of compound [XIII].
  • the acid that can be used in this reaction include mineral acids such as hydrochloric acid, hydrobromic acid, and sulfuric acid, or organic acids such as formic acid, acetic acid, methanesulfonic acid, 4-toluenesulfonic acid, and trifluoromethanesulfonic acid.
  • the amount of the acid used may be appropriately selected from the range of 0.01 to 5 mol, preferably 0.05 to 1.5 mol, per 1 mol of compound [XVI].
  • the reaction temperature of this reaction may be usually selected from the range of any temperature from room temperature to the reflux temperature in the reaction system, preferably in the range of room temperature to 150 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 1 to 120 hours.
  • the compound [I-6] can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating. The isolated compound [I-6] can be further purified by column chromatography, recrystallization or the like, if necessary.
  • the compound represented by the general formula [I-8] can be produced, for example, using the compound represented by the general formula [I-9] according to the method consisting of the reaction formulas exemplified below. it can.
  • the compound represented by the general formula [I-8] is obtained by reacting the compound [I-9] with an appropriate dehydrating agent in an appropriate solvent in the presence or absence of an appropriate base.
  • the amount of the dehydrating agent used in this reaction may be appropriately selected from the range of usually 1-30 mol, preferably 1-10 mol, per 1 mol of compound [I-9].
  • Examples of the solvent that can be used in this reaction include those similar to Production Method 5.
  • the solvent is used in an amount of 0.1 to 100 liters, preferably 0.3 to 20 liters, per 1 mol of compound [II].
  • dehydrating agents examples include halogenating agents such as thionyl chloride and phosphorus oxychloride; mineral acids such as hydrochloric acid and sulfuric acid; formic acid, acetic acid, methanesulfonic acid, 4-toluenesulfonic acid, trifluoromethanesulfonic acid, and the like.
  • Organic acids or sulfonylating agents such as methanesulfonyl chloride.
  • the base examples include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide, sodium carbonate, potassium carbonate and the like.
  • Inorganic bases such as alkali metal carbonates, alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal salts of alcohols such as sodium methoxide, sodium ethoxide and potassium tert-butoxide, or triethylamine, N , N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, and organic bases such as 1,8-diazabicyclo [5.4.0] -7-undecene.
  • the amount of the base used may be appropriately selected from the range of 0 to 10 mol, preferably 0 to 5 mol, relative to 1 mol of the dehydrating agent.
  • the reaction temperature of this reaction may be usually selected from the range of any temperature from 0 ° C.
  • the compound [I-8] can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating. The isolated compound [I-8] can be further purified by column chromatography, recrystallization or the like, if necessary.
  • a compound represented by the general formula [II] is produced according to a method consisting of the reaction formula illustrated below using, for example, a compound represented by the general formula [X] or the general formula [XI]. be able to.
  • the compound represented by the general formula [II] is produced by reacting the compound [X] or the compound [XI] with the compound [XII] in the presence of a suitable base in a suitable solvent.
  • Compound [X] can be produced according to the method described in International Publication Patent Publication No. WO2007 / 067836 or a method thereof.
  • Compound [XI] can be produced according to the method described in J. Org. Chem., Vol. 67, p.3149 (2002) or according to the method.
  • the amount of compound [XII] used in this reaction may be appropriately selected from the range of usually 0.5 to 2 moles relative to 1 mole of compound [X] or compound [XI], preferably 0.8 to 1.2 moles.
  • the solvent that can be used in this reaction include ethers such as diethyl ether, tetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; dichloromethane, chloroform, 1,2-dichloroethane, and the like.
  • Halogenated hydrocarbons such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; methanol, ethanol, 2-propanol, etc.
  • Alcohols such as pentane, hexane, cyclohexane and heptane; esters such as ethyl acetate; water or a mixed solvent thereof.
  • the amount of the solvent to be used is 0.1 to 100 liters, preferably 0.5 to 10 liters, per 1 mol of compound [VIII] or compound [IX].
  • Examples of the base that can be used in this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide, sodium carbonate, potassium carbonate and the like.
  • Inorganic bases such as alkali metal carbonates, alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxide, sodium ethoxide, Metal salts of alcohols such as potassium tert-butoxide or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene, etc.
  • Organic bases etc. can be mentioned.
  • the amount of the base used may be appropriately selected from the range of 1 to 10 mol, preferably 1 to 5 mol, relative to 1 mol of compound [XII].
  • the reaction temperature of this reaction may be selected from the range of any temperature usually from room temperature to the reflux temperature in the reaction system, preferably in the range of room temperature to 120 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 30 minutes to 24 hours.
  • the compound [II] can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating.
  • the isolated compound [II] can be further purified by column chromatography, recrystallization or the like, if necessary.
  • the compound represented by the general formula [III] can be produced, for example, using the compound represented by the general formula [XIII] according to the method consisting of the reaction formulas exemplified below.
  • the compound represented by the general formula [III] can be produced by reacting the compound [XIII] with an appropriate reducing agent in an appropriate solvent.
  • Compound [XIII] can be produced according to the method described in J. Chem. Soc., P. 5976 (1965) or according to the method.
  • Examples of the reducing agent that can be used in this reaction include reducing agents such as alkali metal salts of aluminum hydride compounds such as sodium bis (2-methoxyethoxy) aluminum hydride or organic aluminum hydride compounds such as diisobutylaluminum hydride. Can do.
  • the amount of the reducing agent used may be appropriately selected from the range of usually 0.5 to 2 mol, preferably 1.0 to 1.5 mol, per 1 mol of compound [XIII].
  • Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, tetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; dichloromethane, chloroform, 1,2-dichloroethane, and the like. And halogenated hydrocarbons; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; or a mixed solvent thereof.
  • the amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 20 liters, per 1 mol of compound [XIII].
  • the reaction temperature of this reaction may be usually selected from an arbitrary temperature range from ⁇ 70 ° C. to the reflux temperature in the reaction system, and preferably from ⁇ 70 ° C. to room temperature.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 6 hours.
  • compound [III] can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating.
  • the isolated compound [III] can be further purified by column chromatography, recrystallization or the like, if necessary.
  • Step 1 The compound represented by the general formula [XIV] is obtained by combining the compound [XV] and hydroxylamine or a mineral acid salt of hydroxylamine such as hydrochloric acid or sulfuric acid in the presence or absence of a suitable base. It can manufacture by making it react.
  • the compound [XV] is described in International Patent Publication No. WO2010 / 115736, International Publication Patent Publication No. WO2008 / 031501, Syn. Lett., P.1172 (2000) or International Publication Patent Publication No. WO2014 / 172190. It can manufacture according to the method or its method.
  • the amount of hydroxylamine or a salt thereof used in this reaction may be appropriately selected from the range of 1 to 5 mol, preferably 1.0 to 2.0 mol, per 1 mol of compound [XV].
  • the solvent that can be used in this reaction include ethers such as diethyl ether, tetrahydrofuran and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; N, N-dimethylformamide, Aprotic polar solvents such as N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide and sulfolane; Nitriles such as acetonitrile and propionitrile; Methanol, ethanol and 2-propanol Alcohols such as dichloromethane; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; aliphatic hydrocarbons such as pentan
  • Examples of the base that can be used in this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide, sodium carbonate, potassium carbonate and the like.
  • Inorganic bases such as alkali metal carbonates, alkali metal bicarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate;
  • Metal hydrides such as sodium hydride and potassium hydride;
  • Carboxylic acids such as sodium acetate and potassium acetate Metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide; or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8 -Organic bases such as diazabicyclo [5.4.0] -7-undecene It can be mentioned.
  • the amount of the base used may be appropriately selected from the range of 0 to 2 moles relative to
  • the reaction temperature of this reaction may be usually selected from the range of any temperature from 0 ° C. to the reflux temperature in the reaction system, preferably in the range of room temperature to 100 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 6 hours.
  • the compound [XIV] can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating.
  • the isolated compound [XIV] can be further purified by column chromatography, recrystallization or the like, if necessary.
  • the compound represented by the general formula [XII] can be produced by reacting the compound [XIV] with a halogenating agent in an appropriate solvent.
  • a halogenating agent examples include N-chlorosuccinimide, sodium hypochlorite, tert-butyl hypochlorite, chlorine, N-bromosuccinimide, and bromine.
  • the amount of the halogenating agent to be used may be appropriately selected from the range of usually 1 to 3 mol, preferably 1.0 to 1.5 mol, per 1 mol of compound [XIV].
  • Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, tetrahydrofuran, and 1,4-dioxane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, Aprotic polar solvents such as dimethyl sulfoxide and sulfolane; nitriles such as acetonitrile and propionitrile; alcohols such as methanol, ethanol and 2-propanol; dichloromethane, chloroform, 1, 2 -Halogenated hydrocarbons such as dichloroethane; Aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; water or a mixed solvent thereof.
  • the solvent is used in an amount of 0.1 to 100 liters, preferably 0.3 to 10 liters, per 1 mol of compound [XIV].
  • the reaction temperature of this reaction may be usually selected from the range of any temperature from 0 ° C. to the reflux temperature in the reaction system, preferably 0 ° C. to 50 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 6 hours.
  • the compound [XII] can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating.
  • the isolated compound [XII] can be further purified by column chromatography, recrystallization or the like, if necessary. It is also possible to use the reaction mixture as it is for the reaction exemplified in ⁇ Production Method 9> without isolating the compound [XII] after completion of the reaction.
  • the plant disease control agent for agricultural and horticultural use of the present invention is characterized by containing an isoxazole derivative represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof as an active ingredient.
  • the plant disease control agent for agricultural and horticultural use of the present invention can contain an additive component (carrier) usually used in agricultural chemical preparations, if necessary.
  • an additive component such as a solid carrier or a liquid carrier, a surfactant, a binder or a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, an antifreezing agent, an anti-caking agent, A disintegrating agent, a decomposition inhibitor, etc. are mentioned, In addition, you may use a preservative, a plant piece, etc. as an additional component as needed.
  • these additive components may be used alone or in combination of two or more.
  • the said additive component examples include pyrophyllite clay, kaolin clay, meteorite clay, talc, diatomaceous earth, zeolite, bentonite, acid clay, activated clay, attapulgus clay, vermiculite, perlite, pumice, white carbon (synthetic silicic acid, Synthetic silicates, etc.), mineral carriers such as titanium dioxide; plant carriers such as wood flour, corn stalks, walnut shells, fruit nuclei, rice straw, sawdust, bran, soybean flour, powdered cellulose, starch, dextrin, saccharides; Inorganic salt carriers such as calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride; polymer carriers such as polyethylene, polypropylene, polyvinyl chloride, polyvinyl acetate, ethylene-vinyl acetate copolymer, urea-aldehyde resin, etc. it can.
  • liquid carrier examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, butanol, and cyclohexanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • monohydric alcohols such as methanol, ethanol, propanol, isopropanol, butanol, and cyclohexanol
  • polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • Polyhydric alcohol derivatives such as propylene glycol ethers; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, isophorone; ethers such as ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran; Aliphatic hydrocarbons such as normal paraffin, naphthene, isoparaffin, kerosene, mineral oil; toluene, C 9 —C 10 alkylbenzene, xylene, solvent naphtha, alkylnaphthalene, aromatic hydrocarbons such as high-boiling aromatic hydrocarbons; halogenated hydrocarbons such as dichloroethane, chloroform, carbon tetrachloride; ethyl acetate, diisopropyl phthalate, dibutyl phthalate Est
  • the surfactant is not particularly limited, but is preferably one that gels in water or exhibits swelling properties.
  • sorbitan fatty acid ester polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid Esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyoxyethylene dialkyl phenyl ethers, polyoxyethylene alkyl phenyl ether formalin condensates, polyoxyethylene polyoxy Propylene block polymer, alkyl polyoxyethylene polypropylene block polymer ether, polyoxyethylene alkylamine, polyoxyethylene fat Acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxyalkylene-added acetylene di
  • binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000 to 20000.
  • thickeners examples include xanthan gum, guar gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch derivatives, water-soluble polymers such as polysaccharides; inorganic fine powders such as high-purity bentonite and white carbon Can be mentioned.
  • the colorant examples include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue; organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.
  • the spreading agent examples include silicone surfactants, cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, crosslinked polyvinylpyrrolidone, maleic acid and styrenes, methacrylic acid copolymer, polyhydric alcohol polymer, A half ester with a dicarboxylic acid anhydride, a water-soluble salt of polystyrene sulfonic acid, and the like can be given.
  • the spreading agent examples include various surfactants such as sodium dialkylsulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene fatty acid ester; paraffin, terpene, polyamide resin, polyacrylate, Examples include polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, and synthetic resin emulsion.
  • the antifreezing agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
  • anti-caking agent examples include polysaccharides such as starch, alginic acid, mannose, and galactose; polyvinylpyrrolidone, white carbon, ester gum, and petroleum resin.
  • disintegrating agents include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylic acid ester copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride
  • examples thereof include a copolymer and a starch / polyacrylonitrile graft copolymer.
  • decomposition inhibitor examples include desiccants such as zeolite, quicklime, and magnesium oxide; phenol-based, amine-based, sulfur-based, phosphoric acid-based antioxidants; salicylic acid-based, benzophenone-based ultraviolet absorbers, and the like. be able to.
  • the content ratio is usually 5 to 95%, preferably 20 to 90% for a carrier such as a solid carrier or a liquid carrier on a mass basis.
  • the surfactant is usually selected in the range of 0.1 to 30%, preferably 0.5 to 10%, and the other additives are selected in the range of 0.1 to 30%, preferably 0.5 to 10%.
  • the pest control agent of the present invention is powder, granule, granule, wettable powder, water solvent, granule wettable powder, tablet, jumbo agent, emulsion, oil agent, liquid agent, flowable agent, emulsion agent, microemulsion agent. , Suspoemulsion agent, microdispersion agent, microcapsule agent, smoking agent, aerosol agent, bait agent, paste agent and the like.
  • preparations containing the compound of the present invention or dilutions thereof are generally performed by a commonly used application method, that is, spraying (for example, spraying, misting, atomizing, dusting, dusting, water surface application, box application, etc. ), Soil application (for example, mixing, irrigation, etc.), surface application (for example, application, powder coating, coating, etc.), immersion, poison bait, smoke application, and the like. It is also possible to feed the livestock with the above-mentioned active ingredient mixed with feed to control the occurrence and growth of harmful insects, particularly harmful insects, in the excreta.
  • the mixture ratio (mass%) of the active ingredient in the pest control agent of this invention selects suitably as needed.
  • a powder granule, fine granule, etc., 0.01 to 20%, preferably 0.05 to 10%
  • the pest control agent of the present invention When the pest control agent of the present invention is used after being diluted with a diluent, it is generally applied at an active ingredient concentration of 0.1 to 5000 ppm. When the preparation is used as it is, the application amount per unit area is 0.1 to 5000 g per ha as an active ingredient compound, but is not limited thereto.
  • the plant disease control agent for agricultural and horticultural use of the present invention is sufficiently effective even if the compound of the present invention alone is used as an active ingredient.
  • the agricultural and horticultural composition in the present invention comprises the isoxazole derivative represented by the general formula [I] or an agriculturally acceptable salt thereof, and an agriculturally acceptable carrier.
  • the pesticide-acceptable carrier include the aforementioned additive components and diluents.
  • the agricultural and horticultural composition of the present invention further includes the other fertilizers and agricultural chemicals described above, such as fungicides, antiviral agents, insecticides, acaricides, nematicides, synergists, attractants, weeding.
  • An agent, a plant growth regulator, and the like may be contained.
  • Bactericidal active ingredient Azaconazole, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbisoyl, amethoctrazine , Isopyrazam, isofetamid, isoprothiolane, ipconazole, iprodione, iprovalicas, iprobenizar, iprobenfos il), iminoctadine-tribesate, iminoctadate acetate, imibenconazole, ethifenfos, ethaconazol, ethaconazol ), Ethoxyquin, etridiazole, enestroburin, enoxastrobin, epoxiconazole, organic oils, x dixyl), oxazinylazole, oxathiapiproline, oxy
  • Folpet phthalide, bupirimate, fuberidazole, blasticidin-S, furamethpyr, furaxyl, furaxyl, furaxyl (Fluazinam), fluoxastrobin, fluopicolide, fluopyram, fluorimide, fluxapiroxad, fluquinconazole (flucoconazole) ole), fluconazole-cis, fludioxonil, flusilazole, flusulfamide, fluthianil, flutoranol, flutrianol, flutrianol ), Flumetover, fluromorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole, prothioconazole on Bronopol, propamocarb-hydrochloride, propiconazole, propinebole, probenazole, bromconazole, and bromconazole.
  • Benalaxyl-M benodanyl, benomyl, pefurazoate, penconazole, pencyclon, benzobindiflupyr (benzyl) hizole, Benchavaricarb-isopropyl, pentiopyrad, penflufen, boscalid, fosetyl, polycium, polycium, polycium polycarbamate, Bordeaux liquid, mancozeb, mandipropamide, mandestrobin, manneb, microbutanil, mycrobutilmin Rudiomycin, metasulfocarb, metham, metalaxyl, metalaxyl M laxyl-M), methylam, metconazole, metminostrobin, metraphenone, mepanipirim, meptyldino
  • Herbicidal active ingredient Ioxynil, aclonifen, acrolein, azafenidin, acifluorfen (including salts such as sodium), azimsulfuron,fugm,stagem- acetochlor, atrazine, anilofos, amicarbazone, amidosulfuron, amitrole, aminocyclopyrachlor, aminopyrochlor, aminopyrochlor os-methyl), amethrin, alachlor, alloxydim, isouron, isoxachlortole, isoxaflutole, isoxaben, isoxaben ), Ipfencarbazone, imazaquin, imazapic (including salts with amines, etc.), imazapyr (including salts such as isopropylamine), imazametabenz methyz-thiamez ), Imazamox, ima
  • chlorthiamid chlorphthalim, chlorflulenol-methyl, chlorpropham, chlorbromuron, chloroxuron, chlorotoluron otorururon, saflufenacil, cyanazine, cyanamide, diuron, diethatyl-ethyl, dicamba (amine, diamine) Including salts such as lithium), cycloate, cycloxydim, dicloslam, cyclosulfamuron, cyclopyrimorate, diclobenil, dichlorohop diclopop-P-meth l), diclohop-methyl, dichlorprop, dichlorprop-P, diquat, dithiopyr, siduron, dinitramine, initramine Cynidon-ethyl, cinosulfuron, dinoterb, cyhalohop-butyl, diphenamid, difenzoquan, difluzolfen, diflufencan , Simazine
  • Plant growth regulator 1-naphthylacetamide, 1-methylcyclopropene, 1,6-diisopropylnaphthalene, 4-CPA (4-CPA) (4-chlorophenoxyacetic acid) 4-oxo-4- (2-phenylethyl) aminobutyric acid (chemical name, CAS Registry Number: 1083-55-2), aviglycine, ancymidol, inabenfide, indoleacetic acid ( indole acetic acid), indole butyric acid (uniconazole), uniconazole-P (unico) azole-P), ethiclozate, etephon, epocholeone, carbonone, cloxyfonac, cloxyphonac-potoploprop Chlormequat, cytokinins, cyclanilide, dikeglucac, gibberellins, dimethipin, dithith, zintofron, zitofen, sintofen
  • N-decanol triacontanol, trinexapac-ethyl, paclobutrazol, flumetralin, flurprimollu, flurprimollu , Prohydrojasmon, prohexadione-calcium, benzylaminopurine, forchlorfenuron, maleic hydrazide (maleic hydrazide) de), mefluidide (mefluidide).
  • AD-67 (4-dichloroacetyl-1-oxa-4-azaspiro [4.5] decane), DKA-24 (N1, N2-diallyl-N2-dichloroacetylglycinamide), MG-191 (2-dichloromethyl) -2-methyl-1,3-dioxane), MON4660 (code number), N- (2-methoxybenzoyl) -4-[(methylaminocarbonyl) amino] benzenesulfonamide (chemical name, CAS registry number: 129531-) 12-0), PPG-1292 (2,2-dichloro-N- (1,3-dioxan-2-ylmethyl) -N- (2-propenyl) acetamide), R-29148 (3-dichloroacetyl-2, 2,5-trimethyl-1,3-oxazolidine), TI-35 (code number), isoxa
  • Trichoderma sp. Trichoderma sp.
  • Burkholderia plantarii White leaf blight (Xanthomonas oryzae), Rice blast blight (Burkholderia glumae), Rice brown disease (Acidovorax avenae), Endemic browning disease (Erwinia ananas) ), Wheat powdery mildew (Erysiphe graminis f.sp.hordei; f.sp.tritici), leafy leaf disease (Pyrenophora graminea), net leaf disease (Pyrenophora teres), leaf blight (Gibberella zeae), rust disease (Puccinia striiformis; Puccinia.
  • Gray mold disease (Botrytis cinerea), mycorrhizal disease (Sclerotinia sclerotiorum), buckwheat brown patch disease (Rhizoctonia solani), dollar spot disease (Sclerotinia homoeocarpa) ), Curvularia geniculata, Rust (Puccinia zoysiae), Helmintosporium leaf (Cochliobolus sp.), Cloud disease (Rhynchosporium secalis), Blight (Gaeumannomyces graminis), Anthracnose ( Colletotrichum graminicola), snow rot brown sclerotia nuclear disease (Typhula incarnata), snow rot black sclerotia nuclear disease (Typhula ishikariensis), snow rot large sclerotia nuclear disease (Sclerotinia borealis), fairy ring (Marasmius oreades etc.), pisium disease
  • the plant disease control agent for agricultural and horticultural use according to the present invention exhibits the control effect on the plant disease and the like exemplified above, which has acquired resistance to the existing plant disease control agent for agricultural and horticultural use.
  • the plant disease control agent for agricultural and horticultural use of the present invention can also be used for plants that have acquired characteristics such as pest resistance, disease resistance, and herbicide resistance by genetic recombination, artificial mating, and the like.
  • Example 1 (1) Production of 4,4-difluoro-1- (pyridin-3-yl) pentane-1,3-dione 31.0 g (276 mmol) of potassium tert-butoxide was dissolved in 160 ml of tetrahydrofuran and dissolved at 10 ° C. A solution of 24.2 g (200 mmol) of acetylpyridine and 25.0 g (181 mmol) of ethyl 2,2-difluoropropionate in tetrahydrofuran (180 ml) was added dropwise, and the mixture was stirred at room temperature for 20 hours.
  • a citric acid aqueous solution was added to the reaction solution to adjust the pH to about 4, and ethyl acetate was added for extraction.
  • the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.
  • Example 2 (1) Production of 4-methoxy-1- (pyridin-3-yl) butane-1,3-dione 2.15 g of sodium hydride (purity: about 60%, 53.8 mmol) was suspended in 50 ml of tetrahydrofuran, 0.20 g (2.56 mmol) of dimethyl sulfoxide was added. Subsequently, a solution of 6.46 g (53.3 mmol) of 3-acetylpyridine and 6.00 g (50.8 mmol) of ethyl methoxyacetate in tetrahydrofuran (30 ml) was added dropwise at 60 ° C., and the mixture was heated to reflux for 3 hours.
  • sodium hydride purity: about 60%, 53.8 mmol
  • Example 3 (1) Production of 2- (4-fluorophenyl) pyrimidine-5-carbaldehyde 3.49 g (20.0 mmol) of 4-fluorobenzimide amide hydrochloride, produced by the method described in US Published Patent Publication US2006 / 194801 2-dimethylaminomethylene-1,3-bis (dimethylimmonio) propane bis (tetrafluoroborate) 7.14 g (20 0.0 mmol) and 9.67 g (70.0 mmol) of potassium carbonate were suspended in 60 ml of tetrahydrofuran and heated to reflux for 4 hours. After allowing to cool at room temperature, the reaction mixture was poured into an aqueous citric acid solution and extracted with ethyl acetate.
  • Example 5 (1) Production of 4,4,4-trifluoro-1- (pyridin-3-yl) butane-1,3-dione 52.1 g (464 mmol) of potassium tert-butoxide was dissolved in 350 ml of tetrahydrofuran, and the mixture was heated to 10 ° C. A solution of 43.2 g (357 mmol) of 3-acetylpyridine and 50.7 g (357 mmol) of ethyl trifluoroacetate in tetrahydrofuran (200 ml) was added dropwise, and the mixture was stirred at room temperature for 20 hours.
  • a citric acid aqueous solution was added to the reaction solution to adjust the pH to about 4, and ethyl acetate and tetrahydrofuran were added for extraction.
  • the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.
  • the obtained crystals were washed with ethyl acetate to obtain 66.0 g (yield 85%) of the desired product.
  • Example 6 (1) Production of 4-methyl-1- (pyridin-3-yl) pentane-1,3-dione 19.6 g (0.175 mol) of potassium tert-butoxide was suspended in 150 ml of tetrahydrofuran and then at room temperature. 20.0 g (0.146 mol) of methyl nicotinate was added. Subsequently, a solution of 13.2 g (0.153 mol) of isopropyl methyl ketone in tetrahydrofuran (30 ml) was added dropwise at room temperature, and the mixture was stirred at room temperature for 4 hours.
  • Example 7 (1) Production of 4-methoxy-1- (pyridin-3-yl) pentane-1,3-dione 1.37 g of sodium hydride (purity: about 60%, 34.3 mmol) was suspended in 70 ml of tetrahydrofuran, 0.22 g (2.8 mmol) of dimethyl sulfoxide was added. Subsequently, a solution of 3.45 g (28.5 mmol) of 3-acetylpyridine and 3.36 g (28.4 mmol) of methyl 2-methoxypropanoate in hexane (15 ml) was added dropwise at 60 ° C., and the mixture was heated to reflux for 3 hours. .
  • Example 8 (1) Production of (EZ) -6- (3-trifluoromethyl-1H-pyrazol-1-yl) pyridine-3-carbaldehyde oxime It was produced according to the method described in International Patent Publication WO2014 / 172190. 2.44 g (10.1 mmol) of 6- (3-trifluoromethyl-1H-pyrazol-1-yl) pyridine-3-carbaldehyde, 0.91 g (13.1 mmol) of hydroxylamine hydrochloride and 1.08 g of sodium acetate (13.2 mmol) was dissolved in tetrahydrofuran (100 ml) and water (1.5 ml), and the mixture was stirred for 3 hours with heating under reflux.
  • Example 9 (1) Production of 1- ⁇ 3,4'-difluoro- (1,1'-biphenyl) -4-yl ⁇ -4,4-difluorobutane-1,3-dione (4-fluorophenyl) boronic acid 4 .20 g (30.0 mmol), 1- (4-bromo-2-fluorophenyl) ethanone 6.51 g (30.0 mmol), diacetoxypalladium 0.34 g (1.5 mmol), and sodium carbonate 7.95 g (75 0.0 mmol) was dissolved in a mixed solvent of 1,2-dimethoxyethane (100 ml) and water (100 ml), and the mixture was stirred at 80 ° C.
  • Example 10 (1) Production of 3-cyclopropyl-1- (pyridin-3-yl) -2-propyn-1-ol ethynylcyclopropane (5.00 g, 75.6 mmol) was dissolved in tetrahydrofuran (500 ml) and a nitrogen atmosphere- After cooling to 70 ° C. or lower, 57 ml of n-butyllithium (hexane solution, 1.60 M, 91 mmol) was added dropwise and stirred for 10 minutes. Subsequently, 8.10 g (75.6 mmol) of nicotinaldehyde was added and stirred at room temperature for 3 hours.
  • n-butyllithium hexane solution, 1.60 M, 91 mmol
  • Example 11 (1) Preparation of 4-methyl-1- (pyrimidin-5-yl) -2-pentyn-1-ol 1.04 g (15.3 mmol) of 3-methyl-1-butyne was dissolved in 15 ml of tetrahydrofuran, and a nitrogen atmosphere After cooling to below ⁇ 70 ° C., 5.60 ml of n-butyllithium (hexane solution, 2.60 M, 14.6 mmol) was added dropwise and stirred for 30 minutes. Subsequently, a tetrahydrofuran solution of 1.50 g (13.9 mmol) of pyrimidine-5-carbaldehyde was added dropwise at ⁇ 60 ° C.
  • the reaction mixture was diluted with diisopropyl ether and ethyl acetate, water was added, and insoluble materials were removed by filtration.
  • the obtained organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.70 g (yield 99%) of the desired product. .
  • Example 13 (1) 1- [3- ⁇ (1,1′-biphenyl) -4-yl ⁇ -5- (methoxymethyl) isoxazol-4-yl] -1- (pyridin-3-yl) ethanol (compound of the present invention) Number: D-0007) [3- ⁇ (1,1′-biphenyl) -4-yl ⁇ -5- (methoxymethyl) isoxazol-4-yl] (pyridin-3-yl) methanone 0.40 g ( 1.1 mmol) and 0.27 g (1.1 mmol) of cerium chloride were dissolved in 5 ml of tetrahydrofuran at room temperature and cooled to ⁇ 70 ° C. or lower.
  • Example 15 (1) 3- ⁇ (1,1′-biphenyl) -4-yl ⁇ -4- ⁇ chloro (pyridin-3-yl) methyl ⁇ -5- (methoxymethyl) isoxazole (the present compound number: A-0217 ) [3- ⁇ (1,1′-biphenyl) -4-yl ⁇ -5- (methoxymethyl) isoxazol-4-yl] (pyridin-3-yl) methanol 1.05 g (2.82 mmol) It melt
  • Example 16 (1) 3- ⁇ (1,1′-biphenyl) -4-yl ⁇ -5- (methoxymethyl) -4- ⁇ 1- (pyridin-3-yl) ethyl ⁇ isoxazole (the present compound number: A- 0218) 3- ⁇ (1,1′-biphenyl) -4-yl ⁇ -4- ⁇ chloro (pyridin-3-yl) methyl ⁇ -5- (methoxymethyl) isoxazole 0.40 g (1.0 mmol) Was dissolved in 12 ml of toluene, 6.00 ml of trimethylaluminum (hexane solution, 1.40 M, 8.40 mmol) was added dropwise at room temperature, and the mixture was heated to reflux for 16 hours under a nitrogen atmosphere.
  • reaction mixture was diluted with diisopropyl ether, 0.32 g (0.99 mmol) of sodium sulfate decahydrate was added and stirred, and the precipitated aluminum salt was removed by filtration.
  • Example 17 (1) Production of 4,4-dimethoxy-1- (pyridin-3-yl) butane-1,3-dione 3.00 g (24.8 mmol) of 3-acetylpyridine was dissolved in 60 ml of tetrahydrofuran, and a nitrogen atmosphere was used. Cooled to below 70 ° C. 49.5 ml of lithium hexamethyldisilazide (tetrahydrofuran solution, 1.00 M, 49.5 mmol) was added dropwise, and the mixture was stirred at ⁇ 70 ° C. or lower for 20 minutes.
  • Example 18 (1) Production of 5-methoxymethyl-3- (2-phenylpyrimidin-5-yl) -4- ⁇ 1- (pyridin-3-yl) vinyl ⁇ isoxazole (the present compound number: E-0012) 1 ⁇ 5-methoxymethyl-3- (2-phenylpyrimidin-5-yl) isoxazol-4-yl ⁇ -1- (pyridin-3-yl) ethanol (0.36 g, 0.93 mmol) was dissolved in 3 ml of acetonitrile, At room temperature, 0.28 g (2.4 mmol) of thionyl chloride was added, and the mixture was stirred at 60 ° C. for 2.5 hours.
  • Wheat red rust prevention effect test 1 Wheat seeds were sown in a pot, and a chemical solution adjusted to an active ingredient concentration of 50 ppm was sprayed on the grown seedlings. Thereafter, wheat red rust fungus was spray-inoculated, transferred to a wet room, and kept under dark conditions to promote the invasion of pathogenic bacteria. After that, it was managed in the greenhouse, and after 7-10 days, the degree of morbidity of each first leaf was indexed according to the criteria in Table 122 shown below. The control value was determined by the formula shown. The results are shown in Tables 123 to 127.
  • N Total number of leaves n0: Number of leaves with disease index 0 n1: Number of leaves with disease index 1 n2: Number of leaves with disease index 2 n3: Number of leaves with disease index 3 n4: Number of leaves with disease index 4
  • the comparative compounds 1 and 3 in the table are compounds described in WO2006 / 031631, and the comparative compounds 2 and 4 are compounds described in WO2010 / 069881, and have the following structures.
  • Wheat leaf blight prevention effect test 1 The spore suspension is prepared by scraping the bacterial flora of Septoria tritici (wheat leaf blight) plated in a plate and suspending it in a liquid medium containing 1% yeast extract and 1% sucrose. Prepared. A solution in which the test compound was dissolved in dimethyl sulfoxide was placed in a microtiter plate (96-well plate), and this spore suspension was added to adjust the concentration to 10 ppm. The test plate was incubated using a shaking incubator, and after 5 days of culture, the inhibition of proliferation was measured with a photometer, and the growth inhibition rate was calculated. The results of evaluation according to the evaluation scale shown in Table 134 are shown in Table 135 to Table 144.
  • Wheat leaf blight prevention effect test 2 The spore suspension is prepared by scraping the bacterial flora of Septoria tritici (wheat leaf blight) plated in a plate and suspending it in a liquid medium containing 1% yeast extract and 1% sucrose. Prepared. A solution in which the test compound was dissolved in dimethyl sulfoxide was placed in a microtiter plate (96-well plate), and this spore suspension was added to adjust the concentration to 0.01 ppm. The test plate was incubated using a shaking incubator, and after 5 days of culture, the inhibition of proliferation was measured with a photometer, and the growth inhibition rate was calculated. The results of evaluation according to the evaluation scale shown in Table 134 are shown in Table 145.

Abstract

L'invention concerne un agent supérieur de lutte contre les maladies des plantes agricoles/horticoles, et un intermédiaire de production pour cet agent. L'invention porte sur un agent de lutte contre les maladies des plantes agricoles/horticoles, et sur un intermédiaire de production de cet agent, ledit agent contenant, en tant que matière active, un dérivé de l'isoxazole représenté par la formule générale (I) (dans laquelle X est un groupe alkyle en C1 à C6, un groupe halogènalkyle en C1 à C6 ou analogues, Y1 est un groupe hydroxyle, un groupe alcoxy en C1 à C6 ou analogues, Y2 est un atome d'hydrogène ou analogues, Q1 est un groupe phényle, un groupe pyrazolyle ou analogues, Q2 est un groupe phényle, un groupe pyridyle, un groupe pyrimidinyle ou analogues, Q3 est un groupe pyridyle, un groupe pyrimidinyle ou analogues, et Q1, Q2 et Q3 peuvent chacun être substitués par un atome d'halogène ou analogues), ou un sel pharmaceutiquement acceptable de celui-ci.
PCT/JP2015/055487 2014-02-28 2015-02-25 Dérivé d'isoxazole, et agent de lutte contre les maladies de plantes agricoles/horticoles WO2015129773A1 (fr)

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WO2018202487A1 (fr) * 2017-05-04 2018-11-08 Basf Se 5-(haloalkyl)-5-hydroxy-isoxazoles substitués pour lutter contre des champignons phytopathogènes
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WO2019122393A1 (fr) 2017-12-22 2019-06-27 Bayer Aktiengesellschaft Hydroxyisoxazolines et leurs dérivés
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WO2020254490A1 (fr) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Phénoxyphényl hydroxyisoxazolines et analogues utilisés en tant que nouveaux agents antifongiques
WO2020254493A1 (fr) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Thiénylhydroxyisoxazolines et leurs dérivés
WO2020254486A1 (fr) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Hydroxyisoxazolines et leurs dérivés
WO2020254489A1 (fr) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Benzylphényl hydroxyisoxazolines et analogues en tant que nouveaux agents antifongiques
WO2020254492A1 (fr) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Hydroxyisoxazolines et leurs dérivés
WO2020254488A1 (fr) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Hydroxyisoxazolines et leur utilisation comme fongicides
WO2020254487A1 (fr) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Hydroxyisoxazolines et leurs dérivés
CN113149927A (zh) * 2021-05-07 2021-07-23 北京农学院 香草醛异噁唑类化合物及其制备方法和应用

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