WO2014104268A1 - Composé de tétrazolinone et ses applications - Google Patents

Composé de tétrazolinone et ses applications Download PDF

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WO2014104268A1
WO2014104268A1 PCT/JP2013/085023 JP2013085023W WO2014104268A1 WO 2014104268 A1 WO2014104268 A1 WO 2014104268A1 JP 2013085023 W JP2013085023 W JP 2013085023W WO 2014104268 A1 WO2014104268 A1 WO 2014104268A1
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group
methyl
compound
reaction
atom
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PCT/JP2013/085023
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Japanese (ja)
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隆之 塩田
貞幸 有森
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住友化学株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings

Definitions

  • the present invention relates to a tetrazolinone compound and its use.
  • the present invention provides a compound having an excellent control effect against pests.
  • the present inventors have found that the tetrazolinone compound represented by the following formula (1) has an excellent control effect against pests.
  • the present invention has been completed. That is, the present invention is as follows.
  • R 1 , R 2 , R 3 and R 11 are each hydrogen atom, halogen atom, cyano group, nitro group, amino group, hydroxy group, thiol group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2- C6 alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C8 alkylamino group, C1-C8 haloalkylamino group, C1-C6 alkylthio group, C1-C6 haloalkylthio group C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, pentafluoros
  • C1-C6 may be alkyl groups having a group selected from the group P 1, Or a group optionally may be C3-C6 cycloalkyl group having a selected from the group P 1;
  • R 4 and R 5 each represent a hydrogen atom, a halogen atom or a C1-C3 alkyl group;
  • R 7 , R 8 and R 9 are each a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C2-C3 haloalkenyl group, a C1-C3 alkoxy group, or C1 Represents a -C3 haloalkoxy group;
  • R 10 is a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C2-C3 alkenyl group
  • Group P 1 halogen atom, cyano group, C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C4 alkylthio group and C1-C4 haloalkylthio group
  • a group consisting of Group P 2 halogen atom, cyano group, amino group, hydroxy group, thiol group, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C2-C6 alkenyl Group, C2-C6 haloalkenyl group, C2-C6 alkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C8 alkylamino group, C1-C6 alkyl
  • R 12 is a C2-C6 alkyl group, a C3-C6 cycloalkyl group, A phenyl group which may have a group selected from the group P 3, [1] or [2] which is a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, or a C3-C6 halocycloalkyl group
  • Group P 3 A group consisting of a halogen atom, a C1-C3 alkyl group, and a C1-C3 haloalkyl group.
  • R 13 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C6 cycloalkyl group.
  • group, C3-C6 cycloalkenyl group or a tetrazolinone compound according to any one of is also good benzyl group optionally having a group selected from the group P 3 [1] to [3],.
  • R 1 is a C1-C3 alkyl group optionally having a halogen atom, or a halogen atom;
  • a method for controlling pests comprising treating an effective amount of the tetrazolinone compound according to any one of [1] to [8] on a plant or soil.
  • pests can be controlled.
  • the compound of the present invention is a tetrazolinone compound represented by the formula (1).
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the C1-C8 alkyl group represents a linear or branched alkyl group having 1 to 8 carbon atoms, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl. Group, tert-butyl group, pentyl group, neopentyl group, hexyl group, heptyl group, octyl group and the like.
  • the C1-C6 alkyl group represents a linear or branched alkyl group having 1 to 6 carbon atoms, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl. Group, tert-butyl group, pentyl group, neopentyl group and hexyl group.
  • the C2-C6 alkyl group represents a linear or branched alkyl group having 2 to 6 carbon atoms, for example, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert. -A butyl group, a pentyl group, a neopentyl group, and a hexyl group are mentioned.
  • Examples of the C1-C3 alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • the C1-C8 haloalkyl group represents a group in which at least one hydrogen atom of a linear or branched alkyl group having 1 to 8 carbon atoms is substituted with a halogen atom, such as a monofluoromethyl group, monochloro Methyl group, dichloromethyl group, difluoromethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group Chlorofluoromethyl group, dichlorofluoromethyl group, chlorodifluoromethyl group, 2,2-difluoroethyl group, 2-chloro-2-fluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2- Dichloro-2-fluoroethyl group, 2-fluoropropyl group, 3-fluoroprop
  • the C1-C6 haloalkyl group represents a group in which at least one hydrogen atom of a linear or branched alkyl group having 1 to 6 carbon atoms is substituted with a halogen atom, such as a monofluoromethyl group, monochloro Methyl group, dichloromethyl group, difluoromethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group Chlorofluoromethyl group, dichlorofluoromethyl group, chlorodifluoromethyl group, 2,2-difluoroethyl group, 2-chloro-2-fluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2- Dichloro-2-fluoroethyl group, 2-fluoropropyl group, 3-fluoroprop
  • Examples of the C1-C3 haloalkyl group include a chloromethyl group, a dichloromethyl group, a fluoromethyl group, a difluoromethyl group, a chlorofluoromethyl group, a dichlorofluoromethyl group, a chlorodifluoromethyl group, a trifluoromethyl group, a trichloromethyl group, Tribromomethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloroethyl group, 2,2-dichloroethyl group, 2,2,2-trichloro Ethyl group, pentafluoroethyl group, pentachloroethyl group, 2-chloro-2-fluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2-fluoropropyl group, 3-fluoropropyl group, 2,2
  • the halomethyl group represents a group in which at least one hydrogen atom of the methyl group is substituted with a halogen atom.
  • a fluoromethyl group, a chloromethyl group, a bromomethyl group, a fluoromethyl group, a dichloromethyl group, a dibromomethyl group examples thereof include a trifluoromethyl group, a trichloromethyl group, and a tribromomethyl group.
  • the C3-C6 cycloalkyl group represents a cyclic alkyl group having 3 to 6 carbon atoms and includes a cycloalkyl group having an alkyl group.
  • Examples include cyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, and 2,3-dimethylcyclopropyl group.
  • the C3-C5 cycloalkyl group represents a cyclic alkyl group having 3 to 5 carbon atoms, and includes a cycloalkyl group having an alkyl group, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 1-methylcyclopropyl group. 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, 2,3-dimethylcyclopropyl group.
  • the C3-C6 halocycloalkyl group represents a group in which at least one hydrogen atom of the cycloalkyl group having 3 to 6 carbon atoms is substituted with a halogen atom, such as 1-fluorocyclopropyl group, 2-fluorocyclopropyl group, and the like.
  • the C3-C5 halocycloalkyl group represents a group in which at least one hydrogen atom of a cycloalkyl group having 3 to 5 carbon atoms is substituted with a halogen atom, such as a 1-fluorocyclopropyl group, 2-fluorocyclopropyl group, and the like.
  • Propyl group 2,2-difluorocyclopropyl group, 1-chlorocyclopropyl group, 2-chloro-2-fluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, 2, 2-difluoro-1-methylcyclopropyl group, 2,2-dichloro-1-methylcyclopropyl group, 2,2-dibromo-1-methylcyclopropyl group, 1- (trifluoromethyl) cyclopropyl group, 2, 2,3,3-tetrafluorocyclobutyl group, 2,2,3,3-tetrafluorocyclobutyl group, 2-chlorocyclope Butyl group, and a 3-chloro cyclopentyl group.
  • the C3-C6 cycloalkenyl group represents a cyclic alkenyl group having 3 to 6 carbon atoms, and includes a cycloalkenyl group having an alkyl group, for example, a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, 2 -A methylcyclopentynyl group is mentioned.
  • the C3-C6 halocycloalkenyl group represents a group in which at least one hydrogen atom of the C3-C6 cycloalkenyl group is substituted with a halogen atom, such as a 1-fluorocyclopropenyl group, 2-chlorocycloalkenyl group.
  • a halogen atom such as a 1-fluorocyclopropenyl group, 2-chlorocycloalkenyl group.
  • the C2-C6 alkenyl group represents a linear or branched alkenyl group having 2-6 carbon atoms, such as a vinyl group, 1-propenyl group, isopropenyl group, 2-propenyl group, 1-butenyl group.
  • the C2-C6 haloalkenyl group represents a linear or branched alkenyl group having 2 to 6 carbon atoms in which at least one hydrogen atom is substituted with a halogen atom, such as a 2-chlorovinyl group.
  • Examples of the C2-C3 alkenyl group include a vinyl group, 1-propenyl group, isopropenyl group, and 2-propenyl group.
  • Examples of the C2-C3 haloalkenyl group include 2-chlorovinyl group, 2-bromovinyl group, 2-iodovinyl group, 3-chloro-2-propenyl group, 3-bromo-2-propenyl group, and 1-chloro.
  • Methyl vinyl group 2-bromo-1-methyl vinyl group, 1-trifluoromethyl vinyl group, 3,3,3-trichloro-1-propenyl group, 3-bromo-3,3-difluoro-1-propenyl group, 2,3,3,3-tetrachloro-1-propenyl group, 1-trifluoromethyl-2,2-difluorovinyl group, 2-chloro-2-propenyl group, 3,3-difluoro-2-propenyl group, A 2,3,3-trichloro-2-propenyl group may be mentioned.
  • the C2-C6 alkynyl group represents a C2-C6 alkynyl group which may be linear or branched, and includes, for example, an ethynyl group, a propargyl group, a 1-butyn-3-yl group, Examples include 3-methyl-1-butyn-3-yl group, 2-butynyl group, 3-butynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group, and 5-hexynyl group. .
  • the C2-C6 haloalkynyl group represents a linear or branched alkynyl group having 2 to 6 carbon atoms in which at least one hydrogen atom is substituted with a halogen atom, such as a fluoroethynyl group, 3 -Fluoro-2-propynyl group, 3-chloro-2-propynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group, 3-chloro-1-propynyl group, 5-chloro- 4-pentynyl group, 3,3,3-trifluoro-1-propynyl group, 3,3-difluoro-1-propynyl group, 4,4,4-trifluoro-2-butynyl group, perfluoro-2-butynyl group Perfluoro-2-pentynyl group, perfluoro-3-pentynyl group, and perfluoro-1-he
  • Examples of the C2-C3 alkynyl group include ethynyl group, 1-propynyl group and 2-propynyl group.
  • Examples of the C2-C3 haloalkynyl group include a fluoroethynyl group, 3-fluoro-2-propynyl group, 3-chloro-2-propynyl group, 3-bromo-2-propynyl group, and 3-iodo-2- Examples include propynyl group, 3-chloro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group and 3,3-difluoro-1-propynyl group.
  • the C1-C6 alkoxy group represents a C1-6 alkoxy group which may be linear or branched, and includes, for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy Group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, pentyloxy group, isoamyloxy group, neopentyloxy group, 2-pentyloxy group, 3-pentyloxy group, 2-methylbutyloxy group, hexyloxy Group, isohexyloxy group, 3-methylpentyloxy group, 4-methylpentyloxy group.
  • the C1-C4 alkoxy group represents a C 1-4 alkoxy group which may be linear or branched, and includes, for example, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group , Isobutyloxy group, sec-butyloxy group, and tert-butyloxy group.
  • Examples of the C1-C3 alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group.
  • the C1-C6 haloalkoxy group represents a group in which at least one hydrogen atom of a linear or branched alkoxy group having 1 to 6 carbon atoms is substituted with a halogen atom, such as a trifluoromethoxy group, Trichloromethoxy group, chloromethoxy group, dichloromethoxy group, fluoromethoxy group, difluoromethoxy group, chlorofluoromethoxy group, dichlorofluoromethoxy group, chlorodifluoromethoxy group, pentafluoroethoxy group, pentachloroethoxy group, 2,2,2 -Trichloroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-tribromoethoxy group, 2,2,2-triiodoethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2-difluoroethoxy group, 2-chloro-2-fluoroethoxy group, 2-c B
  • the C1-C4 haloalkoxy group represents a group in which at least one hydrogen atom of a linear or branched alkoxy group having 1 to 4 carbon atoms is substituted with a halogen atom, such as a trifluoromethoxy group, Trichloromethoxy group, chloromethoxy group, dichloromethoxy group, fluoromethoxy group, difluoromethoxy group, chlorofluoromethoxy group, dichlorofluoromethoxy group, chlorodifluoromethoxy group, pentafluoroethoxy group, pentachloroethoxy group, 2,2,2 -Trichloroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-tribromoethoxy group, 2,2,2-triiodoethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 2-c 2-fluor
  • the C1-C3 haloalkoxy group represents a group in which at least one hydrogen atom of a linear or branched alkoxy group having 1 to 3 carbon atoms is substituted with a halogen atom, such as a trifluoromethoxy group, Trichloromethoxy group, chloromethoxy group, dichloromethoxy group, fluoromethoxy group, difluoromethoxy group, chlorofluoromethoxy group, dichlorofluoromethoxy group, chlorodifluoromethoxy group, pentafluoroethoxy group, pentachloroethoxy group, 2,2,2 -Trichloroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-tribromoethoxy group, 2,2,2-triiodoethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 2-c 2-fluor
  • the C1-C6 alkylthio group represents a linear or branched alkylthio group having 1-6 carbon atoms, and examples thereof include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, Examples thereof include n-butylthio group, sec-butylthio group, tert-butylthio group, n-pentylthio group, isopentylthio group, neopentylthio group, n-hexylthio group, isohexylthio group, and sec-hexylthio group.
  • the C1-C6 haloalkylthio group represents a group in which at least one hydrogen atom of a linear or branched alkylthio group having 1 to 6 carbon atoms is substituted with a halogen atom, such as a monofluoromethylthio group, Difluoromethylthio group, trifluoromethylthio group, trichloromethylthio group, tribromomethylthio group, triiodomethylthio group, chlorofluoromethylthio group, pentafluoroethylthio group, pentachloroethylthio group, pentabromoethylthio group, pentaiodoethylthio group 2,2,2-trichloroethylthio group, 2,2,2-trifluoroethylthio group, 2,2,2-tribromoethylthio group, 2,2,2-triiodoethylthio group, 2,2 -Difluoro
  • Examples of the C1-C4 alkylthio group include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, and a tert-butylthio group.
  • the C1-C4 haloalkylthio group represents a group in which at least one hydrogen atom of a linear or branched alkylthio group having 1 to 4 carbon atoms is substituted with a halogen atom, such as a monofluoromethylthio group, Difluoromethylthio group, trifluoromethylthio group, trichloromethylthio group, tribromomethylthio group, triiodomethylthio group, chlorofluoromethylthio group, pentafluoroethylthio group, pentachloroethylthio group, pentabromoethylthio group, pentaiodoethylthio group 2,2,2-trichloroethylthio group, 2,2,2-trifluoroethylthio group, 2,2,2-trifluoroethylthio group, 2,2,2-tribromoethylthio group, 2, 2,2-triiodoeth
  • the C1-C8 alkylamino group is an alkyl group in which one or two hydrogen atoms on the nitrogen having a linear or branched alkyl group having 1 to 8 carbon atoms are the same or different from each other.
  • the C1-C8 haloalkylamino group represents an alkylamino group having 1 to 8 carbon atoms in which one or more hydrogen atoms are substituted with halogen atoms.
  • 2,2,2-trifluoroethyl Examples include an amino group, N, N- (2,2-ditrifluoroethyl) -amino group, N, N- (2,2-ditrichloroethyl) -amino group, and pentafluoropropylamino group.
  • the C2-C6 alkylcarbonyl group represents a straight or branched alkylcarbonyl group having 1 to 5 carbon atoms and having 1 to 5 carbon atoms, such as methylcarbonyl group, ethylcarbonyl group, n -Propylcarbonyl group, isopropylcarbonyl group, pivaloyl group, n-butylcarbonyl group, n-pentylcarbonyl group can be mentioned.
  • the C2-C6 alkoxycarbonyl group represents a straight or branched alkoxycarbonyl group having 1-5 carbon atoms and having 1-5 carbon atoms, such as a methoxycarbonyl group, ethoxycarbonyl group, propyloxy group.
  • Carbonyl group isopropyloxycarbonyl group, butyloxycarbonyl group, isobutyloxycarbonyl group, sec-butyloxycarbonyl group, tert-butyloxycarbonyl group, pentyloxycarbonyl group, isoamyloxycarbonyl group, neopentyloxycarbonyl group, 2- Examples thereof include a pentyloxycarbonyl group, a 3-pentyloxycarbonyl group, and a 2-methylbutyloxycarbonyl group.
  • C2-C9 alkylaminocarbonyl group represents an aminocarbonyl group in which one or two hydrogen atoms on nitrogen are substituted with the same or different linear or branched C1-C4 alkyl group, For example, methylaminocarbonyl group, ethylaminocarbonyl group, propylaminocarbonyl group, isopropylaminocarbonyl group, butylaminocarbonyl group, N, N-dimethylaminocarbonyl group, N, N-diethylaminocarbonyl group, N, N-dipropyl Examples thereof include an aminocarbonyl group and an N, N-diisopropylaminocarbonyl group.
  • the C3-C12 trialkylsilyl group represents an alkylsilyl group in which three hydrogen atoms on the silyl group are substituted with the same or different C1-C4 alkyl group, and the alkyl group is linear or branched Examples thereof include a trimethylsilyl group, a tert-butyl-dimethylsilyl group, a triethylsilyl group, an isopropyldimethylsilyl group, and a triisopropylsilyl group.
  • the C1-C6 alkylsulfonyl group represents a linear or branched alkylsulfonyl group having a C1-6 alkyl group, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group.
  • the C1-C6 haloalkylsulfonyl group represents a group in which at least one hydrogen atom of a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms is substituted with a halogen atom, for example, trifluoromethylsulfonyl Group, trichloromethylsulfonyl group, tribromomethylsulfonyl group, triiodomethylsulfonyl group, pentafluoroethylsulfonyl group, pentachloroethylsulfonyl group, pentabromoethylsulfonyl group, pentaiodoethylsulfonyl group, 2,2,2 -Trichloroethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 2,2,2-tribromoethylsulfonyl group
  • the C1-C6 alkylsulfinyl group represents a linear or branched alkylsulfinyl group having 1-6 carbon atoms, such as a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group.
  • the C1-C6 haloalkylsulfinyl group represents a group in which at least one hydrogen atom of a linear or branched alkylsulfinyl group having 1-6 carbon atoms is substituted with a halogen atom, such as trifluoromethylsulfinyl.
  • the group may C1-C6 alkyl group which may have a selected from the group P 1, which may be substituted with one or more atoms or groups in which a hydrogen atom bonded to a carbon atom selected from the group P 1 C1 -C6 alkyl, is C1-C6 alkyl group, and when two or more atoms or groups selected from the group P 1, even the atom or group selected from these groups P 1 identical to one another, or They may be different from each other.
  • the group may C2-C6 alkyl group which may have a selected from the group P 1, which may be substituted with one or more atoms or groups in which a hydrogen atom bonded to a carbon atom selected from the group P 1 C2 -C6 alkyl, C2-C6 alkyl group, and when two or more atoms or groups selected from the group P 1, even the atom or group selected from these groups P 1 identical to one another, or They may be different from each other.
  • the C3-C6 cycloalkyl group optionally having a group selected from Group P 1 may be substituted with one or more atoms or groups selected from Group P 1 in the hydrogen atom bonded to the carbon atom.
  • the phenyl group optionally having a group selected from group P 2 represents a phenyl group in which a hydrogen atom bonded to a carbon atom may be substituted with one or more atoms or groups selected from group P 2 , phenyl group, and when two or more atoms or groups selected from the group P 2, atom or group selected from these groups P 2 can be identical to each other, or may be the same or different.
  • phenyl group which may have a group selected from the group P 2 include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 2-ethylphenyl group, and 3- Ethylphenyl group, 4-ethylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3 -Bromophenyl group, 4-bromophenyl group, 2-trifluorophenyl group, 3-trifluorophenyl group, 4-trifluorophenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-ethoxyphenyl group, 3-ethoxyphenyl group, 4-ethoxyphenyl group, 4-
  • the benzyl group optionally having a group selected from group P 2 represents a benzyl group in which a hydrogen atom on the benzene ring may be substituted with one or more atoms or groups selected from group P 2 ; a benzyl group, and when two or more atoms or groups selected from the group P 2, atom or group selected from these groups P 2 can be identical to each other, or may be the same or different.
  • Examples of the benzyl group optionally having a group selected from group P 2 include a benzyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3- Chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl group, 3-bromobenzyl group, 4-bromobenzyl group, 2-cyanobenzyl group, 3-cyanobenzyl group, 4-cyanobenzyl group, 2-aminobenzyl Group, 3-aminobenzyl group, 4-aminobenzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-ethylbenzyl group, 3-ethylbenzyl group, 4-ethylbenzyl group, 2-propylbenzyl group, 3-propylbenzyl group, 4-propylbenzyl group, 2-cyclopropylbenzyl group, 3-cyclopropy
  • the phenyl group optionally having a group selected from group P 3 represents a phenyl group in which a hydrogen atom bonded to a carbon atom may be substituted with one or more atoms or groups selected from group P 3. , phenyl group, and when two or more atoms or groups selected from the group P 3, atom or group selected from these groups P 3 will be identical to each other, or may be the same or different.
  • the phenyl group which may have a group selected from the group P 3, for example, a phenyl group, a 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-ethylphenyl group, 3- Ethylphenyl group, 4-ethylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3 -Bromophenyl group, 4-bromophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylophenyl group, 4-trifluoromethylphenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group 2,5-difluorophenyl group, 2,6-difluorophenyl group, 3,4-d
  • the benzyl group optionally having a group selected from group P 3 represents a benzyl group in which a hydrogen atom bonded to a carbon atom may be substituted with an atom or group selected from group P 3; but when two or more atoms or groups selected from the group P 3, atom or group selected from these groups P 3 will be identical to each other, or may be the same or different.
  • the benzyl group which may have a group selected from the group P 3, for example, benzyl, 2-methylbenzyl group, 3-methylbenzyl, 4-methylbenzyl group, 2-ethylbenzyl group, 3- Ethylbenzyl group, 4-ethylbenzyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl Group, 3-bromobenzyl group, 4-bromobenzyl group, 2-trifluorobenzyl group, 3-trifluorobenzyl group, 4-trifluorobenzyl group, 2,3-difluorobenzyl group, 2,4-difluorobenzyl group 2,5-difluorobenzyl group, 2,6-difluorobenzyl group, 3,4-difluorobenzyl group, 3,5-d
  • Examples of the C1-C3 alkyl group optionally having a halogen atom include a methyl group, an ethyl group, a propyl group or an isopropyl group, a chloromethyl group, a dichloromethyl group, a fluoromethyl group, a difluoromethyl group, and a chlorofluoromethyl group.
  • Dichlorofluoromethyl group chlorodifluoromethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloroethyl group, 2,2-dichloroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, pentachloroethyl group, 2-chloro-2-fluoroethyl group, 2-chloro-2,2 -Difluoroethyl group, 2-fluoropropyl group, 3-fluoropropyl group, 2,2- Fluoropropyl group, 2,3-difluoro-propyl, 3,3,3-trifluoropropyl group, heptafluoropropyl group, 1-include (fluoromethyl) -2-fluoroethyl
  • R 1 is a hydrogen atom, a methyl group, an ethyl group, a propyl group, a methoxy group, a trifluoromethyl group, a cyclopropyl group, a 2-propenyl group, a chlorine atom or a bromine atom
  • R 3 is a methyl group, an ethyl group, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom
  • R 2 is a methyl group, an ethyl group, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom
  • R 4 is a hydrogen atom or a fluorine atom
  • a compound in which R 5 is a hydrogen atom or a fluorine atom
  • a compound in which R 7 is a hydrogen atom or a fluorine atom
  • R 8 is
  • a compound in which R 1 is a methyl group, an ethyl group, a trifluoromethyl group, a chlorine atom or a bromine atom;
  • the compound wherein R 4 is a hydrogen atom;
  • the compound wherein R 5 is a hydrogen atom;
  • the compound wherein R 7 is a hydrogen atom;
  • the compound wherein R 8 is a hydrogen atom;
  • the compound wherein R 9 is a hydrogen atom;
  • the compound wherein R 11 is a hydrogen atom;
  • a compound in which R 2 is a hydrogen atom;
  • a compound in which R 3 is a hydrogen atom or a methyl group;
  • a compound in which R 10 is a methyl group, an ethyl group, a difluoromethyl group or a 2,2-difluoroethyl group;
  • a compound in which R 10 is a methyl group;
  • a compound in which X is an oxygen atom;
  • a compound in which X is
  • R 12 is an ethyl group, a cyclopropyl group, or a phenyl group; Compounds wherein R 12 is an ethyl group, a propyl group, an isopropyl group, a butyl group, a neopentyl group, a cyclopropyl group, a cyclohexyl group or a phenyl group; A compound wherein R 12 is a trifluoromethyl group, a 2-propenyl group or a 1-cyclohexenyl group; A compound in which R 12 is a C2-C6 alkyl group, a C3-C6 cycloalkyl group, a phenyl group or a hydrogen atom; R 12 is a C2-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkynyl group, a
  • R 13 is a methyl group, an ethyl group, a 2,2-dimethylethyl group, a 3-propenyl group, a 3-propynyl group or a benzyl group;
  • a compound in which R 13 is a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group or a benzyl group optionally having a group selected from the group P 2 ;
  • R 13 is benzyl group, 2-methylbenzyl group, 3-methylbenzy
  • R 1 is a hydrogen atom, methyl group, ethyl group, propyl group, methoxy group, trifluoromethyl group, cyclopropyl group, 2-propenyl group, chlorine atom or bromine atom
  • R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 2 and R 3 are hydrogen atoms or methyl groups
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is a C2-C6 alkyl group , C1-C6 haloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group or group P have a group selected from 2 is also a phenyl group
  • R 13 is C1-
  • R 1 is a hydrogen atom, methyl group, ethyl group, propyl group, methoxy group, trifluoromethyl group, cyclopropyl group, 2-propenyl group, chlorine atom or bromine atom
  • R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 2 and R 3 are hydrogen atoms or methyl groups
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is a phenyl group, 2- Methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl Group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-
  • R 1 is a hydrogen atom, methyl group, ethyl group, propyl group, methoxy group, trifluoromethyl group, cyclopropyl group, 2-propenyl group, chlorine atom or bromine atom
  • R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 2 and R 3 are hydrogen atoms or methyl groups
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is an ethyl group, a propyl group , Isopropyl group, butyl group, neopentyl group, cyclopropyl group,
  • a compound which is a benzyl group is a hydrogen atom, methyl group, ethyl group, propyl group, methoxy group, trifluoromethyl group, cyclopropyl group, 2-propenyl group, chlorine atom or bromine atom, and R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms, R 2 and R 3 are hydrogen atoms or methyl groups, R 10 is a methyl group, X is an oxygen atom, R 12 is an ethyl group, cyclopropyl A compound wherein R 13 is a methyl group, an ethyl group, a 2,2-dimethylethyl group, a 3-propenyl group, a 3-propynyl group or a benzyl group;
  • R 1 is an optionally substituted C1-C3 alkyl group or a halogen atom
  • R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 2 and R 3 is a hydrogen atom or a methyl group
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is a C2-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 halo alkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, a C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, or a phenyl group which may have a group selected from the group P 2
  • R 13 is C1-C6 alkyl group, C2-C6 alkenyl group, have a C2-C
  • R 1 is an optionally substituted C1-C3 alkyl group or a halogen atom
  • R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 2 and R 3 is a hydrogen atom or a methyl group
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is an ethyl group, a propyl group, an isopropyl group, a butyl group, a neopentyl group, a cyclopropyl group, a cyclohexyl group, A phenyl group, a trifluoromethyl group, a 2-propenyl group or a 1-cyclohexenyl group
  • R 13 is a methyl group, an ethyl group, a 2,2-dimethylethyl group, a butyl group, a 3-propenyl group, a benzyl group, 2
  • R 1 is an optionally substituted C1-C3 alkyl group or a halogen atom
  • R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 2 and R 3 is a hydrogen atom or a methyl group
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is an ethyl group, a propyl group, an isopropyl group, a butyl group, a neopentyl group, a cyclopropyl group, a cyclohexyl group or A phenyl group and R 13 is a methyl group, ethyl group, 2,2-dimethylethyl group, butyl group, 3-propenyl group,
  • R 1 is an optionally substituted C1-C3 alkyl group or a halogen atom
  • R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 2 and R 3 is a hydrogen atom or a methyl group
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is a C2-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 halo alkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, a C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, or a phenyl group which may have a group selected from the group P 2
  • R 13 is C1-C6 alkyl group, C2-C6 alkenyl group, have a C2-C
  • R 1 is a C1-C3 alkyl group optionally having a halogen atom or a halogen atom
  • R 2 and R 3 are a hydrogen atom or a methyl group
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is an ethyl group, propyl group, isopropyl group, butyl group, neopentyl group, cyclopropyl group, cyclohexyl group, phenyl group, trifluoromethyl group, 2-propenyl group or 1-cyclohexenyl group
  • R 13 Is a benzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-ethylbenzyl group, 3-ethylbenzyl group, 4-ethylbenzyl group, 2-fluorobenzyl group, 3-flu
  • R 1 is an optionally substituted C1-C3 alkyl group or a halogen atom
  • R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 2 and R 3 is a hydrogen atom or a methyl group
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is an ethyl group, a propyl group, an isopropyl group, a butyl group, a neopentyl group, a cyclopropyl group, a cyclohexyl group, A phenyl group, a trifluoromethyl group, a 2-propenyl group or a 1-cyclohexenyl group
  • R 13 is a methyl group, an ethyl group, a 2,2-dimethylethyl group, a butyl group, a 3-propenyl group, a benzyl group, 2
  • R 1 is an optionally substituted C1-C3 alkyl group or a halogen atom
  • R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 2 and R 3 is a hydrogen atom or a methyl group
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is an ethyl group, a propyl group, an isopropyl group, a butyl group, a neopentyl group, a cyclopropyl group, a cyclohexyl group or A phenyl group and R 13 is a methyl group, ethyl group, 2,2-dimethylethyl group, butyl group, 3-propenyl group,
  • R 1 is a methyl group, an ethyl group, a trifluoromethyl group, a chlorine atom or a bromine atom
  • R 2 , R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is a C2-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkynyl group group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, a C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, or a phenyl group which may have a group selected from the group P 2, R 13 C1-C6 alkyl group, C2-C6
  • R 1 is a methyl group, an ethyl group, a trifluoromethyl group, a chlorine atom or a bromine atom
  • R 2 , R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, 2- Ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2-fluorophenyl group, 3-flu
  • a compound which is R 1 is a methyl group, an ethyl group, a trifluoromethyl group, a chlorine atom or a bromine atom
  • R 2 , R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 3 Is a hydrogen atom or a methyl group
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, 2- Ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2 -Bromophenyl group, 3-bromophenyl group,
  • R 1 is a methyl group, an ethyl group, a trifluoromethyl group, a chlorine atom or a bromine atom
  • R 2 , R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 3 Is a hydrogen atom or a methyl group
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is an ethyl group, propyl group, isopropyl group, butyl group, neopentyl group, cyclopropyl group, cyclohexyl group, phenyl Group, trifluoromethyl group, 2-propenyl group or 1-cyclohexenyl group
  • R 13 is benzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-ethylbenzyl
  • R 1 is a methyl group, an ethyl group, a trifluoromethyl group, a chlorine atom or a bromine atom
  • R 2 , R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 3 Is a hydrogen atom or a methyl group
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is an ethyl group, propyl group, isopropyl group, butyl group, neopentyl group, cyclopropyl group, cyclohexyl group or phenyl a group
  • R 13 is a C1-C6 alkyl group, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl group or benzyl group that may have a group selected from the group P 2 Compound
  • R 1 is a methyl group, an ethyl
  • R 1 is a methyl group, an ethyl group, a trifluoromethyl group, a chlorine atom or a bromine atom
  • R 2 , R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 3 Is a hydrogen atom or a methyl group
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is an ethyl group, propyl group, isopropyl group, butyl group, neopentyl group, cyclopropyl group, cyclohexyl group or phenyl
  • R 13 is a methyl group, an ethyl group, a 2,2-dimethylethyl group, a 3-propenyl group, a 3-propynyl group or a benzyl group
  • R 1 is a methyl group, an ethyl group, a trifluoromethyl group, a
  • R 1 is a methyl group
  • R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is an ethyl group, propyl group, isopropyl group, butyl group, neopentyl group, cyclopropyl group, cyclohexyl group, phenyl group, trifluoromethyl group, 2-propenyl group or 1-cyclohexenyl group
  • R 13 Is a methyl group, ethyl group, 2,2-dimethylethyl group, butyl group, 3-propenyl group, benzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group or 4-chlorobenzyl group
  • R 1 is a methyl group
  • R 1 is a methyl group,
  • R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms,
  • R 10 is a methyl group,
  • X is an oxygen atom
  • R 12 is an ethyl group, a cyclopropyl group or a phenyl group
  • R 13 is a methyl group, an ethyl group, a 2,2-dimethylethyl group, a 3-propenyl group, a 3-propynyl group or a benzyl group;
  • R 1 is a methyl group,
  • R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms,
  • R 10 is a methyl group
  • X is an oxygen atom
  • R 12 is
  • R 1 is a C1-C6 alkyl group
  • R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 10 is a C1-C3 alkyl group
  • X is an oxygen atom
  • R 12 is a C2-C6 alkyl group, a C3-C6 cycloalkyl group, a phenyl group or a hydrogen atom
  • R 13 is a C1-C8 alkyl group
  • R 1 is a C1-C3 alkyl group
  • R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 11 are hydrogen atoms
  • R 10 is a C1-C3 alkyl group
  • X is an oxygen atom
  • R 12 is a C2-C6 alkyl group, a C3-C6 cycloalkyl group, a phenyl group or a hydrogen atom
  • R 13 is a C1-C3 alkyl group
  • the compound of the present invention represented by formula (1) is composed of a compound represented by formula (A-1) (hereinafter referred to as compound (A-1)) and a compound represented by formula (A-2) (hereinafter referred to as compound). (Referred to as (A-2)) in the presence of a base.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and X represent the same meaning as above, Z 11 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, or a p-toluenesulfonyloxy group.
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, water and mixtures thereof.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichlor
  • Examples of the base used in the reaction include triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene and the like.
  • Alkali metal carbonates such as organic bases, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, lithium hydroxide, hydroxide
  • Alkali metal hydroxides such as sodium, potassium hydroxide and cesium hydroxide
  • alkali metal halides such as sodium fluoride, potassium fluoride and cesium fluoride
  • alkali metals such as lithium hydride, sodium hydride and potassium hydride Hydrogenation , Sodium tert- butoxide, alkali metal alkoxides such as potassium tert- butoxide.
  • the compound (A-2) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol.
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • sodium iodide, tetrabutylammonium iodide or the like may be added as necessary. These compounds are usually added in an amount of 0.001 to 1.2 mol per 1 mol of compound (A-1). It is used in the ratio.
  • the compound of the present invention represented by the formula (1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer.
  • the compound of the present invention represented by the formula (1) can be isolated by performing post-treatment operations such as filtration and concentration of the reaction mixture.
  • the isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
  • the compound of the present invention represented by formula (1) is composed of a compound represented by formula (B-1) (hereinafter referred to as compound (B-1)) and a compound represented by formula (B-2) (hereinafter referred to as compound). (B-2)) in the presence of a base.
  • Z 21 represents a leaving group such as a chlorine atom, bromine atom, iodine atom, methanesulfonyloxy group, methoxysulfonyloxy group, trifluoromethanesulfonyloxy group or p-toluenesulfonyloxy group.
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, water and mixtures thereof.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichlor
  • a commercially available product can be used.
  • chlorodifluoromethane methyl bromide, ethyl bromide, n-propyl bromide, methyl iodide, ethyl iodide, n-propyl bromide, allyl bromide, cyclopropyl bromide, 1,1-difluoro-2 Alkyl halides such as iodoethane, dimethyl sulfate, methyl p-toluenesulfonate, ethyl p-toluenesulfonate, n-propyl p-toluenesulfonate, methyl methanesulfonate, ethyl methanesulfonate, n-methanesulfonate
  • alkyl or aryl sulfates such as propyl.
  • Examples of the base used in the reaction include triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene and the like.
  • Alkali metal carbonates such as organic bases, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, lithium hydroxide, hydroxide
  • Alkali metal hydroxides such as sodium, potassium hydroxide and cesium hydroxide
  • alkali metal halides such as sodium fluoride, potassium fluoride and cesium fluoride
  • alkali metals such as lithium hydride, sodium hydride and potassium hydride Hydrogenation , Lithium hydride, sodium hydride, an alkali metal hydride such as potassium hydride, sodium tert- butoxide, alkali metal alkoxides such as potassium tert- butoxide.
  • the compound (B-2) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 0.5 to 10 mol.
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention represented by the formula (1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer.
  • the isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
  • Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as tellurium, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, nitriles such as acetonitrile, propionitrile, etc. And mixtures thereof.
  • the sulfiding agent used in the reaction include phosphorus pentasulfide, Lawesson's reagent (2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane 2,4-disulphide) and the like.
  • a sulfurizing agent is usually used at a ratio of 0.5 to 10 moles relative to 1 mole of the compound (1-O).
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • an organic base such as pyridine or triethylamine, an inorganic base such as an alkali metal hydroxide or an alkali metal carbonate, or the like may be added.
  • the amount of the base to be added is the compound (1-O). The amount is usually 0.5 to 10 moles.
  • the compound of the present invention represented by the formula (1-S) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. .
  • the isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
  • R 42 represents a C1-C3 alkyl group, C1-C3 haloalkyl group, C2-C3 alkenyl or C2-C3 haloalkenyl group
  • Z 42 is B (OH) 2 , a boronic acid ester, or a trifluoroborate salt BF 3 ⁇ K + is represented. ]
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, methanol, ethanol, propanol, alcohols such as butanol, water and mixtures thereof.
  • halogenated hydrocarbons such as carbon t
  • the compound (D-2-2) used in the reaction a commercially available compound is usually used, or N.I. Miyaura and A.M. Suzuki, Chem. Rev. 1995, 95, 2457 and Molander et al. Acc. Chem. Res. , 2007, 40, 275, etc. can be used.
  • the catalyst used in the reaction include palladium (II) acetate, dichlorobis (triphenylphosphine) palladium, tetrakistriphenylphosphinepalladium (0), palladium (II) acetate / triscyclohexylphosphine, bis (diphenylphosphaneferro).
  • Examples of the base used in the reaction include triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene and the like.
  • Alkali metal carbonates such as organic bases, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, lithium hydroxide, hydroxide
  • Alkali metal hydroxides such as sodium, potassium hydroxide and cesium hydroxide
  • alkali metal halides such as sodium fluoride, potassium fluoride and cesium fluoride
  • alkali metals such as lithium hydride, sodium hydride and potassium hydride
  • Hydrogenation Alkali metal phosphates such as tripotassium phosphate, sodium methoxide, sodium ethoxide, sodium tert- butoxide, alkali metal alkoxides such as potassium tert- butoxide.
  • the compound (D-2-2) is usually 1 to 10 mol
  • the base is usually 1 to 10 mol
  • the catalyst is usually 0.0001 to Used in a proportion of 1 mole.
  • the reaction temperature of the reaction is usually in the range of 0 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention represented by the formula (1-1-2) is isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. Can do.
  • the isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
  • a compound represented by the formula (1-1-3) wherein R 8 is R 42 (hereinafter referred to as a compound) (Referred to as (1-1-3)) is a compound represented by formula (D-4) (hereinafter referred to as compound (D-4)) and a compound represented by formula (D-2-2) ( Hereinafter, the compound (D-2-2)) can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst.
  • a compound represented by the formula (1-1-4) wherein R 9 is R 42 (hereinafter referred to as a compound) (Referred to as (1-1-4)) is a compound represented by formula (D-5) (hereinafter referred to as compound (D-5)) and a compound represented by formula (D-2-2) ( Hereinafter, the compound (D-2-2)) can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst.
  • R 51 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C6 cycloalkyl group. Or represents a C3-C6 halocycloalkyl group.
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, methanol, ethanol, propanol, alcohols such as butanol, water and mixtures thereof.
  • halogenated hydrocarbons such as carbon t
  • the compound (E-2) used for the reaction a commercially available compound is generally used, or N.I. Miyaura and A.M. Suzuki, Chem. Rev. 1995, 95, 2457 and Molander et al. Acc. Chem. Res. , 2007, 40, 275, etc. can be used.
  • the catalyst used in the reaction include palladium (II) acetate, dichlorobis (triphenylphosphine) palladium, tetrakistriphenylphosphinepalladium (0), palladium (II) acetate / triscyclohexylphosphine, bis (diphenylphosphaneferro).
  • Examples of the base used in the reaction include organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene and diazabicyclononene.
  • organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene and diazabicyclononene.
  • Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc., lithium hydroxide, sodium hydroxide, Alkali metal hydroxides such as potassium hydroxide and cesium hydroxide, alkali metal halides such as sodium fluoride, potassium fluoride and cesium fluoride, alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride ,Rin Alkali metal phosphates such as tripotassium, sodium methoxide, sodium ethoxide, sodium tert- butoxide, alkali metal alkoxides such as potassium tert- butoxide.
  • the compound (E-2) is usually 1 to 10 mol
  • the base is usually 1 to 10 mol
  • the catalyst is usually 0.0001 to 1 mol. It is used in the ratio.
  • the reaction temperature of the reaction is usually in the range of 0 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention represented by the formula (1-2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. .
  • the isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
  • a compound represented by the formula (1-2-2) wherein R 2 is R 51 (hereinafter referred to as the compound (1) -2-2)) is a compound represented by formula (E-3) (hereinafter referred to as compound (E-3)) and a compound represented by formula (E-2) (hereinafter referred to as compound ( E-2) can be prepared by subjecting it to a coupling reaction in the presence of a base and a catalyst.
  • a compound represented by the following formula (1-2-3) wherein R 3 is R 51 (hereinafter referred to as a compound ( 1-2-3)) is a compound represented by the following formula (E-4) (hereinafter referred to as a compound (E-4)) and a compound represented by the following formula (E-2) (hereinafter referred to as a compound (E-2)).
  • E-4 a compound represented by the following formula (E-4)
  • E-2) a compound represented by the following formula (E-2)
  • Compound (E-2)) can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst.
  • a compound represented by the formula (1-2-4) wherein R 11 is R 51 (hereinafter referred to as the compound (1) 2-4)) is a compound represented by formula (E-5) (hereinafter referred to as compound (E-5)) and a compound represented by formula (E-2) (hereinafter referred to as compound ( E-2) can be prepared by subjecting it to a coupling reaction in the presence of a base and a catalyst.
  • the compound of the present invention represented by formula (1) is composed of a compound represented by formula (F-1) (hereinafter referred to as compound (F-1)) and a compound represented by formula (F-2) (hereinafter referred to as compound). (F-2)) or a salt thereof can be reacted.
  • F-1 a compound represented by formula (F-1)
  • F-2 a compound represented by formula (F-2)
  • (F-2)) or a salt thereof can be reacted.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , and X represent the same meaning as described above.
  • Examples of the solvent used in the reaction include alcohols such as methanol, ethanol, propanol and butanol, hydrocarbons such as water, n-heptane, n-hexane, cyclohexane, n-pentane, toluene and xylene, and diethyl ether.
  • alcohols such as methanol, ethanol, propanol and butanol
  • hydrocarbons such as water, n-heptane, n-hexane, cyclohexane, n-pentane, toluene and xylene, and diethyl ether.
  • Examples of the salt that can be used in the reaction include hydrochloride, sulfate, and carbonate.
  • (F-2) or a salt thereof is usually used at a ratio of 1 to 10 mol per 1 mol of compound (F-1).
  • additives may be added as necessary, for example, triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicyclone.
  • Organic bases such as decene and diazabicyclononene, alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate and cesium carbonate, alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and cesium hydrogen carbonate
  • alkali metal acetates such as sodium acetate and potassium acetate
  • quaternary ammonium salts such as tetra (n-butyl) ammonium hydroxide.
  • These additives are usually used at a ratio of 0.5 to 10 mol with respect to 1 mol of the compound (F-1).
  • the reaction temperature is usually in the range of 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 72 hours.
  • the compound (1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • a compound represented by formula (XA3) (hereinafter referred to as compound (XA3)) is a compound represented by formula (XA1) (hereinafter referred to as compound (XA1)) or a compound represented by (XA2) ( Hereinafter, it can be produced by reacting compound (XA2)) with an azidating agent.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 11 , R 12 , R 13 and X represent the same meaning as described above, and R 101 represents P 11 , P 12 or P 13 , R 91 represents a C1-C12 alkyl group, Z 101 represents a chlorine atom or a bromine atom, and ⁇ represents a binding site.
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, acetonitrile, nitriles and mixtures thereof, such as propionitrile and the like.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-d
  • the azidating agent used in the reaction examples include inorganic azides such as sodium azide, barium azide or lithium azide, and organic azides such as trimethylsilyl azide and diphenylphosphoryl azide.
  • the azidating agent is usually used in a proportion of 1 to 10 mol per 1 mol of the compound (XA1) or the compound (XA2).
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • a Lewis acid such as aluminum chloride or zinc chloride may be added as necessary, and these compounds are usually added in an amount of 0.05 to 5 to 1 mol of the compound (XA1) or the compound (XA2).
  • the compound (XA3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer.
  • the isolated compound (XA3) can be further purified by chromatography, recrystallization and the like.
  • Compound (XA1) can be produced by reacting a compound represented by the following formula (XB1) (hereinafter referred to as compound (XB1)) with an isocyanate forming agent.
  • XB1 a compound represented by the following formula (XB1)
  • an isocyanate forming agent e.g., a compound represented by the following formula (XB1)
  • R 7 , R 8 , R 9 , R 101 and X represent the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether and diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane and chlorobenzene, esters such as ethyl acetate and methyl acetate , Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile and propionitrile, and mixtures thereof.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane and chlorobenzene
  • esters such as ethyl acetate and methyl acetate
  • Ketones such as acetone, methyl eth
  • Examples of the isocyanate agent used in the reaction include phosgene, diphosgene, triphosgene, and thiophosgene, N, N-carbodiimidazole, N, N-thiocarbodiimidazole, and the like.
  • the isocyanate agent is usually used at a ratio of 1 to 10 moles with respect to 1 mole of the compound (XB1).
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction may be carried out by using organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene, etc.
  • organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene, etc.
  • Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate
  • alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium bicarbonate, potassium bicarbonate, and cesium bicarbonate may be added.
  • the compound is usually used in a proportion of 0.05 to 5 mol with
  • the compound (XA1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • Compound (XA2) can be produced by reacting a compound represented by the formula (XC1) (hereinafter referred to as compound (XC1)) with a halogenating agent.
  • a compound represented by the formula (XC1) hereinafter referred to as compound (XC1)
  • a halogenating agent wherein, R 7 , R 8 , R 9 , R 101 and Z 101 represent the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether and diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane and chlorobenzene, esters such as ethyl acetate and methyl acetate , Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile and propionitrile, and mixtures thereof.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane and chlorobenzene
  • esters such as ethyl acetate and methyl acetate
  • Ketones such as acetone, methyl eth
  • halogenating agent used in the reaction examples include phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride, thionyl chloride, phosphorus oxybromide, phosphorus tribromide, phosphorus pentabromide, phosphorus triiodide, and dichloride.
  • Examples include oxalyl, oxalyl dibromide, triphosgene, diphosgene, phosgene, and sulfuryl chloride.
  • the halogenating agent is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (XC1).
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • a catalyst may be added, and examples thereof include N, N-dimethylformamide.
  • the amount of the catalyst used is usually 0.001 to 1 mol with respect to 1 mol of compound (XC1).
  • the reaction may further include triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene and the like.
  • Alkali metal carbonates such as organic base, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc. may be added, These compounds are usually used in a proportion of 0.05 to 5 mol with respect to 1 mol of compound (XC1).
  • the compound (XA2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • Compound (XA1) is obtained by reacting compound (XB1) with a carbamate agent to obtain a compound represented by the formula (XD1) (hereinafter referred to as compound (XD1)), and then compound (XD1) and isocyanate. It can be produced by reacting with an agent.
  • R 7 , R 8 , R 9 and R 101 represent the same meaning as described above, and R 111 represents a C1-C12 alkyl group or a phenyl group.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, water and mixtures thereof.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichlor
  • Examples of the carbamate agent used in the reaction include phenyl chlorocarbonate, methyl chlorocarbonate, ethyl chlorocarbonate, n-propyl chlorocarbonate, isopropyl chlorocarbonate, n-butyl chlorocarbonate, tert-butyl chlorocarbonate, dicarbonate dicarbonate. -Tert-butyl, dimethyl dicarbonate, diethyl dicarbonate, phenyl chlorothioformate, methyl chlorothioformate, ethyl chlorothioformate and the like.
  • the carbamate agent is usually used at a ratio of 1 to 10 moles relative to 1 mole of the compound (XB1).
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction may be carried out with an organic base such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene as necessary.
  • Bases such as alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, These bases are generally used in a proportion of 0.05 to 5 mol per 1 mol of compound (XB1).
  • the compound (XD1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include ethers such as tetrahydrofuran, dioxane, ethylene glycol dimethyl ether and methyl tert-butyl ether, aromatic hydrocarbons such as toluene and xylene, carbon tetrachloride, chloroform or Halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone and N-methylpyrrolidone, Examples thereof include sulfoxides such as dimethyl sulfoxide, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, and mixtures thereof.
  • Examples of the isocyanate agent used in the reaction include phosphorus pentachloride, phosphorus oxychloride, diphosphorus pentoxide, trichlorosilane, dichlorosilane, monochlorosilane, boron trichloride, 2-chloro-1,3,2- Benzodioxaborol, diiodinated silane, methyltrichlorosilane, dimethyldichlorosilane, chlorotrimethylsilane, and the like can be used.
  • the isocyanate agent is usually used at a ratio of 1 to 10 moles relative to 1 mole of the compound (XD1).
  • the reaction temperature is usually in the range of ⁇ 20 to 250 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction may be carried out by organic compounds such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diinpropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene, as necessary.
  • Bases such as bases, alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal bicarbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate may be added.
  • the compound (XA1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • a compound represented by formula (XE2) (hereinafter, compound (XE2) is produced by reacting a compound represented by formula (XE1) (hereinafter referred to as compound (XE1)) with hydrogen in the presence of a catalyst. can do.
  • a compound represented by formula (XE1) hereinafter referred to as compound (XE1)
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 11 and Q represent the same meaning as described above, and R 181 represents a hydrogen atom or P 21 . , ⁇ represents a binding site.
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include alcohols such as methanol, ethanol, propanol and butanol, esters such as ethyl acetate and butyl acetate, carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, Halogenated hydrocarbons such as chlorobenzene, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisole, methyl tert-butyl ether, diisopropyl ether, n-heptane, n-hexane , Hydrocarbons such as cyclohexane, n-pentane, toluene, xylene, acetic acid, water, and mixtures thereof.
  • alcohols such as methanol, ethanol, propanol and butanol
  • the catalyst used in the reaction examples include palladium on carbon (Pd / C), platinum on carbon (Pt / C), osmium on carbon (Os / C), ruthenium on carbon (Ru / C), rhodium on carbon ( Rh / C), Raney nickel and the like.
  • the catalyst is usually used in a proportion of 0.1 to 1 mol and hydrogen in an excess amount.
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (XE2) can be isolated by post-treatment such as filtration of the catalyst and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • Compound (XE2) can be produced by reacting compound (XE1) with a reducing agent in the presence of an acid.
  • a reducing agent in the presence of an acid.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include aliphatic carboxylic acids such as acetic acid, alcohols such as methanol and ethanol, water, and mixtures thereof.
  • the reducing agent used in the reaction include tin compounds such as tin chloride, zinc compounds such as zinc chloride, and iron.
  • the acid used in the reaction examples include hydrochloric acid, sulfuric acid, acetic acid, and an aqueous ammonium chloride solution.
  • the reducing agent is usually used in a proportion of 1 to 30 mol and the acid in a proportion of 1 to 100 mol.
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (XE2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • a compound represented by formula (XG2) (hereinafter referred to as compound (XG2)) is obtained by combining a compound represented by formula (XG1) (hereinafter referred to as compound (XG1)) with compound (B-2). It can manufacture by making it react in presence of. [Wherein, R 7 , R 8 , R 9 , R 10 , X and Z 11 represent the same meaning as described above, and R 191 represents P 12 or P 13 . ] This reaction can be carried out according to the above Production Method B.
  • a compound represented by the formula (XH2) (hereinafter referred to as the compound (XH2)) is obtained by combining a compound represented by the formula (XH1) (hereinafter referred to as the compound (XH1)) with a halogenating agent. It can manufacture by making it react in presence.
  • a compound represented by the formula (XH1) hereinafter referred to as the compound (XH1)
  • a halogenating agent e.g., R 4 , R 5 , R 7 , R 8 , R 9 , R 10 and X represent the same meaning as described above, R 100 represents a halogen atom, and R 201 represents P 51 or a nitro group.
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as tellurium, anisole, methyl tert-butyl ether, diisopropyl ether, carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, fluorobenzene, difluorobenzene, trifluorobenzene, chlorobenzene, dichlorobenzene, trichlorobenzene , ⁇ , ⁇ , ⁇ -trifluorotoluene, halogenated hydrocarbons such as ⁇ , ⁇ , ⁇ -trichlorotoluene, esters such as ethyl acetate and methyl acetate, acetone, methyl ethyl ketone, methyl Ketones such as isobutyl ketone, acetonitrile, nitriles and mixtures thereof, such as propionitrile and the like.
  • the halogenating agent that can be used in the reaction is a chlorinating agent, a brominating agent or an iodinating agent.
  • a chlorinating agent e.g., chlorine, bromine, iodine, sulfuryl chloride, N-chlorosuccinimide, N-bromosuccinimide, 1, 3-dibromo-5,5-dimethylhydantoin, iodosuccinimide, tert-butyl hypochlorite, N-chloroglutarimide, N-bromoglutarimide, N-chloro-N-cyclohexyl-benzenesulfonimide, N-bromophthalimide Etc.
  • radical initiator used in the reaction examples include benzoyl peroxide, azobisisobutyronitrile (AIBN), 1,1-azobis (cyanocyclohexane), diacyl peroxide, dialkylperoxydicarbonate, tert-alkylperoxyester. , Monoperoxycarbonate, di (tert-alkylperoxy) ketal and ketone peroxide, triethylborane and the like.
  • the halogenating agent is usually used in a proportion of 1 to 10 mol and the radical initiator is usually used in a proportion of 0.01 to 5 mol with respect to 1 mol of the compound (XH1).
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (XH2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • a compound represented by formula (XI2) (hereinafter referred to as compound (XI2)) is obtained by reacting compound (XH2) with a compound represented by formula (XI1) (hereinafter referred to as compound (XI1)).
  • compound (XI2) is obtained by reacting compound (XH2) with a compound represented by formula (XI1) (hereinafter referred to as compound (XI1)).
  • XI1 a compound represented by formula (XI1)
  • Can be manufactured a compound represented by formula (XI2)
  • R 4 , R 5 , R 7 , R 8 , R 9 , R 100 , R 201 and R 111 represent the same meaning as described above, and M represents sodium, potassium, or lithium.
  • the reaction is usually performed in a solvent.
  • solvent used in the reaction examples include ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisole, methyl tert-butyl ether, diisopropyl ether, n-heptane, n -Hydrocarbons such as hexane, cyclohexane, n-pentane, toluene, xylene, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, acetonitrile, propionitrile, etc.
  • ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisole, methyl tert-butyl ether, diiso
  • Examples of the compound (XI1) include sodium methoxide, sodium ethoxide, sodium n-propoxide, sodium n-butoxide, sodium isopropoxide, sodium sec-butoxide, sodium tert-butoxide, potassium methoxide, potassium ethoxide.
  • compound (XI1) is usually used at a ratio of 1 to 10 mol per 1 mol of compound (XH2).
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (XI2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • a compound represented by formula (XJ1) (hereinafter referred to as compound (XJ1)) can be produced by reacting compound (XH2) with water in the presence of a base. [Wherein R 4 , R 5 , R 7 , R 8 , R 9 , R 100 and R 201 represent the same meaning as described above. ] The reaction is usually performed in water or a solvent containing water.
  • solvent used in the reaction examples include ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisole, methyl tert-butyl ether, diisopropyl ether, n-heptane, n -Hydrocarbons such as hexane, cyclohexane, n-pentane, toluene, xylene, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, acetonitrile, propionitrile, etc.
  • ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisole, methyl tert-butyl ether, diiso
  • Nitriles N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, Ketones such as Louis Seo ketone, methanol, ethanol, propanol, and mixtures thereof, such as butanol.
  • Examples of the base used in the reaction include triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene and the like.
  • Organic bases metal organic acid salts such as lithium formate, lithium acetate, sodium formate, sodium acetate, potassium formate and potassium acetate, metal nitrates such as silver nitrate and sodium nitrate, alkalis such as lithium carbonate, sodium carbonate, potassium carbonate and cesium carbonate
  • Alkali metal hydrogen carbonates such as metal carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, Natri Mumetokishido, sodium ethoxide, sodium tert- butoxide, alkali metal alkoxides such as potassium tert- butoxide.
  • the base is usually used at a ratio of 1 to 100 mol per 1 mol of the compound (XH2).
  • water is usually used in a proportion of 1 mol to large excess with respect to 1 mol of compound (XH2).
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (XJ1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • Compound (XH2) can be produced by reacting compound (XI2) with a halogenating agent.
  • a halogenating agent e.g., n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane.
  • Halogenated hydrocarbons such as chlorobenzene, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile and propionitrile, organic acids such as formic acid, acetic acid and trifluoroacetic acid, water and mixtures thereof.
  • Examples of the halogenating agent used in the reaction include hydrochloric acid, hydrobromic acid, and hydriodic acid.
  • the halogenating agent is usually used in a proportion of 1 mol or more per 1 mol of the compound (XI2).
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (XH2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • Compound (XH2) can also be produced by reacting compound (XJ1) with a halogenating agent.
  • a halogenating agent e.g., n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as tellurium, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, esters such as ethyl acetate and methyl acetate , Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile and propionitrile, organic acids such as formic acid, acetic acid and trifluoroacetic acid, water and mixtures thereof.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene
  • esters such as ethyl a
  • halogenating agent used in the reaction examples include bromine, chlorine, sulfuryl chloride, hydrochloric acid, hydrobromic acid, hydroiodic acid, boron tribromide, phosphorus tribromide, trimethylsilyl chloride, trimethylsilyl bromide.
  • the halogenating agent is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (XJ1).
  • additives may be added depending on the halogenating agent used, for example, zinc chloride for acetyl chloride, triphenylphosphine for carbon tetrabromide, and N-bromosuccinimide.
  • Dimethyl sulfide, boron trifluoride diethyl ether complex for sodium iodide, boron trifluoride diethyl ether complex for acetyl bromide, triethylamine and methanesulfonyl chloride for lithium chloride, chloride for sodium iodide Trimethylsilyl chloride etc. are mentioned with respect to aluminum and sodium iodide.
  • the amount of the additive used is usually 0.01 to 5 moles per mole of compound (XJ1).
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (XH2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • the compound represented by the formula (XM2) (hereinafter referred to as the compound (XM2)) is composed of (the compound (XJ1) and the compound represented by the formula (XM1) (hereinafter referred to as the compound (XM1)) in the presence of a base. It can manufacture by making it react.
  • R 901 represents a p-methylphenyl group, a methyl group, or a trifluoromethyl group
  • 301 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group or a trifluoromethanesulfonyloxy group.
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as tellurium, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, nitriles such as acetonitrile, propionitrile, etc.
  • the base used in the reaction include triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene and the like.
  • Alkali metal carbonates such as organic bases, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, lithium hydroxide, hydroxide
  • Alkali metal hydroxides such as sodium, potassium hydroxide and cesium hydroxide
  • alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride, sodium methoxide, sodium ethoxide and sodium tert-butoxide
  • Alkali metal alkoxides such as potassium tert- butoxide.
  • compound (XJ1) is usually used in a proportion of 1 to 10 mol, and base is usually used in a proportion of 1 to 5 mol.
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • sodium iodide, tetrabutylammonium iodide or the like may be added as necessary, and these additives are usually added in an amount of 0.001 to 1.2 mol with respect to 1 mol of the compound (XJ1). Used in proportions.
  • the compound (XM2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer.
  • the isolated compound (XM2) can be further purified by chromatography, recrystallization, and the like.
  • the compound represented by the formula (XN22) (hereinafter referred to as the compound (XN22)) is the same as the compound represented by the formula (XN21) (hereinafter referred to as the compound (XN21)) and the compound (D-2-2). It can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst. [Wherein R 4 , R 5 , R 8 , R 9 , R 10 , R 42 , R 501 , X, Z 41 and Z 42 represent the same meaning as described above. ] The reaction can be carried out according to Production Method D.
  • the compound represented by the formula (XN32) (hereinafter referred to as the compound (XN32)) is the same as the compound represented by the formula (XN31) (hereinafter referred to as the compound (XN31)) and the compound (D-2-2). It can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst. [Wherein R 4 , R 5 , R 7 , R 9 , R 10 , R 42 , R 501 , X, Z 41 and Z 42 represent the same meaning as described above. ] The reaction can be carried out according to Production Method D.
  • the compound represented by the formula (XN42) (hereinafter referred to as the compound (XN42)) is the same as the compound represented by the formula (XN41) (hereinafter referred to as the compound (XN41)) and the compound (D-2-2). It can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst. [Wherein, R 4 , R 5 , R 7 , R 8 , R 10 , R 42 , R 501 , X, Z 41 and Z 42 represent the same meaning as described above. ] The reaction can be carried out according to Production Method D.
  • a compound represented by formula (XO22) (hereinafter referred to as compound (XO22)) is a compound represented by formula (XO21) (hereinafter referred to as compound (XO21)) and a compound (D-2-2).
  • XO22 is a compound represented by formula (XO21) (hereinafter referred to as compound (XO21)) and a compound (D-2-2).
  • R 8 , R 9 , R 10 , R 42 , R 91 , X, Z 41 and Z 42 represent the same meaning as described above.
  • the reaction can be carried out according to Production Method D.
  • the compound represented by the formula (XO32) (hereinafter referred to as the compound (XO32)) is the same as the compound represented by the formula (XO31) (hereinafter referred to as the compound (XO31)) and the compound (D-2-2). It can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst. [Wherein, R 7 , R 9 , R 10 , R 42 , R 91 , X, Z 41 and Z 42 represent the same meaning as described above. ] The reaction can be carried out according to Production Method D.
  • the compound represented by the formula (XO42) (hereinafter referred to as the compound (XO42)) is the same as the compound represented by the formula (XO41) (hereinafter referred to as the compound (XO41)) and the compound (D-2-2). It can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst. [Wherein R 7 , R 8 , R 10 , R 42 , R 91 , X, Z 41 and Z 42 represent the same meaning as described above. ] The reaction can be carried out according to Production Method D.
  • the compound represented by formula (XP3) (hereinafter referred to as compound (XP3)) is represented by the following formula (XP1) in the presence of a reaction accelerator. It can be produced by reacting with a compound represented by (XP2) (hereinafter referred to as compound (XP2)). [Wherein, R 7 , R 8 , R 9 and R 91 represent the same meaning as described above. ] The reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile and mixtures thereof, may also be used compound (XP2) as solvent.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dich
  • Examples of the compound (XP2) that can be used in the reaction include methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, t-butanol, and n-pentanol.
  • reaction accelerator used in the reaction examples include acids such as hydrochloric acid and sulfuric acid, carbodiimides such as dicyclohexylcarbodiimide, diisopropylcarbodiimide, N ′-(3-dimethylaminopropyl) -N-ethylcarbodiimide, methanesulfonic acid, Examples thereof include organic acids such as toluenesulfonic acid, Mitsunobu reaction reagents such as triphenylylphosphine / diethyl azodicarboxylate, thionyl chloride, and boron trifluoride-ethyl ether complex.
  • acids such as hydrochloric acid and sulfuric acid
  • carbodiimides such as dicyclohexylcarbodiimide, diisopropylcarbodiimide, N ′-(3-dimethylaminopropyl) -N-ethylcarbodiimide, methanes
  • the reaction accelerator is usually used in a proportion of 0.01 to 10 mol with respect to 1 mol of the compound (XP1).
  • the reaction may be carried out as necessary with an organic base such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene, etc.
  • Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate
  • alkali metal bicarbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc.
  • the compound is usually used at a ratio of 0.001 to 5 mol with respect to 1 mol of the compound (XP1).
  • an excess of compound (XP2) is used relative to compound (XP1).
  • the reaction temperature is usually in the range of ⁇ 78 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (XP3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile and mixtures thereof, may also be used compound (XP2) as solvent.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dich
  • Examples of the compound (XP2) that can be used in the reaction include methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, t-butanol, and n-pentanol.
  • compound (XP2) is usually used at a ratio of 1 to 50 mol with respect to 1 mol of compound (XQ1).
  • the reaction temperature is usually in the range of ⁇ 78 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (XP3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • Compound (XP3) can be produced by reacting compound (XP1) with an alkylating agent.
  • R 7 , R 8 , R 9 and R 91 represent the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, water and mixtures thereof.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichlor
  • alkylating agent examples include diazo compounds such as diazomethane and trimethylsilyldiazomethane, chlorodifluoromethane, methyl bromide, ethyl bromide, n-propyl bromide, methyl iodide, ethyl iodide, Alkyl halides such as n-propyl bromide, allyl bromide, cyclopropyl bromide, benzyl bromide, 1,1-difluoro-2-iodoethane, sulfuric acid such as dimethyl sulfate, diethyl sulfate, di-n-propyl sulfate Dialkyls, alkyl or aryl sulfates such as methyl p-toluenesulfonate, ethyl p-toluenesulfonate, n-propyl p-tol
  • the alkylating agent is usually used at a ratio of 1 to 10 moles relative to 1 mole of the compound (XP1).
  • additives may be added as necessary, for example, triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicyclone.
  • Organic bases such as decene and diazabicyclononene, alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate and cesium carbonate, alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and cesium hydrogen carbonate And quaternary ammonium salts such as tetra (n-butyl) ammonium hydroxide.
  • alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate and cesium carbonate
  • alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and cesium hydrogen carbonate
  • quaternary ammonium salts such as tetra (n-butyl) ammonium hydroxide.
  • the compound (XP3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • a compound represented by formula (XS2) (hereinafter referred to as compound (XS2)) is produced by reacting a compound represented by formula (XS1) (hereinafter referred to as compound (XS1)) with a reducing agent. can do.
  • a compound represented by formula (XS1) hereinafter referred to as compound (XS1)
  • R 7 , R 8 , R 9 and R 10 represent the same meaning as described above, and represent an R 92 hydrogen atom or a C1-C3 alkyl group.
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, methanol, ethanol, propanol, butanol, etc. Alcohols, water and mixtures thereof.
  • Examples of the reducing agent that can be used in the reaction include lithium triethylborohydride, diisobutylaluminum hydride, lithium aminoborohydride, lithium borohydride, sodium borohydride, borane, borane dimethyl sulfide complex, and borane tetrahydrofuran. And complex.
  • the reducing agent is usually used at a ratio of 1 to 10 moles relative to 1 mole of the compound (XS1).
  • the reaction temperature is usually in the range of ⁇ 78 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (XS2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • a compound represented by formula (XT2) (hereinafter referred to as compound (XT2)) is produced by reacting a compound represented by formula (XT1) (hereinafter referred to as compound (XT1)) with a reducing agent. can do. [Wherein, R 7 , R 8 and R 9 represent the same meaning as described above. ] The reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, sulfoxides such as dimethyl sulfoxide, nitriles such as acetonitrile and propionitrile, methanol, ethanol, propanol, Alcohols such as ethanol, water and mixtures thereof.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide,
  • Examples of the reducing agent that can be used in the reaction include borane, borane tetrahydrofuran complex, and borane dimethyl sulfide complex.
  • Borane generated by mixing borohydride salts such as sodium borohydride and potassium borohydride with acids such as sulfuric acid, hydrochloric acid, methanesulfonic acid and boron trifluoride diethyl ether complex is also used.
  • the reducing agent is usually used at a ratio of 1 to 10 moles relative to 1 mole of the compound (XT1).
  • the reaction temperature of the reaction is usually in the range of -20 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 72 hours.
  • the compound (XT2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • Compound (A-2) can be produced by reacting a compound represented by formula (YA1) (hereinafter referred to as compound (YA1)) with (F-2) or a salt thereof.
  • YA1 a compound represented by formula (YA1)
  • F-2) or a salt thereof.
  • R 1 , R 2 , R 3 , R 11 , R 12 and R 13 represent the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include alcohols such as methanol, ethanol, propanol and butanol, hydrocarbons such as water, n-heptane, n-hexane, cyclohexane, n-pentane, toluene and xylene, and diethyl ether.
  • Examples of the salt that can be used in the reaction include hydrochloride, sulfate, and carbonate.
  • (F-2) or a salt thereof is usually used at a ratio of 1 to 10 moles with respect to 1 mole of the compound (YA1).
  • Examples of the acid used in the reaction include hydrochloric acid, sulfuric acid, nitric acid, acetic acid, trifluoroacetic acid, and p-toluenesulfonic acid.
  • the base examples include triethylamine, pyridine, N-methylmorpholine, N -Organic bases such as methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, aqueous ammonia, diazabicyclononene, metal hydrides such as sodium hydride and potassium hydride, formic acid Metal organic acid salts such as lithium, lithium acetate, sodium formate, sodium acetate, potassium formate and potassium acetate, metal nitrates such as silver nitrate and sodium nitrate, alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate and cesium carbonate, Lithium bicarbonate, sodium bicarbonate Alkali metal hydrogen carbonates such as lithium, potassium hydrogen carbonate, cesium hydrogen carbonate, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide,
  • the reaction temperature is usually in the range of 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 72 hours.
  • the compound (A-2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • Compound (YA1) can be produced by reacting a compound represented by formula (YB1) (hereinafter referred to as compound (YB1)) in the presence of Lewis acid or Bronsted. [Wherein R 1 , R 2 , R 3 , R 11 and R 12 represent the same meaning as described above. ] The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Examples include ethers such as tellurium, anisole, methyl tert-butyl ether, diisopropyl ether, chlorobenzene, nitromethane, and mixtures thereof.
  • Examples of the Lewis acid that can be used in the reaction include aluminum chloride and titanium tetrachloride.
  • Examples of the Bronsted acid include hydrogen fluoride and perchloric acid.
  • compound (YB2) is usually used at a ratio of 0.5 to 10 mol with respect to 1 mol of compound (YB1).
  • the reaction temperature is usually in the range of ⁇ 90 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 72 hours.
  • the compound (YA1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
  • the compound (YB1) is obtained by reacting a compound represented by the formula (YC1) (hereinafter referred to as the compound (YC1)) and a compound represented by the formula (YC2) (hereinafter referred to as the compound (YC2)).
  • YC1 a compound represented by the formula (YC1)
  • YC2 a compound represented by the formula (YC2)
  • R 1 , R 2 , R 3 , R 11 and R 12 represent the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether and diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane and chlorobenzene, esters such as ethyl acetate and methyl acetate , Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile and propionitrile, and mixtures thereof.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane and chlorobenzene
  • esters such as ethyl acetate and methyl acetate
  • Ketones such as acetone, methyl eth
  • additives may be added as necessary, for example, triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicyclone.
  • Organic bases such as decene and diazabicyclononene, alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate and cesium carbonate, alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and cesium hydrogen carbonate
  • alkali metal acetates such as sodium acetate and potassium acetate
  • quaternary ammonium salts such as tetra (n-butyl) ammonium hydroxide.
  • These additives are usually used at a ratio of 0.5 to 10 mol with respect to 1 mol of the compound (YA1).
  • (YC2) is usually used at a ratio of 1 to 10 moles relative to compound (YC1).
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (YB1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer.
  • the isolated compound (YB1) can be further purified by chromatography, recrystallization and the like.
  • Compound (YB1) can be produced by reacting compound (YC1) with a compound represented by formula (YD1) (hereinafter referred to as compound (YD1)).
  • YD1 a compound represented by formula (YD1)
  • R 1 , R 2 , R 3 , R 11 and R 12 represent the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether and diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane and chlorobenzene, esters such as ethyl acetate and methyl acetate , Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile and propionitrile, and mixtures thereof.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane and chlorobenzene
  • esters such as ethyl acetate and methyl acetate
  • Ketones such as acetone, methyl eth
  • additives may be added as necessary, for example, triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicyclone.
  • Organic bases such as decene and diazabicyclononene, alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate and cesium carbonate, alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and cesium hydrogen carbonate
  • alkali metal acetates such as sodium acetate and potassium acetate
  • quaternary ammonium salts such as tetra (n-butyl) ammonium hydroxide.
  • These additives are usually used at a ratio of 0.5 to 10 mol with respect to 1 mol of the compound (YA1).
  • (YC2) is usually used at a ratio of 1 to 10 moles relative to compound (YC1).
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (YB1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer.
  • the isolated compound (YB1) can be further purified by chromatography, recrystallization and the like.
  • Compound (F-1) can be produced by reacting compound (A-1) with compound (YA1) in the presence of a base.
  • a base a base
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Z 11 , and X represent the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether.
  • Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, water and mixtures thereof.
  • halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichlor
  • Examples of the base used in the reaction include triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene and the like.
  • Alkali metal carbonates such as organic bases, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, lithium hydroxide, hydroxide
  • Alkali metal hydroxides such as sodium, potassium hydroxide and cesium hydroxide
  • alkali metal halides such as sodium fluoride, potassium fluoride and cesium fluoride
  • alkali metals such as lithium hydride, sodium hydride and potassium hydride Hydrogenation , Sodium tert- butoxide, alkali metal alkoxides such as potassium tert- butoxide.
  • the compound (YA1) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol.
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • sodium iodide, tetrabutylammonium iodide or the like may be added as necessary. These compounds are usually added in an amount of 0.001 to 1.2 mol per 1 mol of compound (A-1). It is used in the ratio.
  • the compound (F-1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer.
  • compound (F-1) can be isolated by performing post-treatment operations such as filtration and concentration of the reaction mixture.
  • the isolated compound (F-1) can be further purified by chromatography, recrystallization and the like.
  • the form of the compound of the present invention may be the compound of the present invention alone.
  • the compound of the present invention is mixed with a solid carrier, a liquid carrier, a surfactant, etc., and if necessary, a fixing agent or a dispersing agent.
  • Additives for preparations such as stabilizers, wettable powder, granular wettable powder, flowable, granule, dry flowable, emulsion, aqueous liquid, oil, smoke, aerosol, microcapsule It is used by formulating it.
  • These preparations contain the compound of the present invention in a weight ratio of usually 0.1 to 99%, preferably 0.2 to 90%.
  • Examples of the solid support include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fusamic clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon). , Calcium carbonate, hydrated silica) and the like.
  • Examples of the liquid carrier include water, alcohols (eg, methanol, ethanol), ketones (eg, acetone).
  • Methyl ethyl ketone aromatic hydrocarbons (for example, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (for example, n-hexane, cyclohexanone, kerosene), esters (for example, ethyl acetate, acetic acid) Butyl), nitriles (eg acetonitrile, isobutyronitrile), ethers (eg Dioxane, diisopropyl ether), acid amides (for example, N, N-dimethylformamide (hereinafter sometimes referred to as DMF), dimethylacetamide), halogenated hydrocarbons (for example, dichloroethane, trichloroethylene, tetra Carbon chloride).
  • aromatic hydrocarbons for example, benzene, toluene, xylene, ethylbenzen
  • Surfactants include, for example, alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylene compounds, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugars Examples include alcohol derivatives.
  • formulation adjuvants include, for example, fixing agents, dispersants, and stabilizers.
  • fixing agents for example, casein, gelatin, polysaccharides (for example, starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives.
  • Bentonite saccharides, synthetic water-soluble polymers (for example, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylpheno-) ), BHA (mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, fatty acid or ester thereof.
  • synthetic water-soluble polymers for example, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids
  • PAP isopropyl acid phosphate
  • BHT 2,6-di-tert-butyl-4-methylpheno-
  • BHA mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol
  • vegetable oil mineral oil, fatty acid or ester thereof.
  • the method of applying the compound of the present invention is not particularly limited as long as the compound of the present invention can be applied substantially, but for example, treatment of plants such as foliage spraying, soil treatment, etc. Treatment to seeds such as treatment to cultivated land and seed disinfection.
  • oils such as mineral oil and vegetable oil, or surfactant.
  • Oils that can be specifically mixed and used as surfactants include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark) , Nufilm (registered trademark), Emulator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N ( Recorded trademark), BANOLE (registered trademark), Nimbus (registered trademark),
  • control agent of the present invention can be used simultaneously with or without mixing with other fungicides, insecticides, acaricides, nematicides, and plant growth regulators.
  • other bactericides include the following.
  • Azol fungicides propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, fluconol, teconazole Flusilazole, diniconazole, bromconazole, epoxyconazole, difenoconol, cyproconazole, diproconazole, cyproconazole, diproconazole. (Triflumizole), Tet Teconconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, triticol ter.
  • Examples of such other insecticides include the following. (1) Organophosphorus compounds Acephate, Aluminum phosphide, Butathiofos, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlorfenvinphos folpyphos , Chlorpyrifos-methyl, Cyanophos (CYAP), Diazinon, DCIP (Dichlorodipropionic ether), Dichlorfenthion (ECP), Dichlorvos (Dchlo-D) (Dimethoate), dimethylvinphos, disulfoton, EPN, ethion, ethoprofos, etrimfos, fenthion: MPP, phenothione (Fothiazate), formothion (formulation), hydrogen phosphide (isofenphos), isoxathion (isoxathion), malathion (malathion), mesulfenfos (mes
  • nereistoxin compound cartap bensultap, thiocyclam, monosultap, bisultap, etc .
  • Neonicotinoid compounds imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefurin (6)
  • Benzoylurea compounds Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucyclolone, flucyclolone (Flufenoxuron), hexaflumuron, lufenuron, novaluron, novifluuron, teflubenzuron, triflumuron, triflumuron, etc.
  • Phenylpyrazole compound Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, pyrafluprole, etc .
  • acaricide examples include, for example, acequinocyl, amitraz, benzoxymate, biphenate, phenisobromolate, quinopropyrate, (Chinomethionat), Chlorbenzilate, CPCBS (Chlorfenson), Clofentezine, Cyflumetofen, Kelsen (dicophor), Etofazol tin oxide (etoxazole) (Fenothiocarb) , Fenpyroximate, fluacrylpyrim, fluproxyfen, hexythiazox, propargite (BP), polynactin complex (pi), polynactin complex (pi) Tebufenpyrad, tetradiphon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet, cienopyramet, cienopyramet yrafen), and the like.
  • acequinocyl amitraz, benzoxymate, biphenate, phenis
  • nematicides include, for example, DCIP, fostiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartrate. tartarate), imiciafos, fluensulfone and the like.
  • Examples of such other plant growth regulators include the following. Gibberellin A (Kibberdelin A), abscisicin acid (abscisinic acid), abscisicin acid (abscisinic acid) (Benzyladene), 1,3-diphenylurea, forchlorfenuron, thidiazuron, 4-oxo-4- (2-phenylethyl) aminobutyric acid, 5- (trifluoromethyl) benzo [b] thiophene Methyl-2-carboxylate, 5- (trifluoromethyl) benzo [b] thiophene-2-carboxylic acid Etc..
  • the application amount of the present control agent varies depending on weather conditions, formulation form, application time, application method, application place, target disease, target crop, etc., but the amount of the present compound in the present control agent is 1000 m 2.
  • the amount is usually 1 to 500 g, preferably 2 to 200 g.
  • Emulsions, wettable powders, suspensions and the like are usually diluted with water and applied.
  • the concentration of the compound of the present invention after dilution is usually 0.0005 to 2% by weight, preferably 0.005 to It is 1% by weight, and powders, granules and the like are usually applied as they are without dilution.
  • the amount of the compound of the present invention in the control agent of the present invention is usually 0.001 to 100 g, preferably 0.01 to 50 g per 1 kg seed.
  • the present control agent can be used as a plant disease control agent in farmland such as fields, paddy fields, lawns, orchards.
  • the control agent of the present invention can control diseases of the farmland in the farmland where the “plants” and the like listed below are cultivated.
  • the organisms and parasites that parasitize the vertebrate are systemically administered. Or it can be exterminated non-systemically.
  • Such internal administration methods include oral administration, anal administration, transplantation, subcutaneous, intramuscular and intravenous administration by injection.
  • External administration includes transdermal administration. Moreover, it can feed livestock animals and control sanitary pests generated in the excrement of the animals.
  • the dosage can vary widely depending on the administration method, etc. Is preferably administered so that the active ingredient (the compound of the present invention or a salt thereof) per kg of animal weight is 0.1 mg to 2000 mg, preferably 0.5 mg to 1000 mg.
  • the compound of the present invention or the control agent of the present invention can be used as a plant disease control agent in farmland such as fields, paddy fields, lawns, orchards.
  • the compound of the present invention can control diseases of the cultivated land in cultivated lands where the “plants” and the like listed below are cultivated.
  • Agricultural crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc., vegetables; solanaceous vegetables (eggplant, tomato, pepper , Pepper, potato, etc.), cucurbitae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), cruciferous vegetables (radish, turnip, horseradish, colrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower -), Asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), Liliaceae vegetables (leek, onion, garlic, asparagus), Aceraceae vegetables (carrots, parsley, celery, American redfish, etc.) , Red vegetables (spinach, chard, etc.), perilla vegetables (perilla, mint, basil) ), Strawberry, sweet potato, yam, taro, etc., flowers, foliage plants, Fruit
  • Trees other than fruit trees tea, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, red-footed bean, fu, sycamore, zelkova, black beet, black bean, tuna, nezu, Pine, spruce, yew).
  • plants include genetically modified crops.
  • Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiotic seedling (Gibberella fujikuroi) or yellow rot sorghum Graminis), red mold disease (Fusarium graminearum, F. avenaceum, F. culmorum, Microdochium nitrile), rust disease (Puccinia striformis), P. graminis, P. recondetic color. Nuclear disease ( yphula sp.), naked scab (Ustilago tritici), Namagusa smut (Tilletia caries, T.
  • Leafy leaf disease Panophora graminea
  • lambaria disease Roso-cygni
  • Rhizoctonia solani corn rust disease
  • Herpes disease Setosph aeria turcica, sesame leaf blight (Cochliobolus heterotrophus), anthracnose (Colletotrichum glaminicola), gray leaf spot disease (Cercospora zeae-maisedaea)
  • Cotton anthracnose Colletotrichum gossypi
  • mildew Ramuraria areola
  • black spot Alternaria macrospora, A.
  • coffee rust Hemileia vastatrix
  • rape mycorrhizal disease Sterotinia sclerotior
  • apple monilia disease Monilia disease
  • rot Valsa ceratoperaterperaterpera
  • powdery mildew Podosphaera leaf
  • Black star disease Venturia inaequalis
  • anthracnose Glomerella cingulata
  • pear black star disease Venturia nashicola, V. pirina
  • black spot disease Alternaria alternamoe peape morbidity
  • Seedling blight (Phythium sp.); Tomato ring-rot (Alternaria solani), leaf mold (Cladosporium fulvum), scab (Pseudocercospora fuligena), plague (Phytophthora inspot) vexans), powdery mildew (Erysiphe cichoacearum); black spot disease of the cruciferous vegetables (Alternaria japonica), white spot disease (Cercosporella brassicae), root-knot disease (Plasmodiophora brasicae disease) (Puccinia allii); die Purpura (Cercosporakikuchii), black pepper (Elsinoe glycines), sunspot disease (Diaporthephaseolum var.
  • Sojae Sojae
  • rust disease Posora pachyrismi, crimson rot
  • Leaf rot Rhizoctonia solani
  • brown spot Septoria glycines
  • spot disease Cercospora sojina
  • bean anthracnose Colletotrichum lindemthianum
  • Ospora arachidicola Ospora arachidicola
  • white silkworm Sclerotium olfsiii
  • Pea powdery mildew Erysiphe pisii
  • Potato summer plague Alternaria solanitis
  • Phytophthora insitalia Hemitophysium vinegar
  • Bacterial Red Star Disease (Alternaria longipes), Powdery Mildew (Erysiphe cichoracerarum), Anthracnose (Colletotrichum tabacum), Downy Mildew (Peronospora tabacetae), Phytophthoratibola disease Rot disease (Thanatephorus cucumeris), root rot disease (Thanatephorus cucumeris), black root disease (Aphanomyces cochlioides); black spot disease of rose (Diplocarpon rosacea), powdery mildew (Sphaerotheposis) themi-indici), white rust (Puccinia horiana); vitiligo leaf blight of onions (Botrytis cinerea, B.
  • Hemiptera small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), Sejirounka (Sogatella furcifera) planthoppers such as, green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens) leafhoppers such as, cotton aphid (Aphis gossypii) , Peaches aphids (Myzus persicae), radish aphids (Brevicoryne brassicae), tulip beetle aphids (Macrosiphum euphorbiae), potato beetle aphids (Aulacorthum solani) Aphids such as wheat beetle (Rhopalosiphum padi), citrus black aphid (Toxoptera citriticidus), Nesara antenis worms (Rip
  • Lepidoptera rice stem borer (Chilo suppressalis), Sankameiga (Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Japanese medusa such as Shibata toga (Pediasia teterrellus), Spodoptera litura, Spodoptera exigua, Ayuyotoga (Pseudaletia sepata), Atoga assicae), Agrotis ipsilon, Tamanaginawaba (Prusia nigrisigna), Trichopulsia, Heliotis, Helicoberpa, etc.
  • Leguminivora glycinivolora Leguminivora glycinivolora
  • Azusa yamashiga Matsusumuraeses azukikivora
  • Apple wolfberry Adoxophyes orana fasciata
  • Chanokokumon hamakiki Adoxophaki. Fusocopreanus, Cydia pomonella, and other species, Euphoria of the genus Cyptolia, Cypridia isp, etc.
  • Species of the genus Kutis, Suga such as Plutella xylostella, Pterophora gossypiella potato moth (Phthorimaea operculella), and the like anslucens), webbing clothes moth (Tineola bisselliella) Hirozukoga such as such.
  • Thysanoptera western flower thrips (Frankliniella occidentalis), Minami thrips (Thrips palmi), yellow tea thrips (Scirtothrips dorsalis), green onion thrips (Thrips tabaci), Hirazuhanaazamiuma (Frankliniella intonsa), tobacco thrips (Frankliniella fusca) thrips, such as Etc.
  • Diptera Housefly (Musca domestica), Culex (Culex pipiens pallens), gadfly (Tabanus trigonus), onion maggot (Hylemya antiqua), seedcorn maggot (Hylemya platura), Anopheles sinensis (Anopheles sinensis), rice leafminer (Agromyza oryzae), rice Hydrelia griseola, Bluefly flies (Chloropsoryzae), Green flies (Dacus cucurbitae), Ceratitis capitata, Lime folii y (fmati folii y)
  • Coleoptera beetle, Epilachna vigintioctopunctata (Epilachna vigintioctopunctata), cucurbit leaf beetle (Aulacophora femoralis), Kisujinomihamushi (Phyllotreta striolata), Inedorooimushi (Oulema oryzae), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), boll weevil (Anthonomus grandis), Azuki beetle (Callosobruchus chinensis), Shibahorusu weevil (Sphenophorus venatus), Japanese beetle (Popilia japonica), Douganebububu (Anomala cupre) ), Corn rootworm mate (Diabrotica spp.), Colorado potato beetle (Leptinotarsa decemlineat
  • Direct insect pests Locusta migratoria, Kelly (Gryllotalpa africana), Oxya yezoensis, Oyana japonica, and the like.
  • Hymenoptera Athalia rosae, Achillyrmex spp., Fire ant (Solenopsis spp.) And the like.
  • Nematodes Rice moth nematode (Aphelenchoides besseyy), Strawberry nematode (Heterodera glycines) .
  • Cockroach pests German cockroaches (Blatella germanica), Black cockroaches (Periplaneta furiginosa), American cockroaches (Periplaneta americana), Japanese cockroach (Peripraneta brunet)
  • Acarina Tetranychus urticae, Pandychus citri, Odonidus spp., Acarops pelekassi, Mite, Phyphagotaris Mite, such as Typhophagus putrescentiae, Mite, Dermatophagoides falinae, Mite, Mite censis), Tsumedani such as Minami Tsumedani (Cheyletus moorei), chicken mites, and the like.
  • the preparation containing the compound of the present invention or a salt thereof is used in the field of livestock disease treatment and livestock industry, and in vertebrates such as humans, cows, sheep, goats, pigs, poultry, dogs, cats and fish. It can be used to maintain public health by combating organisms and parasites that parasitize inside and / or outside.
  • some of the pests include ticks (Ixodes spp.) (Eg, Ixodes scapularis), bovine ticks (Boophilus spp.) (Eg, Boophilus microplus), larvae ticks (Amblyomamma spp.). Hyalmma spp.), Rhipicphalus spp.
  • pp phylums (Culicodes spp.), houseflies (Musca spp.), cow flies (Hypoderma spp.), frogs (Gasterophilus spp.), flies (Haematobia sppp), cows (Haematobia sppp) Scallops (Simulium spp.), Triatomas spp., Lice (Phythraptera) (e.g.
  • Damalinia spp. Linognathus spp., Haematopinus spp.), Fleas (ceno, ce (Cen) felis.), Xenosylla spp.), Himeari (Monomorium pharaonis) and nematodes [eg hair-like nematodes (for example Nippostrongylus brasiliensis, Trichostrongylus axei, Trichostrongylus colubriformis), trichinosis (such Trichinella spiralis), Haemonchus (Haemonchus contortus), Nematojirusu (such Nematodirus battus ), Ostertag gastroworm (Ostertagia circucumcincta), Couperia (Cooperia spp. ), Hymenolepis nana] and the like.
  • nematodes eg hair-like nematodes (for example Nippostrongylus brasiliensis, Trichostrongy
  • Production Example 2 In Production Example 1, 2-methyl-4- (1-methoxyimino-1-cyclopropyl-methyl) described in Reference Production Example 3 instead of 2-methyl-4- (1-methoxyimino-propyl) phenol The same reaction was performed using phenol, and 1- ⁇ 2- [2-methyl-4- (1-methoxyimino-1-cyclopropyl-methyl) phenoxymethyl] phenyl ⁇ -4-methyl-1,4- Dihydrotetrazol-5-one (hereinafter referred to as the present compound 2) was obtained.
  • Production Example 3 In Production Example 1, 2-methyl-4- (1-methoxyimino-2-methyl-propyl) phenol described in Reference Production Example 4 instead of 2-methyl-4- (1-methoxyimino-propyl) phenol 1- ⁇ 2- [2-methyl-4- (1-methoxyimino-2-methyl-propyl) phenoxymethyl] phenyl ⁇ -4-methyl-1,4-dihydrotetrazole -5-one (hereinafter referred to as the present compound 3) was obtained.
  • Production Example 4 In Production Example 1, 2-methyl-4- (1-methoxyimino-1-cyclohexyl-methyl) phenol described in Reference Production Example 5 instead of 2-methyl-4- (1-methoxyimino-propyl) phenol 1- ⁇ 2- [2-Methyl-4- (1-methoxyimino-1-cyclohexyl-methyl) phenoxymethyl] phenyl ⁇ -4-methyl-1,4-dihydrotetrazole -5-one (hereinafter referred to as the present compound 4) was obtained.
  • Production Example 5 In Production Example 1, instead of 2-methyl-4- (1-methoxyimino-propyl) phenol, 2-methyl-4- (1-methoxyimino-pentyl) phenol described in Reference Production Example 6 was used, A similar reaction was carried out, and 1- ⁇ 2- [2-methyl-4- (1-methoxyimino-pentyl) phenoxymethyl] phenyl ⁇ -4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present invention). Invented compound 5)) was obtained.
  • Production Example 6 In Production Example 1, 2-methyl-4- (1-methoxyimino-1-phenylmethyl) phenol described in Reference Production Example 7 was used instead of 2-methyl-4- (1-methoxyimino-propyl) phenol. 1- ⁇ 2- [2-methyl-4- (1-methoxyimino-1-phenyl-methyl) phenoxymethyl] -phenyl ⁇ -4-methyl-1,4-dihydrotetrazole -5-one (hereinafter referred to as the present compound 6) was obtained.
  • Production Example 7 In Production Example 1, instead of 2-methyl-4- (1-methoxyimino-propyl) phenol, 2-methyl-4- (1-methoxyimino-methyl) phenol described in Reference Production Example 8 was used, A similar reaction was carried out to give 1- ⁇ 2- [2-methyl-4- (1-methoxyimino-methyl) phenoxymethyl] phenyl ⁇ -4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present invention). Invented compound 7)) was obtained.
  • Production Example 8 In Production Example 1, 2-methyl-4- ⁇ 1-methoxyimino-1- (2-chlorophenyl) described in Reference Production Example 23 instead of 2-methyl-4- (1-methoxyimino-propyl) phenol The same reaction is carried out using methyl ⁇ phenol and 1- ⁇ 2- [2-methyl-4- ⁇ 1-methoxyimino-1- (2-chlorophenyl) methyl ⁇ -phenoxymethyl] phenyl ⁇ -4-methyl. -1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 8) was obtained.
  • Production Example 9 In Production Example 1, 2-methyl-4- ⁇ 1-methoxyimino-1- (3-chlorophenyl) described in Reference Production Example 26 instead of 2-methyl-4- (1-methoxyimino-propyl) phenol The same reaction is carried out using methyl ⁇ phenol, and 1- ⁇ 2- [2-methyl-4- ⁇ 1-methoxyimino-1- (3-chlorophenyl) methyl ⁇ -phenoxymethyl] phenyl ⁇ -4-methyl is obtained. -1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 9) was obtained.
  • Production Example 10 In Production Example 1, instead of 2-methyl-4- (1-methoxyimino-propyl) phenol, 2-methyl-4- ⁇ 1-methoxyimino-1- (4-chlorophenyl) described in Reference Production Example 29 was used. The same reaction is carried out using methyl ⁇ phenol, and 1- ⁇ 2- [2-methyl-4- ⁇ 1-methoxyimino-1- (4-chlorophenyl) methyl ⁇ -phenoxymethyl] phenyl ⁇ -4-methyl is obtained. -1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 10) was obtained.
  • Production Example 11 In Production Example 1, 2-methyl-4- ⁇ 1-methoxyimino-1- (3-methylphenyl) described in Reference Production Example 32 instead of 2-methyl-4- (1-methoxyimino-propyl) phenol ) Methyl ⁇ phenol was used to carry out the same reaction, and 1- ⁇ 2- [2-methyl-4- ⁇ 1-methoxyimino-1- (3-methylphenyl) methyl ⁇ -phenoxymethyl] phenyl ⁇ -4 -Methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 11) was obtained.
  • Production Example 12 In Production Example 1, 2-methyl-4- ⁇ 1-methoxyimino-1- (3-methoxyphenyl) described in Reference Production Example 33 instead of 2-methyl-4- (1-methoxyimino-propyl) phenol ) Methyl ⁇ phenol was used to carry out the same reaction, and 1- ⁇ 2- [2-methyl-4- ⁇ 1-methoxyimino-1- (3-methoxyphenyl) methyl ⁇ -phenoxymethyl] phenyl ⁇ -4 -Methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 12) was obtained.
  • Reference production example 1 1- (2-Bromomethyl-phenyl) -4-methyl-1,4-dihydrotetrazol-5-one was produced by the following steps (1) to (3).
  • Step (2)> To a mixture of 69.8 g of 1- (2-methylphenyl) -1,4-dihydrotetrazol-5-one and 380 mL of N, N-dimethylformamide was added 18.2 g of 55% sodium hydride under ice cooling. . After stirring for 20 minutes, 59.4 g of methyl iodide was added. The mixture was warmed to room temperature and stirred for 2.5 hours. Water was poured into the reaction mixture, and the mixture was extracted with methyl tert-butyl ether. The organic layer was washed with 10% hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
  • Step (3)> A mixture of 18.0 g of 1- (2-methylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one, 19.4 g of N-bromosuccinimide and 166 mL of chlorobenzene was brought to 96 ° C., 2.57 g of '-azobis (cyclohexane-1-carbonitrile) was added and stirred at 100 ° C. for 3 hours. After cooling, water was poured into the reaction solution and extracted with methyl tert-butyl ether. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 30.4 g of a residue.
  • Reference production example 3 In Reference Production Example 2, cyclopropyl- (4-hydroxy-3-methylphenyl) -methanone described in Reference Production Example 16 was used instead of 1- (4-hydroxy-3-methylphenyl) propan-1-one. The same reaction was carried out to obtain 2-methyl-4- (1-methoxyimino-1-cyclopropylmethyl) phenol.
  • Reference production example 4 In Reference Production Example 2, 1- (4-hydroxy-3-methylphenyl) -2-methyl described in Reference Production Example 17 was used instead of 1- (4-hydroxy-3-methylphenyl) propan-1-one. Using 2-propan-1-one, the same reaction was performed to obtain 2-methyl-4- (1-methoxyimino-2-methyl-propyl) phenol.
  • Reference production example 5 In Reference Production Example 2, cyclohexyl- (4-hydroxy-3-methyl-phenyl) -methanone described in Reference Production Example 18 is used instead of 1- (4-hydroxy-3-methyl-phenyl) propan-1-one. The same reaction was carried out using 2-methyl-4- (1-methoxyimino-1-cyclohexyl-methyl) phenol.
  • Reference production example 7 In Reference Production Example 2, (4-hydroxy-3-methylphenyl) -phenyl-methanone described in Reference Production Example 20 was used instead of 1- (4-hydroxy-3-methylphenyl) propan-1-one. The same reaction was performed to obtain 2-methyl-4- (1-methoxyimino-1-phenylmethyl) phenol.
  • Reference Production Example 16 In Reference Production Example 15, the same reaction was carried out using cyclopropanecarboxylic acid 2-methylphenyl ester described in Reference Production Example 10 instead of propionic acid 2-methylphenyl ester, and cyclopropyl- (4-hydroxy- 3-Methylphenyl) -methanone was obtained.
  • Reference Production Example 17 In Reference Production Example 15, the same reaction was carried out using 2-methylpropionic acid 2-methylphenyl ester described in Reference Production Example 11 instead of propionic acid 2-methylphenyl ester, and 1- (4-hydroxy- 3-Methylphenyl) -2-methyl-propan-1-one was obtained.
  • Reference Production Example 18 In Reference Production Example 15, the same reaction was carried out using cyclohexanecarboxylic acid 2-methylphenyl ester described in Reference Production Example 12 instead of propionic acid 2-methylphenyl ester, and cyclohexyl- (4-hydroxy-3- Methylphenyl) -methanone was obtained.
  • Reference Production Example 22 In Reference Production Example 21, the same reaction was carried out using 2-chlorobenzoic acid 2-methylphenyl ester described in Reference Production Example 21 instead of propionic acid-o-toluyl ester, and 2-chlorophenyl- (4- Hydroxy-3-methylphenyl) -methanone was obtained.
  • Reference Production Example 25 In Reference Production Example 15, the same reaction was carried out using 3-chlorobenzoic acid 2-methylphenyl ester described in Reference Production Example 24 instead of propionic acid-o-toluyl ester, and 3-chlorophenyl- (4- Hydroxy-3-methylphenyl) -methanone was obtained.
  • Reference Production Example 28 In Reference Production Example 15, the same reaction was carried out using 4-chlorobenzoic acid 2-methylphenyl ester described in Reference Production Example 27 instead of propionic acid-o-toluyl ester, and 4-chlorophenyl- (4- Hydroxy-3-methylphenyl) -methanone was obtained.
  • the mixture was poured into 50 ml of ice water and extracted with chloroform.
  • the organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
  • the obtained residue was subjected to silica gel column chromatography to obtain a crude product.
  • 0.84 g of O-methylhydroxyamine hydrochloride, 1 ml of pyridine, and 20 ml of ethanol were added, followed by stirring at room temperature for 4 hours. Saturated aqueous sodium hydrogen carbonate was added, extracted three times with chloroform, washed with saturated brine, and the organic layer was concentrated under reduced pressure.
  • EP1A-0001 to EP1A-2492, EP1B-0001 to EP1B-2492, EP1C-0001 to EP1C-2492, EP1D-0001 to EP1D-2492, EP1E-0001 to EP1E-2492, EP1F-0001 EP1F-2492, EP1G-0001 to EP1G-2492, EP1H-0001 to EP1H-2492 can be obtained.
  • a part represents a weight part.
  • Formulation Example 1 A preparation is obtained by thoroughly pulverizing and mixing 50 parts of any one of the present compounds 1 to 12, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic silicon hydroxide.
  • Formulation Example 2 20 parts of any one of the compounds 1 to 12 of the present invention and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol and pulverized by a wet pulverization method. Thereafter, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and stirred to obtain a preparation.
  • Formulation Example 3 A preparation is obtained by thoroughly pulverizing and mixing 2 parts of any one of the compounds 1 to 12 of the present invention, 88 parts of kaolin clay and 10 parts of talc.
  • Formulation Example 4 A preparation is obtained by thoroughly mixing 5 parts of any one of the compounds 1 to 12 of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.
  • Formulation Example 5 After thoroughly mixing 2 parts of any one of the compounds 1 to 12 of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, add water and knead well. The preparation is obtained by granulating and drying.
  • Formulation Example 6 Formulation by mixing 10 parts of any one of the compounds 1 to 12 of the present invention; 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt; and 55 parts of water, and pulverizing the mixture by a wet pulverization method. Get.
  • control agent of the present invention when used in combination with other fungicides, insecticides, acaricides, nematicides, and plant growth regulators, specifically, it can be used in the following forms.
  • a plant disease control composition comprising any one of the present compound 1 to or present compound 12 and prothioconazole in a ratio of 0.1: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and prothioconazole in a ratio of 1: 1, a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and prothioconazole in a ratio of 10: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and bromconazole in a ratio of 0.1: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and bromconazole in a ratio of 1: 1, a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and bromconazole in a ratio of 10: 1; Any one compound from the present compound 1 to the present compound 12
  • the present invention compound 1 or the present compound 12 and tebuconazole are contained in a ratio of 1: 1 in a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and tebuconazole in a ratio of 10: 1; Any one compound from the present compound 1 to the present compound 12
  • the present invention compound 1 or the present compound 12 and tetraconazole are contained in a ratio of 0.1: 1 to a plant disease controlling composition; Any one compound from the present compound 1 to the present compound 12
  • the present invention compound 1 or the present compound 12 and tetraconazole are contained in a ratio of 1: 1 in a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present
  • any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and flusilazole in a ratio of 0.1: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and flusilazole in a ratio of 1: 1, a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and flusilazole in a ratio of 10: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and prochloraz in a ratio of 0.1: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and prochloraz in a ratio of 1: 1; a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and prochloraz in a ratio of 10: 1;
  • any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and bixaphene in a ratio of 0.1: 1 to a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and bixaphene are contained in a ratio of 1: 1 in a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and bixaphene in a ratio of 10: 1, plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and isopyrazam in a ratio of 0.1: 1 plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and isopyrazam in a ratio of 1: 1, a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and isopyrazam in a
  • any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and benzobin diflupyr in a ratio of 0.1: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and benzobin diflupyr in a ratio of 1: 1, a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and benzobin diflupyr in a ratio of 10: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and floxapyroxad in a ratio of 0.1: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and fluxapiroxad are contained in a ratio of 1: 1 at a plant disease control composition; Any one compound from the present compound 1 to the present compound 12; a plant disease control composition comprising the present compound 1 or the present compound 12 and fluxapyroxad in
  • Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and boscalid in a ratio of 0.1: 1, a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and boscalid are contained at a ratio of 1: 1 in a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and boscalid in a ratio of 10: 1; Any one compound from the present compound 1 to the present compound 12 The present compound 1 or the present compound 12 and N- [2- (3,4-difluorophenyl) phenyl] -3-trifluoromethylpyrazine-2- A plant disease control composition comprising a carboxylic acid amide in a ratio of 0.1: 1; Any one compound from the present compound 1 to the present compound 12 The present compound 1 or the present compound 12 and N- [2- (3,4-difluorophenyl) pheny
  • any one compound from the present compound 1 to the present compound 12 The present compound 1 or the present compound 12 and (R)-(-)-N- (1,1,3-trimethylindan-4-yl)- A plant disease control composition containing 1-methyl-3-difluoromethylpyrazole-4-carboxylic acid amide in a ratio of 0.1: 1; Any one compound from the present compound 1 to the present compound 12 The present compound 1 or the present compound 12 and (R)-(-)-N- (1,1,3-trimethylindan-4-yl)- A plant disease control composition containing 1-methyl-3-difluoromethylpyrazole-4-carboxylic acid amide in a ratio of 1: 1; Any one compound from the present compound 1 to the present compound 12 The present compound 1 or the present compound 12 and (R)-(-)-N- (1,1,3-trimethylindan-4-yl)- A plant disease control composition comprising 1-methyl-3-difluoromethylpyrazole-4-carboxylic acid amide in a ratio
  • any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and fenpropimorph in a ratio of 0.1: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and fenpropimorph in a ratio of 1: 1; a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and fenpropimorph in a ratio of 10: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and fenpropidin in a ratio of 0.1: 1, a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and fenpropidin in a ratio of 1: 1, a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and fenpropidin in a ratio of 1: 1,
  • any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and cyprodinil in a ratio of 0.1: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and cyprodinil are contained at a ratio of 1: 1 in a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and cyprodinil in a ratio of 10: 1, plant disease control composition; Any one compound from the present compound 1 to the present compound 12, the present compound 1 or the present compound 12 and pyrimesanil in a ratio of 0.1: 1; a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and pyrimesanil are contained in a ratio of 1: 1 in a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and pyrimesan
  • the present invention compound 1 or the present compound 12 and fludioxonil are contained in a ratio of 1: 1 in a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and fludioxonil in a ratio of 10: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and procymidone in a ratio of 0.1: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and procymidone in a ratio of 1: 1, a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and procymidone in a ratio of 10: 1; Any one compound
  • any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and phorpet in a ratio of 0.1: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and phorpet, containing a plant disease in a ratio of 1: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and phorpet in a ratio of 10: 1; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and methylam are contained in a ratio of 0.1: 1 to a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and methylam are contained in a ratio of 1: 1 in a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and methylam in a ratio of 10: 1 plant disease control composition;
  • any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and clothianidin are contained in a ratio of 1: 1 in a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and clothianidin are contained in a ratio of 1:10 in a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and clothianidin are contained at a ratio of 1:50 in a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and imidacloprid are contained in a ratio of 1: 1 in a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and imidacloprid in a ratio of 1:10; Any one of the present compounds 1 to 12 The present compound 1 or the present compound 12 and imidacloprid in a ratio of 1
  • any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and sulfoxafurol are contained at a ratio of 1: 1 in a plant disease control composition; Any one compound from the present compound 1 to the present compound 12, the present compound 1 or the present compound 12 and sulfoxafurol in a ratio of 1:10; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and sulfoxafurol in a 1:50 ratio; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and chlorantraniliprole in a ratio of 1: 1; a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and chlorantraniliprole in a ratio of 1:10; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and chlorantraniliprole in a ratio of 1:50
  • Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and abamectin in a ratio of 1: 1, a plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and abamectin in a 1:10 ratio; Any one compound from the present compound 1 to the present compound 12 The present invention compound 1 or the present compound 12 and abamectin in a 1:50 ratio; Any one compound from the present compound 1 to the present compound 12 The present compound 1 or the present compound 12 and 4-oxo-4- (2-phenylethyl) aminobutyric acid are contained at a ratio of 5: 1.
  • Plant disease control composition Any one compound from the present compound 1 to the present compound 12 The present compound 1 or the present compound 12 and 4-oxo-4- (2-phenylethyl) aminobutyric acid are contained at a ratio of 1:10. Plant disease control composition; Any one compound from the present compound 1 to the present compound 12 The present compound 1 or the present compound 12 and 4-oxo-4- (2-phenylethyl) aminobutyric acid are contained at a ratio of 1:50.
  • Plant disease control composition Any one compound from the present compound 1 to the present compound 12 The present compound 1 or the present compound 12 and methyl 5- (trifluoromethyl) benzo [b] thiophene-2-carboxylate Plant disease control composition containing in proportions; Any one compound from the present compound 1 to the present compound 12 The present compound 1 or the present compound 12 and methyl 5- (trifluoromethyl) benzo [b] thiophene-2-carboxylate Plant disease control composition containing in proportions; Any one compound from the present compound 1 to the present compound 12 The present compound 1 or the present compound 12 and methyl 5- (trifluoromethyl) benzo [b] thiophene-2-carboxylate Plant disease control composition containing in proportions; Any one compound from the present compound 1 to the present compound 12 The present compound 1 or the present compound 12 and 5- (trifluoromethyl) benzo [b] thiophene-2-carboxylate Plant disease control composition containing in proportions; Any one compound from the present compound 1 to the present compound 12 The present compound
  • test examples show that the compounds of the present invention are useful for controlling plant diseases.
  • the control effect is to visually observe the area of the lesion on the test plant at the time of the survey, and to compare the area of the lesion on the plant treated with the compound of the present invention and the area of the lesion on the untreated plant. It was evaluated by.
  • an untreated plant is a plant tested on the same conditions as a test example except not spraying the foliage of the water dilution of the formulation containing this invention compound.
  • Test example 1 A plastic pot was filled with soil, rice (cultivar; Nipponbare) was sown therein, and grown in a greenhouse for 20 days. Thereafter, the compounds 1, 2, 3, and 6 of the present invention were formulated according to Formulation Example 2 above, diluted with water to a predetermined concentration (500 ppm), and sprayed on the foliage so that they adhered well to the rice leaf surface . After spraying, the plants were air-dried, and the sprayed rice was contacted with rice seedlings (variety: Nihonbare) affected by rice blast fungus (Magnaporthe grisea) under high humidity at 24 ° C in the daytime and 20 ° C at night After leaving for days, the lesion area was examined. As a result, the lesion area in the plant treated with the present compounds 1, 2, 3, 6 was 30% or less of the lesion area in the untreated plant.
  • Test example 2 A plastic pot was filled with soil, and wheat (variety: Shirogane) was sown therein and allowed to grow in a greenhouse for 9 days.
  • the compounds 2 and 6 of the present invention were prepared according to Formulation Example 2 above, diluted with water to a predetermined concentration (500 ppm), and sprayed on the foliage so as to adhere well to the leaves of the wheat. After spraying, the plants were air-dried and cultivated at 20 ° C. under illumination for 5 days, and then sprinkled with spores of wheat rust fungus (Puccinia recondita). After inoculation, the plants were placed at 23 ° C. under dark and humid conditions for 1 day, then cultivated at 20 ° C. under illumination for 8 days, and the lesion area was examined. As a result, the lesion area in the plant treated with the present compounds 2 and 6 was 30% or less of the lesion area in the untreated plant.
  • Test example 3 A plastic pot was filled with soil, and barley (variety: Mikamo Golden) was sown there and allowed to grow in a greenhouse for 7 days.
  • the compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12 of the present invention were formulated according to the above Formulation Example 2 and then diluted with water to give a predetermined concentration (500 ppm). Then, the stems and leaves were sprayed so as to adhere well to the leaf surface of the barley. After spraying, the plants were air-dried, and two days later, an aqueous suspension of barley net spore fungus (Pyrenophora teres) spores was spray-inoculated.
  • the plants were placed under high humidity in a greenhouse at 23 ° C. during the day and 20 ° C. during the night, and then cultivated in the greenhouse for 7 days.
  • the lesion areas in the plants treated with the compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 of the present invention are all the lesion areas in the untreated plants. It was 30% or less.
  • Test example 4 A plastic pot was stuffed with soil, seeded with green beans (variety; Nagahama peas) and grown in a greenhouse for 8 days.
  • the compounds 1, 2, 3, 4, 6, 7, 11, and 12 of the present invention were formulated according to Formulation Example 2, respectively, and then diluted with water to a predetermined concentration (500 ppm), and sufficiently adhered to the kidney leaf
  • the foliage was sprayed like so. After spraying, the plants were air-dried, and a mycelia-containing PDA medium of sclerotia sclerotium was placed on the kidney leaf surface. After the inoculation, all kidney beans were placed under high humidity only at night, and the lesion area was examined 4 days after the inoculation. As a result, the lesion area in the plant treated with any one of the compounds 1, 2, 3, 4, 6, 7, 11, 12 of the present invention was 30% or less of the lesion area in the untreated plant. It was.
  • Test Example 5 A plastic pot was filled with soil, and wheat (variety: Apogee) was sown therein and grown in a greenhouse for 10 days.
  • the compounds 1, 2, 3, 4, 6, and 7 of the present invention were formulated according to Formulation Example 2, respectively, and then diluted with water to a predetermined concentration (500 ppm) so that they would adhere well to the leaves of the wheat.
  • the foliage was sprayed on. After spraying, the plants were air-dried, and after 4 days, sprayed with a water suspension of Septoria tritici spores. After inoculation, the plants were placed under high humidity at 18 ° C. for 3 days, then placed under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the compounds 1, 2, 3, 4, 6, and 7 of the present invention was 30% or less of the lesion area in the untreated plant.
  • Test Example 6 A plastic pot was filled with soil, and cucumber (variety: Sagamihanjiro) was sown there and allowed to grow in a greenhouse for 12 days.
  • the compounds 1, 2, 3, 4, 6, 7, 11, and 12 of the present invention were formulated according to Formulation Example 2, respectively, and then diluted with water to a predetermined concentration (500 ppm), which was sufficient for the cucumber leaves.
  • the foliage was sprayed to adhere.
  • the plants were air-dried and sprinkled with spore powdery mildew (Sphaerotheca furiginea) spores.
  • the plants were cultivated in a greenhouse at 24 ° C. during the day and 20 ° C. during the night for 8 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the present compounds 1, 2, 3, 4, 6, 7, 11, 12 was 30% or less of the lesion area in the untreated plant.
  • Test Example 7 A plastic pot was filled with soil, rice (cultivar; Nipponbare) was sown therein, and grown in a greenhouse for 20 days. Thereafter, the compounds 1, 2, 3, and 6 of the present invention were formulated according to Formulation Example 2 above, and then diluted with water to a predetermined concentration (200 ppm), so that the foliage was sufficiently attached to the rice leaf surface. Scattered. After spraying, the plants were air-dried, and the sprayed rice was contacted with rice seedlings (variety: Nihonbare) affected by rice blast fungus (Magnaporthe grisea) under high humidity at 24 ° C in the daytime and 20 ° C at night After leaving for days, the lesion area was examined. As a result, the lesion area in the plant treated with the present compounds 1, 2, 3, 6 was 30% or less of the lesion area in the untreated plant.
  • Test Example 8 A plastic pot was filled with soil, and wheat (variety: Shirogane) was sown therein and allowed to grow in a greenhouse for 9 days.
  • the compounds 1, 2, 3, and 6 of the present invention were formulated according to Formulation Example 2 above, diluted with water to a predetermined concentration (200 ppm), and sprayed with foliage so as to adhere well to the leaves of the wheat. .
  • the plants were air-dried and cultivated at 20 ° C. under illumination for 5 days, and then sprinkled with spores of wheat rust fungus (Puccinia recondita). After inoculation, the plants were placed at 23 ° C. under dark and humid conditions for 1 day, then cultivated at 20 ° C. under illumination for 8 days, and the lesion area was examined. As a result, the lesion area in the plant treated with the present compounds 1, 2, 3, 6 was 30% or less of the lesion area in the untreated plant.
  • Test Example 9 A plastic pot was filled with soil, and barley (variety: Mikamo Golden) was sown there and allowed to grow in a greenhouse for 7 days.
  • the compounds 1, 2, 3, 4, 6, and 7 of the present invention are formulated according to Formulation Example 2, respectively, and then diluted with water to a predetermined concentration (200 ppm) so that they adhere well to the leaves of the barley.
  • the foliage was sprayed on the ground. After spraying, the plants were air-dried, and two days later, an aqueous suspension of barley net spore fungus (Pyrenophora teres) spores was spray-inoculated. After inoculation, the plants were placed under high humidity in a greenhouse at 23 ° C.
  • the lesion area in the plant treated with the compounds 1, 2, 3, 4, 6, and 7 of the present invention was 30% or less of the lesion area in the untreated plant.
  • Test Example 10 A plastic pot was stuffed with soil, seeded with green beans (variety; Nagahama peas) and grown in a greenhouse for 8 days.
  • the compounds 4 and 7 of the present invention were formulated according to Formulation Example 2 above, diluted with water to a predetermined concentration (200 ppm), and sprayed on the foliage so as to adhere well to the kidney leaf surface. After spraying, the plants were air-dried, and a mycelia-containing PDA medium of sclerotia sclerotium was placed on the kidney leaf surface. After the inoculation, all kidney beans were placed under high humidity only at night, and the lesion area was examined 4 days after the inoculation. As a result, the lesion area in the plant treated with any of the compounds 4 and 7 of the present invention was 30% or less of the lesion area in the untreated plant.
  • Test Example 11 A plastic pot was filled with soil, and wheat (variety: Apogee) was sown therein and grown in a greenhouse for 10 days.
  • the compounds 1, 2, 3, 4 and 6 of the present invention were formulated according to Formulation Example 2, respectively, and then diluted with water to a predetermined concentration (200 ppm), and the foliage so that it was sufficiently attached to the leaves of the wheat. Scattered. After spraying, the plants were air-dried, and after 4 days, sprayed with a water suspension of Septoria tritici spores. After inoculation, the plants were placed under high humidity at 18 ° C. for 3 days, then placed under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the compounds 1, 2, 3, 4 and 6 of the present invention was 30% or less of the lesion area in the untreated plant.
  • Test Example 12 A plastic pot was filled with soil, and cucumber (variety: Sagamihanjiro) was sown there and allowed to grow in a greenhouse for 12 days.
  • the compounds 1, 2, 3, 4, 6, and 7 of the present invention were formulated in accordance with Formulation Example 2 above, and then diluted with water to a predetermined concentration (200 ppm) so that they adhered sufficiently to the cucumber leaf surface.
  • the foliage was sprayed. After spraying, the plants were air-dried and sprinkled with spore powdery mildew (Sphaerotheca furiginea) spores.
  • the plants were cultivated in a greenhouse at 24 ° C. during the day and 20 ° C. during the night for 8 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the compounds 1, 2, 3, 4, 6, and 7 of the present invention was 30% or less of the lesion area in the untreated plant.
  • Test Example 13 A plastic pot was filled with soil, and soybeans (variety: Kurosengoku) were sown therein and grown in a greenhouse for 13 days.
  • the compounds 1, 2, 3, 4 and 6 of the present invention were formulated according to Formulation Example 2, respectively, and then diluted with water to a predetermined concentration (200 ppm), so that the foliage was sufficiently attached to the leaves of the soybean. Scattered. After spraying, the plants were air-dried, and after 2 days, spray-inoculated with a water suspension of soybean rust fungus (Phakopsora pachyrhizi). After inoculation, the plants were placed in a greenhouse at 23 ° C. during the day and 20 ° C. during the night under high humidity for 3 days. As a result, the lesion area in the plant treated with the compounds 1, 2, 3, 4 and 6 of the present invention was 30% or less of the lesion area in the untreated plant.
  • Test Example 14 A plastic pot was filled with soil, and barley (variety: Mikamo Golden) was sown there and allowed to grow in a greenhouse for 7 days.
  • the compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12 of the present invention were formulated according to the above Formulation Example 2 and then diluted with water to give a predetermined concentration (200 ppm). Then, the stems and leaves were sprayed so as to adhere well to the leaf surface of the barley. After spraying, the plants were air-dried, and after 2 days, sprayed with a water suspension of barley cloud spore (Rhynchosporium secalis) spores. After inoculation, the plants were placed under high humidity in a greenhouse at 23 ° C.
  • the lesion areas in the plants treated with the compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 of the present invention are all the lesion areas in the untreated plants. It was 30% or less.

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Abstract

Le composé de tétrazolinone représenté par la formule (1) a un excellent effet de lutte contre les organismes nuisibles. [Dans la formule : R1, R2, R3 et R11 représentent chacun un groupe alkyle en C1-C3, qui peut avoir un atome d'halogène, ou similaire ; R4 et R5 représentent chacun un atome d'hydrogène, un atome d'halogène, un groupe alkyle en C1-C3, ou similaire ; R7, R8 et R9 représentent chacun un atome d'hydrogène, un atome d'halogène, ou similaire ; R10 représente un groupe alkyle en C1-C3 ou similaire ; R12 représente un groupe alkyle en C2-C6, un groupe cycloalkyle en C3-C6, un atome d'hydrogène ou similaire ; et R13 représente un groupe alkyle en C1-C6, un groupe alcényle en C2-C6 ou similaire].
PCT/JP2013/085023 2012-12-27 2013-12-19 Composé de tétrazolinone et ses applications WO2014104268A1 (fr)

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9314023B2 (en) 2012-09-28 2016-04-19 Sumitomo Chemical Company, Limited Tetrazolinone compounds and their use as pesticides
US9560850B2 (en) 2012-12-27 2017-02-07 Sumitomo Chemical Company, Limited Tetrazolinone compound and use thereof
US9675072B2 (en) 2013-05-29 2017-06-13 Sumitomo Chemical Company, Limited Tetrazolinone compound and application of same
US9725423B2 (en) 2012-11-29 2017-08-08 Sumitomo Chemical Company, Limited Tetrazolinone compound and applications thereof
US9730448B2 (en) 2013-08-29 2017-08-15 Sumitomo Chemical Company, Limited Tetrazolinone compound and use of same
US9822095B2 (en) 2014-03-28 2017-11-21 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
US9828389B2 (en) 2012-09-28 2017-11-28 Sumitomo Chemical Company, Limited Tetrazolinone compounds and their use as pesticides
US9826741B2 (en) 2014-03-28 2017-11-28 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
US9867372B2 (en) 2013-04-26 2018-01-16 Sumitomo Chemical Company, Limited Tetrazolinone compound and use of same
US9888688B2 (en) 2013-07-12 2018-02-13 Sumitomo Chemical Company, Limited Tetrazolinone compounds and applications thereof
US10070646B2 (en) 2014-03-28 2018-09-11 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
US10077254B2 (en) 2013-10-17 2018-09-18 Sumitomo Chemical Company, Limited Tetrazolinone compound and use thereof
US10091998B2 (en) 2013-10-28 2018-10-09 Sumitomo Chemical Company, Limited Tetrazolinone compound and use thereof

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JPH09208565A (ja) * 1996-02-07 1997-08-12 Sumitomo Chem Co Ltd テトラゾリノン誘導体、その用途およびその製造中間体
JP2002506060A (ja) * 1998-03-09 2002-02-26 ビーエーエスエフ アクチェンゲゼルシャフト ヘテロアリール置換ベンジルフェニルエーテル、その製造方法、並びに有害菌類及び有害動物防除用としての使用法
JP2003509415A (ja) * 1999-09-15 2003-03-11 ビーエーエスエフ アクチェンゲゼルシャフト 不飽和オキシムエーテル並びに有害な菌類及び家畜害虫を防除するためのその使用
WO2013092224A1 (fr) * 2011-12-21 2013-06-27 Basf Se Utilisation de composés de type strobilurine pour combattre des champignons phytopathogènes résistants aux inhibiteurs du site qo

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Publication number Priority date Publication date Assignee Title
JPH09208565A (ja) * 1996-02-07 1997-08-12 Sumitomo Chem Co Ltd テトラゾリノン誘導体、その用途およびその製造中間体
JP2002506060A (ja) * 1998-03-09 2002-02-26 ビーエーエスエフ アクチェンゲゼルシャフト ヘテロアリール置換ベンジルフェニルエーテル、その製造方法、並びに有害菌類及び有害動物防除用としての使用法
JP2003509415A (ja) * 1999-09-15 2003-03-11 ビーエーエスエフ アクチェンゲゼルシャフト 不飽和オキシムエーテル並びに有害な菌類及び家畜害虫を防除するためのその使用
WO2013092224A1 (fr) * 2011-12-21 2013-06-27 Basf Se Utilisation de composés de type strobilurine pour combattre des champignons phytopathogènes résistants aux inhibiteurs du site qo

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9828389B2 (en) 2012-09-28 2017-11-28 Sumitomo Chemical Company, Limited Tetrazolinone compounds and their use as pesticides
US9554576B2 (en) 2012-09-28 2017-01-31 Sumitomo Chemical Company, Limited Tetrazolinone compounds and their use as pesticides
US9314023B2 (en) 2012-09-28 2016-04-19 Sumitomo Chemical Company, Limited Tetrazolinone compounds and their use as pesticides
US9725423B2 (en) 2012-11-29 2017-08-08 Sumitomo Chemical Company, Limited Tetrazolinone compound and applications thereof
US9560850B2 (en) 2012-12-27 2017-02-07 Sumitomo Chemical Company, Limited Tetrazolinone compound and use thereof
US9867372B2 (en) 2013-04-26 2018-01-16 Sumitomo Chemical Company, Limited Tetrazolinone compound and use of same
US9675072B2 (en) 2013-05-29 2017-06-13 Sumitomo Chemical Company, Limited Tetrazolinone compound and application of same
US9888688B2 (en) 2013-07-12 2018-02-13 Sumitomo Chemical Company, Limited Tetrazolinone compounds and applications thereof
US9730448B2 (en) 2013-08-29 2017-08-15 Sumitomo Chemical Company, Limited Tetrazolinone compound and use of same
US10077254B2 (en) 2013-10-17 2018-09-18 Sumitomo Chemical Company, Limited Tetrazolinone compound and use thereof
US10091998B2 (en) 2013-10-28 2018-10-09 Sumitomo Chemical Company, Limited Tetrazolinone compound and use thereof
US9822095B2 (en) 2014-03-28 2017-11-21 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
US9826741B2 (en) 2014-03-28 2017-11-28 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
US10070646B2 (en) 2014-03-28 2018-09-11 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof

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