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WO2018190326A1 - Composition de lutte contre les nuisibles contenant un composé pyridone et un composé à base de quinoléine et procédé de lutte contre les nuisibles, et nouveau composé à base de quinoléine - Google Patents

Composition de lutte contre les nuisibles contenant un composé pyridone et un composé à base de quinoléine et procédé de lutte contre les nuisibles, et nouveau composé à base de quinoléine Download PDF

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Publication number
WO2018190326A1
WO2018190326A1 PCT/JP2018/015011 JP2018015011W WO2018190326A1 WO 2018190326 A1 WO2018190326 A1 WO 2018190326A1 JP 2018015011 W JP2018015011 W JP 2018015011W WO 2018190326 A1 WO2018190326 A1 WO 2018190326A1
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group
substituent
optionally substituted
formula
compound represented
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PCT/JP2018/015011
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Japanese (ja)
Inventor
健志 福元
豪毅 梅谷
伊藤　寛之
敏明 小原
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三井化学アグロ株式会社
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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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to a pest control composition containing a pyridone compound and one or more quinoline compounds as active ingredients, and a novel quinoline compound.
  • 1,3,5,6-substituted-2-pyridone compounds for example, 1,3,5,6-substituted-2 having an aryl group or heteroaryl group at the 3-position as a GABA alpha-2 / 3 ligand.
  • -Pyridone compounds have been disclosed (see eg WO 98/55480).
  • 1,3,5,6-substituted-2-pyridone compounds having a carboxyl group at the 3-position have been disclosed as therapeutic agents for bacterial infections (see, for example, European Patent No. 0308020).
  • the uses of the compounds described in WO 98/55480 and EP 0308020 are all related to medicines and are different from the technical field to which the pest control composition according to the present invention belongs. To do.
  • Patent Documents 3 and 4 disclose that rice blasts of rice blast (Pyricularia oryzae) and tomato, cucumber and kidney beans are gray as quinoline compounds as fungicides. It has been disclosed that a disease control such as fungus disease (Botrytis cinerea), cucumber vine split disease (Fusarium oxysporum) and the like can be controlled by treatment methods such as foliage spraying, soil treatment, seed treatment, and the like.
  • Patent Documents 5 and 6 disclose mixing of the quinoline compound represented by the formula (2a) or the formula (2b) with a certain fungicide, but mixing with the pyridone compound of the present invention. Is not disclosed.
  • An object of the present invention is to provide a pest control composition having a useful control effect including a combination of a novel pyridone compound or a salt thereof and a quinoline compound, a method of using the same, and a novel quinoline compound having a useful control effect Is to provide.
  • a pest control composition comprising, as active ingredients, a compound group having an aryl group or heteroaryl group having a substituent at the ortho position with respect to the 6-position in the 2-pyridone skeleton, and one or more quinoline compounds;
  • the present inventors have found that a novel quinoline compound exhibits excellent pest control activity and has completed the present invention. That is, the present invention is as follows.
  • R1 is a hydroxyl group, A cyano group, A C1-C6 alkyl group optionally substituted with substituent A, A C1-C6 haloalkyl group, A C3-C8 cycloalkyl group optionally substituted with the substituent A, A C2-C6 alkenyl group optionally substituted with the substituent A, A C2-C6 haloalkenyl group, A C2-C6 alkynyl group optionally substituted with substituent A, A C2-C6 haloalkynyl group, A C1-C6 alkoxy group optionally substituted with the substituent A, A C1-C6 haloalkoxy group, A C3-C8 cycloalkoxy group optionally substituted with the substituent A, A C2-C6 alkenyloxy group optionally substituted with the substituent A, A C2-C6 haloalkenyloxy group, A C3-C6 alkynyloxy group
  • R20C ( ⁇ O) O— (wherein R20 has the same meaning as above), A 3- to 6-membered group containing 1 to 2 oxygen atoms, R23-L2- (wherein, R23 represents a C1 alkyl group ⁇ C6 or C1 ⁇ C6 haloalkyl group,, L2 represents S, SO, or SO 2.), R21R22N- (wherein R21 and R22 are as defined above), Or R24C ( ⁇ O) N (R25) — (wherein R24 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or R21R22N— (wherein R21 and R22 have the same meanings as described above), and R25 is optional
  • Substituent B1 is At least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, and a C3-C8 cycloalkoxy group
  • Substituent C is Hydroxyl group, cyano group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, R31R32N- (wherein R31 and R32 are the same as R21 And R22), and R30-L3- (wherein R30 has the same meaning as R14 and L3 has the same meaning as L1), and at least one selected from the group consisting of Seeds
  • Substituent D is At least one selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C
  • R1 is a cyano group, A C1-C6 alkyl group optionally substituted with substituent A, A C1-C6 haloalkyl group, A C3-C8 cycloalkyl group optionally substituted with the substituent A, A C2-C6 alkenyl group optionally substituted with the substituent A, A C2-C6 haloalkenyl group, A C2-C6 alkynyl group optionally substituted with substituent A, Or R10R11N- (wherein R10 and R11 are each independently a hydrogen atom or a C1-C6 alkyl group); R2 is a halogen atom, Hydroxyl group, A cyano group, A C1-C6 alkyl group optionally substituted with the substituent B, A C1-C6 haloalkyl group, A C1-C6 alkoxy group optionally substituted with the substituent B, A C1-C6
  • R1 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group optionally substituted with the substituent A
  • R2 represents a halogen atom, a C1-C6 alkyl group optionally substituted with the substituent B, or a C1-C6 alkoxy group optionally substituted with the substituent B
  • R3 represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally substituted with a substituent C.
  • R2a and R2b are each independent, A C1-C6 alkyl group optionally substituted with a substituent E1; R2c and R2d are each independent, A hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent E1, or a halogen atom, R2e is a hydrogen atom or a C1-C6 alkyl group optionally substituted with a substituent E1, X1 is a halogen atom, X2 is a halogen atom, n1 represents an integer of 0 to 4, The pest control composition according to [1], wherein n2 represents an integer of 0 to 6.
  • the quinoline compound represented by formula (2a) or formula (2b) is represented by formula (2c) or formula (2d).
  • R2f represents a hydrogen atom or a methyl group
  • X3, X4 and X5 each independently represent a hydrogen atom or a fluorine atom
  • X6 and X7 each independently represent a hydrogen atom, a methyl group or a fluorine atom.
  • the pesticidal composition according to [1] which is a quinoline compound represented by the formula:
  • the quinoline compound represented by the formula (2a) or the formula (2b) is 3- (4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, 3- (4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) -8-fluoroquinoline, 8-Fluoro-3- (5-fluoro-3,3,4,4-tetramethyl-1,2,3,4-tetrahydroisoquinolin-1-yl) quinoline and 8-fluoro-3- (5-fluoro-).
  • the pest control composition according to [4] which is at least one selected from the group consisting of 3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline.
  • [7] A method for controlling pests by applying the pest control composition according to [1].
  • a composition containing, as an active ingredient, a pyridone compound represented by the formula (1) according to [1] or a salt thereof, and a quinoline system represented by the formula (2a) or the formula (2b) according to [1] A method for controlling pests by simultaneously applying a compound or a salt thereof as an active ingredient.
  • a composition containing, as an active ingredient, a pyridone compound represented by formula (1) according to [1] or a salt thereof, or a quinoline system represented by formula (2a) or formula (2b) according to [1] A method of controlling pests by applying one of the compositions containing a compound or a salt thereof as an active ingredient and then applying the other composition.
  • a method for controlling pests comprising a compound of the formula (I) or a salt thereof and the formula (2a) or formula described in [1] on a plant individual, seed, soil, seedling box, or cell tray in need thereof
  • a method comprising applying an effective amount of the quinoline compound represented by (2b) or a salt thereof.
  • a pest control composition useful for controlling pests containing a novel active ingredient a method for using the same, and a novel quinoline compound.
  • Cx-Cy has x to y carbon atoms.
  • optionally substituted means substituted or unsubstituted. When this term is used, the number of substituents is 1 when the number of substituents is not specified.
  • the C1-C6 alkyl group may be linear or branched, and is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl.
  • the halogen atom is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
  • the C1-C6 haloalkyl group represents a group in which the hydrogen in the C1-C6 alkyl group is optionally substituted with one or more halogen atoms.
  • the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent.
  • C1-C6 haloalkyl group examples include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a monobromomethyl group, a monoiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, 1 -Fluoroethyl group, 2-fluoroethyl group, 1,1-difluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group , Pentafluoroethyl group, 2,2,2-trichloroethyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 2,2,2
  • the C1-C6 fluoroalkyl group represents a group in which hydrogen in the C1-C6 alkyl group is optionally substituted with one or more fluorine atoms.
  • Specific examples of the C1-C6 fluoroalkyl group include monofluoromethyl group, difluoromethyl group, trifluoromethyl group, 1-fluoroethyl group, 2-fluoroethyl group, 1,1-difluoroethyl group, 2,2- Difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, pentafluoroethyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl Group, heptafluoropropyl group, heptafluoroisopropyl group, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, nonafluorobut
  • the C3-C8 cycloalkyl group includes a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like.
  • the C2-C6 alkenyl group represents an unsaturated hydrocarbon group which has one or more double bonds and is linear or branched.
  • C2 to C6 alkenyl groups include vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, and 3-pentenyl.
  • the C2-C6 haloalkenyl group represents a group in which the hydrogen atom in the C2-C6 alkenyl group is optionally substituted with one or more halogen atoms.
  • the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent.
  • C2-C6 haloalkenyl group examples include 2-fluorovinyl group, 2,2-difluorovinyl group, 2,2-dichlorovinyl group, 3-fluoroallyl group, 3,3-difluoroallyl group, 3, Examples include 3-dichloroallyl group, 4,4-difluoro-3-butenyl group, 5,5-difluoro-4-pentenyl group, 6,6-difluoro-5-hexenyl group and the like.
  • the C2-C6 alkynyl group represents an unsaturated hydrocarbon group having one or more triple bonds and being linear or branched. Specific examples of the C2-C6 alkynyl group include ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, and 3-pentynyl.
  • the C2-C6 haloalkynyl group represents a group in which the hydrogen atom in the C2-C6 alkynyl group is optionally substituted with one or more halogen atoms.
  • the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent.
  • C2-C6 haloalkynyl group examples include 2-fluoroethynyl group, 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3,3-difluoro-1-propynyl group, 3-chloro -3,3-difluoro-1-propynyl group, 3-bromo-3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl Group, 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro-1-butynyl group, 4-chloro-4,4-difluoro-2-butynyl group, 4-bromo-4,4 -Difluoro-1-butynyl group, 4-bromo-4,4-Di
  • the C1-C6 alkoxy group represents a C1-C6 alkyl group bonded through an oxygen atom.
  • Specific examples of the C1-C6 alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a t-butoxy group, a pentyloxy group, and an isopentyloxy group.
  • the C1-C6 haloalkoxy group represents a group in which the hydrogen atom in the C1-C6 alkoxy group is optionally substituted with one or more halogen atoms.
  • the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent.
  • C1-C6 haloalkoxy group examples include difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2,2-difluoroethoxy group, 2,2,2 -Trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, pentafluoroethoxy group, 2,2,2-trichloroethoxy group, 3,3-difluoropropyloxy group, 3,3,3-tri Fluoropropyloxy group, heptafluoropropyloxy group, heptafluoroisopropyloxy group, 2,2,2-trifluoro-1- (trifluoromethyl) -ethoxy group, nonafluorobutoxy group, nonafluoro-sec-butoxy group, 3 , 3,4,4,5,5,5-heptafluoropentyloxy group Undecafluoro pent
  • the C3-C8 cycloalkoxy group represents a group in which the C3-C8 cycloalkyl group is bonded via an oxygen atom.
  • Specific examples of the C3-C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, and a cyclooctyloxy group.
  • the C2-C6 alkenyloxy group is a group in which the C2-C6 alkenyl group is bonded through an oxygen atom.
  • E-form and Z-form or a mixture of E-form and Z-form in an arbitrary ratio, is not particularly limited as long as it is within the specified carbon number range. None happen.
  • C2-C6 alkenyloxy group examples include vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group, 2-pentenyloxy group 3-pentenyloxy group, 4-pentenyloxy group, 3-methyl-2-butenyloxy group, 1-hexenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group Group, 4-methyl-3-pentenyloxy group, 3-methyl-2-pentenyloxy group and the like.
  • the C2-C6 haloalkenyloxy group represents a group in which the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent.
  • Specific examples of the C2-C6 haloalkenyloxy group include 2-fluorovinyloxy group, 2,2-difluorovinyloxy group, 2,2-dichlorovinyloxy group, 3-fluoroallyloxy group, 3,3-difluoro.
  • the C3-C6 alkynyloxy group represents a group in which the C3-C6 alkynyl group is bonded via an oxygen atom among the C2-C6 alkynyl groups.
  • Specific examples of the C3-C6 alkynyloxy group include propargyloxy group, 2-butynyloxy group, 3-butynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, 1,1 -Dimethyl-2-propynyloxy group, 2-hexynyloxy group, 3-hexynyloxy group, 4-hexynyloxy group, 5-hexynyloxy group and the like.
  • the C3-C6 haloalkynyloxy group represents a group in which the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted with one or more halogen atoms.
  • the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent.
  • C3-C6 haloalkynyloxy group examples include 1,1-difluoro-2-propynyloxy group, 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro-2-butynyloxy group 4-bromo-4,4-difluoro-2-butynyloxy group, 4,4,4-trifluoro-2-butynyloxy group, 5,5-difluoro-3-pentynyloxy group, 5-chloro-5,5 -Difluoro-3-pentynyloxy group, 5-bromo-5,5-difluoro-3-pentynyloxy group, 5,5,5-trifluoro-3-pentynyloxy group, 6,6-difluoro-4 -Hexynyloxy group, 6-chloro-6,6-difluoro-4-hexynyloxy group, 6-bromo-6
  • the C2-C6 alkoxyalkoxy group is a group in which the hydrogen atom in the C1-C5 alkoxy group in the C1-C6 alkoxy group is optionally substituted with one or more C1-C5 alkoxy groups Represents. There is no particular limitation as long as the total number of carbon atoms is within the specified carbon number range.
  • C2-C6 alkoxyalkoxy groups include methoxymethoxy, ethoxymethoxy, propyloxymethoxy, isopropyloxymethoxy, methoxyethoxy, ethoxyethoxy, propyloxyethoxy, isopropyloxyethoxy, methoxypropyl Examples thereof include an oxy group, an ethoxypropyloxy group, a propyloxypropyloxy group, and an isopropyloxypropyloxy group.
  • the C2-C12 alkoxyalkyl group represents a group in which the C1-C6 alkoxy group is bonded to the C1-C6 alkyl group. There is no particular limitation as long as the total number of carbon atoms is within the specified carbon number range. Specific examples of the C2-C12 alkoxyalkyl group include a methoxymethyl group, an ethoxymethyl group, a 2-methoxyethyl group, and a 2-ethoxyethyl group.
  • the C2-C7 alkyloxycarbonyl group represents a carbonyl group bonded to the C1-C6 alkoxy group.
  • Specific examples of the C2-C7 alkyloxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a 1-butyloxycarbonyl group, a 2-butyloxycarbonyl group, and a 1-pentyloxycarbonyl group. Group, 1-ethylpropyloxycarbonyl group, 1-hexylcarbonyl group and the like.
  • the C1-C6 alkylthio group is a group in which a sulfur atom is bonded to the C1-C6 alkyl group.
  • Specific examples of the C1-C6 alkylthio group include methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, sec-butylthio group, t-butylthio group, pentylthio group, isopentylthio group, 2 -Methylbutylthio group, neopentylthio group, 1-ethylpropylthio group, hexylthio group, 4-methylpentylthio group, 3-methylpentylthio group, 2-methylpentylthio group, 1-methylpentylthio group, 3 , 3-dimethylbutylthio group, 2,2-dimethylbutylthio group, 1,1-
  • the C2-C7 acyl group represents a carbonyl group bonded to the C1-C6 alkyl group.
  • Specific examples of the C2 to C7 acyl group include acetyl group, propanoyl group, 1-butanoyl group, 2-methylpropanoyl group, 1-pentanoyl group, 2-methylbutanoyl group, 1-hexanoyl group, 2-methylpenta Examples include noyl group and 2-ethylbutanoyl group.
  • the C3-C8 alkylsulfonylethyl group represents a group in which the C1-C6 alkyl group is bonded to the sulfur atom of the sulfonylethyl group. There is no particular limitation as long as the total number of carbon atoms is within the specified carbon number range.
  • Examples of the C3-C8 alkylsulfonylethyl group include 2-methylsulfonylethyl group, 2-ethylsulfonylethyl group, 2- (1-propylsulfonyl) ethyl group, 2- (2-propylsulfonyl) ethyl group, 1-methyl- 2-methylsulfonylethyl group, 1-ethyl-2-methylsulfonylethyl group, 2-methyl-2-methylsulfonylethyl group, 2-ethyl-2-ethylsulfonylethyl group, 1-methyl-2-methyl-2-methyl A sulfonylethyl group etc. are mentioned.
  • the aryl group represents a C6 to C14 1 to 3 aromatic ring.
  • Specific examples of the aryl group include a phenyl group, a naphthyl group, and an anthracenyl group.
  • the heteroaryl group represents a 5- to 14-membered 1 to 3 ring aromatic ring containing one or two or more identical or different ring-constituting heteroatoms.
  • the kind of hetero atom is not specifically limited, A nitrogen atom, an oxygen atom, a sulfur atom, etc. can be illustrated.
  • heteroaryl groups include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, dihydroisoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl , Tetrazolyl group, pyridyl group, azepinyl group, oxazepinyl group, etc.
  • the aralkyl group represents a group in which one or more hydrogen atoms of the C1-C6 alkyl group are substituted with the aryl group.
  • Specific examples of the aralkyl group include benzyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, anthracenylmethyl group, phenanthrenylmethyl group, acenaphthylenylmethyl group, diphenylmethyl group, 1-phenethyl group.
  • 2-phenethyl group 1- (1-naphthyl) ethyl group, 1- (2-naphthyl) ethyl group, 2- (1-naphthyl) ethyl group, 2- (2-naphthyl) ethyl group, 3-phenylpropyl Group, 3- (1-naphthyl) propyl group, 3- (2-naphthyl) propyl group, 4-phenylbutyl group, 4- (1-naphthyl) butyl group, 4- (2-naphthyl) butyl group, 5- Phenylpentyl group, 5- (1-naphthyl) pentyl group, 5- (2-naphthyl) pentyl group, 6-phenylhexyl group, 6- (1-naphthyl) hexyl group, 6- (2-naphthyl) ) Hexyl group
  • the C3-C10 cycloalkyl ring includes a cyclopropyl ring, a cyclobutyl ring, a cyclopentyl ring, a cyclohexyl ring, a cycloheptyl ring, a cyclooctyl ring, and the like.
  • the N-hydroxyalkaneimidoyl group includes a hydroxyiminomethyl group, an N-hydroxyethaneimidoyl group, an N-hydroxypropanimidyl group, an N-hydroxybutanimidoyl group, and the like.
  • 3- to 6-membered ring group containing 1 to 2 oxygen atoms include 1,2-epoxyethanyl group, oxetanyl group, oxolanyl group, oxanyl group, 1,3-dioxolanyl group, 1,3- Examples thereof include a dioxanyl group and a 1,4-dioxanyl group.
  • the pest control composition of the present invention (hereinafter sometimes simply referred to as the composition of the present invention) is a pyridone compound represented by the following formula (1) or a salt thereof (herein, simply represented by the formula (1)).
  • R1 in the formula (1) is a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 optionally substituted with a substituent A.
  • a hydrogen atom or an alkyl group C1 ⁇ C6,) represents a.
  • R1 is a cyano group, a C1-C6 alkyl group optionally substituted with the substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with the substituent A, a substituted group.
  • a C1-C6 alkyl group or a C1-C6 haloalkyl group which may be optionally substituted with the substituent A is preferable.
  • the “substituent A” in the formula (1) is a hydroxyl group, a cyano group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, R12R13N.
  • R12 and R13 are each independently a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or R12 and R13 are , Together with the nitrogen atom to which it is attached, represents an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group), and R14-L1- (where R14 is represents a C1 alkyl group ⁇ C6 or C1 ⁇ C6 haloalkyl group,, L1 is, S, SO, or SO 2 Represents at least one selected from the group consisting of:
  • the substituent A is preferably a cyano group, a C1-C6 alkoxy group, or R14-L1- (wherein R14 and L1 are as defined above), In particular, a cyano group or a C1-C6 alkoxy group is preferable.
  • substituent A examples include a hydroxyl group; a cyano group; As a C3-C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; A methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group as the C1-C6 alkoxy group; C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group; As a C3-C8 cycloalkoxy group, a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclo
  • substituent A a hydroxyl group; a cyano group; A cyclopropyl group and a cyclobutyl group as the C3-C8 cycloalkyl group; A methoxy group and an ethoxy group as the C1-C6 alkoxy group; A difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group; A cyclopropyloxy group and a cyclobutoxy group as a C3-C8 cycloalkoxy group; R12R13N- (wherein R12 and R13 have the same meanings as described above), dimethylamino group, ethylmethylamino group, and diethylamino group; And R14-L1- (wherein R14 and L1 are as defined above) include a methylthio
  • R1 in the formula (1) includes a hydroxyl group and a cyano group.
  • the C1-C6 alkyl group of the “C1-C6 alkyl group optionally substituted with the substituent A” in R1 of the formula (1) has the same definition as above, preferably a methyl group, an ethyl group , A propyl group, an isopropyl group, a butyl group, or an isobutyl group, and more preferably a methyl group or an ethyl group.
  • the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.
  • the “C1-C6 haloalkyl group” in R1 of the formula (1) has the same definition as described above, preferably a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoro group.
  • the C3-C8 cycloalkyl group in the “C3-C8 cycloalkyl group optionally substituted with the substituent A” in R1 of the formula (1) has the same definition as above, preferably a cyclopropyl group , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group.
  • the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent A.
  • the C2-C6 alkenyl group of the “C2-C6 alkenyl group optionally substituted with the substituent A” in R1 of the formula (1) has the same definition as above, preferably a vinyl group, 1- It is a propenyl group or an allyl group, more preferably a vinyl group or an allyl group.
  • the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent A.
  • the “C2-C6 haloalkenyl group” in R1 of the formula (1) has the same definition as above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or A 3,3-difluoroallyl group, more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.
  • the C2-C6 alkynyl group of the “C2-C6 alkynyl group optionally substituted with the substituent A” in R1 of the formula (1) has the same meaning as defined above, preferably a propargyl group, 2- It is a butynyl group or a 3-butynyl group, more preferably a propargyl group.
  • the hydrogen atom in the C2-C6 alkynyl group is optionally substituted by the substituent A.
  • the “C2-C6 haloalkynyl group” in R1 of the formula (1) has the same definition as above, and is preferably a 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro- 2-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group or 4,4,4-trifluoro-2-butynyl group, more preferably 4,4-difluoro-2-butynyl Or a 4,4,4-trifluoro-2-butynyl group.
  • the C1-C6 alkoxy group of the “C1-C6 alkoxy group optionally substituted with the substituent A” in R1 of the formula (1) has the same definition as above, preferably a methoxy group, an ethoxy group , A propyloxy group, an isopropyloxy group, a butoxy group, or an isobutoxy group, and more preferably a methoxy group or an ethoxy group.
  • the hydrogen atom in the C1-C6 alkoxy group is optionally substituted by the substituent A.
  • the “C1-C6 haloalkoxy group” in R1 of the formula (1) has the same definition as above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group, or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group Or a 2,2,2-trifluoroethoxy group.
  • the C3-C8 cycloalkoxy group in the “C3-C8 cycloalkoxy group optionally substituted with the substituent A” in R1 of the formula (1) has the same definition as described above, preferably cyclopropyloxy Group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, and more preferably a cyclopropyloxy group or a cyclobutoxy group.
  • the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted with the substituent A.
  • the C2-C6 alkenyloxy group of “C2-C6 alkenyloxy group optionally substituted with substituent A” in R1 of formula (1) has the same definition as above, preferably a vinyloxy group, It is a 1-propenyloxy group or an allyloxy group, and more preferably a vinyloxy group.
  • the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent A.
  • the “C2-C6 haloalkenyloxy group” in R1 of the formula (1) has the same definition as above, preferably 2-fluorovinyloxy group, 2,2-difluorovinyloxy group, 3-fluoro An allyloxy group or a 3,3-difluoroallyloxy group, more preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.
  • the C3-C6 alkynyloxy group of “C3-C6 alkynyloxy group optionally substituted with substituent A” in R1 of formula (1) has the same definition as above, preferably a propargyloxy group , 2-butynyloxy group, or 3-butynyloxy group, and more preferably a propargyloxy group.
  • the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent A.
  • the “C3-C6 haloalkynyloxy group” in R1 of the formula (1) has the same definition as described above, and is preferably a 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4- A difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group, or a 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2 -Butynyloxy group or 4,4,4-trifluoro-2-butynyloxy group.
  • R10R11N— The C1-C6 alkyl group of “R10R11N—” in R1 of the formula (1) (wherein R10 and R11 are each independently a hydrogen atom or a C1-C6 alkyl group) Synonymous with definition.
  • R10R11N— is preferably an amino group, a dimethylamino group, an ethylmethylamino group, and a diethylamino group, more preferably an amino group and a dimethylamino group.
  • R2 is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group that may be optionally substituted with a substituent B, a C1-C6 haloalkyl group, and a C3-optionally substituted C3- A C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with substituent B, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent B, C2- C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent B, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent B, substituted C2-C6 alkenyloxy group optionally substituted with group B, C2-C6 haloalkenyloxy group, C3-
  • R24C ( ⁇ O) N (R25) (wherein R24 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group) , A C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R21R22N— (wherein R21 and R22 have the same meanings as described above), and R25 is a hydrogen atom or a substituent B1. Place Which may be C1 ⁇ C6 alkyl group, a cycloalkyl group of haloalkyl group having C1 ⁇ C6 or C3 ⁇ C8,. ).
  • R2 is a halogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C1-C6 optionally substituted with a substituent B.
  • Substituent B in formula (1) is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2 To C6 alkoxyalkoxy groups, R21R22N- (wherein R21 and R22 are as defined above), R23-L2- (wherein R23 and L2 are as defined above), R26R27R28Si- ( Here, R26, R27, and R28 are each independently a C1-C6 alkyl group.), R26R27R28Si— (CH 2 ) s—O— (wherein s is an integer of 1 to 3) R26, R27, and R28 are as defined above, R20C ( ⁇ O) — (wherein R20 is as defined above for R20), and ⁇ Represents at least one member selected from the group consist
  • the substituent B is a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C2-C6 alkoxyalkoxy group, R23-L2- (wherein R23 and L2 are as defined above).
  • R26R27R28Si— wherein R26, R27, and R28 are as defined above
  • R26R27R28Si— CH 2 ) s—O—
  • s, R26, R27, and R28 are R20C ( ⁇ O) —
  • R20 is as defined above
  • a 3- to 6-membered ring group containing 1 to 2 oxygen atoms is preferred, In particular, a cyano group or a C1-C6 alkoxy group is preferable.
  • Preferred specific examples of the substituent B include a hydroxyl group; a cyano group; As a C3-C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; A C1-C6 alkoxy group as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, and an isobutoxy group; C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group; As a C3-C8 cycloalkoxy group, a cyclopropyloxy group, a cyclobutoxy group, a
  • substituent B a hydroxyl group; a cyano group; A cyclopropyl group and a cyclobutyl group as the C3-C8 cycloalkyl group; A methoxy group and an ethoxy group as the C1-C6 alkoxy group; A difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group; A cyclopropyloxy group and a cyclobutoxy group as a C3-C8 cycloalkoxy group; A methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, and an ethoxyethoxy group as the C2-C6 alkoxyalkoxy group; R21R22N— (wherein R21 and R22 have the same meanings as described above),
  • Examples of the 3- to 6-membered ring group containing 1 to 2 oxygen atoms include a 1,3-dioxolanyl group and a 1,3-dioxanyl group.
  • the “substituent B1” in the formula (1) is at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, and a C3-C8 cycloalkoxy group.
  • the substituent B1 is preferably a cyano group or a C1-C6 alkoxy group.
  • substituent B1 examples include a cyano group;
  • a C1-C6 alkoxy group as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, and an isobutoxy group;
  • C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
  • examples of the C3-C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group.
  • substituent B1 a cyano group; A methoxy group and an ethoxy group as the C1-C6 alkoxy group; A difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group; As the C3-C8 cycloalkoxy group, a cyclopropyloxy group and a cyclobutoxy group can be mentioned.
  • the halogen atom in R2 of the formula (1) has the same definition as described above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • R2 in the formula (1) includes a hydroxyl group, a cyano group, and a nitro group.
  • the C1-C6 alkyl group in the “C1-C6 alkyl group optionally substituted with the substituent B” in R2 of the formula (1) has the same definition as above, preferably a methyl group, an ethyl group , A propyl group, an isopropyl group, a butyl group, or an isobutyl group, and more preferably a methyl group, an ethyl group, a propyl group, or an isopropyl group.
  • the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent B.
  • the “C1-C6 haloalkyl group” in R2 of the formula (1) has the same definition as above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, 2,2,2 A trifluoroethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, or 2,2,2-trifluoroethyl group.
  • the C3-C8 cycloalkyl group in the “C3-C8 cycloalkyl group optionally substituted with the substituent B” in R2 of the formula (1) is as defined above, and preferably a cyclopropyl group , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group.
  • the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent B.
  • the C2-C6 alkenyl group of “C2-C6 alkenyl group optionally substituted with substituent B” in R2 of formula (1) has the same definition as above, preferably a vinyl group, 1- A propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, or an allyl group.
  • the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent B.
  • the “C2-C6 haloalkenyl group” in R2 of the formula (1) has the same definition as above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group. , 3-fluoroallyl group, 3,3-difluoroallyl group, or 3,3-dichloroallyl group, more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.
  • the C2-C6 alkynyl group of the “C2-C6 alkynyl group optionally substituted with the substituent B” in R2 of the formula (1) has the same definition as above, preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group, a 1-propynyl group, or a propargyl group.
  • the hydrogen atom in the C2-C6 alkynyl group is optionally substituted by the substituent B.
  • the “C2-C6 haloalkynyl group” in R2 of the formula (1) has the same definition as above, preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -Propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- A 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group.
  • the C1-C6 alkoxy group of the “C1-C6 alkoxy group optionally substituted with the substituent B” in R2 of the formula (1) is as defined above, preferably a methoxy group, an ethoxy group Propyloxy group, isopropyloxy group, butoxy group, isobutoxy group or pentyloxy group, more preferably methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group or pentyloxy group.
  • the hydrogen atom in the C1-C6 alkoxy group is optionally substituted by the substituent B.
  • the “C1-C6 haloalkoxy group” in R2 of the formula (1) has the same definition as above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group, or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group Or a 2,2,2-trifluoroethoxy group.
  • the C3-C8 cycloalkoxy group of the “C3-C8 cycloalkoxy group optionally substituted with the substituent B” in R2 of the formula (1) has the same definition as described above, preferably cyclopropyloxy Group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, and more preferably a cyclopropyloxy group or a cyclobutoxy group.
  • the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent B.
  • the C2-C6 alkenyloxy group of the “C2-C6 alkenyloxy group optionally substituted with the substituent B” in R2 of the formula (1) has the same definition as above, preferably a vinyloxy group, A 1-propenyloxy group, an allyloxy group, a 1-butenyloxy group, a 2-butenyloxy group, or a 3-butenyloxy group, and more preferably a vinyloxy group, a 1-propenyloxy group, or an allyloxy group.
  • the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent B.
  • the “C2-C6 haloalkenyloxy group” in R2 of the formula (1) has the same definition as above, and preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2- A dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group, or a 3,3-dichloroallyloxy group, more preferably a 2-fluorovinyloxy group or 2,2-difluoro It is a vinyloxy group.
  • the C3-C6 alkynyloxy group of “C3-C6 alkynyloxy group optionally substituted with substituent B” in R2 of formula (1) is as defined above, preferably a propargyloxy group , 2-butynyloxy group, or 3-butynyloxy group, and more preferably a propargyloxy group.
  • the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent B.
  • the “C3-C6 haloalkynyloxy group” in R2 of the formula (1) has the same definition as above, and is preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro group.
  • R20C ( ⁇ O) — in R2 of the formula (1) (wherein R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group) , A C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R21R22N— (wherein R21 and R22 are each independently a hydrogen atom or a C1-C6 group optionally substituted with a substituent B1).
  • R20C ( ⁇ O) — is preferably an acetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, pyrrolidinylcarbonyl group, and piperidinylcarbonyl group More preferably, acetyl group, difluoroacetyl group, trifluoroacetyl group, methoxycarbonyl group, ethoxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl
  • R20 of “R20C ( ⁇ O) O—” in R2 of the formula (1) has the same meaning as described above.
  • “R20C ( ⁇ O) O—” is preferably an acetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, 2 , 2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, cyclopropyloxycarbonyloxy group, aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethylmethylaminocarbonyloxy group, diethylaminocarbonyloxy group Group, pyrrolidinylcarbonyloxy group, and piperidinylcarbonyloxy group, more preferably acetyloxy group,
  • Shi group methoxycarbonyloxy group, ethoxycarbonyloxy group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylamino carbonyloxy groups, and diethylamino carbonyl group.
  • the “3- to 6-membered ring group containing 1 to 2 oxygen atoms” in R2 of the formula (1) has the same definition as above, and preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group Or a 1,3-dioxanyl group, and more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.
  • R23-L2- in R2 of Formula (1) (wherein R23 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L2 represents S, SO, or SO 2 ). ) Are as defined above. “R23-L2-” is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, a trifluoromethanesulfonyl group, a (chloromethyl) thio group, or a (chloromethane) sulfinyl group.
  • chloromethane sulfonyl group, more preferably, methylthio group, methanesulfinyl group, methanesulfonyl group, (chloromethyl) thio group, (chloromethane) sulfinyl group, and (chloromethane) sulfonyl group. It is done.
  • R21 and R22 of “R21R22N-” in R2 of the formula (1) have the same meanings as described above.
  • “R21R22N—” preferably includes an amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a pyrrolidinyl group, and a piperidinyl group, and more preferably a dimethylamino group, an ethylmethylamino group, and a diethylamino group. Is mentioned.
  • R24C ( ⁇ O) N (R25) — in R2 of the formula (1) (wherein R24 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group) , C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are as defined above), and R25 represents hydrogen.
  • R24 is preferably a hydrogen atom, methyl group, ethyl group, difluoromethyl group, trifluoromethyl group, cyclopropyl group, methoxy group, ethoxy group, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy.
  • Group cyclopropyloxy group, amino group, dimethylamino group, ethylmethylamino group, diethylamino group, pyrrolidinyl group, and piperidinyl group, and more preferably a hydrogen atom, a methyl group, a difluoromethyl group, a trifluoromethyl group.
  • R25 is preferably a hydrogen atom, methyl group, ethyl group, propyl group, methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, cyanomethyl group, 2-cyanoethyl group, 2,2-difluoroethyl.
  • Group, 2,2,2-trifluoroethyl group, and cyclopropyl group more preferably hydrogen atom, methyl group, ethyl group, methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, A cyanomethyl group, a 2,2-difluoroethyl group, and a 2,2,2-trifluoroethyl group can be mentioned.
  • N in the formula (1) is an integer of 0 to 5.
  • n 2 or more
  • two or more R2s each represent an independent substituent, may be the same or different, and can be arbitrarily selected.
  • R3 in formula (1) may be optionally substituted with a hydrogen atom, a halogen atom, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, or a substituent C.
  • R3 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group that may be optionally substituted with a substituent C, a C3-C8 cycloalkyl group that may be optionally substituted with a substituent C, or a substituent C as appropriate.
  • a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally substituted with a substituent C is preferable.
  • the “substituent C” in formula (1) is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, R31R32N. -(Wherein R31 and R32 are as defined above for R21 and R22), and R30-L3- (wherein R30 is as defined above for R14, and L3 is as defined above for L1).
  • the substituent C is preferably a cyano group, a C1-C6 alkoxy group, or R30-L3- (wherein R30 and L3 are as defined above), In particular, a cyano group or a C1-C6 alkoxy group is preferable.
  • substituent C examples include a hydroxyl group; a cyano group; As a C3-C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; A C1-C6 alkoxy group as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, and an isobutoxy group; C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group; As a C3-C8 cycloalkoxy group, a cyclopropyloxy group, a cyclobutoxy group, a
  • substituent C a hydroxyl group; a cyano group; A cyclopropyl group and a cyclobutyl group as the C3-C8 cycloalkyl group; A methoxy group and an ethoxy group as the C1-C6 alkoxy group; A difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group; A cyclopropyloxy group and a cyclobutoxy group as a C3-C8 cycloalkoxy group; R31R32N— (wherein R31 and R32 have the same meanings as described above), a dimethylamino group, an ethylmethylamino group, and a diethylamino group; And R30-L3- (wherein R30 and L3 are as defined above) include
  • R3 in the formula (1) includes a hydrogen atom and a nitro group.
  • the “halogen atom” in R3 of the formula (1) has the same definition as described above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • the C1-C6 alkyl group in the “C1-C6 alkyl group optionally substituted with substituent C” in R3 of the formula (1) has the same definition as described above, preferably a methyl group, an ethyl group , A propyl group, an isopropyl group, a butyl group, or an isobutyl group, and more preferably a methyl group, an ethyl group, or a propyl group.
  • the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent C.
  • the “C1-C6 haloalkyl group” in R3 of the formula (1) has the same meaning as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, 2,2,2 A trifluoroethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, or 2,2,2-trifluoroethyl group.
  • the C3-C8 cycloalkyl group in the “C3-C8 cycloalkyl group optionally substituted with the substituent C” in R3 of the formula (1) has the same definition as above, preferably a cyclopropyl group , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group.
  • the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent C.
  • the C1-C6 alkoxy group of the “C1-C6 alkoxy group optionally substituted with the substituent C” in R3 of the formula (1) has the same definition as above, preferably a methoxy group, an ethoxy group , A propyloxy group, an isopropyloxy group, a butoxy group, or an isobutoxy group, and more preferably a methoxy group, an ethoxy group, a propyloxy group, or an isopropyloxy group.
  • the hydrogen atom in the C1-C6 alkoxy group is optionally substituted with the substituent C.
  • the “C1-C6 haloalkoxy group” in R3 of the formula (1) has the same definition as above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group, or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group Or a 2,2,2-trifluoroethoxy group.
  • the C2-C6 alkenyl group of “C2-C6 alkenyl group optionally substituted with substituent C” in R3 of formula (1) is as defined above, preferably a vinyl group, 1- A propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, or an allyl group.
  • the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent C.
  • the “C2-C6 haloalkenyl group” in R3 of the formula (1) has the same definition as above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group. , 3-fluoroallyl group, 3,3-difluoroallyl group, or 3,3-dichloroallyl group, more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.
  • the C2-C6 alkynyl group of the “C2-C6 alkynyl group optionally substituted with the substituent C” in R3 of the formula (1) has the same definition as defined above, preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group, a 1-propynyl group, or a propargyl group.
  • the hydrogen atom in the C2-C6 alkynyl group is optionally substituted by the substituent C.
  • the “C2-C6 haloalkynyl group” in R3 of the formula (1) has the same definition as described above, and is preferably a 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -Propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- A 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group.
  • R30-L3- in R3 of the formula (1), R30 has the same meaning as R23, and L3 has the same meaning as L2.
  • R30-L3- preferably includes a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group. Groups, and methanesulfonyl groups.
  • R31R32N— in R3 of the formula (1) has the same meaning as R21 and R22, and is preferably an amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a pyrrolidinyl group, or A piperidinyl group, more preferably a dimethylamino group, an ethylmethylamino group, or a diethylamino group.
  • R33C ( ⁇ O) — (wherein R33 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group) in R3 of the formula (1).
  • Terminology is as defined above.
  • “R33C ( ⁇ O) —” preferably includes an acetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, and a cyclopropanecarbonyl group, and more preferably an acetyl group, a difluoroacetyl group, and a triphenyl group.
  • a fluoroacetyl group is mentioned.
  • X in the formula (1) represents an oxygen atom or a sulfur atom.
  • Preferred X is an oxygen atom.
  • Y in Formula (1) represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group.
  • the substituent D is substituted at the ortho position, and the substituent D1 is independently independently substituted with 0 to 4 appropriately.
  • the substituent D is substituted at the ortho position, and the substituent D1 is independently independently selected from 0 to 3 Replace.
  • the substituent D is substituted at the ortho position, and the substituent D1 is independently independently substituted with 0-2.
  • “Substituent D” in formula (1) is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group Represents at least one kind.
  • the substituent D is preferably a halogen atom or a C1-C6 alkyl group, In particular, a halogen atom is preferable.
  • substituent D As a preferable specific example of the substituent D, As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; A methyl group, an ethyl group, and a propyl group as the C1-C6 alkyl group; A difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, and a 2,2,2-trifluoroethyl group as the C1-C6 haloalkyl group; A C1-C6 alkoxy group as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, and a t-butoxy group; And C1-C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-d
  • examples of the C1-C6 haloalkoxy group include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group.
  • the “substituent D1” in formula (1) is a hydroxyl group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 And at least one selected from the group consisting of C3-C8 cycloalkoxy groups.
  • the substituent D1 is preferably a hydroxyl group, a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, or a C1-C6 haloalkyl group, More preferably, a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group is preferable.
  • substituent D1 a hydroxyl group;
  • a halogen atom a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom;
  • a methyl group, an ethyl group, and a propyl group as the C1-C6 alkyl group;
  • a C3-C8 cycloalkyl group a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
  • a C1-C6 alkoxy group as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group,
  • substituent D1 a hydroxyl group; A halogen atom, a fluorine atom, a chlorine atom, and a bromine atom; A methyl group and an ethyl group as the C1-C6 alkyl group; A difluoromethyl group and a trifluoromethyl group as a C1-C6 haloalkyl group; A cyclopropyl group and a cyclobutyl group as the C3-C8 cycloalkyl group; A methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group as the C1-C6 alkoxy group; A difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group; As the C3-C8 cycloalkoxy
  • Y is a phenyl group
  • Y is represented by the formula (a) (Wherein D and D1 are as defined above, and ma represents an integer of 0 to 4).
  • ma represents an integer of 0 to 4.
  • 2 or more D1s each represent an independent substituent, may be the same or different, and can be arbitrarily selected.
  • the ortho position means the position of the phenyl group having the substituent D as shown in the formula (a).
  • the phenyl group in which the substituent D is located in the ortho position is a feature of the present invention.
  • a preferred combination of the formula (a) is a 2-D-6-D1-phenyl group, a 2-D-4-D1-phenyl group, or a 2-D-4-D1-6-D1-phenyl group.
  • 2-D-6-D1-phenyl group means a disubstituted phenyl group having a substituent D at the 2-position and a substituent D1 at the 6-position, and the following description is also the same.
  • Y is a group represented by the formula (b) (Wherein D and D1 are as defined above, and mb represents an integer of 0 to 3).
  • G1, G2, G3 and G4 in the formula (b) are each independently a carbon atom or a nitrogen atom. However, at least one of G1, G2, G3 and G4 is a nitrogen atom. Preferred G1, G2, G3 and G4 are any one of G1, G2, G3 and G4 being a nitrogen atom. That is, it is a pyridyl group.
  • mb represents an integer of 0 to 3. When mb in the formula (b) is 2 or more, 2 or more D1s each represent an independent substituent, may be the same or different, and can be arbitrarily selected.
  • the ortho position means a 6-membered ring having a substituent D as shown in the formula (b).
  • Means the position of Specific examples of the partial structure of the formula (b) are shown below.
  • a pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, or tetrazinyl group in which the substituent D is located in the ortho position is a feature of the present invention.
  • Preferred combinations of formula (b) are 3-D-2-pyridyl group, 3-D-5-D1-2-pyridyl group, 2-D-3-pyridyl group, 2-D-4-D1-3- Pyridyl group, 2-D-6-D1-3-pyridyl group, 2-D-4-D1-6-D1-3-pyridyl group, 4-D-3-pyridyl group, 4-D-2-D1- 3-pyridyl group, 4-D-6-D1-3-pyridyl group, 4-D-2-D1-6-D1-3-pyridyl group, 3-D-4-pyridyl group, or 3-D-5 -D1-4-pyridyl group.
  • Y is a group represented by the formula (c-1) Formula (c-2) Or the formula (c-3) (Wherein D and D1 are as defined above, and mc represents an integer of 0 to 2).
  • G5 and G6 in formula (c-1), formula (c-2) and formula (c-3) are each independently a carbon atom or a nitrogen atom.
  • mc represents an integer of 0 to 2.
  • D1 in 2 represents an independent substituent, and may be the same or different and arbitrarily selected can do.
  • the ortho position is represented by the formula (c-1), the formula (c-2), and the formula (c-3).
  • the thienyl group, thiazolyl group, isothiazolyl group, or thiadiazolyl group in which the substituent D is located in the ortho position is a feature of the present invention.
  • the bond including the broken line in Equation (1) is This represents the location represented by.
  • the bond including the broken line part in Formula (1) represents a double bond or a single bond.
  • R3 in the formula (1b) is a substituent other than hydrogen, only one of the R-form and S-form, or a mixture of the R-form and the S-form in an arbitrary ratio.
  • the compound represented by formula (1) may have one or two axial asymmetry.
  • the isomer ratio is a single or an arbitrary mixing ratio, and is not particularly limited.
  • the compound represented by Formula (1) may contain an asymmetric atom.
  • the isomer ratio is a single or an arbitrary mixing ratio, and is not particularly limited.
  • the compound represented by Formula (1) may contain geometric isomers.
  • the isomer ratio is a single or an arbitrary mixing ratio, and is not particularly limited.
  • the compound represented by the formula (1) may be able to form a salt.
  • a salt examples thereof include acid salts such as hydrochloric acid, sulfuric acid, acetic acid, fumaric acid and maleic acid, and metal salts such as sodium, potassium and calcium, but are not particularly limited as long as they can be used as agricultural chemicals.
  • specific compounds of the pyridone compound represented by the formula (I) according to the present invention include the structural formula shown in Table 1, (R2) n shown in Table 2, and X which is an oxygen atom or a sulfur atom. It is represented by the combination. These compounds are for illustrative purposes, and the present invention is not limited thereto.
  • the description “2-F—” in Table 2 means that a fluorine atom is bonded to the 2-position of the phenyl group to which (R2) n is bonded, and “2-F-3”
  • the description “—HO—” means that a fluorine atom is bonded to the 2-position and a hydroxyl group is bonded to the 3-position.
  • the description of “2,3-di-F” means that the 2-position and 3 This means that a fluorine atom is bonded to the position, and other descriptions are the same.
  • R4 is a hydrogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group that may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-optionally substituted C3- A C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent A, C2- C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent A, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A, substituted A C2-C6 alkenyloxy group optionally substituted with the group A, a C2-C6 haloalkenyloxy group, a C3-C8
  • Production method A is a method for obtaining a compound represented by the formula (1b-a) containing the compound of the present invention and a production intermediate of the compound of the present invention, wherein the compound represented by formula (3) and R4NH 2 are obtained. , A production method comprising reacting in the presence of an acid.
  • R4NH 2 used in this reaction can be produced by obtaining or known manner as a commercially available product.
  • R4NH 2 are hydrochloric, may be those forming a salt with an acidic compound such as acetic acid, it is not particularly limited as long as the reaction proceeds to the desired.
  • R4NH 2 used in this reaction may if 1 equivalent or more relative to the compound represented by formula (3), but are not particularly limited as long as the reaction proceeds to the desired, preferably, 1 Equivalent to 200 equivalents.
  • Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, methanesulfonic acid, and p-toluenesulfonic acid, and are particularly limited as long as the target reaction proceeds. Although not preferred, acetic acid is preferred. Further, when using salts with R4NH 2 and the acidic compound, the use of acid is not essential.
  • the amount of the acid used in this reaction may if 1 equivalent or more relative to the R4NH 2, is not limited in particular as long as the reaction proceeds to the desired, preferably, one or more equivalents 200 equivalent or less is there.
  • the acid to be used is a liquid, it can also be used as a solvent.
  • a solvent can be used for this reaction, it is not necessarily essential.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxy Ether solvents such as ethane, tetrahydrofuran, dioxane, alcohol solvents such as methanol, ethanol, isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ethyl acetate, isopropyl acetate, butyl acetate, etc.
  • Ester solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea systems such as 1,3-dimethyl-2-imidazolidinone solvent Dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or in admixture of two or more.
  • the solvent is preferably an acidic solvent, more preferably acetic acid.
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by formula (3). is there.
  • the temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but is usually 50 ° C. or higher and 180 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (1b-a) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (1b-a) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1b-a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • the compound represented by formula (2) which can be produced when R4 represents a hydrogen atom in the compound represented by formula (1b-a), It can be a useful production intermediate for obtaining the compound represented by 1b).
  • a specific example of the production intermediate represented by the formula (2) is represented by a combination of the structural formula shown in Table 3, (R2) n shown in Table 2, and X which is an oxygen atom or a sulfur atom. These compounds are for illustrative purposes, and the present invention is not limited thereto.
  • Lv represents a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group, a leaving group such as a halogen atom, and R1, R2, R3, X, Y, and n are as defined above.
  • Production method B is a method for obtaining a compound represented by formula (1b), which comprises reacting the production intermediate represented by formula (2) with R1Lv in a solvent in the presence of a base. It is a manufacturing method.
  • R1Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • the amount of R1Lv used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (2), and is not particularly limited as long as the target reaction proceeds. 1 equivalent or more and 10 equivalents or less.
  • Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride, but are particularly limited as long as the intended reaction proceeds. It will never be done.
  • the amount of the base used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (2), and is not particularly limited as long as the target reaction proceeds. 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, Alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, Ch
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by formula (2). is there.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually 0 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, sodium thiosulfate, sulfurous acid
  • An aqueous solution or a salt solution in which a salt containing sulfur such as sodium is dissolved can be arbitrarily used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl
  • Solvents that are not compatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add.
  • these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio.
  • the number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (1b) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (1b) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • SR represents a sulfurizing agent
  • R1, R2, R3, Y, and n are as defined above.
  • Production method C is a production method for obtaining a compound represented by formula (1b-c) among the compounds represented by formula (1b), wherein the compound represented by formula (1b-b) is sulfurated. It is a manufacturing method including making an agent (SR) react in a solvent.
  • SR agent
  • sulfurizing agent examples include Lawesson's reagent (2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetan-2,4-disulfide).
  • the amount of the sulfurizing agent used in this reaction may be 0.5 equivalent or more with respect to the compound represented by the formula (1b-b), and is not particularly limited as long as the target reaction proceeds. However, it is preferably 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, Examples thereof include benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. These solvents can be used alone or in admixture of two or more.
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1b-b). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but is usually 50 ° C. or higher and 180 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl
  • Solvents that are not compatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane.
  • liquid separation operation is not essential.
  • the reaction mixture containing the compound represented by the formula (1b-c) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but it is not essential.
  • the reaction mixture containing the compound represented by the formula (1b-c) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1b-c) obtained after the solvent is distilled off can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • R3a is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent C2-C6 alkenyl group optionally substituted with C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, or C2-C6 haloalkynyl group , Lv, R1, R2, X, Y, and n are as defined above.
  • R3a is optionally substituted with a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a substituent C, which may be optionally substituted with a substituent C.
  • R3aLv used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • the amount of R3aLv used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (1b-d), and is not particularly limited as long as the target reaction proceeds, but is preferably Is 1 equivalent or more and 1.8 equivalent or less.
  • Bases used in this reaction include metal hydrides such as sodium hydride, organic lithiums such as methyl lithium, butyl lithium, sec-butyl lithium, t-butyl lithium, hexyl lithium, lithium diisopropylamide, hexamethyldisilazane
  • metal hydrides such as sodium hydride
  • organic lithiums such as methyl lithium, butyl lithium, sec-butyl lithium, t-butyl lithium, hexyl lithium, lithium diisopropylamide, hexamethyldisilazane
  • metal amides such as lithium, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
  • the amount of the base used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (1b-d), and is not particularly limited as long as the target reaction proceeds, but preferably Is 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, Examples thereof include benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. These solvents can be used alone or in admixture of two or more.
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1b-d). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually from ⁇ 80 ° C. to 100 ° C. or the boiling point of the solvent.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, sodium thiosulfate, sulfurous acid
  • An aqueous solution or a salt solution in which a salt containing sulfur such as sodium is dissolved can be arbitrarily used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl
  • a solvent that is not compatible with water such as an ether solvent such as t-butyl ether, a halogen solvent such as dichloromethane, dichloroethane, or chloroform, or a hydrocarbon solvent such as hexane, heptane, cyclohexane, or methylcyclohexane.
  • these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio.
  • the number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (1b-e) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (1b-e) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1b-e) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • Ox represents an oxidizing agent
  • R1, R2, R3, X, Y, and n are as defined above.
  • Production method E is a method for obtaining a compound represented by formula (1a), which comprises reacting a compound represented by formula (1b) with an oxidizing agent (Ox) in a solvent. is there.
  • oxidizing agent used in this reaction examples include metal oxides such as manganese dioxide, benzoquinones such as 2,3-dichloro-5,6-dicyano-p-benzoquinone, azobisisobutyronitrile, and benzoyl peroxide.
  • the oxidizing agent is a metal oxide.
  • the amount of the oxidizing agent used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1b). Equivalent to 200 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, dichloromethane, dichloroethane, chloroform, And halogen-based solvents such as carbon tetrachloride. These solvents can be used alone or in admixture of two or more.
  • the amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by formula (1b). is there.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually 0 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl
  • Solvents that are not compatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane.
  • liquid separation operation is not essential.
  • the reaction mixture containing the compound represented by the formula (1a) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (1a) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • the oxidizing agent is a benzoquinone.
  • the amount of the oxidizing agent used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1b). Equivalent to 20 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, dichloromethane, dichloroethane, chloroform, And halogen-based solvents such as carbon tetrachloride. These solvents can be used alone or in admixture of two or more.
  • the amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by formula (1b). is there.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually 0 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl
  • Solvents that are not compatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane.
  • liquid separation operation is not essential.
  • the reaction mixture containing the compound represented by the formula (1a) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (1a) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • the oxidizing agent is a combination of a radical initiator and a halogenating agent. If the amount of the radical initiator and the halogenating agent used in this reaction is 0.01 equivalent or more and 1.0 equivalent or more with respect to the compound represented by the formula (1b), the target reaction proceeds. As long as it does, it will not specifically limit.
  • the radical initiator is 0.01 equivalent to 1 equivalent and the halogenating agent is 1 equivalent to 3 equivalent.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but halogenated benzene solvents such as chlorobenzene and dichlorobenzene, and ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate.
  • halogenated benzene solvents such as chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate.
  • the solvent include halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. These solvents can be used alone or in admixture of two or more.
  • the amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by formula (1b). is there.
  • the temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but is usually 20 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, sodium thiosulfate, sulfurous acid
  • An aqueous solution or a salt solution in which a salt containing sulfur such as sodium is dissolved can be arbitrarily used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl
  • a solvent that is not compatible with water such as an ether solvent such as t-butyl ether, a halogen solvent such as dichloromethane, dichloroethane, or chloroform, or a hydrocarbon solvent such as hexane, heptane, cyclohexane, or methylcyclohexane.
  • these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio.
  • the number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (1a) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (1a) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • R3b represents a halogen atom
  • HalR represents a halogenating agent
  • R1, R2, X, Y, and n are as defined above.
  • Production method F is a production method for obtaining a compound represented by formula (1a-b) in which R3b represents a halogen atom among the compounds represented by formula (1a), which is represented by formula (1a-a). And a halogenating agent (HalR) in a solvent.
  • selectfluoro N-fluoro-N′-triethylenediamine bis (tetrafluoroborate)
  • N-chlorosuccinimide N-bromosuccinimide
  • N-iodosuccinimide 1 1,3-Dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like.
  • the amount of the halogenating agent used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1a-a). Preferably, it is 1 equivalent or more and 10 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as the target reaction proceeds as long as it is 0.5 equivalent or more, and preferably 1 equivalent or more and 5 equivalents or less.
  • the halogenating agent used in this reaction is an iodinating agent
  • an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid, or trifluoromethanesulfonic acid.
  • the amount of acid used is 0.01 equivalent or more with respect to the compound represented by formula (1a-a), although it does not restrict
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid and trifluoromethanesulfonic acid, diethyl ether , Ether solvents such as diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene Ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1a-a). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually 0 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, sodium thiosulfate, sulfurous acid
  • An aqueous solution or a salt solution in which a salt containing sulfur such as sodium is dissolved can be arbitrarily used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl
  • Solvents that are not compatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add.
  • these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio.
  • the number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (1a-b) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (1a-b) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1a-b) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • R3c is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent C
  • J represents an oxygen atom or a sulfur atom
  • Q represents a hydrogen atom or a metal
  • R1, R2, R3b, X, Y, and n have the same meanings as described above.
  • R3c is optionally substituted with a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a substituent C, which may be optionally substituted with a substituent C.
  • C3-C8 cycloalkyl group C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 optionally substituted with substituent C Or a haloalkynyl group of C2 to C6, wherein J is an oxygen atom or a sulfur atom, and is a method of synthesizing a compound represented by the formula (1a-b) A compound obtained by a coupling reaction in which R3c-JQ is reacted in the presence of a transition metal.
  • R 3b is a chlorine atom, a bromine atom, or an iodine atom.
  • R3c-JQ used in this reaction is obtained as a commercial product or can be produced by a known method.
  • Preferred Q is a hydrogen atom or an alkali metal such as sodium or potassium.
  • the amount of R3c-JQ used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1a-b).
  • Q is a hydrogen atom, it can also be used as a solvent.
  • the transition metal used in this reaction may have a ligand, such as palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis ( Palladiums such as triphenylphosphine) palladium and bis (triphenylphosphine) palladium dichloride.
  • a ligand such as palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis ( Palladiums such as triphenylphosphine) palladium and bis (triphenylphosphine) palladium dichloride.
  • the amount of the transition metal used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (1a-b), but is particularly limited as long as the target reaction proceeds. None happen.
  • triphenylphosphine 1,1′-bis (diphenylphosphino) ferrocene, 2-dicyclohexylphosphino-2′4′6′-triisopropylbiphenyl, 2-di-t -A phosphine ligand such as butylphosphino-2'4'6'-triisopropylbiphenyl can be added.
  • the amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (1a-b), but is particularly limited as long as the target reaction proceeds. It will never be done.
  • the base used in this reaction is an inorganic base such as sodium carbonate, potassium carbonate or cesium carbonate, or an organic base such as triethylamine, tributylamine or diisopropylethylamine.
  • the amount of the base used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1a-b). 1 equivalent or more and 50 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but R3c-JH (wherein R3c has the same meaning as described above and J is an oxygen atom).
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1a-b). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but is usually 30 ° C. or higher and 200 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl
  • Solvents that are not compatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane.
  • these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio.
  • the number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield. Further, it is possible to remove insoluble matters by performing a filtration operation, but this is not essential.
  • the reaction mixture containing the compound represented by the formula (1a-c) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1a-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • R3d is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent C Represents an optionally substituted C2-C6 alkenyl group or C2-C6 haloalkenyl group, R3d-B represents an organic boronic acid, and R1, R2, R3b, X, Y and n are as defined above. It is.
  • R3d in the compound represented by the formula (1a) is optionally substituted with a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a substituent C, which may be optionally substituted with a substituent C.
  • a compound represented by the formula (1a-d) which may be a C3-C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent C, or a C2-C6 haloalkenyl group.
  • a method of synthesis comprising obtaining a compound of formula (1a-b) and an organoboronic acid (R3d-B) by a Suzuki-Miyaura coupling in the presence of a transition metal and a base Is the method.
  • R 3b is a chlorine atom, a bromine atom, or an iodine atom.
  • R3d-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronic acid ester, and can be obtained as a commercial product or produced by a known method.
  • the amount of R3d-B used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1a-b). Preferably, it is 1 equivalent or more and 10 equivalents or less.
  • the transition metals used in this reaction are palladium, nickel, ruthenium, etc., and may have a ligand.
  • Palladium is mentioned.
  • the amount of the transition metal used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (1a-b), but is particularly limited as long as the target reaction proceeds. None happen.
  • phosphine ligands such as triphenylphosphine and tricyclohexylphosphine can be added.
  • the amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (1a-b), but is particularly limited as long as the target reaction proceeds. It will never be done.
  • the base used in this reaction includes inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and tripotassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium t-butoxide.
  • inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and tripotassium phosphate
  • metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium t-butoxide.
  • the amount of the base used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1a-b). 1 equivalent or more and 50 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but an ether such as an aqueous solvent, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc.
  • benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. These solvents can be used alone or in admixture of two or more.
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1a-b). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but is usually 30 ° C. or higher and 200 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl
  • Solvents that are not compatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane.
  • these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio.
  • the number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield. Further, it is possible to remove insoluble matters by performing a filtration operation, but this is not essential.
  • reaction mixture containing the compound represented by the formula (1a-d) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by formula (1a-d) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • R3e represents a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent C
  • R1, R2, R3b, X, Y and n are as defined above.
  • R3e is a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent C (1a-)
  • R 3b is a chlorine atom, a bromine atom, or an iodine atom.
  • the terminal alkyne compound used in this reaction can be obtained as a commercial product or produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to perform desilylation after introducing a trimethylsilylethynyl group into the compound represented by the formula (1a-b).
  • For the desilylation Journal of the American Chemical Society, Vol. 131, No. 2, pp. 634-643 (2009), Journal of the American Chemical Society. And Journal of Organometallic Chemistry (Vol. 696, No. 25, pages 4039-4045 (2011)), Journal of Organometallic Chemistry (Journal of Organometallic Chemistry). It can carry out with reference to nonpatent literatures, such as.
  • the amount of the terminal alkyne compound used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1a-b). Preferably, it is 1 equivalent or more and 10 equivalents or less.
  • the transition metal used in this reaction may have a ligand, such as palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis ( Palladiums such as triphenylphosphine) palladium and bis (triphenylphosphine) palladium dichloride.
  • a ligand such as palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis ( Palladiums such as triphenylphosphine) palladium and bis (triphenylphosphine) palladium dichloride.
  • coppers such as copper chloride, copper bromide and copper iodide are also used at the same time.
  • the amount of the transition metal used in this reaction may be 0.001 equivalent or more with respect to the compound represented by the formula (1a-b) for palladium and the like, respectively, and the target reaction proceeds. There is no particular limitation as long as it does. A preferable amount is 0.001 equivalent or more and 1 equivalent or less for both.
  • Examples of the base used in this reaction include organic amines such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine and diisopropylethylamine, and inorganic bases such as sodium carbonate, potassium carbonate and cesium carbonate.
  • organic amines such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine and diisopropylethylamine
  • inorganic bases such as sodium carbonate, potassium carbonate and cesium carbonate.
  • the amount of the base used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1a-b). 1 equivalent or more and 50 equivalents or less.
  • the organic base when it is liquid, it can be used as a solvent.
  • a phosphine ligand such as tri-t-butylphosphine or 2-dicyclohexylphosphino-2'4'6'-triisopropylbiphenyl can be added to allow the reaction to proceed efficiently, but it is not essential. .
  • the amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (1a-b), but is particularly limited as long as the target reaction proceeds. It will never be done.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N, N-dimethylformamide Amide solvents such as N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, tri
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1a-b). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually 0 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl
  • Solvents that are not compatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane.
  • these solvents can be used alone, or two or more of them can be mixed in an arbitrary ratio.
  • the number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield. Further, it is possible to remove insoluble matters by performing a filtration operation, but this is not essential.
  • the reaction mixture containing the compound represented by the formula (1a-e) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1a-e) obtained after the solvent is distilled off can be purified with an appropriate solvent by washing, reprecipitation, recrystallization, column chromatography or the like. What is necessary is just to set suitably according to the target purity.
  • R2a represents a C1 to C6 alkoxy group
  • nb represents an integer of 0 to 4 (provided that when nb is 2 or more, each of R2 and 2 represents an independent substituent)
  • R1 , R2, R3, X, Y and the broken line part have the same meanings as described above.
  • Production method J is a method for synthesizing a compound represented by formula (1-b) having a hydroxyl group among the compounds represented by formula (1), wherein R2a is a C1-C6 alkoxy group ( This is a production method comprising obtaining the compound represented by 1-a) by reacting with an acid.
  • the acid used for this reaction includes boron halides such as boron trichloride and boron tribromide.
  • the amount of acid used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (1-a), and is not particularly limited as long as the target reaction proceeds, but preferably Is 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and nitrile solvents such as acetonitrile. And halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents can be used alone or in admixture of two or more.
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1-a). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually from ⁇ 80 ° C. to 100 ° C. or the boiling point of the solvent.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (1-b) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • the reaction mixture containing the compound represented by the formula (1-b) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1-b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • R2b—O— is a C1-C6 alkoxy group optionally substituted with the substituent B, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy optionally substituted with the substituent B.
  • R2b—O— may be optionally substituted with a substituent B, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a substituent C3-C8 cycloalkoxy group optionally substituted with B, C2-C6 alkenyloxy group optionally substituted with substituent B, C2-C6 haloalkenyloxy group, optionally substituted with substituent B
  • a process for synthesizing a compound represented by formula (1-b) comprising reacting a compound represented by formula (1-b) with R2b-Lv in a solvent in the presence of a base.
  • R2b-Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • R2b-Lv used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (1-b), and is not particularly limited as long as the target reaction proceeds, but preferably Is 1 equivalent or more and 10 equivalents or less.
  • Bases used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine, and lutidine.
  • inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride
  • organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine, and lutidine.
  • organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine, and lutidine.
  • the base used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (1-b), and is not particularly limited as long as the target reaction proceeds. 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, Alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, Ch
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1-b). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually ⁇ 20 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, sodium thiosulfate, sulfurous acid
  • An aqueous solution or a salt solution in which a salt containing sulfur such as sodium is dissolved can be arbitrarily used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl
  • Solvents that are not compatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add.
  • these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio.
  • the number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (1-c) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but it is not essential.
  • the reaction mixture containing the compound represented by the formula (1-c) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • R2c represents a halogen atom
  • R2d is a C1-C6 alkyl group optionally substituted with the substituent B, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with the substituent B
  • R2d-B represents an organic boronic acid, R1, R2, R3, nb, X, Y, and the broken line are as defined above.
  • R2d is optionally substituted with a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a substituent B which may be optionally substituted with a substituent B.
  • R2d is optionally substituted with a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a substituent B which may be optionally substituted with a substituent B.
  • the compound represented by the formula (1-e) which may be a C3-C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with the substituent B, or a C2-C6 haloalkenyl group.
  • a synthesis method comprising obtaining by a Suzuki-Miyaura coupling in which a compound represented by the formula (1-d) and an organic boronic acid (R2d-B) are reacted.
  • R2c is preferably a chlorine atom, a bromine atom, or an iodine atom.
  • production method H By using the compound represented by formula (1a-b) and R3d-B in production method H instead of the compound represented by formula (1-d) and R2d-B, respectively, production method H
  • the production method L can be carried out according to the above.
  • R2e represents a C2-C6 alkynyl group or a C2-C6 haloalkynyl group which may be optionally substituted with the substituent B, and R1, R2, R2c, R3, nb, X, Y and the broken line part It is synonymous with the above.
  • R2e is a C2-C6 alkynyl group or a C2-C6 haloalkynyl group which may be optionally substituted with a substituent B
  • a method for synthesizing the compound represented by f which comprises obtaining the compound represented by the formula (1-d) by Sonogashira coupling with a terminal alkyne compound.
  • R2c is a chlorine atom, a bromine atom, or an iodine atom.
  • the production method M can be carried out according to the production method I. .
  • Da represents a halogen atom
  • D1a represents a halogen atom
  • D1b represents a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, or a C3-C8 cycloalkoxy group
  • E represents a halogen atom.
  • R 1, R 2, R 3, n, X, Q, and a broken line part are as defined above.
  • D1b is a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, or a C3-C8 cycloalkoxy group
  • E is a halogen atom.
  • D1b-Q used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • Preferred Q is a hydrogen atom or an alkali metal such as sodium or potassium.
  • the amount of D1b-Q used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1-g). Preferably, it is 1 equivalent or more and 30 equivalent or less. Moreover, when Q represents a hydrogen atom, it can be used as a solvent.
  • the base used in this reaction is preferably an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate or sodium hydride. Further, when Q is an alkali metal, the use of a base is not essential.
  • the amount of the base used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1-g). 1 equivalent or more and 30 equivalent or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but alcohol solvents represented by D1b-H, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxy Ether solvents such as ethane, tetrahydrofuran and dioxane, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform, carbon te
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1-g). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually 0 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (1-h) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but it is not essential.
  • the reaction mixture containing the compound represented by the formula (1-h) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1-h) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • R2e represents a C1-C6 alkoxy group that may be optionally substituted with the substituent B
  • R2f represents a C1-C6 alkoxy group that may be optionally substituted with the substituent B
  • R2g represents a halogen atom.
  • HalR, R1, R3, X, Y and the broken line part are as defined above.
  • R2e is a C1-C6 alkoxy group which may be appropriately substituted with the substituent B
  • R2f may be appropriately substituted with the substituent B.
  • selectfluoro N-fluoro-N′-triethylenediamine bis (tetrafluoroborate)
  • N-chlorosuccinimide N-bromosuccinimide
  • N-iodosuccinimide 1 1,3-Dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like.
  • the amount of the halogenating agent used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1-i). Preferably, it is 1 equivalent or more and 10 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as the target reaction proceeds as long as it is 0.5 equivalent or more, and preferably 1 equivalent or more and 5 equivalents or less.
  • the halogenating agent used in this reaction is an iodinating agent
  • an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid, or trifluoromethanesulfonic acid.
  • the halogenating agent used in this reaction is an iodinating agent
  • the amount of acid used is 0.01 equivalent or more with respect to the compound represented by formula (1-i), and the target reaction
  • it is 0.1 equivalent or more and 3 equivalent or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid and trifluoromethanesulfonic acid, diethyl ether , Ether solvents such as diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene Ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but usually 3 to 200 times by weight with respect to the compound represented by the formula (1-i). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually 0 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, sodium thiosulfate, sulfurous acid
  • An aqueous solution or a salt solution in which a salt containing sulfur such as sodium is dissolved can be arbitrarily used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl
  • Solvents that are not compatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add.
  • these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio.
  • the number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (1-j) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (1-j) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (1-j) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • La represents S
  • Lb represents SO or SO 2
  • Ox ′ represents an oxidizing agent
  • Production method P during the compound represented by formula (1) a process for the preparation of a compound represented by R1, Lb contained in R2 and R3 is SO or SO 2 wherein (Lb), the formula ( In 1), it is a production method comprising reacting a compound represented by the formula (La) in which La contained in R1, R2 or R3 is S with an oxidizing agent (Ox ′) in a solvent.
  • oxidizing agent used in this reaction examples include peroxides such as hydrogen peroxide and meta-chloroperbenzoic acid.
  • transition metals such as sodium tungstate can be added.
  • the amount of the oxidizing agent used in this reaction is usually 1.0 equivalent or more and 1.2 equivalent or less with respect to the compound represented by the formula (La) when producing SO, and produces SO 2 . When doing, it is usually 2 equivalents or more and 10 equivalents or less. Moreover, when adding transition metals, it is 0.001 equivalent or more and 1 equivalent or less normally.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but an aqueous solvent, an acidic solvent such as acetic acid, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc.
  • an acidic solvent such as acetic acid, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc.
  • examples thereof include benzene solvents, nitrile solvents such as acetonitrile, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in admixture of two or more.
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 times the weight of the compound represented by the formula (1) having the formula (La). More than 200 weight times.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually ⁇ 10 ° C. or higher and 120 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, sodium thiosulfate, sulfurous acid
  • An aqueous solution or a salt solution in which a salt containing sulfur such as sodium is dissolved can be arbitrarily used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl
  • Solvents that are not compatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add.
  • these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio.
  • the number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (Lb) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (Lb) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (Lb) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • R2, R3, R5, n, X and Y have the same meanings as described above.
  • Production method Q is a production method of a production intermediate represented by formula (3), in which a compound represented by formula (4) and a compound represented by formula (5) are mixed in a solvent in the presence of a base. It is a manufacturing method including making it react with.
  • the compound represented by the formula (4) used in this reaction is, for example, Green Chemistry, Vol. 41, pages 580-585, The Journal of Organic Chemistry, No. 65, No. 20, pages 6458-6461 (2000). Etc. can be synthesized by reference.
  • the compound represented by Formula (5) used for this reaction can be obtained as a commercial product or can be produced by a known method.
  • the amount of the compound represented by the formula (5) used in this reaction is particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (4). However, it is preferably 1 equivalent or more and 3 equivalents or less.
  • the base used in this reaction includes inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and tripotassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium t-butoxide.
  • inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and tripotassium phosphate
  • metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium t-butoxide.
  • the base used in this reaction can be carried out in a catalytic amount, and is not particularly limited as long as the target reaction proceeds, but preferably the compound represented by formula (4) is used. On the other hand, it is 0.01 equivalent or more and 3 equivalent or less.
  • Solvents used in this reaction are ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, Ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl -2-Urea solvents such as imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, sulfur solvents such as dimethyl sulfox
  • the amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by formula (4). is there.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually ⁇ 50 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (3) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (3) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by the formula (3) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • R5a represents a C1 to C6 alkyl group
  • R2, R3, n, X, and Y are as defined above.
  • Production method R is a production method of a production intermediate represented by formula (3b) among the compounds represented by formula (3), wherein the compound represented by formula (3a) is subjected to acidic conditions or a base. It is a manufacturing method including making it react in a solvent on sexual conditions.
  • the reaction under acidic conditions will be described.
  • the acid used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, and phosphoric acid, and organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid, and trifluoroacetic acid.
  • inorganic acids such as hydrochloric acid, hydrobromic acid, and phosphoric acid
  • organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid, and trifluoroacetic acid.
  • the amount of the acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the target reaction proceeds.
  • the amount of the acid is 0. 0 with respect to the compound represented by the formula (3a). 01 equivalents or more.
  • liquid acids can be used as solvents.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but is not limited to an aqueous solvent, an acidic solvent such as acetic acid or methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t- Ether solvents such as butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ethyl acetate, isopropyl acetate and acetic acid Ester solvents such as butyl, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-d
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by formula (3a). is there.
  • the temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but is usually 0 ° C. or higher and 180 ° C. or lower or the boiling point of the solvent or lower.
  • Examples of the base used in this reaction include inorganic bases such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, but are not particularly limited as long as the target reaction proceeds.
  • the base used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by formula (3a), but preferably 1 equivalent or more. 30 equivalents or less,
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but an ether such as an aqueous solvent, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc.
  • an ether such as an aqueous solvent, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc.
  • Solvents alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitriles such as acetonitrile Solvents, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane Down, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or in admixture of two or more.
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by formula (3a). is there.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually ⁇ 20 ° C. or higher and 180 ° C. or lower or the boiling point of the solvent or lower.
  • reaction under acidic conditions and the reaction under basic conditions can be performed by a common method.
  • a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, etc. are dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved, saline, etc. are optional.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (3b) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (3b) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • the reaction mixture containing the compound represented by formula (3b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. What is necessary is just to set suitably according to the target purity.
  • the compound represented by the formula (3b) is represented by the formula (3b ′) (Wherein R2, R3, n, X and Y are as defined above.)
  • the compound represented by the formula (3b ′) can be handled in the same manner as the compound represented by the formula (3b), and the production method A can be applied. Further, the compound represented by the formula (3b ′) contains an asymmetric carbon, but the isomer mixing ratio may be single or a mixture of any ratio. Further, it may be a mixture of the compound represented by the formula (3b) and the compound represented by the formula (3b ′), and the isomer mixing ratio may be a single compound or a mixture of any ratio.
  • the compound represented by the formula (1) can be produced by arbitrarily combining the production methods A to R shown above. Alternatively, the compound represented by the formula (1) can also be produced by arbitrarily combining known methods and production methods A to R.
  • R2a and R2b in the formula (2a) and the formula (2b) are each independent, a C1-C6 alkyl group which may be appropriately substituted with a substituent E1, an aryl group which may be optionally substituted with a substituent E2, Represents a heteroaryl group optionally substituted with a substituent E3, or an aralkyl group optionally substituted with a substituent E2, or R2a and R2b together with the carbon atom to which they are bonded together A C3-C10 cycloalkyl ring optionally substituted with E4 may be formed.
  • R2a and R2b are independent of each other, and are preferably a C1-C6 alkyl group, particularly a C1-C6 alkyl group, and more preferably a methyl group, which may be appropriately substituted with the substituent E1.
  • R2c and R2d in the formula (2a) and the formula (2b) are each independently a hydrogen atom, a C1-C6 alkyl group, a halogen atom, a C1-C6 alkoxy group which may be optionally substituted with a substituent E1, Or a hydroxyl group, or R2c and R2d together with the carbon atom to which they are attached may form a C3-C10 cycloalkyl ring that may be optionally substituted with a carbonyl group or substituent E4.
  • R2c and R2d are independent of each other, and are preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent E1, particularly a C1-C6 alkyl group, or a halogen atom.
  • a group or a fluorine atom is more preferred.
  • R2e in the formulas (2a) and (2b) represents a hydrogen atom, a C2 to C7 acyl group, or a C1 to C6 alkyl group optionally substituted with a substituent E1.
  • R2e is preferably a hydrogen atom or a C1-C6 alkyl group which may be optionally substituted with a substituent E1, particularly a C1-C6 alkyl group, and more preferably a hydrogen atom or a methyl group. Most preferred is a hydrogen atom.
  • X1 in formula (2a) and formula (2b) is a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent E5, a C2-C6 alkenyl group optionally substituted with a substituent E6, C2-C6 alkynyl group optionally substituted with substituent E7, aryl group optionally substituted with substituent E2, heteroaryl group optionally substituted with substituent E3, alkoxy group with C1-C6 Represents an amino group optionally substituted with a substituent E8, an acyl group of C2 to C7, a cyano group, or an N-hydroxyalkaneimidoyl group in which a hydrogen atom of a hydroxyl group may be substituted with a substituent E9.
  • X1 is preferably a halogen atom, more preferably a fluorine atom.
  • X2 in the formulas (2a) and (2b) represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group or a hydroxyl group.
  • X2 is preferably a halogen atom, more preferably a fluorine atom.
  • n1 represents an integer of 0 to 4
  • n2 represents an integer of 0 to 6.
  • n1 is preferably an integer of 0 to 1
  • n2 is preferably an integer of 0 to 2, particularly preferably an integer of 0 to 1.
  • the substituent E1 in the formulas (2a) and (2b) is at least one selected from the group consisting of a halogen atom, a C1-C6 alkoxy group, a C1-C6 alkylthio group, and a phenoxy group.
  • the substituent E2 in the formula (2a) and the formula (2b) is a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or an amino optionally substituted with a substituent E8. And at least one selected from the group consisting of a group, a nitro group, a cyano group, a hydroxyl group, a mercapto group, and a C1-C6 alkylthio group.
  • the substituent E3 in the formulas (2a) and (2b) is at least one selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, and a C1-C6 alkoxy group. .
  • the substituent E4 in the formulas (2a) and (2b) is at least one selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a phenoxy group.
  • the substituent E5 in the formula (2a) and the formula (2b) is at least one selected from the group consisting of a halogen atom, a C1-C6 alkoxy group, a hydroxyl group, a C2-C7 alkyloxycarbonyl group, and a phenoxy group. .
  • the substituent E6 in the formula (2a) and the formula (2b) is at least one selected from the group consisting of a halogen atom, a C1-C6 alkoxy group, a C2-C7 alkyloxycarbonyl group, and a phenoxy group.
  • the substituent E7 in the formula (2a) and the formula (2b) is at least one selected from the group consisting of a halogen atom, a C1-C6 alkoxy group and a phenoxy group.
  • the substituent E8 in the formulas (2a) and (2b) is at least one selected from the group consisting of C1-C6 alkyl groups and C2-C7 acyl groups.
  • Substituent E9 in formula (2a) and formula (2b) is selected from the group consisting of C1-C6 alkyl groups, C2-C6 alkenyl groups, C2-C6 alkynyl groups, aralkyl groups, aryl groups and heteroaryl groups Is at least one kind.
  • the quinoline compound represented by the formula (2a) or the formula (2b) is represented by the formula (2c) or the formula (2d).
  • R2f represents a hydrogen atom or a methyl group
  • X3, X4 and X5 each independently represent a hydrogen atom or a fluorine atom
  • X6 and X7 each independently represent a hydrogen atom, a methyl group or a fluorine atom.
  • the quinoline type compound represented by this is preferable.
  • a quinoline compound represented by the formula (2a) or (2b) 3- (4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline (compound number: (2) -1), 3- (4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) -8-fluoroquinoline (compound number: (2) -2), 8-fluoro-3- (5-fluoro-3,3,4,4-tetramethyl-1,2,3,4-tetrahydroisoquinolin-1-yl) quinoline (compound number: (2) -3), Or 8-fluoro-3- (5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline (compound number: (2) -4) Most preferably.
  • the quinoline compound represented by the above formula (2c) or (2d), wherein X3 or X4, and particularly X3 is a fluorine atom, is gray mold disease, rice blast disease, apple black spot disease, cucumber anthracnose It has been found that the effect is remarkably improved against diseases such as diseases, which is preferable.
  • a certain quinoline compound or a salt thereof is preferable because it exhibits a remarkable effect on diseases such as gray mold disease, rice blast disease, apple black spot disease, and cucumber anthracnose.
  • the quinoline compounds (2) -2, (2) -3, and (2) -4 are preferable, and the quinoline compounds (2) -2 and (2) -3 are particularly preferable.
  • the quinoline compounds (2) -3 and (2) -4 have an environmental kinetic property that has a half-life of 7 to 55 days in a soil residual test in a container and a remarkably low soil residual property. This is also found and preferred.
  • quinoline-based compound represented by the formula (2a) or the formula (2b) its biological activity or a method for controlling pests using the component can be determined according to known literature (for example, International Publication No. 05/070917 or International Publication No. 08/0666148) may be referred to.
  • known literature for example, International Publication No. 05/070917 or International Publication No. 08/0666148
  • it is well-known literature for example, international publication 05/070917, international publication 08/066148, international Reference can be made to publication 13/047749, international publication 13/047750 or international publication 13/047751).
  • the pest control composition of the present invention can be produced according to a conventional method relating to the production of general agricultural chemicals. That is, the pest control composition contains two or more active ingredients of the compound of the present invention and a quinoline compound, and if necessary, a carrier and an auxiliary agent are mixed to contain both active ingredients. A composition can be produced. Moreover, after manufacturing the composition containing any one of this invention compound and a quinoline-type compound previously, the other may be added to it and the composition containing both active ingredients may be manufactured. Usually, the mixture containing both active ingredients is preferably prepared to produce the pest control composition. Alternatively, the pest control composition of the present invention can be produced by mixing a quinoline-based compound with an active ingredient, if necessary, a carrier and an auxiliary agent according to a conventional method for producing general agricultural chemicals. .
  • auxiliary agents such as surfactants, binders, disintegrants, stabilizers, pH adjusters, antibacterial antifungal agents (preservatives), thickeners, antifoaming agents, wetting agents, fixing agents, coloring agents, etc.
  • dosage forms such as wettable powder, flowable powder, wettable powder granule, OD drug, powder, liquid, emulsion, granule, pack, etc. in a timely manner according to conventional methods.
  • the form is not particularly limited as long as the effect is exhibited.
  • the pest control composition of the present invention may be an embodiment in which the compound of the present invention and the quinoline compound are formulated in one dosage form, or each is formulated in separate dosage forms. Alternatively, both sets may be used.
  • the carrier used in the composition of the present invention means a synthetic or natural inorganic compound formulated to help the active ingredient reach the site to be treated and to facilitate the storage, transport and handling of the active ingredient compound. Or it means an organic substance, and any solid, liquid or gas can be used as long as it is usually used for agricultural chemicals.
  • the carrier is not particularly limited as long as the effect is exhibited.
  • solid carrier examples include inorganic substances such as bentonite, montmorillonite, diatomaceous earth, white clay, talc, and clay, plant organic substances such as wood flour and sawdust, and urea. be able to.
  • liquid carriers examples include aromatic hydrocarbons such as xylene and toluene, aliphatic hydrocarbons such as naphthenes, n-paraffins, and liquid paraffin, acetone, methyl ethyl ketone, and the like. Ketones, dioxane, ethers such as diethylene glycol dimethyl ether, alcohols such as ethanol and ethylene glycol, carbonates such as ethylene carbonate, aprotic solvents such as dimethylformamide, water, and the like.
  • the gas carrier examples include nitrogen and carbon dioxide.
  • adjuvants can also be used to enhance the efficacy of the compounds in the compositions of the present invention.
  • the use form can be used alone or in combination depending on the purpose in consideration of the dosage form of the preparation, the treatment method, and the like.
  • adjuvants include surfactants, binders, disintegrants, stabilizers, pH adjusters, antibacterial and antifungal agents, thickeners, antifoaming agents, antifreeze agents, and the like.
  • a surfactant that is usually used for the purpose of emulsifying, dispersing, spreading or / and wetting the agricultural chemical preparation can be used.
  • the surfactant include sorbitan fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene polyoxypropylene block polymer, alkyl polyoxyethylene polyoxypropylene block polymer ether
  • Nonionic surfactants such as polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene bisphenyl ethers, polyoxyalkylene adducts of higher alcohols, polyoxyethylene ethers, ester type silicones, fluorosurfactants Agent; Alkyl sulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylene benzyl phenyl ether sulfate, polyoxyethylene styryl
  • binder examples include sodium alginate, polyvinyl alcohol, gum arabic, sodium carboxymethyl cellulose, bentonite and the like.
  • disintegrant examples include carboxymethylcellulose CMC sodium and croscarmellose sodium.
  • stabilizer examples include hindered phenol-based antioxidants, benzotriazole-based and hindered amine-based ultraviolet absorbers, and the like.
  • Examples of the pH adjuster include phosphoric acid, acetic acid, sodium hydroxide and the like.
  • antibacterial / antifungal agent examples include industrial bactericides such as sodium benzoate, potassium sorbate, parahydroxybenzoate ester, 1,2-benzisothiazolin-3-one, and antibacterial / antifungal agents. .
  • thickener examples include xanthan gum, guar gum, sodium carboxymethylcellulose, gum arabic, polyvinyl alcohol, montmorillonite and the like.
  • antifoaming agents examples include silicone compounds.
  • antifreezing agent examples include propylene glycol and ethylene glycol.
  • the adjuvants described above are examples, and the adjuvants used in the composition of the present invention are not particularly limited as long as the effects are exhibited.
  • the content of the compound of the present invention in the composition of the present invention is not particularly limited as long as the effect is exhibited, but is usually in the range of 0.01 to 99% by weight, preferably It is in the range of 0.1 to 90%, more preferably in the range of 1 to 80%.
  • the content of the quinoline compound in the composition of the present invention is not particularly limited as long as the effect is exhibited, but it is usually in the range of 0.01 to 99% by weight, preferably Is in the range of 0.1 to 90%, more preferably in the range of 1 to 80%.
  • the total content of the compound of the present invention and the quinoline compound in the composition of the present invention is not particularly limited as long as the effect is exhibited, but is usually in the range of 0.01 to 99% by weight. Yes, preferably in the range of 0.1 to 90%, more preferably in the range of 1 to 80%.
  • the mixing ratio of the compound of the present invention and the quinoline compound in the composition of the present invention is not particularly limited as long as the effect is exhibited, but the quinoline compound is usually in a weight ratio with respect to the compound of the present invention.
  • the ratio is 0.001 to 1000, and preferably the ratio is 0.01 to 100.
  • composition of the present invention can be used for pest control in fields, paddy fields, tea gardens, orchards, pastures, lawns, forests, gardens, roadside trees, and the like.
  • foliage spraying treatment to plant individuals for example, foliage spraying treatment to plant individuals, seedling box treatment, cell tray treatment, soil surface dispersion treatment, soil mixing after soil surface dispersion treatment, soil Infusion into soil, soil mixing after infusion treatment in soil, soil irrigation treatment, soil mixing after soil irrigation treatment, spraying treatment on plant seeds, smearing treatment on plant seeds, immersion treatment in plant seeds Or the dressing process etc. to a plant seed are mentioned.
  • application methods utilized by those skilled in the art can be used.
  • the method for controlling pests in the present invention includes a method for applying the pest control composition of the present invention, a composition containing the compound of the present invention as an active ingredient, and a composition containing a quinoline compound as an active ingredient. After applying either one of the method of applying at the same time, the composition containing the compound of the present invention as an active ingredient, or the composition containing a quinoline compound as an active ingredient, the other composition is applied. Methods and the like.
  • a method of applying the pest control composition of the present invention a method of applying the pest control composition manufactured to contain two or more kinds of active ingredients of the compound of the present invention and the quinoline compound, or the present invention.
  • a composition containing the compound of the present invention and a quinoline compound is prepared by a user mixing a composition containing the compound as an active ingredient and a composition containing a quinoline compound as an active ingredient before use. The method to use etc. are mentioned.
  • the time (period) until the other composition is applied is: Although it is not particularly limited as long as the effect is exhibited, for example, it is 1 minute to 2 weeks after applying any one of the compositions, preferably after applying any one of the compositions The period is 5 minutes to 1 week, and more preferably 10 minutes to 3 days after applying any one of the compositions.
  • the application amount and dilution rate of the composition of the present invention are appropriately selected according to the target crop, the target pest, the degree of occurrence of the pest, the dosage form of the composition of the present invention, the application method, various environmental conditions, and the like. Can be determined.
  • the application amount is not particularly limited as long as the effect is exhibited, but it is usually 1 to 10,000 g per hectare in terms of the amount of active ingredient, preferably 10 to 5000 g per hectare.
  • the application amount is not particularly limited as long as the effect is exhibited, but usually 0.001 per 1 kg of seed in terms of the amount of active ingredient. -100 g, preferably 0.01-50 g.
  • the dilution factor is particularly limited as long as the effect is exhibited. However, it is usually 5 to 50000 times, preferably 10 to 10000 times.
  • the plant means those that live without photosynthesis and exercise, for example, grains such as rice, wheat, barley, corn, grapes, apples, pears, peaches, sweet potatoes, oysters, citrus.
  • Fruit trees such as soybeans, green beans, green peas, fruits such as strawberries, watermelons, potatoes, sweet potatoes, taros, konjacs, etc., cabbage, lettuce, tomatoes, cucumbers, eggplant, sugar beet, spinach, pumpkins, Examples include, but are not limited to, vegetables such as peppers, rapes such as oilseed rape, cotton, sunflower, tulip, chrysanthemum, sugarcane, tobacco, turf, and the like.
  • seed means a nutrient stored for germination of a young plant and used for agricultural reproduction, for example, corn, soybean, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, Seeds such as cucumber, eggplant, spinach, sweet pea, pumpkin, sugar cane, tobacco, pepper and rape; seed pods such as taro, potato, sweet potato and konjac; seed balls such as edible lily, bulbs such as tulips and raccoons; or genes Is a plant produced by artificially manipulating, for example, soybean, corn, cotton, etc. imparted with herbicide resistance that does not naturally exist in nature; rice adapted to cold regions, Tobacco, etc .; transformed with maize, cotton, potato, etc., which have the ability to produce insecticides Child like although not limited thereto.
  • pests mean organisms that adversely affect the growth of plants such as pathogens such as bacteria, fungi and viruses, pests and weeds.
  • Pathogenic bacteria infect plants and cause plant diseases. Pests infest and infest plants. Weeds compete with plants in terms of photosynthesis and nutrient absorption by proliferating at or near the plant's growing location. For these reasons, pests are harmful to plants because they cause poor plant growth, wither and die, and decrease in yield.
  • the composition and control method of the present invention are effective against these pests.
  • specific pathogenic bacteria and pests to be controlled by the present invention are exemplified.
  • pathogens examples include rice blast fungus (Magnaporthe grisea), blight fungus (Thanatephorus cucumeris), brown sclerotia fungus (Ceratobasidium setariae), brown bacterium Bacterial rot fungus (Waitea citrus fungus), cucumeris, sclerotium hydrophilum, red sclerotia (Wairea circinata), staphylococcal fungus (Entyloma dactylidis), bacilli (Magneportorcium cerevisiae) Disease-causing bacteria (Cochliobolus Miyabeanus), Leaf blight fungus (Sphaerulina oryzina), Leaf seedling fungus (Gibberella fujikuroi), Seedling fungus (Pythium spp., Fusarium spp., Trichoderma spp., Rhizopus spp.
  • Tritici Tritici
  • rust fungus Pierinia graminis, Pucciria recondita, Puccinia recondita, Puccinaor fungus
  • Pyrenophora teres Fusarium mold fungus (Gibberella zeae), Fusarium culmorum, Fusarium avenaceum, Monographella phnephalis fungus (Typhila incarnathia) Stilago nuda), Tuna scab (Tilletia caries), Tilletia controversa (Pseudocercosporella phytotrophic) Phaeosphaeria nodorum), Fusarium spp., Pythium spp., Rhizoctonia spp., Septoria spp., Pyrenophorra spp.
  • Um graminicola ergot fungus (Claviceps purpurea), spot fungus (Cochliobolus sativus), black clause fungus (Pseudomonas syringae pv syringae); Corn fungus (Gibberella zeae, etc.), Seedling fungus (Fusarium avenaceum, Penicillium spp, Phythium spp.), Rhizoctonia sph.
  • Ustilago maydis, Anthracnose fungus (Colletotrichum graminicola), Northern spotted fungus (Cochliobolus caribonum), Brown rot fungus (Acidovorax avenae suburb), Staphylococcus aureus .
  • Mi pv zeae wilt bacterium fungus (Erwinia stewartii); Grape downy mildew (Plasmopara viticola), rust fungus (Physopella ampelopsidis), powdery mildew (Uncinula necator), black mold fungus (Elsinoe ampelina), late rot fungus (Glomerulumuleum, mullet) ), Vine split fungus (Phoropsis viticola), soot spot fungus (Zygophiala jamaicensis), gray mold fungus (Bottrytis cinerea), diatomote moss aid, trix), crown gall tumefaciens (Agrobacterium vitis); Apple powdery mildew (Podosphaera leukotricha), black rot (Venturia inaequalis), spot leaf rot (Alternaria mali), red rot (Gymnosporangium
  • Erwinia sp. Erwinia sp.
  • Agrobacterium tumefaciens Rust radish blight fungus (Erwinia chrysanthemi pv. Chrysanthemispiring), Pseudomonasy symptom Pesticides of pear (Phytophthoraca bacterium, Phytophthora syringae), bacterial wilt (Erwinia sp.); Peach black rot fungus (Cladosporium carpophilum), homoposis spoilage fungus (Phomopsis sp.), Plague fungus (Phytophthora sp.
  • Agrobacterium tumefaciens Sugar beetle fungus (Glomerella cingulata), larvae fungus (Monilinia kusanoi), Aspergillus fungus (ingi) aingacterial syrup (Agrobacterium tumefaciens); Oyster anthracnose fungus (Glomerella singulata), deciduous fungus (Cercospora kaki; Mycosphaerella nawae), powdery mildew (Phyllactinia kakikora), root cancer fungus (Agrobacteria) Citrus black spot fungus (Diaporthe citrus), green mold fungus (Penicillium digitatum), green mold fungus (Penicillium italicum), scab fungus (Elsinophatophanthocorii) Pseudomonas syringae pv.
  • Botrytis cinerea such as tomato, cucumber, beans, strawberry, potato, cabbage, eggplant, lettuce
  • Sclerotinia sclerotiorum such as tomato, cucumber, beans, strawberry, potato, rapeseed, cabbage, eggplant, lettuce, etc .
  • Seedling blight fungi (Rhizoctonia spp., Phythium spp., Phytophthora spp., Phytophthora spp., Sclerotrin, etc.) Ralstonia solanacerum, a solanaceous plant; Downy mildew of cucurbits (Pseudoperonospora cubensis), powdery mildew (Sphaerotheca fuliginea), anthracnose fungus (Colletotrichum orbiculare), vine blight (Didymella bryoniae), Fusarium fungus (Fusarium oxysporum), Phytophthora (Phytophthora parasitica, Phytophthora melonis , Phytophthora nicotianae, Phytophthora drechsleri, Phytophthora capsici, etc.), Xanthomonas campestris pv.
  • Brassicaceae black spot fungus (Alternaria brassicae, etc.), white spot fungus (Cercosporella brassicae), root rot fungus (Phoma lingam), root-knot fungus (Plasmodiophora brassicae), black mold fungus (Panthophora brassicae), mildew fungus (Panthophora brassicae) pv. campestris), black spot bacteria (Pseudomonas syringae pv. maculacola), soft rot fungus (Erwinia carotovora subsp.
  • Carotovora spot bacterial pathogen (Pseudomonas syringae pv. Syringae), Rot (Erwinia rhapontici), a scale-Rot (Burkholderia gladioli), yellows fungus (Phytoplasma asteris ); Soft rot of garlic (Erwinia carotovora subsp. Carotovora), spring rot (Pseudomonas marginalis pv.
  • Soybean purpura fungus (Cercospora kikuchii), black rot fungus (Elsinoe glycines), black spot fungus (Diaporthe phasororum), rhizobonia hormonal fungus (Rhizotonia soloni), Phygopsora pachyrhizi, Anthracnose fungus (Colletotrichum truncatum, etc.), leaf-burning fungus (Xhanthomonas campestris pv.
  • Kidney anthracnose fungus (Colletotrichum lindemuthianum), bacterial wilt fungus (Ralstonia solanacearum), bacterial wilt fungus (Pseudomonas syringae pv.
  • Groundnut black fungus Mycosphaerella berkeleyi
  • brown spot fungus Mycosphaerella arachidis
  • bacterial wilt (Ralstonia solanaceram)
  • Pea powdery mildew fungus (Erysiphe pisi), downy mildew fungus (Peronospora pisi), vine blight fungus (Pseudomonas syringae pv.
  • Pisi vine rot fungus
  • Xhanthomonas campestris pestis Broad bean fungus (Peronospora viciae), Phytophthora nicotianae; Potato summer blight fungus (Alternaria solani), black rot fungus (Thanatephorus cucumeris), blight fungus (Phytophthora infestans), silver rot fungus (Helminosporum solani), dry rot fungus (Fusarium sorghum) Spongospora subterranea, bacterial wilt (Ralstonia solanacearum), black rot (Erwinia carotovora subsp.
  • Atroseptica rot fungus (Streptomyces scabipes, rot fungi .. A subsp carotovora), viscous Rot (Crostridium spp), Wakusa Fungus (Clavibacter michiganensis subsp.sepedonicus); Streptomyces ipomoeae; Sugar beet blight fungus (Cercospora beticola), downy mildew fungus (Peronospora schachtii), black root fungus (Aphanomyces cochioides), snake eye blight fungus (Phomabecto sect) (Agrobacter fungus) , Pseudomonas syringae pv.
  • Carotovora Ralstonia solanacearum, tobacco mosaic virus (Tobaco mosaic virus); Coffee rust (Hemileia vastatrix); Banana black sigatoga disease (Mycosphaerella fijiensis), Panama disease (Fusarium oxysporum f. Cotton Fusarium oxysporum, Milulaia areola; Sunflower sclerotia (Sclerotinia sclerotiorum), Xanthomonas campestris pv. Malvacearum, cavernous fungus Erwinia carotovora subsp. carotovora), Pseudomonas syringae pv.
  • Myriosclerotinia borealis Fairy Ri Grayed Fungus (Marasmius Oreades etc.), (such as Pythium aphanidermatum) Pythium fungus, Pyricularia oryzae (Pyricularia grisea), and the like.
  • pests examples include, but are not limited to, Adoxophyes honmai, Adoxophies orana faciata, Apples burapipicanus, and Argops reptile. fuscocuppreanus, papaver (Grapholita molesta), chacha maki (Christoneura magnanima), bean thrips (Leguminivora glycinivolores), mulberry papaver (Olethia maki) Nkui (Argyresthia conjugella), Nashihosoga (Spulerrina astaurota), beans Hime Saya insect moth (Matsumuraeses phaseoli), Tobihamaki (Pandemis heparana), Nashichibiga (Bucculatrix pyrivorella), Momohamoguriga (Lyonetia clerkella), peach fruit moth (Carposina niponensis), Gin Mont leafminer ( Lyonetia punifoliella malinella), Chalothosiga (Caloptilia theivora), Golden
  • Coleoptera insects such as Onychiurus folsomi, Siberian whitebill (Onychiurus sibiricus), Bourletiella hortensis, etc., Cockroach (Periplaneta americana), Cockroach (Periplaneta americana), German cockroach (Blattella germanica), cockroach (Peliplaneta Americana), etc.
  • Termite insects such as the termites (Coptothermes formosanus), the Yamato termites (Reticulitermes speratus), the Taiwan termites (Odontotermes formosanus), Cat fleas (Ctenocephalidae felis), Dog fleas (Ctenocephalides canis), Chicken fleas (Echidnophaga gallinacea), Human fleas (Pulex irritans), Ceopus vulgaris (Xenopsylla, etc.) Dipteran insects such as chicken lice (Mecananthus stramineus), bovine lice (Bovicola bovis), Bovine lice (Haematopinus eurysternus), swine lice (Haematopinus suis), bovine white lice (Linognathus vitili), mosquito lice lice (Solenopotes capillus), sheep d Dust mites such as cyclamen dust mites (Phytonemus pallidus), chano mite mites (Polyphago
  • Rice spider mites (Oligonychus shinkajii), citrus red spider mite (Pananychus citri), red spider mite (Pananychus ulmi), tick mite (Tananychus urticae), Tetranichus kanzawai Tea Roh Naga rust mite (Acaphylla theavagrans), Tulip rust mite (Aceria tulipae), tomato rust mite (Aculops lycopersici), mandarin orange rust mite (Aculops pelekassi), apple rust mite (Aculus Lampendali), false pear rust mite (Eriophyes chibaensis), citrus last mite (Phyllocoptruta oleivora ) Coniferous mites such as Robin tick (Rhizoglyphus robini), Kenagakonadani mite (Tyrophagus putrescentiae), Spinach mites (Tyrophagus similis), Leopard mites, such
  • Ticks such as Rocky Mountain Forest Tick (Dermenteror andrsononi), West Coast Tick (Demercentor occidentalis), American Dog Tick (Dermentertor variabilis), Tick Tick (Dermenteror spp.), Crawfish ticks (Cheeletiella yasguri), crayfish ticks (Cheeletiella blackei), etc., Acne mites such as Inodemite mites (Demodex canis), Caterpillar mites (Demodex cati), Cucumber mites such as ovine cucumber mites (Psoroptes ovis), Mite mites such as Sarcoptes scabiei, catfish mite mite (Notoderes cati), chick mite mite (Knemidopoptes spp.), Crustaceans such as Armadillium vulgare, Pomacea caliculata, Achatina falica, slugs (Meghiatum
  • Worms such as Cestoda Ascaris, Toxocara, Toxacaris, Parascaris, Ascaridia, Heterakis, Oxyuris, Capillaria, Capillaria Caterpillars (Trichinella), roundworms (Strongylus, Tridontophorus), hairy nematodes (Trichonema), swine nematodes (Stephanurus), intestinal nodules (Desophagostomum), large intestinal nematodes (Chabertia), moths astragalus (A) , Uncinaria, Necator, Bunostom), Trichostromylus, Coober ciliate nematode (Coo) eria, nematoderus, torsion stomach nematode (Haemonchus), octer dark gastroworm (Ostertagia), lungworm (Dictyocaurus, Metastrungylus), dirofilariae (polyrofilaria) Parafilaria
  • Step 2 Synthesis of 5- (2-chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -1-ethyl-3,4-dihydropyridin-2 (1H) -one (Compound No. 52)
  • the obtained organic layer was washed successively with aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 109 mg off-white solid.
  • the resulting white solid was the title compound, 2.24 g. Further, the filtrate produced when the precipitate was washed was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The white solid obtained from the filtrate was also the title compound, 0.46 g. 1 H-NMR (CDCl 3 ) ⁇ : 7.28-7.26 (1H, m), 7.18 (1H, br s), 6.86-6.83 (1H, m), 6.74- 6.72 (1H, m), 6.61-6.59 (2H, br m), 2.85-2.74 (4H, br m).
  • Step 2 Synthesis of 5- (2-chloro-5-fluorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one (compound Number 320)
  • Step 2 Synthesis of 5- (3,5-dimethoxyphenyl) -1-methyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one
  • Step 1 Synthesis of 2- (2-chloro-5-methoxyphenyl) -1- (2,6-difluorophenyl) ethanone
  • Step 2 Synthesis of ethyl 4- (2-chloro-5-methoxyphenyl) -5- (2,6-difluorophenyl) -5-oxopentanoate
  • Step 3 Synthesis of 4- (2-chloro-5-methoxyphenyl) -5- (2,6-difluorophenyl) -5-oxopentanoic acid
  • Step 1 Synthesis of N ′-(2-chloro-5-fluorobenzylidene) -4-methylbenzenesulfonyl hydrazide
  • Step 2 Synthesis of 2- (2-chloro-5-fluorophenyl) -1- (2,4,6-trifluorophenyl) ethanone
  • Step 3 Synthesis of ethyl 4- (2-chloro-5-fluorophenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoate
  • Step 4 Synthesis of 4- (2-chloro-5-fluorophenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoic acid
  • Step 1 Synthesis of N ′-(3,5-dimethoxybenzylidene) -4-methylbenzenesulfonyl hydrazide
  • Step 2 Synthesis of 2- (3,5-dimethoxyphenyl) -1- (2,4,6-trifluorophenyl) ethanone
  • Step 3 Synthesis of ethyl 4- (3,5-dimethoxyphenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoate
  • Step 4 Synthesis of 4- (3,5-dimethoxyphenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoic acid
  • Structure B represents the following:
  • Structure C represents:
  • Structure D represents:
  • Step 1 Preparation of 3- (3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) -8-fluoroquinoline
  • (Z) -2- (3,3-dimethyl-3 , 4-Dihydroisoquinolin-1-yl) -3-hydroxyacrylaldehyde (23 g, 0.1 mol) and 2-fluoroaniline (16.7 g, 0.16 mol) in xylene (300 ml) were heated to reflux for 3 hours.
  • Eaton's reagent (phosphorus pentoxide-methanesulfonic acid solution, weight ratio 1:10) (300 ml) was added dropwise, and the mixture was further heated to reflux for 3 hours. Water (500 ml) was added to the reaction solution under ice cooling, and the aqueous layer washed with xylene was made alkaline with potassium carbonate, extracted with ethyl acetate, dried over magnesium sulfate, filtered and concentrated.
  • Step 2 Preparation of 3- (4,4-dibromo-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) -8-fluoroquinoline 3- (3,3-dimethyl in a 1 L three-necked flask To a solution of -3,4-dihydroisoquinolin-1-yl) -8-fluoroquinoline (17.7 g, 58 mmol) in chlorobenzene (400 ml), 1,3-dibromo-5,5-dimethylhydantoin (19.1 g, 66.
  • Step 3 Preparation of 3- (4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) -8-fluoroquinoline Triethylamine trioxide in a 500 mL PFA (polytetrafluoroethylene) flask Hydrogen fluoride (18.7 g, 116 mmol) to 3- (4,4-dibromo-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) -8-fluoroquinoline (24.4 g, 58 mmol) Chlorobenzene (45 ml) solution was added, and the mixture was heated with stirring at 85 ° C. for 5 hours.
  • PFA polytetrafluoroethylene
  • Step 1 Preparation of 8-fluoro-3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline
  • sulfuric acid 115 mL
  • 3-cyano-8-fluoroquinoline 20.6 g, 0.12 mol
  • 3- (2-fluorophenyl) -2,3-dimethylbutan-2-ol 28.3 g, 0.12 mol
  • 144 mmol) in dichloroethane (40 ml) was added dropwise and stirred at room temperature for 18 hours.
  • Step 2 Preparation of 8-fluoro-3- (5-fluoro-3,3,4,4-tetramethyl-1,2,3,4-tetrahydroisoquinolin-1-yl) quinoline under nitrogen atmosphere
  • 8-fluoro-3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline (16.7 g, 47.7 mmol) in ethanol (477 mL).
  • Sodium borohydride (5.4 g, 0.14 mol) was added to the solution, and the mixture was stirred at room temperature for 0.5 hour and further heated to reflux for 3 hours.
  • reaction solution was poured into ice water, and the aqueous layer washed with ethyl acetate was made alkaline with aqueous ammonia and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, filtered and concentrated. To the obtained residue was added 10% aqueous sodium hydroxide (50 ml), and the mixture was heated to reflux for 1 hour.
  • a spore suspension of each pathogen (spore density 1 ⁇ 10 5 spores / mL) were dispensed in appropriate amounts and mixed well.
  • the microtiter plate was cultured in a closed container at 18 ° C. in the dark, and the growth degree of the bacteria in the drug-treated group and the drug-untreated group was measured after 0 to 7 days.
  • the growth inhibition rate of bacteria by chemical treatment was calculated from the following formula.
  • Tomato gray mold: GM After sowing the test plant (tomato variety: large Fuju), it was cultivated until three true leaves were developed. In the test, a diluted solution diluted with distilled water was sprayed so that each compound had a concentration of 50 ppm. The seedlings one day after the spraying were spray-inoculated with conidia of Botrytis cinerea , and then left in an inoculation room at room temperature of 20-23 ° C. for about 48 hours to promote disease. The degree of illness 2 days after inoculation was investigated and the effect was evaluated. (Rice blast: B) After sowing the test plant (rice cultivar: Kofu), the plant was cultivated until the second leaf developed.
  • a diluted solution diluted with distilled water was sprayed so that each compound had a concentration of 50 ppm.
  • the seedlings one day after the spraying were spray-inoculated with conidia of Colletotrichum orbiculare , and then left in an inoculation room at a room temperature of 20 to 23 ° C. for about 24 hours to promote disease.
  • the degree of disease on the 10th day after inoculation was investigated and the effect was evaluated. (Apple black spot disease: AS) After sowing the test plant (apple variety: Wang Lin), the plant was cultivated until four true leaves developed.
  • a diluted solution diluted with distilled water was sprayed so that each compound had a concentration of 50 ppm.
  • the seedlings one day after spraying were spray-inoculated with conidia of Venturia inaequalis and then left in an inoculation room at room temperature of 18 to 20 ° C. for about 24 hours to promote disease.
  • the degree of disease on the 10th day after inoculation was investigated and the effect was evaluated.
  • Cabbage black soot disease: CA After sowing the test plant (cabbage variety: seasonal harvest), it was cultivated until the cotyledon developed. In the test, a diluted solution diluted with distilled water was sprayed so that each compound had a concentration of 250 ppm.
  • the seedlings one day after the spraying were spray-inoculated with conidia of cabbage black soot fungus (Alternaria brassicicola) and then left in an inoculation room at room temperature of 20 to 23 ° C. for about 48 hours to promote the onset of disease.
  • the degree of illness 2 days after inoculation was investigated and the effect was evaluated.
  • compounds against tomato gray mold, rice blast, cucumber anthracnose, apple black spot, cabbage black soot (2) -2, (2) -3 and (2) -4 showed a high control effect with a control value of 95% or more.
  • Test Example 3 Antibacterial test against various pathogens
  • quinoline compounds Fusarium oxysporum f. Sp. Cucumerinum, Anthracnose fungus (Glomerella cingulata), rice Antibacterial activity against sesame leaf blight fungus (Cochrobulus Miyabeanus) and grape black rot fungus (Elinoe ampelina) was measured.
  • compound (2) -2, (2) -3, (2) -4 was found to be effective against cucumber vine split fungus, anthrax fungus, rice sesame leaf blight fungus, and grape black rot fungus. The growth of each pathogen was completely prevented.
  • the pest control composition and the novel quinoline compound according to the present invention have an excellent pest control effect and thus have utility value as an agrochemical.

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

Abstract

L'invention concerne une composition de lutte contre les nuisibles contenant un nouvel ingrédient actif et étant utile pour repousser les organismes nuisibles et son procédé d'utilisation, et un nouveau composé à base de quinoléine. L'invention concerne une composition de lutte contre les nuisibles contenant, comme ingrédients actifs, un composé exprimé par la formule (1) ou un sel de celui-ci, et un ou plusieurs types d'ingrédients choisis parmi des composés à base de quinoléine et présentant une activité de lutte contre les nuisibles, et un nouveau composé à base de quinoléine présentant une activité de lutte contre les nuisibles. Dans la formule, R1 représente un groupe alkyle en C1-C6 remplaçable, un groupe halogénoalkyle en C1-C6, etc., R2 représente un atome d'halogène, un groupe alkyle en C1-C6 remplaçable, un groupe alcoxy en C1-C6 remplaçable, etc., R3 représente un atome d'hydrogène, un atome d'halogène, un groupe alkyle en C1-C6 remplaçable, etc., n représente un nombre entier compris entre 0 et 5, X représente un atome d'oxygène ou un atome de soufre, Y représente un groupe phényle comportant un substituant en position ortho, un groupe pyridyle, etc., et la liaison comprenant une ligne en pointillés représente une liaison double ou une liaison simple.
PCT/JP2018/015011 2017-04-10 2018-04-10 Composition de lutte contre les nuisibles contenant un composé pyridone et un composé à base de quinoléine et procédé de lutte contre les nuisibles, et nouveau composé à base de quinoléine WO2018190326A1 (fr)

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JP2017077868A JP2020121925A (ja) 2017-04-10 2017-04-10 ピリドン化合物とキノリン系化合物を含有する有害生物防除組成物および有害生物の防除方法、ならびに新規キノリン系化合物
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Cited By (4)

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WO2021023193A1 (fr) * 2019-08-08 2021-02-11 漳州片仔癀药业股份有限公司 Procédé de préparation d'un composé de pyrazine-2 (1h)-cétone
WO2021074309A1 (fr) * 2019-10-16 2021-04-22 Syngenta Crop Protection Ag Dérivés de 1-(3-quinolyl)-3,4-dihydroisoquinoléine utilisés en tant que fongicides pour lutter contre des phytopathogènes spécifiques
WO2021074311A1 (fr) * 2019-10-16 2021-04-22 Syngenta Crop Protection Ag Dérivés de 1-(3-quinolyl)-1,2,3,4-tétrahydroisoquinoléine utilisés en tant que fongicides pour lutter contre des phytopathogènes spécifiques
CN112979621A (zh) * 2021-03-11 2021-06-18 西华大学 2,3,4,6-四取代吡啶类化合物及其在农药中的用途

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CN114988994B (zh) * 2022-05-30 2023-04-21 中国科学院山西煤炭化学研究所 一种一步制备二芳基乙酮的方法

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WO2021023193A1 (fr) * 2019-08-08 2021-02-11 漳州片仔癀药业股份有限公司 Procédé de préparation d'un composé de pyrazine-2 (1h)-cétone
CN114174272A (zh) * 2019-08-08 2022-03-11 漳州片仔癀药业股份有限公司 吡嗪-2(1h)-酮类化合物的制备方法
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WO2021074309A1 (fr) * 2019-10-16 2021-04-22 Syngenta Crop Protection Ag Dérivés de 1-(3-quinolyl)-3,4-dihydroisoquinoléine utilisés en tant que fongicides pour lutter contre des phytopathogènes spécifiques
WO2021074311A1 (fr) * 2019-10-16 2021-04-22 Syngenta Crop Protection Ag Dérivés de 1-(3-quinolyl)-1,2,3,4-tétrahydroisoquinoléine utilisés en tant que fongicides pour lutter contre des phytopathogènes spécifiques
CN112979621A (zh) * 2021-03-11 2021-06-18 西华大学 2,3,4,6-四取代吡啶类化合物及其在农药中的用途
CN112979621B (zh) * 2021-03-11 2023-08-29 山东淏源生物科技有限公司 2,3,4,6-四取代吡啶类化合物及其在农药中的用途

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