WO2018230516A1 - Composé de pyridone et agent antimicrobien l'utilisant comme ingrédient actif pour l'agriculture et l'horticulture - Google Patents

Composé de pyridone et agent antimicrobien l'utilisant comme ingrédient actif pour l'agriculture et l'horticulture Download PDF

Info

Publication number
WO2018230516A1
WO2018230516A1 PCT/JP2018/022279 JP2018022279W WO2018230516A1 WO 2018230516 A1 WO2018230516 A1 WO 2018230516A1 JP 2018022279 W JP2018022279 W JP 2018022279W WO 2018230516 A1 WO2018230516 A1 WO 2018230516A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
optionally substituted
substituent
substituents
defined above
Prior art date
Application number
PCT/JP2018/022279
Other languages
English (en)
Japanese (ja)
Inventor
豪毅 梅谷
駿 岡谷
光児 益富
健志 福元
暉 小石原
友美 白川
Original Assignee
三井化学アグロ株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 三井化学アグロ株式会社 filed Critical 三井化学アグロ株式会社
Priority to JP2019525423A priority Critical patent/JP7118961B2/ja
Publication of WO2018230516A1 publication Critical patent/WO2018230516A1/fr

Links

Classifications

    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to a pyridone compound and an agrochemical containing the compound as an active ingredient.
  • Controlling diseases of agricultural and horticultural crops plays an important role in ensuring stable agricultural production. For this reason, various bactericides are used, but the use of bactericides for many years has led to the emergence of drug-resistant bacteria. Has been.
  • 1,3,5,6-substituted-2-pyridone compounds having an aryl group or a heteroaryl group at the 3-position are disclosed as GABA alpha-2 / 3 ligands (for example, WO 98/55480). reference).
  • GABA alpha-2 / 3 ligands for example, WO 98/55480. reference.
  • 1,3,5,6-substituted-2-pyridone compounds having a carboxyl group at the 3-position have been disclosed (see, for example, European Patent No. 0308020).
  • 1,3,5,6-substituted-2-pyridone compounds in which 4,4-dimethylpentanoic acid is introduced at the 1-position are disclosed as anti-HIV agents (for example, International Publication No. 2016/012913). reference).
  • An object of the present invention is to provide a novel pyridone compound that is effective as an agricultural and horticultural fungicide.
  • R1 is 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-C
  • R2 is Hydrogen atom, A cyano group, Nitro group, Halogen atoms, 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 alkyny
  • R4 is Hydrogen atom, A C1-C6 alkyl group optionally substituted with substituent C, A C1-C6 haloalkyl group, A C3-C8 cycloalkyl group optionally substituted with substituent C, A C2-C6 alkenyl group optionally substituted with substituent C, A C2-C6 haloalkenyl group, A C2-C6 alkynyl group optionally substituted with substituent C, A C2-C6 haloalkynyl group, A phenyl group which may be optionally substituted with 0-5 substituents D (however, in the case of two or more substituents D, each is independent); A C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 substituents D (in the case of two or more substituents D, each is independent), A C1-C6 haloalkyl group having a phenyl group which may be optionally
  • the substituent A includes 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, RaRbN— (where Ra And Rb are as defined above) and Rc-L- (wherein Rc and L are as defined above) and are at least one selected from the group consisting of:
  • Substituent B 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 a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 halo
  • Substituent D is a hydroxyl group, cyano group, nitro group, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 optionally substituted with substituent B, C1- At least one selected from the group consisting of a C6 alkoxy group, a C1-C6 haloalkoxy group, and a C3-C8 cycloalkoxy group;
  • Substituent E is a hydroxyl group, cyano group, halogen atom, C1-C6 alkyl group optionally substituted with substituent C, C1-C6 haloalkyl group, C3-C8 optionally substituted with substituent C.
  • R1 is A C1-C6 alkyl group optionally substituted with substituent A, A C1-C6 haloalkyl group, 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 represents a C2-C6 haloalkynyl group;
  • R2 is Hydrogen atom, Halogen atoms, A C1-C6 alkyl group optionally substituted with substituent A, A C1-C6 haloalkyl group, A C2-C6 alkenyl group optionally substituted with the substituent A, A C2-C6 alkynyl group optionally substituted with substituent A, A C1-C6 alkoxy group optionally substituted with the substituent A, A C1-C6 haloalkoxy group, Rc-L-(wherein, Rc represents a halo
  • Each of which may represent a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb together with the nitrogen atom to which they are bonded, is an aziridinyl group, an azetidinyl group Represents a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group).
  • Y is A phenyl group which may be optionally substituted with 0 to 5 by R3 (however, in the case of R3 having 2 or more substitutions, each is independent); Or a pyridyl group optionally substituted with 0 to 4 by R3 (provided that each of R3 having 2 or more substituents is independent); R3 is Hydroxyl group, A cyano group, Halogen atoms, A C1-C6 alkyl group optionally substituted with substituent C, A C1-C6 alkoxy group that may be optionally substituted with a substituent C; A C1-C6 haloalkoxy group, A C2-C6 alkenyloxy group optionally substituted with the substituent C, A C2-C6 haloalkenyloxy group, A C3-C6 alkynyloxy group optionally substituted with substituent C, A C3-C6 haloalkynyloxy group, Or RdC ( ⁇ O) O— (wherein Rd is as
  • R1 is A C1-C6 alkyl group optionally substituted with substituent A, Or represents a C1-C6 haloalkyl group
  • R2 is Halogen atoms, A C1-C6 alkyl group optionally substituted with substituent A, A C2-C6 alkynyl group optionally substituted with substituent A, Or a C1-C6 alkoxy group optionally substituted with the substituent A
  • Y is R3 represents a phenyl group which may be optionally substituted with 0 to 5 (provided that each of R3 having two or more substituents is independent);
  • R3 is A cyano group, Halogen atoms, Or a C1-C6 alkoxy group optionally substituted with a substituent C;
  • R4 is Hydrogen atom, A C1-C6 alkyl group optionally substituted with substituent C, A C3-C8 cycloalkyl group optionally substituted with substituent C, A phenyl group which
  • R5 is Hydrogen atom, A C1-C6 alkyl group optionally substituted with substituent C, Or RdC ( ⁇ O) — (where Rd is a hydrogen atom, a C1-C6 alkyl group optionally substituted with the substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1 -C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are each independently substituted with a hydrogen atom or a substituent B as appropriate).
  • Each of which may represent a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb together with the nitrogen atom to which they are bonded, is an aziridinyl group, an azetidinyl group Represents a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group).
  • R4 and R5 together with the oxime structure to which they are attached (C ⁇ N—O)
  • An isoxazole ring optionally substituted with 0 to 2 substituents E (however, in the case of 2 substituted substituents E, each is independent)
  • An isoxazoline ring optionally substituted with 0 to 4 substituents F (provided that each of substituents F having two or more substituents is independent)
  • Or [2] which represents a benzisoxazole ring which may be optionally substituted with 0 to 4 substituents D (however, in the case of two or more substituents D, each is independent).
  • Or a salt thereof (C ⁇ N—O)
  • R4 is Hydrogen atom, A C1-C6 alkyl group optionally substituted with substituent C, A C3-C8 cycloalkyl group optionally substituted with substituent C, A phenyl group which may be optionally substituted with 0-5 substituents D (however, in the case of two or more substituents D, each is independent); Or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 A cycloalkyl group or Ra and Rb together with the nitrogen atom to which they are attached represent an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group.
  • R5 is Hydrogen atom, A C1-C6 alkyl group optionally substituted with substituent C, Or RdC ( ⁇ O) — (where Rd is a hydrogen atom, a C1-C6 alkyl group optionally substituted with the substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1 -C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are each independently substituted with a hydrogen atom or a substituent B as appropriate).
  • Each of which may represent a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb together with the nitrogen atom to which they are bonded, is an aziridinyl group, an azetidinyl group Represents a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group).
  • R4 and R5 together with the oxime structure to which they are attached (C ⁇ N—O)
  • [5] The compound or a salt thereof according to any one of [1] to [4], wherein R1 is a methyl group, an ethyl group, or a 2,2-difluoroethyl group.
  • Y represents a phenyl group, a 4-cyanophenyl group, a 4-fluorophenyl group, a 2,6-difluorophenyl group, a 2,4,6-trifluorophenyl group, a 2,6-difluoro-4-methoxyphenyl group, 3
  • R4 is a hydrogen atom, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, cyclopentyl group, phenyl group, amino group, or methylamino group, [1] to [ 9] or a salt thereof.
  • R5 is a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, or an acetyl group.
  • R5ON C (R4)-is (hydroxyimino) methyl group, 1- (hydroxyimino) propyl group, 1- (hydroxyimino) -2-methylpropyl group, 1- (hydroxyimino) -2,2 -Dimethylpropyl group, 1- (hydroxyimino) -3-methylbutyl group, (methoxyimino) methyl group, 1- (methoxyimino) ethyl group, 1- (methoxyimino) propyl group, 1- (methoxyimino) -2 -Methylpropyl group, 1- (methoxyimino) -2,2-dimethylpropyl group, 1- (methoxyimino) butyl group, 1- (methoxyimino) -3-methylbutyl group, 1- (methoxyimino) pentyl group, (Methoxyimino) (phenyl) methyl group, 1- (ethoxyimino) propyl group, 1-
  • RgON C (Rh)-(where Rg and Rh are as defined above) and RiRjRkSi- (where Ri, Rj and Rk are as defined above).
  • Substituent E is chlorine, bromine, iodine, methyl, ethyl, isopropyl, hydroxymethyl, 1-hydroxyethyl, trifluoroacetoxymethyl, bromomethyl, difluoromethyl, vinyl, ethynyl
  • R4 and R5 together with the oxime structure to which they are attached (C ⁇ N—O), may be optionally substituted with 0 to 2 substituents E isoxazole rings (in the case of a disubstituted substituent E, Which form an independent group) isoxazol-3-yl group, 4-chloroisoxazol-3-yl group, 4-bromoisoxazol-3-yl group, 4-iodoisoxazole- 3-yl group, 4-methylisoxazol-3-yl group, 5-methylisoxazol-3-yl group, 5- (hydroxymethyl) isoxazol-3-yl group, 5-ethylisoxazole-3 -Yl group, 5- (1-hydroxyethyl) isoxazol-3-yl group, 5-isopropylisoxazol-3-yl group, 5-aminoisoxazol-3-yl group, 5- (trimethylsilyl) iso Sazol-3-yl group,
  • the substituent F is at least one selected from the group consisting of a halogen atom, an alkyl group that may be optionally substituted with the substituent C, and a C1-C6 alkoxy group that may be optionally substituted with the substituent C. , [1] to [3], or a compound or a salt thereof according to any one of [5] to [9].
  • the substituent F is at least one selected from the group consisting of a bromine atom, a methyl group, an ethyl group, and an ethoxy group, and any one of [1] to [3] and [5] to [9] Or a salt thereof.
  • R4 and R5 are combined with an oxime structure (C ⁇ N—O), and isoxazoline ring which may be optionally substituted with 0 to 4 substituents F (provided that the substituent F has 2 or more substituents, Are independently formed from 4-bromo-5,5-dimethyl-4,5-dihydroisoxazol-3-yl group, 5-ethyl-4,5-dihydroisoxazole- A 3-yl group, a 5,5-dimethyl-4,5-dihydroisoxazol-3-yl group, or a 5-ethoxy-4,5-dihydroisoxazol-3-yl group, [1] to [3] The compound or a salt thereof according to any one of [5] to [9].
  • a benzisoxazole ring in which R4 and R5 together with the oxime structure (C ⁇ N—O) to which R4 and R5 are bonded may be optionally substituted with 0 to 4 substituents D (provided that the substituents D have two or more substituents) Each of which is independent of each other) is a benzo [d] isoxazol-3-yl group, any one of [1] to [3] and [5] to [9] Or a salt thereof.
  • An agricultural and horticultural pest control agent comprising the compound according to any one of [1] to [19] or a salt thereof as an active ingredient.
  • [21] An agricultural and horticultural fungicide containing the compound according to any one of [1] to [19] or a salt thereof as an active ingredient.
  • a method for controlling plant diseases which comprises applying the agricultural and horticultural pest control agent according to [20] to plants, plant seeds, or soil in which plants are grown.
  • a method for controlling plant diseases which comprises applying the agricultural and horticultural fungicide according to [21] to a plant, plant seed, or soil in which the plant is cultivated.
  • a novel compound that is effective as an agricultural and horticultural fungicide can be provided.
  • Cx-Cy has x to y carbon atoms.
  • x and y represent integers, and it is understood that all integers existing between x and y are also individually disclosed.
  • C1-C6 is 1, 2, 3, 4, 5, or 6 carbon atoms
  • C1-C5 is 1, 2, 3, 4, or 5 carbon atoms
  • C2-C6 is 2, 3, 4, 5, or 6 carbon atoms
  • C3-C8 is 3, 4, 5, 6, 7, or 8 carbon atoms
  • C3-C6 is 3, 4, 5 Or 6 carbon atoms each.
  • optionally substituted means substituted or unsubstituted.
  • the number of substituents is 1 when the number of substituents is not specified.
  • the number of substituents is designated as “optionally substituted with 0 to 6”, it is understood that all integers existing between 0 and 6 are also individually disclosed. Is done. That is, the number of substituents means none, 1, 2, 3, 4, 5, or 6 substituents.
  • the number of substituents is none, 1, 2, 3, 4, or 5 as “optionally substituted with 0 to 4 as appropriate”.
  • No, 1, 2, 3, or 4 substituents, and “optionally substituted by 0 to 3” means “no, 1, 2, or 3 substituents” “0 to 2 may be substituted” means having none, 1 or 2 substituents, respectively.
  • the C1-C6 alkyl group may be linear or branched, and is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • 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
  • Examples of the C3-C8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
  • the C2-C6 alkenyl group represents an unsaturated hydrocarbon group having one or more double bonds and being linear or branched.
  • the C2-C6 alkenyl group includes vinyl group, 1-propenyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 2-methyl-1-propenyl group, and 1-pentenyl group.
  • 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 group in which the C1-C6 alkyl group is bonded via 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, 2-methyl-1-propenyloxy group, 1 -Pentenyloxy group, 2-pentenyloxy group, 3-pentenyloxy group, 4-pentenyloxy group, 2-methyl-1-butenyloxy group, 3-methyl-2-butenyloxy group, 1-hexenyloxy group, 2-hexenyl Examples thereof include an oxy group, a 3-hexenyloxy group, a 4-hexenyloxy group, a 5-hexenyloxy group, a 4-methyl-3-pentenyloxy group, and a 3-methyl-2-pentenyloxy group.
  • 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
  • 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 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 pyridone compound of the present invention includes a compound represented by the following formula (1) and a salt thereof. (Hereinafter also referred to as the compound of the present invention). Hereinafter, Formula (1) is demonstrated.
  • R1 in 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-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 C2-C6 alkenyloxy group optionally substituted with group A, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with
  • R1 is a C1-C6 alkyl group optionally substituted with the substituent A, a C1-C6 haloalkyl group, a C2-C6 alkenyl group optionally substituted with the substituent A, or a C2-C6 halo.
  • An alkenyl group, a C2-C6 alkynyl group optionally substituted with the substituent A, or a C2-C6 haloalkynyl group is preferred,
  • R1 is preferably a C1-C6 alkyl group or a C1-C6 haloalkyl group which may be optionally substituted with the substituent A.
  • 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, an ethyl group, or a propyl 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.
  • Ra and RbN— in R1 of the formula (1) (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 Each represents a haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb together with the nitrogen atom to which they are attached, represents an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group.
  • the definition of each term of (forms what is formed.) Is synonymous with the said definition.
  • RaRbN— is preferably an amino group, a methylamino group, an ethylamino group, a (methoxymethyl) amino group, a (2-methoxyethyl) amino group, a (cyanomethyl) amino group, a (2-cyanoethyl) amino group, Dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2- A difluoroethylamino group, a 2,2,2-trifluoroethylamino group,
  • R2 in formula (1) is a hydrogen atom, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a substituent A as appropriate.
  • C3-C8 cycloalkyl group which may be substituted, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, C2-C6 optionally substituted with substituent A C6-alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent A, C1-C6 haloalkoxy group, optionally substituted with substituent A C3- C8 cycloalkoxy group, C2-C6 alkenyloxy group optionally substituted with substituent A, C2-C6 haloalkenyloxy group, C3-C6 optionally substituted with substituent A Rukiniruokishi group, haloalkynyl group of C3 ⁇ C6, Rc-L- (wherein, Rc represents a haloalkyl group of alkyl or C1 ⁇ C6 of C1 ⁇ C6, L is S, SO,
  • R2 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a C2-C6 alkenyl group optionally substituted with a substituent A.
  • R2 is optionally substituted with a halogen atom, a C1-C6 alkyl group optionally substituted with the substituent A, a C2-C6 alkynyl group optionally substituted with the substituent A, or the substituent A.
  • Preferred is a C1-C6 alkoxy group.
  • R2 in Formula (1) includes a hydrogen atom, a cyano group, and a nitro group.
  • 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.
  • the C1-C6 alkyl group in the “C1-C6 alkyl group optionally substituted with the substituent A” in R2 of the formula (1) has the same definition as above, preferably a methyl group, an ethyl group , A propyl group, or an isopropyl 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 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 A” 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 A.
  • the C2-C6 alkenyl group in the “C2-C6 alkenyl group optionally substituted with the substituent A” in R2 of the 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 A.
  • 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 A” 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 A.
  • 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 A” in R2 of the formula (1) has the same definition as above, preferably a methoxy group, an ethoxy group , A propyloxy group, or an isopropyloxy 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 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 A” 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 with the substituent A.
  • the C2-C6 alkenyloxy group of “C2-C6 alkenyloxy group optionally substituted with substituent A” in R2 of 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 A.
  • the “C2-C6 haloalkenyloxy group” in R2 of the formula (1) has the same definition as above, and includes a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2-dichlorovinyloxy group. Group, 3-fluoroallyloxy group, 3,3-difluoroallyloxy group, or 3,3-dichloroallyloxy group, more preferably 2-fluorovinyloxy group or 2,2-difluorovinyloxy group It is.
  • the C3-C6 alkynyloxy group of “C3-C6 alkynyloxy group optionally substituted with substituent A” in R2 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 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.
  • Rc-L - in R2 of formula (1) (wherein, Rc represents a haloalkyl group of alkyl or C1 ⁇ C6 of C1 ⁇ C6, L represents S, SO, or SO 2.)
  • Rc—L— is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group or a methanesulfinyl group. Or a methanesulfonyl group.
  • Ra and Rb of “RaRbN—” in R2 of the formula (1) are as defined above.
  • “RaRbN—” is preferably an amino group, methylamino group, ethylamino group, propylamino group, isopropylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, dimethylamino group, ethyl (methyl) amino group, methyl (propyl) amino group, isopropyl (methyl) amino group, diethylamino group, ethyl (propyl) amino group, ethyl (isopropyl) amino group, (Methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2-diflu
  • RdC ( ⁇ O) — in R2 of the formula (1) (where Rd is a hydrogen atom, a C1-C6 alkyl group optionally substituted with the substituent B, a C1-C6 haloalkyl group, C3 -C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above).
  • Rd is a hydrogen atom, a C1-C6 alkyl group optionally substituted with the substituent B, a C1-C6 haloalkyl group, C3 -C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above).
  • C1-C6 alkyl group optionally substituted with substituent B when it has substituent B, the hydrogen atom in C1-C6 alkyl group is optionally substituted with substituent B.
  • RdC ( ⁇ O) — preferably formyl group, acetyl group, methoxyacetyl group, cyanoacetyl group, propionyl group, difluoroacetyl group, trifluoroacetyl group, cyclopropanecarbonyl group, methoxycarbonyl group, ethoxycarbonyl Group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group Ethylaminocarbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxye
  • X in the formula (1) represents an oxygen atom or a sulfur atom.
  • Preferred X is an oxygen atom.
  • Y in formula (1) may be optionally substituted with R3 as a phenyl group which may be optionally substituted with 0 to 5 (provided that each of R3 having two or more substituents is independent), or R3 may be optionally substituted with 0 to 4
  • a good pyridyl group in the case of R3 having two or more substituents, each independently
  • a pyridazinyl group optionally substituted by 0 to 3 with R3 in the case of R3 having two or more substitutions, each independently
  • Pyrimidinyl group optionally substituted with 0-3 by R3 (in the case of R3 having two or more substituents, each independently), pyrazinyl group optionally substituted with 0-3 by R3 ( However, in the case of R3 having two or more substitutions, each is independent.)
  • Y is a phenyl group which may be optionally substituted with 0 to 5 by R3 (however, in the case of R3 having two or more substitutions, each is independent), or a pyridyl group which may be optionally substituted with 0 to 4 by R3 (However, in the case of R3 having two or more substitutions, each is independent.)
  • Y is preferably a phenyl group which may be optionally substituted with 0 to 5 by R3 (however, in the case of R3 having 2 or more substitutions, each is independent).
  • na represents an integer of 0 to 5
  • two or more substituted R3s each represent an independent substituent, which may be the same or different, and may be arbitrarily selected. it can.
  • the “pyridyl group optionally substituted with 0 to 4 by R3” in Y of Formula (1) (however, each of R3 having 2 or more substituents is independent) is represented by Formula (b-1), Formula The following partial structures represented by (b-2) and formula (b-3) are represented.
  • nb represents an integer of 0 to 4, and when nb is 2 or more, two or more substituted R3s are independent substituents. May be the same or different and can be arbitrarily selected.
  • the “pyridazinyl group optionally substituted with 0-3 by R3” in Y of formula (1) (however, each of R3 having 2 or more substituents is independent) is represented by formula (c-1), formula The following partial structures represented by (c-2) and (c-3) are represented.
  • nc represents an integer of 0 to 3, and when nc is 2 or more, two or more substituted R3s are independent substituents. May be the same or different and can be arbitrarily selected.
  • the “pyrimidinyl group optionally substituted with 0-3 by R3” in Y of formula (1) (however, each of R3 having 2 or more substituents is independent) is represented by formula (d-1), formula The partial structures shown below represented by (d-2) and formula (d-3) are represented.
  • “Pyrazinyl group optionally substituted with 0 to 3 by R3 (in the case of R3 having 2 or more substituents)” in Y of Formula (1) is represented by Formula (e)
  • the partial structure shown below is represented.
  • ne represents an integer of 0 to 3
  • two or more substituted R3s each represent an independent substituent, which may be the same or different, and may be arbitrarily selected. it can.
  • a triazinyl group optionally substituted with 0 to 2 by R3” in Y of formula (1) is represented by formula (f-1), formula ( The partial structures shown below are represented by f-2), formula (f-3), formula (f-4) and formula (f-5).
  • nf represents an integer of 0 to 2
  • nf is 2.
  • each disubstituted R3 represents an independent substituent, may be the same or different, and can be arbitrarily selected.
  • the “tetrazinyl group optionally substituted with R3” in Y in formula (1) is a moiety represented by the following formula (g-1), formula (g-2) or formula (g-3) Represents the structure.
  • ng represents an integer of 0 to 1.
  • the “thienyl group optionally substituted with 0 to 3 by R3” in Y of formula (1) (however, each of R3 having 2 or more substituents is independent) is represented by formula (h-1) and formula The partial structure shown below represented by (h-2) is represented.
  • nh represents an integer of 0 to 3
  • nh is 2 or more
  • R3 each represents an independent substituent, and may be the same or different.
  • the “thiazolyl group optionally substituted by 0 to 2 with R3” in Y of the formula (1) is represented by the formula (i-1), the formula ( The partial structure shown below represented by i-2) and formula (i-3) is represented.
  • ni represents an integer of 0 to 2
  • each disubstituted R3 represents an independent substituent. May be the same or different and can be arbitrarily selected.
  • the “isothiazolyl group optionally substituted by 0 to 2 with R3” in Y of formula (1) (in the case of disubstituted R3, each independently) is represented by formula (j-1), formula ( The partial structure shown below represented by j-2) and formula (j-3) is represented.
  • nj represents an integer of 0 to 2
  • each disubstituted R3 represents an independent substituent. May be the same or different and can be arbitrarily selected.
  • the “thiadiazolyl group optionally substituted with R3” in Y in the formula (1) is the formula (k-1), the formula (k-2), the formula (k-3), the formula (k-4), the formula
  • the partial structures shown below represented by (k-5) and formula (k-6) are represented.
  • nk is an integer of 0 to 1 Represents.
  • R3 in Formula (1) is optionally substituted with a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, or 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 Alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 optionally substituted with substituent C
  • R3 represents a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group that may be optionally substituted with a substituent C, a C1-C6 alkoxy group that may be optionally substituted with a substituent C, a C1-C6 group.
  • R3 is preferably a cyano group, a halogen atom, or a C1-C6 alkoxy group optionally substituted with a substituent C.
  • R3 in the formula (1) includes a hydroxyl group, a cyano group, 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, a propyl group, or an isopropyl 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 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.
  • 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 Propyloxy group, isopropyloxy group, butoxy group, isobutoxy group or pentyloxy group, more preferably methoxy group or ethoxy 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 C3-C8 cycloalkoxy group in the “C3-C8 cycloalkoxy group optionally substituted with the substituent C” in R3 of the formula (1) has the same definition as 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 C.
  • the C2-C6 alkenyloxy group of “C2-C6 alkenyloxy group optionally substituted with substituent C” in R3 of formula (1) is as defined 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 C.
  • the “C2-C6 haloalkenyloxy group” in R3 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 C” in R3 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 C.
  • the “C3-C6 haloalkynyloxy group” in R3 of the formula (1) has the same definition as above, and is preferably a 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- A butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.
  • Rd of “RdC ( ⁇ O) —” in R3 of the formula (1) has the same definition as above.
  • RdC ( ⁇ O) — preferably formyl group, acetyl group, methoxyacetyl group, cyanoacetyl group, propionyl group, difluoroacetyl group, trifluoroacetyl group, cyclopropanecarbonyl group, methoxycarbonyl group, ethoxycarbonyl Group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group Ethylaminocarbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxyethyl) aminocarbonyl group, (cyanomethyl) aminocarbonyl group, (2-cyanoe
  • Rd of “RdC ( ⁇ O) O—” in R3 of the formula (1) has the same definition as above.
  • RdC ( ⁇ O) O— preferably formyloxy group, acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group, propionyloxy group, difluoroacetyloxy group, trifluoroacetyloxy group, cyclopropanecarbonyl Oxy group, methoxycarbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, Cyclopropyloxycarbonyloxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl) aminocarbonyloxy group, (2-methoxyethyl) aminocarbon
  • the “3- to 6-membered ring group containing 1 to 2 oxygen atoms” in R3 of the formula (1) is as defined above, and preferably an oxolanyl group, an oxanyl group, or 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.
  • Rc and L of “Rc-L-” in R3 of the formula (1) are as defined above.
  • Rc-L- is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group or a methanesulfinyl group. Or a methanesulfonyl group.
  • Ra and Rb of “RaRbN—” in R3 of the formula (1) are as defined above.
  • “RaRbN—” is preferably an amino group, methylamino group, ethylamino group, propylamino group, isopropylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, dimethylamino group, ethyl (methyl) amino group, methyl (propyl) amino group, isopropyl (methyl) amino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group (Cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, diethylamino group, ethyl (propyl) amino group, ethyl (isopropyl) amino group, ethy
  • ReC ( ⁇ O) N (Rf) — in R3 of the formula (1) (wherein Re and Rf are independent of each other and may be appropriately substituted with a hydrogen atom or a substituent B).
  • An 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 a RaRbN- (where Ra And Rb are as defined above.))) Are the same as defined above.
  • C1-C6 alkyl group optionally substituted with substituent B when it has substituent B, the hydrogen atom in C1-C6 alkyl group is optionally substituted with substituent B.
  • ReC ( ⁇ O) N (Rf) — preferably formylamino group, acetylamino group, methoxyacetylamino group, cyanoacetylamino group, propionylamino group, difluoroacetylamino group, trifluoroacetylamino group, Cyclopropanecarbonylamino group, methoxycarbonylamino group, ethoxycarbonylamino group, 2,2-difluoroethoxycarbonylamino group, 2,2,2-trifluoroethoxycarbonylamino group, 3,3,3-trifluoropropyloxycarbonyl Amino group, cyclopropyloxycarbonylamino group, aminocarbonylamino group, methylamin
  • R4 in formula (1) is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, or a C3-C8 optionally substituted with a substituent C.
  • Has C1-C6 halo Alkyl group (provided that when a 2-substituted or more substituents D, and independent of each other.), Or RaRbN- (wherein, Ra and
  • R4 is a hydrogen atom, 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 substituted group.
  • R4 is a hydrogen 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 D with 0-5 as appropriate.
  • a phenyl group which may be substituted in the case of two or more substituents D, each is independent), or RaRbN- (wherein Ra and Rb are as defined
  • R4 in the formula (1) includes a hydrogen atom.
  • the C1-C6 alkyl group in the “C1-C6 alkyl group optionally substituted with the substituent C” in R4 of the formula (1) has the same definition as above, preferably a methyl group, an ethyl group , Propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, pentyl group or isopentyl group, more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group , An isobutyl group, a sec-butyl group, or a t-butyl group.
  • the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent C.
  • the “C1-C6 haloalkyl group” in R4 of the formula (1) has the same definition as above, 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 of the “C3-C8 cycloalkyl group optionally substituted with the substituent C” in R4 of the formula (1) has the same definition as above, preferably a cyclopropyl group , A cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or a cycloheptyl group, and more preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group.
  • the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent C.
  • the C2-C6 alkenyl group of the “C2-C6 alkenyl group optionally substituted with substituent C” in R4 of the 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 C.
  • the “C2-C6 haloalkenyl group” in R4 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 R4 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 C.
  • the “C2-C6 haloalkynyl group” in R4 of the formula (1) has the same definition as 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- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.
  • C1-C6 alkyl group having a phenyl group which may be optionally substituted with 0 to 5 substituents D in R4 of formula (1) (however, in the case of substituents D having 2 or more substitutions, each is independent)
  • the “phenyl group which may be optionally substituted with 0 to 5 substituents D” and “C1-C6 alkyl group” in the formula (1) are as defined above.
  • the “C1-C6 alkyl group having a phenyl group” is preferably a phenylmethyl group, a 2-phenylethyl group, a 1-phenylethyl group, a 3-phenylpropyl group, a 2-phenylpropyl group, or a 1-phenylpropyl group.
  • 4-phenylbutyl group or 5-phenylpentyl group more preferably phenylmethyl group, 2-phenylethyl group, 1-phenylethyl group or 1-phenylpropyl group.
  • C1-C6 haloalkyl group having a phenyl group which may be optionally substituted with 0 to 5 substituents D in R4 of formula (1) (however, in the case of substituents D having 2 or more substitutions, each is independent
  • the “phenyl group which may be optionally substituted with 0 to 5 substituents D” and “C1-C6 haloalkyl group” in the above) have the same definitions as above.
  • the “C1-C6 haloalkyl group having a phenyl group” is preferably a 2,2,2-trifluoro-1-phenylethyl group or a 2,2-difluoro-1-phenylethyl group, more preferably 2,2,2-trifluoro-1-phenylethyl group.
  • the hydrogen atom in a phenyl group is arbitrarily substituted by the substituent D.
  • Ra and Rb of “RaRbN—” in R4 of the formula (1) are as defined above.
  • Ra and Rb are preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with the substituent B, or a C1-C6 haloalkyl group, and more preferably a hydrogen atom or the substituent B.
  • a C1-C6 alkyl group which may be optionally substituted.
  • RaRbN— is preferably an amino group, methylamino group, ethylamino group, propylamino group, isopropylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, dimethylamino group, ethyl (methyl) amino group, methyl (propyl) amino group, isopropyl (methyl) amino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group (Cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, diethylamino group, ethyl (propyl) amino group, ethyl (isopropyl) amino group, ethyl (methoxymethyl) amino group, ethyl (2-methoxyethyl) amino Group,
  • R5 in formula (1) is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with a substituent C A cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent C, a C2-C6 A haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents D (in the case of 2 or more substituents D, each independently), a substituent D with 0 to 5 substituents as appropriate A C1-C6 alkyl group having an optionally substituted phenyl group (in the case of two or more substituents D, each independently), a phenyl group optionally substituted
  • R5 is a hydrogen atom, 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 substituted group.
  • a C2-C6 alkenyl group optionally substituted with a group C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent C, a C2-C6 haloalkynyl group, or RdC ( ⁇ O) — (wherein Rd is as defined above) is preferable,
  • R5 is preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, or RdC ( ⁇ O) — (wherein Rd has the same meaning as described above).
  • R5 in the formula (1) includes a hydrogen atom.
  • the C1-C6 alkyl group of “C1-C6 alkyl group optionally substituted with substituent C” in R5 of 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 C.
  • the “C1-C6 haloalkyl group” in R5 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 substituent C” in R5 of the formula (1) has the same definition as above, preferably a cyclopropyl group , A cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or a cycloheptyl group, and more preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group.
  • the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent C.
  • the C2-C6 alkenyl group of “C2-C6 alkenyl group optionally substituted with substituent C” in R5 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 R5 of the formula (1) is as defined above, and 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 R5 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 C.
  • the “C2-C6 haloalkynyl group” in R5 of the formula (1) has the same definition as 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.
  • C1-C6 alkyl group having a phenyl group optionally substituted with 0-5 substituents D in R5 of formula (1) (however, in the case of a substituent D having 2 or more substitutions, each is independent)
  • the “phenyl group which may be optionally substituted with 0 to 5 substituents D” and “C1-C6 alkyl group” in the formula (1) are as defined above.
  • the “C1-C6 alkyl group having a phenyl group” is preferably a phenylmethyl group, a 2-phenylethyl group, a 1-phenylethyl group, a 3-phenylpropyl group, a 2-phenylpropyl group, or a 1-phenylpropyl group.
  • 4-phenylbutyl group or 5-phenylpentyl group more preferably phenylmethyl group, 2-phenylethyl group, 1-phenylethyl group or 1-phenylpropyl group.
  • C1-C6 haloalkyl group having a phenyl group which may be optionally substituted with 0 to 5 substituents D in R5 of formula (1) (however, in the case of substituents D having 2 or more substitutions, each is independent)
  • the “phenyl group which may be optionally substituted with 0 to 5 substituents D” and “C1-C6 haloalkyl group” in the above) have the same definitions as above.
  • the “C1-C6 haloalkyl group having a phenyl group” is preferably a 2,2,2-trifluoro-1-phenylethyl group or a 2,2-difluoro-1-phenylethyl group, more preferably 2,2,2-trifluoro-1-phenylethyl group.
  • the hydrogen atom in a phenyl group is arbitrarily substituted by the substituent D.
  • Rd of “RdC ( ⁇ O) —” in R5 of formula (1) has the same definition as above.
  • Rd is preferably a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group that may be optionally substituted with the substituent B, and more preferably with the substituent B.
  • C1-C6 alkyl group which may be substituted.
  • RdC ( ⁇ O) — preferably formyl group, acetyl group, methoxyacetyl group, cyanoacetyl group, propionyl group, difluoroacetyl group, trifluoroacetyl group, cyclopropanecarbonyl group, methoxycarbonyl group, ethoxycarbonyl Group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group Ethylaminocarbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxyethyl) aminocarbonyl group, (cyanomethyl) aminocarbonyl group, (2-cyanoethyl) aminocarbonyl group, dimethylaminocarbonyl group, Ru (methyl) aminocarbonyl group,
  • R4 and R5 together with the oxime structure to be bonded (C ⁇ N—O) together with the isoxazole ring optionally substituted with the substituent E (provided that the disubstituted In the case of the substituent E, each is independent.),
  • a benzisoxazole ring which may be optionally substituted with 0 to 4 substituents D (however, in the case of two or more substituents D, each is independent), or with 0 to 6 substituents as appropriate. It may represent a 5,6-dihydro-4H-1,2-oxazine ring (in the case of two or more substituents F, they are each independent).
  • R4 and R5 together with an oxime structure (C ⁇ N—O) to be bonded together and an isoxazole ring optionally substituted with 0 to 2 substituents E (in the case of a disubstituted substituent E, Each is independent.), An isoxazoline ring optionally substituted with 0 to 4 substituents F (however, in the case of two or more substituents F, each is independent), or a substituent D as appropriate Those which form a benzisoxazole ring which may be substituted by 0 to 4 (however, in the case of the substituent D having two or more substitutions, each is independent), In particular, R4 and R5 together with the oxime structure to which they are bonded (C ⁇ N—O) together with an isoxazole ring optionally substituted with 0 to 2 substituents E (provided that in the case of a disubstituted substituent E, Those which are independent of each other) are preferred.
  • R6 and R7 are each independently a hydrogen atom or a substituent E, and R1, R2, X and Y are as defined above.
  • R6 in formula (2) is specifically a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a substituent.
  • C3-C8 cycloalkyl group optionally substituted with C, C2-C6 alkenyl group optionally substituted with substituent C, haloalkenyl group C2-C6, optionally substituted with substituent C C2-C6 alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, optionally substituted with substituent C C3-C8 cycloalkoxy group, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group, C3-optionally substituted C3 C6 alkynyloxy group, C3 to C6 haloalkynyloxy group, C2 to C6 alkoxyalkoxy group, RaRbN- (wherein Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC ( ⁇
  • R6 is a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group that may be optionally substituted with a substituent C, a C1-C6 haloalkyl group, or a C2-C6 optionally substituted with a substituent C.
  • Rd is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent C, A C2-C6 alkynyl group optionally substituted with a substituent C, RdC ( ⁇ O) — (wherein Rd is as defined above), or RgON ⁇ C (Rh) — (wherein Rg and Rh are as defined above.
  • R7 in the formula (2) is specifically a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a substituent.
  • C3-C8 cycloalkyl group optionally substituted with C, C2-C6 alkenyl group optionally substituted with substituent C, haloalkenyl group C2-C6, optionally substituted with substituent C C2-C6 alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, optionally substituted with substituent C C3-C8 cycloalkoxy group, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group, C3-optionally substituted C3 C6 alkynyloxy group, C3 to C6 haloalkynyloxy group, C2 to C6 alkoxyalkoxy group, RaRbN- (wherein Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC ( ⁇
  • R7 is a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, or a C2-C6 optionally substituted with a substituent C.
  • RdC ( ⁇ O) — (where Rd is as defined above), or RiRjRkSi— (where Ri, Rj, and Rk are each independently a C1-C6 alkyl group).
  • R7 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with the substituent C, a C1-C6 haloalkyl group, RaRbN— (wherein Ra and Rb are as defined above), RdC ( ⁇ O) — (where Rd is as defined above), or RiRjRkSi— (where Ri, Rj and Rk are each independently a C1-C6 alkyl group). Is preferred.
  • R4 and R5 together with the oxime structure to be bonded form an isoxazoline ring optionally substituted with 0 to 4 substituents F (provided that In the case of two or more substituents F, each is independent.)
  • substituents F provided that In the case of two or more substituents F, each is independent.
  • R8, R9, R10 and R11 are each independently a hydrogen atom or a substituent F, and R1, R2, X and Y are as defined above.
  • R8 and R9 in formula (3) are independent of each other. Specifically, a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, C1-C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent C, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, substituted C2-C6 alkynyl group optionally substituted with group C, C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, substituted A C3-C8 cycloalkoxy group optionally substituted with the group C, a C2-C6 alkenyloxy group optionally substituted with the substituent C, a C2-C6 haloalken
  • R8 and R9 are each independently a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, or a C1-C6 haloalkyl group,
  • R8 and R9 are each independently a hydrogen atom or a halogen atom.
  • R10 and R11 in the formula (3) are independent of each other. Specifically, a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent C, C1-C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent C, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, substituted C2-C6 alkynyl group optionally substituted with group C, C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, substituted C3-C8 cycloalkoxy group optionally substituted with group C, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy A
  • R10 and R11 are independent of each other, and are optionally substituted with a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, or a substituent C.
  • Preferred is an optionally substituted C1-C6 alkoxy group, a C2-C6 alkenyloxy group optionally substituted with a substituent C, or a C3-C6 alkynyloxy group optionally substituted with a substituent C.
  • R10 and R11 are each independently a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, or a C1-C6 alkyl group optionally substituted with a substituent C.
  • Alkoxy groups are preferred.
  • R12, R13, R14 and R15 are each independently a hydrogen atom or a substituent D, and R1, R2, X and Y are as defined above.
  • R4 and R5 in formula (1) may be optionally substituted with 0 to 6 substituents F together with the oxime structure to which they are bonded (C ⁇ N—O) , 2-Oxazine ring (in the case of two or more substituents F, each independently) is represented by the formula (5) It is represented by
  • R16, R17, R18, R19, R20 and R21 are each independently a hydrogen atom or a substituent F, and R1, R2, X and Y are as defined above.
  • Substituent A 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, RaRbN- (where Ra and Rb Represents at least one selected from the group consisting of: and Rc-L- (wherein Rc and L are as defined above).
  • the substituent A is preferably a cyano group, a C1-C6 alkoxy group or Rc-L- (wherein Rc and L are as defined above), In particular, a cyano group or a C1-C6 alkoxy group is preferred.
  • substituent A is as defined above.
  • a C3-C8 cycloalkyl group a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
  • C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
  • a C3-C8 cycloalkoxy group a cyclopropyloxy group, a cyclobutoxy group, a cycl
  • 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; RaRbN- (wherein Ra and Rb are as defined above), a dimethylamino group, an ethyl (methyl) amino group, and a diethylamino group; And Rc-L- (wherein Rc and L are as defined above) include a methylthio group,
  • Substituent B represents 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 B is preferably a cyano group or a C1-C6 alkoxy group.
  • Each term of the substituent B is as defined above.
  • substituent B a cyano 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 B 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 substituent C includes 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, Rc-L- (where, Rc and L are as defined above), RdC ( ⁇ O) — (where Rd is as defined above), or RdC ( ⁇ O) O— (wherein Rd is as defined above) Are preferred.) In particular, a hydroxyl group or RdC ( ⁇ O) O— (wherein Rd has the same meaning as described above) is preferable.
  • RdC ( ⁇ O) O— is preferably a C1-C6 alkyl group or a C1-C6 haloalkyl group optionally substituted with the substituent B, and more preferably C1-C6.
  • a haloalkyl group is preferably a C1-C6 alkyl group or a C1-C6 haloalkyl group optionally substituted with the substituent B, and more preferably C1-C6.
  • a haloalkyl group is preferably a C1-C6 alkyl group or a C1-C6 haloalkyl group optionally substituted with the substituent B, and more preferably C1-C6.
  • substituent C a hydroxyl group; a cyano 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, a butoxy group, an isobutoxy group, and a t-butoxy group;
  • C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
  • a C3-C8 cycloalkoxy group a cyclopropyloxy 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, 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; RaRbN- (wherein Ra and Rb are as defined above), a dimethylamino
  • Substituent D is a hydroxyl group, cyano group, nitro group, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 optionally substituted with substituent B, C1- It represents at least one selected from the group consisting of a C6 alkoxy group, a C1-C6 haloalkoxy group, and a C3-C8 cycloalkoxy group.
  • the substituent D is a cyano group, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group, and a C1 to C6 haloalkoxy group that may be optionally substituted with a substituent B.
  • a halogen atom, a C1-C6 alkyl group which may be optionally substituted with the substituent B, and a C1-C6 alkoxy group are preferable.
  • substituent D has the same definition as above.
  • substituent B when it has substituent B, the hydrogen atom in C1-C6 alkyl group is optionally substituted with substituent B. .
  • substituent D a hydroxyl group; a cyano group; a nitro group;
  • substituent B a hydroxyl group; a cyano group; a nitro group;
  • substituent B a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, and 2-cyanoethyl.
  • C1-C6 haloalkyl groups include difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3-difluoropropyl, and 3,3,3 A trifluoropropyl 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, a butoxy group, an isobutoxy group, and a t-butoxy group;
  • C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-
  • substituent D a hydroxyl group; a cyano group; a nitro group; A halogen atom, a fluorine atom, a chlorine atom, and a bromine atom;
  • C1-C6 alkyl group that may be optionally substituted with the substituent B include a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, and 2- A cyanoethyl 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 cyclopropyl group and a cyclobutyl group as the C3-C8 cycloalkyl group; A
  • Substituent E is a hydroxyl group, cyano group, halogen atom, C1-C6 alkyl group optionally substituted with substituent C, C1-C6 haloalkyl group, C3-C8 optionally substituted with substituent C.
  • the substituent E is a C1-C6 alkyl group optionally substituted with a cyano group, a halogen atom, or a substituent C, a C1-C6 haloalkyl group, or a C3-C8 optionally substituted with a substituent C.
  • RaRbN— An optionally substituted C2-C6 alkynyl group, RaRbN— (wherein Ra and Rb are as defined above), RdC ( ⁇ O) — (wherein Rd is as defined above).
  • RgON C (Rh)-(where Rg and Rh are as defined above) and RiRjRkSi- (where Ri, Rj and Rk are as defined above).
  • substituent E has the same definition as above.
  • C1-C6 alkyl group optionally substituted with substituent C when it has substituent C, the hydrogen atom in C1-C6 alkyl group is optionally substituted with substituent C.
  • C3-C8 cycloalkyl group optionally substituted with substituent C when it has substituent C, a hydrogen atom in C3-C8 cycloalkyl group is optionally substituted with substituent C .
  • C2-C6 alkenyl group optionally substituted with substituent C when it has substituent C, a hydrogen atom in C2-C6 alkenyl group is optionally substituted with substituent C.
  • C2-C6 alkynyl group optionally substituted with substituent C when it has substituent C, a hydrogen atom in C2-C6 alkynyl group is optionally substituted with substituent C.
  • C1-C6 alkoxy group optionally substituted with the substituent C when having the substituent C, the hydrogen atom in the C1-C6 alkoxy group is optionally substituted with the substituent C.
  • C3-C8 cycloalkoxy group optionally substituted with substituent C when it has substituent C, a hydrogen atom in C3-C8 cycloalkoxy group is optionally substituted with substituent C .
  • C2-C6 alkenyloxy group optionally substituted with substituent C when it has substituent C, a hydrogen atom in C2-C6 alkenyloxy group is optionally substituted with substituent C .
  • C3-C6 alkynyloxy group optionally substituted with substituent C when it has substituent C, a hydrogen atom in C3-C6 alkynyloxy group is optionally substituted with substituent C .
  • substituent E a hydroxyl group; a cyano group; As halogen atom, fluorine atom, chlorine atom, bromine atom and iodine atom;
  • C1-C6 alkyl group optionally substituted with the substituent C include a methyl group, a hydroxymethyl group, a cyanomethyl group, a cyclopropylmethyl group, a cyclobutylmethyl group, a methoxymethyl group, an ethoxymethyl group, and a difluoromethoxymethyl group.
  • Trifluoromethoxymethyl group Trifluoromethoxymethyl group, cyclopropyloxymethyl group, cyclobutyloxymethyl group, methoxymethoxymethyl group, dimethylaminomethyl group, methylthiomethyl group, methylsulfinylmethyl group, methylsulfonylmethyl group, acetylmethyl group, propionoyl Methyl group, trifluoroacetylmethyl group, methoxycarbonylmethyl group, ethoxycarbonylmethyl group, acetyloxymethyl group, difluoroacetyloxymethyl group, trifluoroacetyloxymethyl group, (1,3-dioxy group) Lan-2-yl) methyl group, (1,3-dioxane-2-yl) methyl group, ethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 1- Methoxyethyl group,
  • 2-trifluoromethoxyvinyloxy group 2-cyclopropyloxyvinyloxy group, 2- (methoxymethoxy) vinyloxy group, 2- (dimethylamino) vinyloxy group, 2-acetylvinyloxy group, 2- (trifluoroacetyl) ) Vinyloxy group, 2- (1,3-dioxolan-2-yl) vinyloxy group, 2- (1,3-dioxane-2-yl) vinyloxy group, 1-propenyloxy group, 3-hydroxy-1-propenyloxy Group, allyloxy group, 1- (methoxymethoxy) allyloxy group, 1- (methyl) Thio) allyloxy group, 1- (methylsulfinyl) allyloxy group, 1- (methylsulfonyl) allyloxy group, 1- (acetyloxy) allyloxy group, 1- (difluoroacetyloxy) allyloxy group, 1- (trifluoroacetyloxy) An allyloxy
  • substituent E a hydroxyl group; a cyano group; As a halogen atom, a chlorine atom, a bromine atom and an iodine atom;
  • C1-C6 alkyl group that may be optionally substituted with the substituent C include a methyl group, a hydroxymethyl group, a methoxymethyl group, an acetyloxymethyl group, a difluoroacetyloxymethyl group, a trifluoroacetyloxymethyl group, an ethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-methoxyethyl group, 1- (acetyloxy) ethyl group, 2- (acetyloxy) ethyl group, 1- (difluoroacetyloxy) ethyl group, 2- (difluoro Acetyloxy) ethyl group, 1- (trifluoroacetyloxy
  • C3-C8 cycloalkoxy groups optionally substituted with substituent C include a cyclopropyloxy group, a cyclobutyloxy group, and a cyclopentyloxy group;
  • a C2-C6 alkenyloxy group optionally substituted with the substituent C includes a vinyloxy group, a 1-propenyloxy group, and an allyloxy group; 2-fluorovinyloxy group and 2,2-difluorovinyloxy group as C2-C6
  • the substituent F is a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group that may be optionally substituted with a substituent C, a C1-C6 haloalkyl group, or a C3-C8 optionally substituted with a substituent C.
  • the substituent F is a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a substituent C optionally substituted with a C3- C8 cycloalkyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, RdC ( ⁇ O) — (where Rd is as defined above) and RdC ( ⁇ O) O— (where Rd is as defined above) are preferred,
  • a halogen atom, a C1-C6 alkyl group that may be optionally substituted with the substituent C, and a C1-C6 alkoxy group that may be optionally substituted with the substituent C are preferable.
  • substituent F is as defined above.
  • C1-C6 alkyl group optionally substituted with substituent C when it has substituent C, the hydrogen atom in C1-C6 alkyl group is optionally substituted with substituent C.
  • C3-C8 cycloalkyl group optionally substituted with substituent C when it has substituent C, a hydrogen atom in C3-C8 cycloalkyl group is optionally substituted with substituent C .
  • C2-C6 alkenyl group optionally substituted with substituent C when it has substituent C, a hydrogen atom in C2-C6 alkenyl group is optionally substituted with substituent C.
  • C2-C6 alkynyl group optionally substituted with substituent C when it has substituent C, a hydrogen atom in C2-C6 alkynyl group is optionally substituted with substituent C.
  • C1-C6 alkoxy group optionally substituted with substituent C when it has substituent C, the hydrogen atom in the C1-C6 alkoxy group optionally substituted with substituent C is substituted.
  • group C when it has substituent C, a hydrogen atom in C3-C8 cycloalkoxy group is optionally substituted with substituent C .
  • C2-C6 alkenyloxy group optionally substituted with substituent C when it has substituent C, a hydrogen atom in C2-C6 alkenyloxy group is optionally substituted with substituent C .
  • C3-C6 alkynyloxy group optionally substituted with substituent C when it has substituent C, a hydrogen atom in C3-C6 alkynyloxy group is optionally substituted with substituent C .
  • substituent F a hydroxyl group; a cyano group;
  • substituent C halogen atom, fluorine atom, chlorine atom, bromine atom and iodine atom
  • substituent C examples include a methyl group, a hydroxymethyl group, a cyanomethyl group, a cyclopropylmethyl group, a cyclobutylmethyl group, a methoxymethyl group, an ethoxymethyl group, and a difluoromethoxymethyl group.
  • Trifluoromethoxymethyl group Trifluoromethoxymethyl group, cyclopropyloxymethyl group, cyclobutyloxymethyl group, methoxymethoxymethyl group, dimethylaminomethyl group, methylthiomethyl group, methylsulfinylmethyl group, methylsulfonylmethyl group, acetylmethyl group, propionoyl Methyl group, trifluoroacetylmethyl group, methoxycarbonylmethyl group, ethoxycarbonylmethyl group, acetyloxymethyl group, difluoroacetyloxymethyl group, trifluoroacetyloxymethyl group, (1,3-dioxy group) Lan-2-yl) methyl group, (1,3-dioxane-2-yl) methyl group, ethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 1- Methoxyethyl group,
  • 2-trifluoromethoxyvinyloxy group 2-cyclopropyloxyvinyloxy group, 2- (methoxymethoxy) vinyloxy group, 2- (dimethylamino) vinyloxy group, 2-acetylvinyloxy group, 2- (trifluoroacetyl) ) Vinyloxy group, 2- (1,3-dioxolan-2-yl) vinyloxy group, 2- (1,3-dioxane-2-yl) vinyloxy group, 1-propenyloxy group, 3-hydroxy-1-propenyloxy Group, allyloxy group, 1- (methoxymethoxy) allyloxy group, 1- (methyl) Thio) allyloxy group, 1- (methylsulfinyl) allyloxy group, 1- (methylsulfonyl) allyloxy group, 1- (acetyloxy) allyloxy group, 1- (difluoroacetyloxy) allyloxy group, 1- (trifluoroacetyloxy) An allyloxy
  • substituent F a hydroxyl group; a cyano group;
  • substituent C a halogen atom, a chlorine atom, a bromine atom and an iodine atom
  • Examples of the C1-C6 alkyl group optionally substituted with the substituent C include a methyl group, a hydroxymethyl group, a methoxymethyl group, an ethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-methoxyethyl group, Propyl group, and isopropyl group;
  • C3-C8 cycloalkyl groups optionally substituted with substituent C include a cyclopropyl group, a cyclobutyl group, and a cyclopentyl group;
  • the wavy line in the compound represented by formula (1) represents an E-form or a Z-form. That is, the formula (1-a) Or a compound represented by the formula (1-b) The compound represented by these is represented.
  • the ratio may be either one alone or a mixture of any ratio, and is not particularly limited.
  • the compound represented by the formula (1) may have axial asymmetry.
  • the isomer ratio is a single or an arbitrary mixing ratio, and is not particularly limited.
  • the compound represented by the 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 the 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.
  • Examples 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 particularly limited as long as they can be used as agricultural and horticultural fungicides. There is no.
  • R1, R2, R3, R4, R5, X, Y, Substituent A, Substituent B, Substituent C, Substituent D, Substituent E and Substituent F described above can be obtained in any desired combination.
  • the range of all the compounds is also described in this specification as the range of the compound represented by the formula (1) of the present invention.
  • the partial structure represented by Za is represented by the following formula (Za).
  • the partial structure represented by Zb is represented by the following formula (Zb).
  • the partial structure represented by Zc is represented by the following formula (Zc).
  • the partial structure represented by Zd is represented by the following formula (Zd).
  • the manufacturing method of the compound represented by Formula (1) of this invention is shown below.
  • the production method of the compound of the present invention is not limited to Production Method A to Production Method AQ.
  • Z1 represents a C1-C6 alkyl group
  • R22 represents a hydrogen atom or a C1-C6 alkyl group
  • R2, X and Y are as defined above.
  • Manufacturing method A is a manufacturing method of the compound represented by Formula (8) which is a manufacturing intermediate of this invention compound, Comprising: When represented by Formula (6), the compound represented by Formula (7) And a reaction method in a solvent in the presence of a base.
  • the compound represented by the formula (6) used in this reaction can be obtained as a commercial product, or can be produced using Reference Examples or known methods.
  • the compound represented by the formula (7) used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • the amount of the compound represented by formula (7) 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 formula (6). Usually, it is 1 equivalent or more and 3 equivalents or less.
  • Bases used in this reaction are inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and tripotassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide, sodium t-butoxide and potassium t-butoxide. Etc.
  • the base used in this reaction is not particularly limited as long as the target reaction proceeds, but is usually 0.01 equivalents or more and 3 equivalents or less with respect to the compound represented by formula (6). .
  • 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 (6). 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.
  • 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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.
  • reaction mixture containing the compound represented by the formula (8) obtained above is sodium sulfate or Although moisture can be removed with a desiccant such as magnesium sulfate, it is not essential.
  • reaction mixture containing the compound represented by the formula (8) 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 (8) obtained after evaporation of 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.
  • R22a represents a C1 to C6 alkyl group
  • R2, X, Y, and Z1 are as defined above.
  • Production method B is a method for obtaining a production intermediate represented by formula (8b) among compounds represented by formula (8), wherein the compound represented by formula (8a) 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 acid used in this reaction may be a catalytic amount and is not particularly limited as long as the target reaction proceeds, but is usually 0.01% with respect to the compound represented by formula (8a). More than equivalent. Further, 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 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 (8a). 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 (8a). It is below the equivalent.
  • 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 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 (8a). 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.
  • the 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (8b) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (8b) 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 (8b) 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 the formula (8b) has the formula (8b ′) (Wherein R2, X, Y and Z1 have the same meanings as described above.) Is also included.
  • the compound represented by the formula (8b ′) can be handled in the same manner as the compound represented by the formula (8b), and can be applied to the production method C, for example.
  • the compound represented by the formula (8b ′) contains an asymmetric carbon, but the isomer mixing ratio may be a single compound or a mixture of any ratio. Further, it may be a mixture of the compound represented by the formula (8b) and the compound represented by the formula (8b ′), and the isomer mixing ratio may be a single compound or a mixture of any ratio.
  • R23 is a hydrogen atom, 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-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, or a C3-optionally substituted
  • Production method C is a method for obtaining a compound represented by formula (9), which is a production intermediate of the compound of the present invention, and reacts a compound represented by formula (8) with R23NH 2 in the presence of an acid. Manufacturing method.
  • R23NH 2 used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • R23NH 2 may be a salt formed with an acidic compound such as hydrochloric acid or acetic acid, and is not particularly limited as long as the intended reaction proceeds.
  • R23NH 2 used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (8), and is not particularly limited as long as the target reaction proceeds, but usually 1 equivalent. More than 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 of R23NH 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 R23NH 2, is not limited in particular as long as the reaction proceeds to the desired, usually not more than 1 equivalent to 200 equivalents .
  • 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 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 (8). 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (9) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (9) 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 (9) 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.
  • Lv represents a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group, a leaving group such as a halogen atom, and R1, R2, X, Y, and Z1 are as defined above.
  • Production method D is a method for obtaining a compound represented by the formula (9b), which is a production intermediate of the compound of the present invention, in which the compound represented by the formula (9a) and R1-Lv are reacted in the presence of a base. It is a manufacturing method including making it react in a solvent.
  • the compound represented by the formula (9a), which is a raw material of the present invention, is produced by the production method C or Journal of Heterocyclic Chemistry, Vol. 20, paragraphs 65-67 (1983). It can synthesize
  • R1-Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • 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 (9a), and is not particularly limited as long as the target reaction proceeds. Equivalent to 10 equivalents.
  • 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 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 (9a). 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (9b) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (9b) 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 (9b) 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, Y, and Z1 are as defined above.
  • Production method E is a method for obtaining a compound represented by formula (9b-2) among compounds represented by formula (9b), wherein the compound represented by formula (9b-1) and a sulfurizing agent (SR) is a production method including reacting in a solvent.
  • SR sulfurizing 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 formula (9b-1), and is not particularly limited as long as the target reaction proceeds. Usually, it 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 (9b-1). 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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.
  • liquid separation operation is not essential.
  • the reaction mixture containing the compound represented by the formula (9b-2) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (9b-2) 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 (9b-2) 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.
  • R2a is 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 substituent C2-C6 alkenyl group optionally substituted with A, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent A, C2-C6 haloalkynyl group, or RdC ( ⁇ O) — (where Rd is as defined above), and R1, X, Y, Z1 and Lv are as defined above.
  • R2a is optionally substituted with a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a substituent A which may be optionally substituted with the substituent A.
  • C3-C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, C2-C6 optionally substituted with substituent A This is a method for obtaining a compound represented by the formula (9b-4), which is an alkynyl group, a C2-C6 haloalkynyl group, or RdC ( ⁇ O) — (wherein Rd is as defined above). And a process comprising reacting a compound represented by the formula (9b-3) with R2a-Lv in a solvent in the presence of a base.
  • R2a-Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • the amount of R2a-Lv used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (9b-3), and is not particularly limited as long as the target reaction proceeds. Usually, it 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 (9b-3), 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, Examples thereof include benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents can be used alone or in admixture of two or more.
  • ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane
  • benzene solvents such as benzene, toluene, x
  • 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 (9b-3). 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (9b-4) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (9b-4) 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 (9b-4) 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, X, Y, and Z1 are as defined above.
  • Production method G is a method for obtaining a compound represented by formula (10), which is a production intermediate of the compound of the present invention, and comprises a compound represented by formula (9b) and an oxidizing agent (Ox) in a solvent. It is a manufacturing method including making it react with.
  • 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 (9b). 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 (9b). 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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.
  • liquid separation operation is not essential.
  • the reaction mixture containing the compound represented by the formula (10) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (10) 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 (10) 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 (9b). 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 (9b). 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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.
  • liquid separation operation is not essential.
  • the reaction mixture containing the compound represented by the formula (10) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (10) 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 (10) 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 radical initiator and 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 (9b), the target reaction proceeds. As long as it does, it will not specifically limit. Usually, 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 (9b). 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (10) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (10) 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 (10) 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 represents a halogen atom
  • Z2 is a C1-C6 alkyl group
  • R5ON C (R4)-(R4 and R5 are as defined above, and the ON bond includes one or an arbitrary proportion of isomers. )
  • HalR represents a halogenating agent
  • R1, X and Y are as defined above.
  • Production method H is a method for obtaining a compound represented by formula (10b) in which R2b represents a halogen atom, and reacting a compound represented by formula (10a) with a halogenating agent (HalR) in a solvent. Manufacturing method.
  • 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 (10a). 1 equivalent or more and 10 equivalents or less.
  • 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 is usually 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.
  • 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 target reaction proceeds. 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 is usually 3 to 200 times by weight with respect to the compound represented by the formula (10a). 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (10b) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (10b) 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 (10b) 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.
  • J represents an oxygen atom or a sulfur atom
  • R2c is a C1-C6 alkyl group, C1-C6 haloalkyl group, or substituent A optionally substituted with the substituent A.
  • J represents an oxygen atom or a sulfur atom
  • R2c may be optionally substituted with a substituent A, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a substituent C3-C8 cycloalkyl group optionally substituted with A, C2-C6 alkenyl group optionally substituted with substituent A, haloalkenyl group C2-C6, optionally substituted with substituent A A C2-C6 alkynyl group, a C2-C6 haloalkynyl group, and when J is a sulfur atom, R2c is represented by the formula (10c), which represents a C1-C6 alkyl group or a C1-C6 haloalkyl group
  • a method for obtaining a compound comprising obtaining a compound represented by the formula (10b) and R2c-JQ by a coupling reaction in the presence of a transition metal.
  • R 2b is a chlorine atom, a bromine atom, or an iodine atom.
  • R2c-JQ used in this reaction can be obtained as a commercially available 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 R2c-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 (10b).
  • 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 usually 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (10b), but is particularly limited as long as the target reaction proceeds. It will never be done.
  • 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 usually 0.001 equivalents or more and 1 equivalent or less with respect to the compound represented by the formula (10b), but particularly as long as the target reaction proceeds. There is no limit.
  • 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 (10b). More than 50 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but R2c-JH (wherein R2c has the same meaning as described above, and J is an oxygen atom).
  • Alcohol 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 Is mentioned.
  • 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 is usually 3 to 200 times by weight with respect to the compound represented by the formula (10b). 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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.
  • 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 (10c) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (10c) 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 (10c) 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.
  • R2d is 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 substituent A Represents an optionally substituted C2-C6 alkenyl group or C2-C6 haloalkenyl group, R2d-B represents an organic boronic acid, and R1, R2b, X, Y and Z2 are as defined above .
  • R2d is 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,
  • This is a production method comprising obtaining a compound and an organic boronic acid (R2d-B) by a Suzuki-Miyaura coupling in which a reaction is performed in the presence of a transition metal and a base.
  • R 2b is a chlorine atom, a bromine atom, or an iodine atom.
  • R2d-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 R2d-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 formula (10b). 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 usually 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (10b), but is particularly limited as long as the target reaction proceeds. It will never be done.
  • phosphine ligands such as triphenylphosphine and tricyclohexylphosphine can be added.
  • the amount of the phosphine ligand used in this reaction is usually 0.001 equivalents or more and 1 equivalent or less with respect to the compound represented by the formula (10b), but particularly as long as the target reaction proceeds. There is no limit.
  • Bases used in this reaction are inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and tripotassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide, sodium t-butoxide and potassium t-butoxide. Etc.
  • 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 (10b). More than 50 equivalents.
  • 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 is usually 3 to 200 times by weight with respect to the compound represented by the formula (10b). 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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.
  • 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 (10d) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (10d) 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 (10d) 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 C2-C6 alkynyl group or a C2-C6 haloalkynyl group which may be optionally substituted with the substituent A, and R1, R2b, X, Y and Z2 are as defined above.
  • Production method K is a method for obtaining a compound represented by the formula (10e), wherein R2e is a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with substituent A,
  • This is a production method including obtaining a compound represented by (10b) and a terminal alkyne compound by Sonogashira coupling in which the compound is reacted in the presence of a transition metal and a base.
  • R 2b 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 can be produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to desilylate after introducing a trimethylsilylethynyl group into the compound represented by the formula (10b).
  • desilylation Journal of the American Chemical Society, Vol. 131, No. 2, pages 634-643 (2009). And Journal of Organometallic Chemistry, Vol. 696, No. 25, pages 4039-4045 (2011). 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 (10b). 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 is usually 0.001 equivalent or more with respect to the compound represented by the formula (10b) in which palladium and the like are each represented by the formula (10b). There is no particular limitation as long as it progresses. 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 (10b). More than 50 equivalents.
  • the organic base when the organic base 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 usually 0.001 equivalents or more and 1 equivalent or less with respect to the compound represented by the formula (10b), but particularly as long as the target reaction proceeds. There is no limit.
  • 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 is usually 3 to 200 times by weight with respect to the compound represented by the formula (10b). 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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.
  • 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 (10e) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (10e) 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 (10e) 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.
  • Z3 represents a halogen atom
  • HalR, R1, R2, X, and Y are as defined above.
  • Production method L is a method for obtaining a compound represented by formula (10f) in which Z3 is a halogen atom, and is represented by formula (10-1) using a radical initiator and a halogenating agent (HalR). It is a manufacturing method including reacting a compound.
  • preferable Z3 is a chlorine atom, a bromine atom, or an iodine atom.
  • radical initiator used in this reaction include azobisisobutyronitrile and benzoyl peroxide.
  • the amount of the radical initiator used in this reaction is not particularly limited as long as the target reaction proceeds, but is usually 0.01 equivalent to the compound represented by the formula (10-1). It is 1.0 equivalent or less.
  • the halogenating agent used in this reaction is N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin 1,3-diiodo-5,5-dimethylhydantoin 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 2 equivalents or more with respect to the compound represented by formula (10-1). Usually, it is 2 equivalents or more and 2.8 equivalents or less.
  • 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 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 (10-1). 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (10f) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (10f) 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 (10f) 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.
  • Production method M is a method for obtaining a compound represented by formula (10g), which is a production intermediate of the compound of the present invention, and comprises hydrolyzing the compound represented by formula (10f) in the presence of water. It is a manufacturing method.
  • Z3 is a chlorine atom, a bromine atom, or an iodine atom.
  • Water is essential for this reaction.
  • silver nitrate can be used in order to make this reaction proceed smoothly.
  • the amount of water used in this reaction is not 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 (10f). Moreover, water can be used as a solvent.
  • the amount of silver nitrate used in this reaction is not limited as long as the target reaction proceeds as long as it is 2 equivalents or more with respect to the compound represented by formula (10f). It is below the equivalent.
  • 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. And nitrile solvents such as acetonitrile and acetonitrile. 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 (10f). 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 ⁇ 10 ° C. or higher and 100 ° 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (10 g) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (10 g) 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 (10 g) 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.
  • R4a 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 A C2-C6 alkenyl group optionally substituted with a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent C, a C2-C6 haloalkynyl group, a substituent D A phenyl group which may be optionally substituted with 0 to 5 (provided that in the case of two or more substituents D, each independently), a phenyl group which may be appropriately substituted with 0 to 5 substituents D C1-C6 alkyl group (in the case of two or more substituents D, each independently), or C1-C6 haloalkyl having a
  • R4a 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 substituted C2-C6 alkenyl group optionally substituted with group C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2-C6 haloalkynyl group, substituted A phenyl group which may be optionally substituted with 0 to 5 by the group D (however, in the case of the substituent D having 2 or more substituents, each is independently), a phenyl group which may be optionally substituted with 0 to 5 by the substituent D Or a C1-C6 alkyl group having a phenyl group which may be optionally substituted with 0-5 substituents D.
  • the Haroa A method for obtaining a compound represented by the formula (10h) which is a kill group (however, in the case of a substituent D having two or more substitutions, each), and a compound represented by the formula (10g) It is a manufacturing method including reacting an organometallic reagent in a solvent.
  • organometallic reagents used in this reaction include organomagnesium halides (R4a-Mg-Hal: where Hal represents a halogen atom and R4a is as defined above), organolithium reagents (R4a-Li: Here, R4a has the same meaning as described above), organomagnesium halide-zinc (II) ate complex reagent ([(R4a) 3 -Zn] - [Mg-Hal] + [Mg- (Hal) 2 ] 2 Where R4a and Hal are as defined above).
  • organometallic reagents can be obtained as commercially available products or can be produced by known methods.
  • the amount of the organometallic reagent used in this reaction may be 1 equivalent or more with respect to the formula (10 g), and is not particularly limited as long as the target reaction proceeds. Usually, it is 1 equivalent or more and 10 equivalents or less.
  • the solvent used in the reaction is not particularly limited as long as the target reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and hexane , Hydrocarbon solvents such as 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 the formula (10 g). 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (10h) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (10h) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (10h) 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.
  • Ox ′ represents an oxidizing agent
  • R1, R2, X, Y, and R4a have the same meanings as described above.
  • Production method O is a method for obtaining a compound represented by formula (10i), which is a production intermediate of the compound of the present invention, in which a compound represented by formula (10h) and an oxidizing agent (Ox ′) are mixed with a solvent. It is a manufacturing method including making it react in.
  • This production method should be carried out by oxidation methods commonly used by those skilled in the art, such as Dess-Martin oxidation, Swern oxidation, Parrick-Doering oxidation, etc. Can do.
  • the oxidation reaction is not particularly limited as long as the target reaction proceeds.
  • the method of the Parrick-Deiling oxidation using dimethyl sulfoxide, pyridine-sulfur trioxide complex and a base in a solvent is described.
  • the dimethyl sulfoxide 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 (10h), and should be used as a solvent. You can also.
  • the pyridine-sulfur trioxide complex 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 (10h). 1 equivalent or more and 20 equivalents or less.
  • Examples of the base used in this reaction include organic amines such as triethylamine, tributylamine and 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 (10h). 50 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, sulfur solvents such as dimethyl sulfoxide, and the like. Can be mentioned. 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 the formula (10h). 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 ⁇ 10 ° 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (10i) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (10i) 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 (10i) 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.
  • R4b is a hydrogen atom, 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.
  • C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2-C6 haloalkynyl group A phenyl group that may be optionally substituted with 0 to 5 substituents D (provided that each of substituents D is 2 or more is independent), and optionally substituted with 0 to 5 substituents D.
  • R4b is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a substituent C
  • R4b is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a substituent C
  • R4b is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a substituent C
  • a substituent C Optionally substituted with a C3-C8 cycloalkyl group optionally substituted with a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, and optionally substituted with a substituent C.
  • a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, and a phenyl group optionally substituted with 0 to 5 substituents D (in the case of a substituent D having 2 or more substituents, each is independent)
  • a process comprising reacting a compound represented by formula (10j) with R5ONH2 in a solvent.
  • R5ONH2 used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • R5ONH2 may be a salt formed with an acidic compound such as hydrochloric acid or sulfuric acid, and can be used in the presence of a base in the reaction system.
  • bases used include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine, and lutidine.
  • bases used include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine, and lutidine.
  • triethylamine tributylamine,
  • the amount of the base used may be 1 equivalent or more with respect to R5ONH2, and is not particularly limited as long as the intended reaction proceeds, but is usually 1 equivalent or more and 20 equivalents or less. It is also possible to use R5ONH2 after desalting by a known method in advance.
  • the amount of R5ONH2 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 (10j). It is 20 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 is usually 3 to 200 times by weight with respect to the compound represented by the formula (10j). 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.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • 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.
  • Production method Q is a method for obtaining a compound represented by formula (1d), which is a production intermediate of the present invention, and reacting a compound represented by formula (1b) with a chlorinating agent in a solvent. It is a manufacturing method including.
  • chlorinating agent used in this reaction examples include N-chlorosuccinimide and 1,3-dichloro-5,5-dimethylhydantoin.
  • the amount of the chlorinating agent used in this reaction is, in the case of N-chlorosuccinimide, as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by formula (1b). Although it does not restrict
  • 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 and carbon tetrachloride.
  • 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 ⁇ 10 ° 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (1d) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (1d) 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 (1d) 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.
  • Production method R is a method for obtaining a compound represented by formula (1e) among compounds represented by formula (1), wherein a compound represented by formula (1d) and an organometallic reagent are mixed with a solvent. It is a manufacturing method including making it react in.
  • organometallic reagents used in this reaction include organomagnesium halides (R4a-Mg-Hal: where Hal represents a halogen atom and R4a is as defined above), organolithium reagents (R4a-Li: Here, R4a is as defined above.
  • organometallic reagents can be obtained as commercially available products or can be produced by known methods.
  • the amount of the organometallic reagent used in this reaction may be 2 equivalents or more with respect to the formula represented by formula (1d), and is not particularly limited as long as the target reaction proceeds. Usually, it is 2 equivalents or more and 10 equivalents or less.
  • the solvent used in the reaction is not particularly limited as long as the target reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and hexane , Hydrocarbon solvents such as heptane, cyclohexane and methylcyclohexane. These solvents can be used alone or in admixture of two or more.
  • 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (1e) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (1e) 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 (1e) 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.
  • Production method S is a method for obtaining a compound represented by formula (1f) among the compounds represented by formula (1), wherein the compound represented by formula (1d) and RaRbNH are mixed in a solvent. It is a manufacturing method including reacting.
  • RaRbNH used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • RaRbNH may be a salt formed with an acidic compound such as hydrochloric acid or sulfuric acid, and can be used in the presence of a base in the reaction system.
  • bases used include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine, and lutidine.
  • bases used include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine, and lutidine.
  • triethylamine tributylamine
  • the amount of the base used may be 1 equivalent or more with respect to RaRbNH, and is not particularly limited as long as the target reaction proceeds, but is usually 1 equivalent or more and 20 equivalents or less. It is also possible to use RaRbNH after desalting by a known method in advance.
  • the amount of RaRbNH used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 2 equivalents or more with respect to the compound represented by formula (1d). It is 20 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, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide and N, N-dimethylacetamide; Urea solvents such as 1,3-dimethyl-2-imidazolidinone, 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 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 (1d). 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 ⁇ 10 ° 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (1f) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (1f) 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 (1f) 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 is a C1-C6 alkyl group optionally substituted with the substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with the 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, C2-C6 haloalkynyl group, substituent A C1-C6 alkyl group having a phenyl group which may be optionally substituted with 0 to 5 by D (however, in the case of two or more substituents D, each is independent); A C1-C6 haloalkyl group having an optionally substituted phenyl group (however, in the case of two or more substituents D, each is independent), or RdC ( ⁇ O) — (where Rd is Synonym
  • Production method T is a method for obtaining a compound represented by formula (1h) among compounds represented by formula (1), wherein a compound represented by formula (1g) and R5a-Lv are converted into a base It is a manufacturing method including making it react in presence.
  • R5a-Lv used in this reaction can be obtained as a commercial product or can be obtained by a known method.
  • R5a-Lv used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (1g), and is not particularly limited as long as the target reaction proceeds. Equivalent to 50 equivalents.
  • Examples of the base used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine and lutidine.
  • examples thereof include transition metals such as silver (I) oxide, but are not particularly limited as long as the target reaction proceeds.
  • the base used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (1g), and is not particularly limited as long as the target reaction proceeds, but usually 1 equivalent or more. 50 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, 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 and carbon tetrachloride.
  • 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 the formula (1 g). 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 ⁇ 10 ° 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (1h) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (1h) 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 (1h) 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 the formula (11) used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • the compound represented by the formula (11) used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (1d), and is not particularly limited as long as the target reaction proceeds. Usually, it is 1 equivalent or more and 20 equivalents or less.
  • Bases used in this reaction are inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and 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 and 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 (1d), and is not particularly limited as long as the target reaction proceeds, but usually 1 equivalent or more. 20 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, 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, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc. Examples include halogen-based solvent media. 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 (1d). 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (3) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • 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.
  • R8a represents a halogen atom
  • R1, R2, R9, R10, R11, X, and Y are as defined above.
  • Production method V is a method of obtaining a compound represented by formula (3b) among compounds represented by formula (3), wherein the compound represented by formula (3a) is converted into a radical initiator and a halogenating agent. And a reaction method in a solvent.
  • radical initiator used in this reaction examples include azobisisobutyronitrile and benzoyl peroxide.
  • the amount of the radical initiator used in this reaction may be 0.01 equivalent or more with respect to the compound represented by formula (3a), and is not particularly limited as long as the target reaction proceeds. Is usually not less than 0.01 equivalent and not more than 1 equivalent.
  • N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethyl Hydantoin, 1,3-diiodo-5,5-dimethylhydantoin and the like can be mentioned.
  • the amount of the halogenating agent used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (3a), and is particularly limited as long as the target reaction proceeds. Usually, it is 1 equivalent or more and 3 equivalents or less.
  • the hydantoins may be 0.5 equivalent or more with respect to the compound represented by the formula (3a), and are not particularly limited as long as the target reaction proceeds. It is 5 equivalents or more and 1.5 equivalents or less.
  • 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 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (3b) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • 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 the formula (3b) 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.
  • R24 represents a C1-C6 alkyl group
  • R1, R2, R8, R10, X and Y are as defined above.
  • Production method W is a production method for obtaining a compound represented by formula (2a) among the compounds represented by formula (2), wherein the compound represented by formula (3c) is dissolved in the presence of an acid in a solvent. It is a manufacturing method including making it react in.
  • Examples of 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. There is no particular limitation as long as the target reaction proceeds.
  • the amount of acid used in this reaction may be a catalytic amount and is not particularly limited as long as the target reaction proceeds, but is usually 0.01% relative to the compound represented by formula (3c). More than equivalent. Further, 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 (3c). 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.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (2a) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (2a) 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 (2a) 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 production method X is a method for obtaining a compound represented by the formula (2).
  • the compound represented by the formula (12) is reacted in a solvent in the presence of a base. It is a manufacturing method containing.
  • the compound represented by the formula (12) used in this reaction can be obtained as a commercially available product or can be produced by a known method.
  • the compound represented by the formula (12) used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (1d), and is not particularly limited as long as the target reaction proceeds. Usually, it is 1 equivalent or more and 100 equivalent or less.
  • Bases used in this reaction are inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and 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 and 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 (1d), and is not particularly limited as long as the target reaction proceeds, but usually 1 equivalent or more. 20 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, 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, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc. Examples include halogen-based solvent media. 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 (1d). 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (2) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (2) 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 (2) 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.
  • R6a represents a halogen atom
  • R1, R2, R7, X and Y have the same meanings as described above.
  • the production method Y is a method for obtaining a compound represented by the formula (2c) among the compounds represented by the formula (2), wherein the compound represented by the formula (2b) and the halogenating agent are mixed with a solvent. It is a manufacturing method including making it react in.
  • 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 (2b). 1 equivalent or more and 100 equivalents or less.
  • 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 is usually 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.
  • 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 target reaction proceeds. 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 is usually 3 to 200 times by weight with respect to the compound represented by the formula (2b). 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.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (2c) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (2c) 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 (2c) 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.
  • Production method Z is a method for obtaining a compound represented by formula (2e) among compounds represented by formula (2), wherein the compound represented by formula (2d) and the fluorine-containing compound are mixed with a solvent. It is a manufacturing method including making it react in.
  • fluorine-containing compound used in this reaction examples include inorganic salts such as sodium fluoride, potassium fluoride and cesium fluoride, and organic salts such as tetrabutylammonium fluoride.
  • the amount of the fluorine-containing 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 (2d). 1 equivalent or more and 20 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, Examples thereof include 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 is usually 3 to 200 times by weight with respect to the compound represented by the formula (2d). 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (2e) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (2e) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (2e) 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.
  • R4c and R5b are each independently a hydrogen atom or a C1-C6 alkyl group, and R1, R2, X and Y are as defined above.
  • Production method AA is a method for obtaining a compound represented by formula (2f) among compounds represented by formula (2), in which a compound represented by formula (1i) is treated with iodine and iodine in the presence of a base. It is a manufacturing method including reacting a metal iodide with a solvent.
  • the compound represented by the formula (1i) used for this reaction can be prepared by the method described in Production Method R.
  • Bases used in this reaction are inorganic bases such as sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, cesium carbonate, cesium bicarbonate, sodium methoxide, sodium ethoxide, sodium t-butoxide, potassium t.
  • Metal alkoxides such as 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 formula (1i). Equivalent to 30 equivalents.
  • the amount of iodine 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 (1i). Equivalent to 30 equivalents.
  • Examples of the metal iodide used in this reaction include sodium iodide and potassium iodide.
  • the amount of metal iodide 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 (1i). 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 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 such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, nitrile solvents such as acetonitrile, amides such as N-methylpyrrolidone, N, N-dimethylformamide and N, N-dimethylacetamide
  • amides such as N-methylpyrrolidone, N, N-dimethylformamide and N, N-dimethylacetamide
  • the solvent include urea solvents such as 1,3-dimethyl-2-imidazolidinone, 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 to 200 times by weight with respect to the compound represented by formula (1i). 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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.
  • 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.
  • reaction mixture containing the compound represented by the formula (2f) 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 (2f) 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.
  • R6b represents a hydrogen atom or a substituent E
  • Ox ′′ represents an oxidizing agent
  • R1, R2, Rh, X, and Y have the same meanings as described above.
  • Production method AB is a method for obtaining a compound represented by formula (2h) among compounds represented by formula (2), and comprises a compound represented by formula (2g) and an oxidizing agent (Ox ′′). And a reaction method in a solvent.
  • This production method should be carried out by oxidation methods commonly used by those skilled in the art, such as Dess-Martin oxidation, Swern oxidation, Parrick-Doering oxidation, etc. Can do.
  • the oxidation reaction is not particularly limited as long as the target reaction proceeds.
  • the method of Dess-Martin oxidation using Dess-Martin reagent in a solvent is demonstrated.
  • the oxidizing agent used in this reaction is Dess-Martin reagent (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (1H) -one), which is a commercially available product. Can be obtained as
  • 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 (2g). It is 20 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, sulfur solvents such as dimethyl sulfoxide, and the like. Can be mentioned. 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 is usually 3 to 200 times by weight with respect to the compound represented by the formula (2g). 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 ⁇ 10 ° 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (2h) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (2h) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (2h) 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.
  • Production method AC is a method for obtaining a compound represented by formula (2j) among compounds represented by formula (2), wherein the compound represented by formula (2i), a fluorinating agent (FR), Is a production method comprising reacting in a solvent.
  • fluorinating agent used in this reaction (diethylamino) sulfur trifluoride, bis (2-methoxyethyl) aminosulfur trifluoride, N, N-diethyl-1,1,2,3,3,3-hexafluoropropyl Amine, 2,2-difluoro-1,3-dimethylimidazolidine and the like.
  • the amount of the fluorinating agent used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (2i), 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, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, nitrile solvents such as acetonitrile, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, hexane, heptane, cyclohexane, methylcyclohexane, etc. Examples include hydrocarbon solvents. 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 is usually 3 to 200 times by weight with respect to the compound represented by the formula (2i). 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 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.
  • the reaction mixture containing the compound represented by the formula (2j) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (2j) 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 (2j) 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.
  • Production method AD is a method for obtaining a compound represented by formula (2k) among compounds represented by formula (2), wherein the compound represented by formula (2g) and RgONH2 are mixed in a solvent. It is a manufacturing method including reacting.
  • the production method AD is carried out according to the production method P by using the compound represented by the formula (10j) and R5ONH2 in the production method P instead of the compound represented by the formula (2g) and RgONH2, respectively. Can do.
  • Rl is a hydrogen atom or a C1-C4 alkyl group
  • R1, R2, R6b, X and Y are as defined above.
  • the C1-C4 alkyl group represents a C1-C6 alkyl group having 1 to 4 carbon atoms.
  • Production method AE is a method for obtaining a compound represented by formula (2m) among compounds represented by formula (2), wherein a compound represented by formula (2l) and a diazophosphonate reagent are mixed with a base. It is a production method in which a reaction is carried out in a solvent in the presence.
  • diazophosphonate reagent used in this reaction examples include dimethyl (1-diazo-2-oxypropyl) phosphonate and dimethyl (diazomethyl) phosphonate.
  • the amount of the diazophosphonate reagent used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (2l), and is not particularly limited as long as the target reaction proceeds. Usually, it is 1 equivalent or more and 10 equivalents or less.
  • Bases used in this reaction are inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride, sodium methoxide, sodium ethoxide, sodium t-butoxide, potassium t- Metal alkoxides such as butoxide.
  • the amount of the base used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (2l), and is not particularly limited as long as the target reaction proceeds. Equivalent to 20 equivalents.
  • 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, isopropanol and the like can be mentioned. 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 (2l). 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 100 ° 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 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.
  • reaction mixture containing the compound represented by the formula (2m) 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 (2m) 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.
  • R6c is a C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 halo optionally substituted with the substituent B.
  • R7a is a C1-C6 alkyl group optionally substituted with the substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with the substituent C, and a substituent C appropriately.
  • An optionally substituted C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent C, a C2-C6 haloalkynyl group, and R1, R2, X and Y are as defined above.
  • Production method AF is a method for obtaining a compound represented by formula (2n) among compounds represented by formula (2), and is represented by a compound represented by formula (1d) and formula (13). This is a production method comprising reacting a compound in a solvent in the presence of a base.
  • the compound represented by the formula (13) used in this reaction can be obtained as a commercially available product or can be produced by a known method.
  • the production method AF can be performed according to the production method X.
  • Production method AG is a method of obtaining formula (2g) among the compounds represented by formula (2), wherein the compound represented by formula (2h) is reacted with a hydride reagent in a solvent. It is a manufacturing method including.
  • Examples of the hydride reagent used in this reaction include borons such as sodium borohydride.
  • the hydride reagent used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more in terms of hydride with respect to the compound represented by formula (2h). 1 equivalent or more and 40 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.
  • the solvent include alcohol solvents such as methanol, ethanol, and isopropanol. 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 the formula (2h). 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (2g) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (2g) 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 (2 g) 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.
  • Rm and Rn are each independently a hydrogen atom or a C1-C4 alkyl group (provided that the total number of carbon atoms of Rm and Rn is 4 or less), and R1, R2, R6b , X and Y are as defined above.
  • the C1-C4 alkyl group represents a C1-C6 alkyl group having 1 to 4 carbon atoms.
  • Production method AH is a method for obtaining a compound represented by formula (2p) among compounds represented by formula (2), wherein the compound represented by formula (2o) is dissolved in a solvent in the presence of an acid. It is a manufacturing method including making it react with.
  • Examples of 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. There is no particular limitation as long as the target reaction proceeds.
  • 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, but usually 0.01% relative to the compound represented by the formula (2o). More than equivalent. Further, 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 the formula (2o). 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.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (2p) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (2p) 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 (2p) 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.
  • Production method AI is a method for obtaining a compound represented by formula (4), wherein a compound represented by formula (1d), a compound represented by formula (14) and a fluorine-containing compound are mixed in a solvent. It is a manufacturing method including reacting.
  • the compound represented by the formula (14) used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • the amount of the compound represented by formula (14) 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 formula (1d). Usually, it is 1 equivalent or more and 30 equivalent or less.
  • fluorine-containing compound used in this reaction examples include inorganic salts such as sodium fluoride, potassium fluoride and cesium fluoride, and organic salts such as tetrabutylammonium fluoride.
  • the amount of the fluorine-containing compound used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 2 equivalents or more with respect to the compound represented by the formula (1d). 2 equivalents or more and 30 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, 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, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc. Halogen type solvent etc. are mentioned. 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 (1d). 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (4) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (4) 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 (4) 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.
  • R3a represents a halogen atom
  • R3b represents a C1-C6 alkoxy group that may be optionally substituted with a substituent C, a C1-C6 haloalkoxy group, and a C3-C8 optionally substituted with a substituent C.
  • R3b is optionally substituted with a C1-C6 alkoxy group, C1-C6 haloalkoxy group, or substituent C optionally substituted with a substituent C.
  • C3-C8 cycloalkoxy group which may be substituted, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group, optionally substituted with substituent C
  • C represents a C3-C6 alkynyloxy group or a C3-C6 haloalkynyloxy group
  • Y1 represents a phenyl group having R3a optionally substituted with R3, or R3a optionally substituted with R3.
  • nA represents an integer of 0 to 4 (however, in the case of R3 having 2 or more substitutions, each is independent), and Y1 is a pyridyl group.
  • nA is a method for obtaining a compound represented by the formula (1j) representing an integer of 0 to 3 (provided that each of R3 having 2 or more substituents is independent), A production method comprising reacting the compound represented by 1j) with R3b-Q in a solvent.
  • R3b-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 R3b-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 formula (1j). 1 equivalent or more and 30 equivalent or less.
  • 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 formula (1j). It is 30 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but alcohol solvents represented by R3b-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 is usually 3 to 200 times by weight with respect to the compound represented by the formula (1j). 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.
  • 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 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 a sulfur atom 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 (1k) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (1k) 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 (1k) 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.
  • R3c represents a C1-C6 alkoxy group
  • R1, R2, R3, R4, R5, nA, X, and Y1 are as defined above.
  • Production method Z is a method for obtaining a compound represented by formula (1m) having a hydroxyl group among the compounds represented by formula (1), and reacting the compound represented by formula (1l) with an acid. It is a manufacturing method including obtaining by making it.
  • Examples of the acid used for this reaction include 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 formula (1l), and is not particularly limited as long as the target reaction proceeds. Equivalent to 10 equivalents.
  • 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 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 (1l). 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (1m) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (1m) 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 (1m) 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 the substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with the 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, C3-C6 haloalkynyl group, or RdC ( ⁇ O) — (where Rd is as defined above), and R1, R2, R3, R4, R5, nA, Lv, X, and Y1 are as defined above.
  • R3d 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.
  • R3d-Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • R3d-Lv used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (1m), and is not particularly limited as long as the target reaction proceeds. Equivalent to 10 equivalents.
  • 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 the formula (1m), and is not particularly limited as long as the target reaction proceeds, but usually 1 equivalent or more. 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 (1m). 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (1n) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (1n) 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 (1n) 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.
  • R3e 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, or a substituent C
  • R3e-B represents an organic boronic acid
  • R1, R2, R3, R3a, R4, R5, nA, X And Y1 are as defined above.
  • R3e 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 production method comprising obtaining by a Suzuki-Miyaura coupling in which a compound represented by the formula (1j) and an organic boronic acid (R3e-B) are reacted in the presence of a transition metal and a base.
  • R 3a is a chlorine atom, a bromine atom, or an iodine atom.
  • R3e-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.
  • AM can be performed.
  • R3f represents a C2 to C6 alkynyl group or a C2 to C6 haloalkynyl group which may be optionally substituted with a substituent C, and R1, R2, R3, R3a, R4, R5, nA, X and Y1 Is as defined above.
  • R3f is a C2 to C6 alkynyl group or a C2 to C6 haloalkynyl group optionally substituted with a substituent C.
  • R 3a 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.
  • the production method AN can be performed according to the production method K.
  • R7b represents a C1-C6 alkyl group optionally substituted with the substituent C
  • R1, R2, X and Y are as defined above.
  • Production method AO is a method of obtaining a compound represented by formula (2q), and reacting a compound represented by formula (1d) represented by formula (1d) in a solvent in the presence of a base. It is a manufacturing method containing.
  • the compound represented by the formula (15) used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • the compound represented by the formula (15) used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (1d), and is not particularly limited as long as the target reaction proceeds. Usually, it is 1 equivalent or more and 20 equivalents or less.
  • Bases used in this reaction are inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and 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 and 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 (1d), and is not particularly limited as long as the target reaction proceeds, but usually 1 equivalent or more. 20 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, 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, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc. Examples include halogen-based solvent media. 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 (1d). 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 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, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (2q) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (2q) 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 (2q) 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.
  • Production method AP is a method for obtaining a compound represented by formula (5), and is a production method comprising reacting a compound represented by formula (1c) in a solvent in the presence of a base.
  • the compound represented by the formula (1c) can be obtained with reference to the production method R and the like.
  • the base used in this reaction is exemplified by inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride, but is not particularly limited as long as the target reaction proceeds.
  • the base used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (1c), and is not particularly limited as long as the target reaction proceeds, but usually 1 equivalent or more. 20 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but alcohol solvents such as tertiary butanol, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, Ether solvents such as tetrahydrofuran and dioxane, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N, N-dimethylformamide, N, N- Examples include amide solvents such as dimethylacetamide and urea solvents such as 1,3-dimethyl-2-imidazolidinone. 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 is usually 3 to 200 times by weight with respect to the compound represented by the formula (1c). 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.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride 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, thiosulfuric acid
  • An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite 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 (5) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (5) 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 (5) 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.
  • Manufacturing method AQ is the compound represented by the formula (1), there a way to obtain the R1, R2, R3, Lb contained in R4 and R5 of formula (Lb) is SO or SO 2 Compound
  • a compound represented by the formula (La) in which La contained in R1, R2, R3, R4 and R5 is S and an oxidizing agent (Ox ′ ′′) A production method including reacting 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 to 200 times by weight with respect to the compound represented by the formula (La). 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 ⁇ 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 a sulfur atom 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.
  • 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 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.
  • the compound represented by the formula (1) can be produced by arbitrarily combining the production methods A to AQ described above. Alternatively, the compound represented by the formula (1) can be produced by arbitrarily combining known methods and production methods A to AQ.
  • the compound of the present invention can control harmful organisms to plants, it can be used as a pesticide, particularly a pesticide for agricultural and horticultural use.
  • a pesticide particularly a pesticide for agricultural and horticultural use.
  • Specific examples include fungicides, insecticides, herbicides, plant growth regulators, and the like.
  • it is a disinfectant.
  • the compound of the present invention can be used as an agricultural and horticultural fungicide in fields, paddy fields, tea gardens, orchards, pastures, lawns, forests, gardens, street trees, etc., for the control of plant diseases.
  • the plant disease as used in the present invention refers to systemic abnormal pathological symptoms such as wilt, withering, yellowing, atrophy, and pupa of plants such as crops, flowers, flowering trees, trees, or spots, leaf wilts, mosaics.
  • partial pathological symptoms such as cigars, branch wilt, root rot, root humps, humps are caused. That is, the plant becomes sick.
  • pathogens that cause plant diseases mainly include fungi, bacteria, spiroplasma, phytoplasma, viruses, viroids, parasitic higher plants, nematodes and the like.
  • the compound of the present invention is effective against fungi, but is not limited thereto.
  • fungi Diseases caused by fungi are mainly fungal diseases.
  • fungi pathogens
  • pathogens include root-knot fungi, oomycetes, zygomycetes, ascomycetous fungi, basidiomycetes, and incomplete fungi.
  • root-knot fungus fungi root-knot fungus
  • potato powdery scab fungus sugar beet root-knot fungus
  • oomycetes plague fungus, downy mildew, Pythium spp.
  • Aphanomyces spp. Aphanomyces spp.
  • peach blight fungus corn sesame leaf blight fungus, rice blast fungus, powdery mildew fungus, anthracnose fungus, red mold fungus, leafy seedling fungus, mycorrhizal fungus, basidiomycetous fungus, rust fungus, purple crest
  • blast fungus blast fungus, blast fungus, blight fungus, and incomplete fungus
  • gray mold Alteria spp., Fusarium spp., Penicillium spp., Rhizoctonia spp.
  • the compound of the present invention is effective against various plant diseases. Specific examples of disease names and pathogen names are shown below.
  • Rice blast Magnaporthe grisea
  • blight Tarephorus cucumeris
  • brown sclerotia Ceratobasidium setariae
  • brown sclerotia Waitea circinata
  • Red sclerotia Wildairea circinata
  • scab Entyloma dactylidis
  • staphylococcal sclerosis Ceratobasidium leaf
  • gray sclerotia Ceratobasidium leaf
  • Blight Sphaerulina oryzina
  • Seedling disease Gibberella fujikuroi
  • Seedling disease Pythium spp., Fusarium spp., Trichoderma spp., Rhizopus spi., Rhizoctonia solpi, spor.
  • Achlya spp. Dictychus spp., Claviceps virens, Black-headed blight (Tillletia barclayana), Brown rice (Curvularia spp., Alternaria spp.), Yellowing atrophy thoracor sprout disease Xanthomonas oryzae pv. Oryzae), brown stripe disease (Acidovora) avenae subsp.
  • Tritici Tritici
  • rust Puccinia striformis, Puccinia graminis, Puccinia recondita, Puccinia h Pyrenophora teres
  • Fusarium head blight Gibberella zeae
  • Fusarium culmorum Fusarium avenaceum, Monographa nivalis, black rot (Typhala incarnata sill) nuda
  • tuna scab Teilletia caries, Tilletia controversa
  • eye rot Pseudocercosporella herpotrichoides
  • bacterial rot Citobasidium gramineum
  • nodorum Fusarium spp., Pythium spp., Rhizoctonia spp., Septoria spp., Pyrenophora spp.
  • Bacterial disease Gaemanomyces graminiol
  • Ergot disease Claviceps pur
  • Syringae Corn red mold (Gibberella zeae, etc.), seedling blight (Fusarium avenaceum, Penicillium spp., Phythium spp.), Rhizoctonia spp. Ustilago maydis, Colletotrichum graminicola, Northern spot disease (Cochliobolus caribonum), Brown scab (Acidovorax avenae subur.
  • Erwinia sp. Erwinia sp.
  • Agrobacterium tumefaciens Rust radiata bacilli (Erwinia chrysanthemia pv. Chrysanthemipy), Pseudomonas syringae disease.
  • s lingae blight blight (Erwinia sp.); peach black scab (Cladosporium carpophilum), homoposis rot (Phomopsis sp.), plague (Phytophthora phlegm morbidity) deformans, perforated bacterial disease (Xhanthomonas campestris pv.
  • ytoplasma asteris yellow dwarf disease (Tobacco leaf curl subgroup III geminiphyrus); Brown spot disease (Pseudomonas cichorrii), stem rot (Pseudomonas corrugata), stem rot (Erwinia chrysanthemi), soft rot (Erwinia carotovora stospor.
  • Black spot disease Alternaria brassicae
  • Black rot Xhanthomonas campestris pv. Campestris
  • Black spot bacterial disease Pseudomonas syringae pv.
  • Maculacola Soft rot disease (Erwina disease) Etc.), white spot disease (Cercosporella brassicae), root rot disease (Phoma lingam), root-knot disease (Plasmophorora brassicae), downy mildew (Peronospora parasitica), black rot (Xhanthomprasc). Pseudomonas sy lingae pv. macrocola), soft rot (Erwinia carotovora subsp.
  • Anthracnose (Colletotrichum lindemuthianum), bacterial wilt (Ralstonia solanacearum), blight (Pseudomonas syringae pv. Phaseolisola), brown bacterial disease (Pseudomonas firla flamp) . phaseoli); Groundnut black blight (Mycosphaerella berkeleyi), brown spot (Mycosphaerella arachidis), bacterial blight (Ralstonia solanacearum); pea mildew (Erysiphe pisi), downy mildew (Peron morse) syringae pv.
  • Streptomyces ipomoeae brown spot of sugar beet (Cercospora bechticola); downy mildew (Peronospora schachtii); black root disease (Aphanomyces cohid); Symptom (Agrobacterium tumefaciens), scab (Streptomyces scabies), spot bacterial disease (Pseudomonas syringae pv. Aptata); Carrot black leaf blight (Alternaria dauci), knot disease (Rhizobacter dauci), root cancer disease (Agrobacterium tumefaciens), Streptomyces or serovar (Strotomyces spp.), Soft rot disease.
  • Strawberry powdery mildew (Sphaerotheca aphanis var. Aphanis), plague (Phytophthora nicotianae, etc.), anthracnose (Glomerella cinulata etc.), bacterial rot (Phythium ultimum), bacterial blight (X) campestris), Bacterial blight (Pseudomonas marginalis pv. Marginalis); Chamodium wilt (Exobasidium reticulosti et al.), Anthracnose (Peludomonas marginalis pv.
  • carotovora damping off (Ralstonia solanacearum) Tobacco mosaic virus; Coffee rust (Hemileia vastatrix); Banana black sigatoga disease (Mycosphaerella fijiensis), Panama disease (Fusarium oxysporum f. Spamur potato disease) (Fusarium oxymarrow) Sclerotinia sclerotiorum, Xanthomonas campestris pv. Malvacearum, cavernous disease (Erwinia carotovora subp. Carotovora), spot bacterial disease (Pseudomosis).
  • Powdery mildew (Sphaerotheca pannosa, etc.), plague (Phytophthora megasperma), downy mildew (Peronospora sparsa), root rot (Agrobacterium terescaiens); ), Plague (Pseudomonas cichoroii), soft rot (Erwinia carotovora subbsp. ifolia); Brown patch disease of turf (Rhizoctonia solani), Dollar spot disease (Sclerotinia homoeocarpa), Curvularia sp.
  • Rhynchosporium secalis Gaeumanomyces graminis, Anthracnose (Colletotrichum sp.), Typhala incarnata, Typhala blackspot Myriosclerotia borealis, fairy ring disease (Marasmius oreades, etc.), Pythium disease (Pythium aphanidermatum, etc.), Blast disease (Pyricularia grisea), etc. are mentioned.
  • the compound of the present invention may be used alone, but is preferably mixed with a solid carrier, liquid carrier, gas carrier, surfactant, fixing agent, dispersant, stabilizer, etc. , Granule wettable powder, aqueous solvent, granular aqueous solvent, granule, emulsion, liquid, microemulsion, aqueous suspension preparation, aqueous emulsion preparation, suspoemulsion preparation and the like. As long as an effect is exhibited, it is not limited to those compositions.
  • composition containing the compound of the present invention (agricultural and horticultural pesticide, agricultural and horticultural fungicide) will be described.
  • Examples of the method of applying the composition containing the compound of the present invention include a method of contacting with a plant body or seeds, or a method of bringing it into cultivated soil and bringing it into contact with plant roots or rhizomes.
  • foliage spraying treatment, injection treatment, seedling box treatment, cell tray treatment, spraying treatment on plant seeds, smearing treatment on plant seeds, immersion treatment in plant seeds, plant seeds Powder coating, soil application, soil mixing after soil application, soil injection, soil injection, soil mixing after soil injection, soil irrigation, soil irrigation Examples include soil mixing. In general, any application method such as that utilized by those skilled in the art will exhibit sufficient efficacy.
  • Plant refers to those that live without moving through photosynthesis. Specific examples include rice, wheat, barley, corn, coffee, banana, grape, apple, pear, peach, sweet potato, oyster, citrus, soybean, green beans, cotton, strawberry, potato, cabbage, lettuce, tomato, cucumber, eggplant, Watermelon, sugar beet, spinach, sweet pea, pumpkin, sugar cane, tobacco, sweet pepper, sweet potato, taro, konjac, cotton, sunflower, rose, tulip, chrysanthemum, turf, etc. and their F1 varieties. It also includes genetically engineered crops that are created by artificially manipulating genes and are not naturally present. For example, soybeans, corn, cotton, etc. that have been given herbicide tolerance have been adapted to cold regions.
  • plants such as corn and cotton that have been provided with the ability to produce insecticides, such as tobacco.
  • insecticides such as tobacco.
  • Further examples include trees such as pine, ash, ginkgo, maple, oak, poplar, and zelkova.
  • the “plant body” as used in the present invention is a general term for all parts constituting the plant individual, and examples thereof include stems, leaves, roots, seeds, flowers, fruits and the like.
  • seed refers to a seed that stores nutrients for germination of young plants and is used for agricultural reproduction.
  • Specific examples include seeds such as corn, soybean, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, green pea, pumpkin, sugar cane, tobacco, sweet pepper, oilseed rape, and their F1 varieties.
  • seeds such as seeds, taro, potato, sweet potato, and konjac, edible lilies, bulbs such as tulips, seed balls such as lacquer, and seeds and tubers of genetically modified crops.
  • the application amount and concentration of the composition containing the compound of the present invention vary depending on the target crop, target disease, degree of occurrence of the disease, compound dosage form, application method and various environmental conditions, but when spraying or irrigating.
  • the amount of active ingredient is suitably 0.1 to 10,000 g per hectare, preferably 10 to 1,000 g per hectare.
  • the amount used in the seed treatment is 0.0001 to 1000 g, preferably 0.001 to 100 g, per kg seed as the amount of active ingredient.
  • the composition containing the compound of the present invention is used as a foliage spraying treatment, a soil surface spraying treatment, a soil injection treatment or a soil irrigation treatment to individual plants, it is diluted with a suitable carrier at an appropriate concentration. Thereafter, processing may be performed.
  • the composition containing the compound of the present invention When the composition containing the compound of the present invention is brought into contact with a plant seed, it may be used after being diluted to an appropriate concentration and then dipped, powdered, sprayed or smeared on the plant seed.
  • the amount of the composition used in the dipping, powder coating, spraying or smearing treatment is usually about 0.05 to 50%, preferably 0.1 to 30% of the weight of the dried plant seeds as the amount of the active ingredient. However, it may be appropriately set depending on the form of the composition and the type of plant seed to be treated, and is not limited to these ranges.
  • the compound of the present invention may contain other pesticides such as bactericides, insecticides (including acaricides and nematicides), herbicides, microbial materials, plant growth regulators, and the like as necessary. It can be used by being mixed with a disease control agent (International Publication No. 2014/062775), a soil conditioner, a fertilizer or the like as an active ingredient.
  • bactericides such as bactericides, insecticides (including acaricides and nematicides), herbicides, microbial materials, plant growth regulators, and the like as necessary. It can be used by being mixed with a disease control agent (International Publication No. 2014/062775), a soil conditioner, a fertilizer or the like as an active ingredient.
  • a method of using the compound of the present invention and other agricultural chemicals in combination a method of using the compound of the present invention and other agricultural chemicals in a single dosage form, both of which are formulated in separate dosage forms Use one of the following methods: Mixing before use, using both formulated in separate dosage forms at the same time, or using both formulated in separate dosage forms The method of using the other after doing is mentioned.
  • bactericide that can be used by mixing with the compound of the present invention are exemplified in the following group b, and include salts, isomers and N-oxides thereof.
  • known disinfectants are not limited to these.
  • Group b b-1: Phenylamide fungicide [b-1.1]: Benalaxyl, [b-1.2] Benalaxyl M or Kiraraxyl, [b-1.1]: [b-1.1] -1.3] furaraxyl, [b-1.4] metalaxyl, [b-1.5] metalaxyl M or mephenoxam (metalaxyl-M or mefenoxam), [b-1.6] oxazyl ( oxadixyl), [b-1.7] offrace and the like.
  • b-2 Mitotic fission and cell division inhibitor [b-2.1] benomyl, [b-2.2] carbendazim, [b- 2.3] fuberidazole, [b-2.4] thiabendazole, [b-2.5] thiophanate, [b-2.6] thiophanate-methyl, [b- 2.7] Dietofencarb, [b-2,8] zoxamide, [b-2.9] ethaboxam, [b-2.10] pencycuron, [b-2. 11] fluopico Examples thereof include fluoriclide, [b-2.12] phenacryl and the like.
  • SDHI agent succinate dehydrogenase inhibitor
  • succinate dehydrogenase inhibitors [b-3.1] benodanil, [b-3.2] benzovindiflupyr, [b-3.3] bixafen (bixafen) ), [B-3.4] boscalid, [b-3.5] carboxin, [b-3.6] fenfuram, [b-3.7] fluopyram [B-3.8] flutolanil, [b-3.9] fluxapyroxad, [b-3.10] furamethpyr, [b-3.11] isofetamide ), [B-3.12] isopyrazam (isop) razam), [b-3.13] mepronil, [b-3.14] oxycarboxin, [b-3.15] pentiopyrad, [b-3.16] penflufen ( penflufen), [b-3.17] pydiflumethofen, [
  • b-4 Quinone external inhibitor (QoI agent) As quinone external inhibitors (QoI agents), [b-4.1] azoxystrobin, [b-4.2] cumoxystrobin, [b-4.3] dimoxist Robin (dimoxystrobin), [b-4.4] enoxastrobin, [b-4.5] famoxadone, [b-4.6] fenamidone, [b-4.7] Phenaminestrobin, [b-4.8] fluphenoxystrobin, [b-4.9] fluoxastrobin, [b-4.10] cresoxime-me hyl), [b-4.11] mandestrobin, [b-4.12] methinostrobin, [b-4.13] oryastrobine, [b-4.14] Picoxystrobin, [b-4.15] Pyraclostrobin, [b-4.16] Pyramethostrobin, [b-4.17] Pyraoxystrobin [B-4.18] Pyribencarb, [b-4.
  • quinone internal inhibitor examples include [b-5.1] cyazofamid (cazofamid), [b-5.2] amisulbrom and the like.
  • Oxidative phosphorylation uncoupling inhibitor As oxidative phosphorylation uncoupling inhibitors, [b-6.1] binapacryl, [b-6.2] meptyldinocap, [b-6.1] b-6.3] dinocap, [b-6.4] fluazinam and the like.
  • b-7 Quinone external stigmaterin binding subsite inhibitor
  • QoSI agent quinone external stigmaterin binding subsite inhibitor
  • Examples of the quinone external stigmateline binding subsite inhibitor (QoSI agent) include [b-7.1] ametoctradin.
  • b-8 Amino acid biosynthesis inhibitors As amino acid biosynthesis inhibitors, [b-8.1] cyprodinil, [b-8.2] mepanipyrim, [b-8.3] pyrimethanil ) And the like.
  • b-9 Protein biosynthesis inhibitor [b-9.1] Streptomycin, [b-9.2] Blasticidin-S, [b-9. 3] Kasugamycin, [b-9.4] oxytetracycline, and the like.
  • b-10 Signaling inhibitor As a signal transduction inhibitor, [b-10.1] fenpiclonil, [b-10.2] fludioxonil, [b-10.3] quinoxyfen, [B-10.4] proquinazid, [b-10.5] clozolinate, [b-10.6] dimethachlone, [b-10.7] iprodione, [b -10.8] procymidone, [b-10.9] vinclozolin and the like.
  • b-11 Lipid and cell membrane biosynthesis inhibitors As lipid and cell membrane biosynthesis inhibitors, [b-11.1] edifenphos, [b-11.2] iprobenfos, [b-11. Pyrazophos, [b-11.4] isoprothiolane, [b-11.5] biphenyl, [b-11.6] chloroneb, [b-11.7] dichlorane (Dicloran), [b-11. 8] quintozene, [b-11.
  • DI agent Demethylation inhibitor
  • DI agents include [b-12.1] azaconazole, [b-12.2] bittertanol, [b-12.3] bromuconazole, [ b-12.4] cyproconazole, [b-12.5] difenoconazole, [b-12.6] diniconazole, [b-12.7] diniconazole-M ), [B-12.8] epoxiconazole, [b-12.9] etaconazole, [b-12.10] fenarimol, [b-12.11.
  • Fenbuconazole [b-12.12] fluquinconazole, [b-12.13] quinconazole, [b-12.14] flusilazole, [b-12 .15] flutriafol, [b-12.16] hexaconazole, [b-12.17] imazaril, [b-12.18] imibenconazole, [B-12.19] ipconazole, [b-12.20] metconazole, [b-12.21] microbutanil [B-12.22] nuarimol, [b-12.23] oxpoconazole, [b-12.24] oxpoconazole fumarate, [b- 12.25] pefurazoate, [b-12.26] penconazole, [b-12.27] prochloraz, [b-12.28] propiconazole, [b- 12.29] Prothioconazole, [b-12.30] Pyrifenox, [b-12.31] Pyrioxazole
  • b-13 Amine fungicide [b-13.1] aldimorph, [b-13.2] dodemorph, [b-13.3] fenpropimorph as amine fungicides ), [B-13.4] tridemorph, [b-13.5] fenpropidin, [b-13.6] piperalin, [b-13.7] spiroxamine. ) And the like.
  • b-14 3-keto reductase inhibitor in C4 demethylation of sterol biosynthesis
  • b-15 Squalene epoxidase inhibitor of sterol biosynthesis As a squalene epoxidase inhibitor of sterol biosynthesis, [b-15.1] pyributicalb, [b-15.2] naphthifine, [b ⁇ 15.3] terbinafine and the like.
  • b-16 Cell wall biosynthesis inhibitor As cell wall biosynthesis inhibitors, [b-16.1] polyoxins (polyoxins), [b-16.2] dimethomorph, [b-16.3] furmorph ( flumorph, [b-16.4] pyrimorph, [b-16.5] benchavaricarb, [b-16.6] benchacarbab-isopropyl, [b -16.7] iprovaricarb, [b-16.8] mandipropamide, [b-17.9] varifenate, and the like.
  • b-17 Melanin biosynthesis inhibitor [b-17.1] Phthalide or fthalide, [b-17.2] Pyroquilone, [b-17.3] Tricyclazole as melanin biosynthesis inhibitors (Tricycazole), [b-17.4] carpropamide, [b-17.5] diclocymet, [b-17.6] phenoxanil, [b-17.7] tolprocarb (tolprocarb) ) And the like.
  • b-18 Host Plant Resistance Inducing Agent
  • b-19 Dithiocarbamate fungicide [b-19.1] Mancozeb or manzeb, [b-19.2] maneb, [b-19.3] as a dithiocarbamate fungicide ] Metiram, [b-19.4] Propineb, [b-19.5] Thiuram, [b-19.6] Zineb, [b-19.7] Diram (Ziram), [b-19.8] ferbam and the like.
  • Phthalimide fungicide [b-20.1] captan, [b-20.2] captafol, [b-20.3] holpet as phthalimide fungicide ), [B-20.4] fluorophorpet, and the like.
  • b-21 Guanidine fungicide [b-21.1] guazatine, [b-21.2] iminoctadin, [b-21.3] iminotadine albecyl salt as guanidine fungicides (Iminoctaline alcoholate), [b-21.4] iminoctadine triacetate, and the like.
  • b-22 Multi-acting point contact active fungicide [b-22.1] Copper oxychloride, [b-22.2] Cupric hydroxide as multi-acting point contact active fungicide (Copper (II) hydrochloride), [b-22.3] basic copper sulfate, [b-22.4] organocopper compound, [b-22.5] dodecylbenzenesulfone Bisethylenediamine copper complex salt [II] (Dodecylbenzensulfonic acid bisethylenediamine copper [II] salt, DBEDC), [b-22.6] sulfur, [b-22.7] fluorimide de), [b-22.8] chlorothalonil, [b-22.9] dichlorofluanid, [b-22.10] tolylfluanid, [b-22.11] Anilazine, [b-22.12] dithianon, [b-22.13] chinomethionate or quinomethionate, [b-22.14] extract from cotyledons of buffalo seed
  • bactericides include [b-23.1] dichlorobenazox, [b-23.2] fenpicoxamide, [b-23.3. ] Dipymetitrone, [b-23.4] Bupirimate, [b-23.5] Dimethilimol, [b-23.6] Ethirimol, [b-23.7] Acetic acid Triphenyltin (fentin acetate), [b-23.8] triphenyltin chloride (fentin chloride), [b-23.9] triphenyltin hydroxide (f-23) (Oxo linic acid), [b-23.11] himexazole, [b-23.12] octylinone, [b-23.13] fosetyl, [b-23.14] phosphorous acid (Phosphorous acid), [b-23.15] sodium phosphite, [b-23.16] ammonium phosphite, [b-23.17]
  • Formula (s26) or Formula (s27) [Wherein, m5 represents an integer of 0 to 5, A30 represents a C1 to C6 alkyl group, A31 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group. And when m5 is 2 or more, two or more A31s each represent an independent substituent, which may be the same or different, and A32 represents a C1-C6 alkyl group, a C2-C6 alkenyl group, or C3 Represents a C6 alkynyl group. ] (See International Publication No. 13/037717),
  • A41 represents a hydrogen atom, a hydroxyl group (—SH), a thiocyanic acid group (—SCN), or a C1-C6 alkylthio group
  • A42, A43, A44 and A45 are each independently Represents a hydrogen atom or a halogen atom.
  • insecticide that can be used in combination with the compound of the present invention are exemplified in the following group c and include salts, isomers and N-oxides thereof.
  • known insecticides are not limited to these.
  • Group c c-1: Carbamate-type acetylcholinesterase (AChE) inhibitor [c-1.1] Phosphocarb, [c-1.2] alanycarb, [c] -1.3] butocarboxim, [c-1.4] butoxycarboxim, [c-1.5] thiodicarb, [c-1.6] thiofanox ), [C-1.7] aldicarb, [c-1.8] bendiocarb, [c-1.9] benfurcarb, [c-1.10] carbaryl ryl), [c-1.11] carbofuran, [c-1.12] carbosulfan, [c-1.13] etiofencarb, [c-1.14] fenocarb ( fenobucarb), [c-1.15] formatenate, [c-1.16] furathiocarb, [c-1.17] isoprocarb, [c-1.18] metiocarb [C-1.19] mesomy
  • c-2 Organophosphorus acetylcholinesterase (AChE) inhibitors As organophosphorus acetylcholinesterase (AChE) inhibitors, [c-2.1] acephate, [c-2.2] azamethiphos, [C-2.3] Azinphos-methyl, [c-2.4] Azinphos-ethyl, [c-2.5] Ethephon, [c-2.6] [Cadusafos], [c-2.7] Chlorethoxyphos, [c-2.8] Chlorfenvinphos, [c-2.9] Chlormephos, [c- 2.10] Black Rupyrifos, [c-2.11] chloropyrifos-methyl, [c-2.12] coumafos, [c-2.13] cyanophos, [c-2.

Landscapes

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

Abstract

L'invention concerne un nouveau composé de lutte contre les maladies des plantes. Le composé de pyridone selon la présente invention est un nouveau composé, et peut lutter contre les maladies des plantes.
PCT/JP2018/022279 2017-06-12 2018-06-11 Composé de pyridone et agent antimicrobien l'utilisant comme ingrédient actif pour l'agriculture et l'horticulture WO2018230516A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2019525423A JP7118961B2 (ja) 2017-06-12 2018-06-11 ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2017-115359 2017-06-12
JP2017115359 2017-06-12

Publications (1)

Publication Number Publication Date
WO2018230516A1 true WO2018230516A1 (fr) 2018-12-20

Family

ID=64660134

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2018/022279 WO2018230516A1 (fr) 2017-06-12 2018-06-11 Composé de pyridone et agent antimicrobien l'utilisant comme ingrédient actif pour l'agriculture et l'horticulture

Country Status (2)

Country Link
JP (1) JP7118961B2 (fr)
WO (1) WO2018230516A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022224924A1 (fr) * 2021-04-23 2022-10-27 日本曹達株式会社 Composé hétéroarylique contenant de l'azote, agent antibactérien agricole et horticole, nématicide et agent antifongique pour utilisations médicales et vétérinaires

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994008968A1 (fr) * 1992-10-14 1994-04-28 Zeneca Limited Derives de l'acide propenoique utiles en tant que fongicides
WO2002066434A1 (fr) * 2001-02-20 2002-08-29 Nippon Soda Co.,Ltd. Compose d'oximether et bactericides agricole et horticoles
JP2002348278A (ja) * 2001-05-23 2002-12-04 Kumiai Chem Ind Co Ltd 複素環式アルキルカーバメート誘導体及び農園芸用殺菌剤
WO2008009406A1 (fr) * 2006-07-17 2008-01-24 Syngenta Participations Ag Nouveaux dérivés de pyridazine
WO2010093595A1 (fr) * 2009-02-10 2010-08-19 E. I. Du Pont De Nemours And Company 2‑pyridones fongicides
WO2014010737A1 (fr) * 2012-07-12 2014-01-16 日産化学工業株式会社 Composé amide substitué par oxime et agent de lutte contre les organismes nuisibles
WO2014135478A1 (fr) * 2013-03-04 2014-09-12 Bayer Cropscience Ag Dérivés de 3-{hétérocyclyl[(hétérocyclylméthoxy)imino]méthyl}-oxadiazolone fongicides

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994008968A1 (fr) * 1992-10-14 1994-04-28 Zeneca Limited Derives de l'acide propenoique utiles en tant que fongicides
WO2002066434A1 (fr) * 2001-02-20 2002-08-29 Nippon Soda Co.,Ltd. Compose d'oximether et bactericides agricole et horticoles
JP2002348278A (ja) * 2001-05-23 2002-12-04 Kumiai Chem Ind Co Ltd 複素環式アルキルカーバメート誘導体及び農園芸用殺菌剤
WO2008009406A1 (fr) * 2006-07-17 2008-01-24 Syngenta Participations Ag Nouveaux dérivés de pyridazine
WO2010093595A1 (fr) * 2009-02-10 2010-08-19 E. I. Du Pont De Nemours And Company 2‑pyridones fongicides
WO2014010737A1 (fr) * 2012-07-12 2014-01-16 日産化学工業株式会社 Composé amide substitué par oxime et agent de lutte contre les organismes nuisibles
WO2014135478A1 (fr) * 2013-03-04 2014-09-12 Bayer Cropscience Ag Dérivés de 3-{hétérocyclyl[(hétérocyclylméthoxy)imino]méthyl}-oxadiazolone fongicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
RAJANARENDAR, E. ET AL: "Synthesis and antimicrobial activity of 1-(5-methyl-3-isoxazolyl)-3, 6-diaryl-4-thioxo-1,3,5-triazin-2-ones", INDIAN JOURNAL OF CHEMISTRY SECTION B: ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, vol. 50B, no. 2, February 2011 (2011-02-01), pages 223 - 228, XP055646382 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022224924A1 (fr) * 2021-04-23 2022-10-27 日本曹達株式会社 Composé hétéroarylique contenant de l'azote, agent antibactérien agricole et horticole, nématicide et agent antifongique pour utilisations médicales et vétérinaires

Also Published As

Publication number Publication date
JP7118961B2 (ja) 2022-08-16
JPWO2018230516A1 (ja) 2020-04-16

Similar Documents

Publication Publication Date Title
JP7037507B2 (ja) ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
KR102498819B1 (ko) 피리돈 화합물 및 그것을 유효성분으로 하는 농원예용 살균제
JP7157738B2 (ja) ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
JP7111731B2 (ja) ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
JP7118961B2 (ja) ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
JP7397800B2 (ja) ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
JP7134946B2 (ja) ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
JP7168556B2 (ja) ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
WO2018190349A1 (fr) Composé pyridone, et bactéricide à usage agricole et horticole ayant ce composé pour principe actif
JP7291151B2 (ja) ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
JP7328222B2 (ja) ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
JP7370998B2 (ja) ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
JP7291143B2 (ja) ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
JP7153645B2 (ja) ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
JP7110190B2 (ja) 含窒素複素環化合物ならびにそれを有効成分とする農園芸用殺菌剤

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18818003

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2019525423

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18818003

Country of ref document: EP

Kind code of ref document: A1