WO2018225816A1 - Composé hétérocyclique contenant de l'azote et bactéricide à usage agricole et horticole le contenant en tant que principe actif - Google Patents

Composé hétérocyclique contenant de l'azote et bactéricide à usage agricole et horticole le contenant en tant que principe actif Download PDF

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WO2018225816A1
WO2018225816A1 PCT/JP2018/021836 JP2018021836W WO2018225816A1 WO 2018225816 A1 WO2018225816 A1 WO 2018225816A1 JP 2018021836 W JP2018021836 W JP 2018021836W WO 2018225816 A1 WO2018225816 A1 WO 2018225816A1
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group
substituent
optionally substituted
formula
substituted
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PCT/JP2018/021836
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Japanese (ja)
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英明 生島
豪毅 梅谷
健志 福元
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三井化学アグロ株式会社
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Priority to JP2019523965A priority Critical patent/JP7110190B2/ja
Publication of WO2018225816A1 publication Critical patent/WO2018225816A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • C07D239/40—One sulfur atom as doubly bound sulfur atom or as unsubstituted mercapto radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D241/18—Oxygen or sulfur atoms

Definitions

  • the present invention relates to a nitrogen-containing heterocyclic 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.
  • 1,5,6-substituted-2-pyrimidinone compounds and 1,5,6-substituted-2-pyrazinone compounds for example, as a dopamine D1 ligand, a heteroaryloxy group at the para position of the 6-position phenyl group 1,5,6-substituted-2-pyrimidinone compounds and 1,5,6-substituted-2-pyrazinone compounds substituted with 1 are disclosed (for example, see Patent Document 1 and Patent Document 2).
  • Patent Document 1 and Patent Document 2 are all related to medicine, and are different from the technical field to which the agricultural and horticultural fungicides according to the present invention belong.
  • An object of the present invention is to provide a novel compound that is effective as an agricultural and horticultural fungicide.
  • the present inventors diligently studied the 1,4,5,6-substituted-2-pyrimidinone compound group and the 1,3,5,6-substituted-2-pyrazinone compound group.
  • a novel compound group in which an aryl group or heteroaryl group having a substituent at the ortho position is introduced at the 6-position in the 2-pyrimidinone and 2-pyrazinone skeletons exhibits excellent control activity against plant diseases.
  • the present invention has been completed.
  • the present invention is as follows.
  • 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-C6 alkynyloxy group optionally
  • R2 is A cyano group, A C1-C6 alkyl group optionally substituted with substituent A, A C1-C6 haloalkyl group, A C3-C8 cycloalkyl group optionally substituted with the substituent A, A C2-C6 alkenyl group optionally substituted with the substituent A, A C2-C6 haloalkenyl group, A C2-C6 alkynyl group optionally substituted with substituent A, 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, RaRbN- (wherein Ra and Rb are as defined above), Rx1C ( ⁇ O) — (wherein Rx1 is a C1-C6 alkyl group, C1-C6 haloalkyl group, C
  • R3 is Hydroxyl group, A cyano group, Nitro group, Halogen atoms, 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 C1-C6 alkoxy group that may be optionally substituted with a substituent C; A C1-C6 haloalkoxy group, A C3-C8 cycloalkoxy group optionally substituted with substituent C, A C2-C6 alkenyloxy group optionally substituted with the substituent C, A C2-C6 haloalkenyloxy group, A C3-C6 alkyn
  • Rx3 represents A hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group optionally substituted with a substituent B).
  • Rx4Rx5C ⁇ N—O— (wherein Rx4 and Rx5 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3- A C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are as defined above).
  • Y is Represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group;
  • R4 is substituted at the ortho position, and R5 is optionally substituted with 0 to 4 (provided that when there are two or more R5s, R5 represents an independent substituent).
  • R4 is substituted at the ortho position, and R5 is optionally substituted by 0 to 3 (however, two or more substituted or more).
  • R5 represents an independent substituent).
  • R4 is substituted at the ortho position, and R5 is optionally substituted by 0 to 2 (provided that when there are two or more substituted R5s, R5 is Represents an independent substituent).
  • R4 is Hydroxyl group, A cyano group, Nitro group, Halogen atoms, 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 C1-C6 alkoxy group that may be optionally substituted with a substituent C; A C1-C6 haloalkoxy group, A C3-C8 cycloalkoxy group optionally substituted with substituent C, A C2-C6 alkenyloxy group optionally substituted with the substituent C, A C2-C6 haloalkenyloxy group, A C3-C6 alkynyloxy
  • Rx3 represents A hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group optionally substituted with a substituent B).
  • Rx4Rx5C ⁇ N—O— (wherein Rx4 and Rx5 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3- A C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are as defined above).
  • R5 has the same meaning as R4 described above;
  • Z1 represents C—R6, or a nitrogen atom,
  • Z2 represents C—R7, or a nitrogen atom, At least one of Z1 and Z2 represents a nitrogen atom;
  • R6 is Hydrogen atom, Halogen atoms, A C1-C6 alkyl group C1-C6 haloalkyl group optionally substituted with substituent A, 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, Or Rc-L
  • R2 is A cyano group, A C1-C6 alkyl group optionally substituted with substituent A, A C1-C6 haloalkyl group, A C3-C8 cycloalkyl group optionally substituted with the substituent A, A C2-C6 alkenyl group optionally substituted with the substituent A, A C2-C6 haloalkenyl group, A C2-C6 alkynyl group optionally substituted with substituent A, 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, 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
  • An alkyl 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.
  • Rx1C ( ⁇ O) — (wherein Rx1 is a C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy optionally substituted with the substituent B) A group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above), Phenyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, thiatriazolyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group
  • R3 is appropriately substituted by 0 to 3 (provided that when there are two or more substituents R3, each R3 represents an independent substituent.
  • R3 is appropriately substituted with 0 to 4 (however, when there are two or more substituted R3s, each R3 is independently Represents a substituted group).
  • R3 is appropriately substituted by 0 to 3 (provided that when R3 has two or more substitutions, R3 represents an independent substituent).
  • R3 is appropriately substituted with 0 to 6 (provided that when there are two or more substituted R3s, each R3 is independent) Represents a substituent).
  • R3 is appropriately substituted with 0 to 5 (provided that when R3 has two or more substitutions, R3 represents an independent substituent).
  • R3 is appropriately substituted with 0 to 5 (however, when there are two or more substituted R3s, each R3 is independent) Represents a substituent).
  • R3 is appropriately substituted with 0 to 6 (provided that when there are two or more substituents R3, each R3 is an independent substituent.
  • R3 is optionally substituted with 0 to 5 (provided that when there are two or more R3s, R3 represents an independent substituent).
  • R3 is appropriately substituted with 0 to 6 (provided that there are two or more substituted R3, R3 represents an independent substituent.
  • R1 is A cyano group, A C1-C6 alkyl group optionally substituted with substituent A, A C1-C6 haloalkyl group, A C3-C8 cycloalkyl group optionally substituted with the substituent A, A C2-C6 alkenyl group optionally substituted with the substituent A, A C2-C6 haloalkenyl group, A C2-C6 alkynyl group optionally substituted with substituent A, Or represents a C2-C6 haloalkynyl group;
  • R2 is 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 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
  • An alkyl 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.
  • Rx1C ( ⁇ O) — (wherein Rx1 is a C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy optionally substituted with the substituent B) A group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above), Phenyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, thiatriazolyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group
  • R3 is appropriately substituted by 0 to 3 (provided that when there are two or more substituents R3, each R3 represents an independent substituent.
  • R3 is appropriately substituted with 0 to 4 (however, when there are two or more substituted R3s, each R3 is independently Represents a substituted group).
  • R3 is appropriately substituted by 0 to 3 (provided that when R3 has two or more substitutions, R3 represents an independent substituent).
  • R3 is Hydroxyl group, A cyano group, Halogen atoms, 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 alkynyl 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 C3-C8 cycloalkoxy group optionally substituted with substituent C, 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, Or represents a C3-C6 haloalkynyloxy group; Y
  • R4 is substituted at the ortho position, and R5 is optionally substituted by 0 to 3 (provided that when there are two or more R5s, R5 represents an independent substituent).
  • R4 is Halogen atoms, A C1-C6 alkyl group optionally substituted with substituent C, A C1-C6 haloalkyl group, A C1-C6 alkoxy group that may be optionally substituted with a substituent C; Or a C1-C6 haloalkoxy group, R5 is Hydroxyl group, A cyano group, Halogen atoms, 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 alkynyl group optionally substituted with substituent C, A C1-
  • R1 is A C1-C6 alkyl group optionally substituted with substituent A, Or represents a C1-C6 haloalkyl group
  • R2 is A C1-C6 alkyl group optionally substituted with substituent A, A C1-C6 haloalkyl group, Rx1C ( ⁇ O) —
  • Rx1 is a C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy optionally substituted with the substituent B
  • R3 is optionally substituted with 0 to 5 (provided that when there are two or more substituents R3, each R3 represents an independent substituent);
  • R4 is Halogen atoms, A C1-C6 alkyl group optionally substituted with substituent C, Or a C1-C6 alkoxy group optionally substituted with a substituent C
  • R5 is A cyano group, Halogen atoms, A C1-C6 alkoxy group that may be optionally substituted with a substituent C; Or a C1-C6 haloalkoxy group
  • R6 is Hydrogen atom, Halogen atoms, A C1-C6 alkyl group optionally substituted with substituent A, Or a C1-C6 haloalkyl group
  • R7 is Hydrogen atom, Or the compound or its salt as described in said [3] which represents a halogen atom.
  • R1 is The compound or a salt thereof according to any one of [1] to [4], which represents a C1-C6 alkyl group or a C1-C6 haloalkyl group.
  • R1 is Any one of [1] to [4], which is a methyl group, an ethyl group, a propyl group, an isobutyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl group, or a 2,2,2-trifluoroethyl group The compound as described in one, or its salt.
  • R1 is The compound or a salt thereof according to any one of [1] to [4], which is a methyl group, an ethyl group, an isobutyl group, or a 2,2-difluoroethyl group.
  • R2 is C1-C6 alkyl group optionally substituted with substituent A, Rx1C ( ⁇ O) — (where Rx1 is a C1-C6 alkyl group optionally substituted with substituent B, 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). Or a phenyl group (in which the R3 is appropriately substituted with 0 to 5 (provided that when there are two or more substituents R3, each R3 represents an independent substituent)).
  • R2 is Methyl group, ethyl group, isopropyl group, isobutyl group, difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, acetyl group, methoxyacetyl group, cyanoacetyl group Difluoroacetyl group, trifluoroacetyl group, methoxycarbonyl group, ethoxycarbonyl group, phenyl group, 2-fluorophenyl group, 2-chlorophenyl group, 2-bromophenyl group, 2-iodophenyl group, 2-methoxyphenyl group, 3-fluorophenyl group, 3-chlorophenyl group, 3-bromophenyl group, 3-iodophenyl group, 3-methoxyphenyl group, 4-chlor
  • R2 is Represents a methyl group, isopropyl group, ethoxycarbonyl group, 2-fluorophenyl group, 2-chlorophenyl group, 2-chloro-5-methoxyphenyl group, or 2-chloro-3,5-difluorophenyl group, [1] to [7] The compound according to any one of [7] or a salt thereof.
  • R3 is The compound or a salt thereof according to any one of [1] to [8], which represents a halogen atom or a C1-C6 alkoxy group optionally substituted with a substituent C.
  • R3 is Any one of [1] to [8], which represents a fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, propyl group, isopropyl group, methoxy group, ethoxy group, propyloxy group, or isopropyloxy group Or a salt thereof.
  • R3 is The compound or a salt thereof according to any one of [1] to [8], which represents a fluorine atom, a chlorine atom, or a methoxy group.
  • Y is Formula (k-1), Formula (k-2), Formula (k-3), Formula (k-4), Formula (k-5), Formula (k-6)
  • Y is Formula (k-1) or Formula (k-4)
  • R4 is The compound or a salt thereof according to any one of [1] to [15], which represents a halogen atom.
  • R4 is The fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, methoxy group, ethoxy group, propyloxy group, or isopropyloxy group, according to any one of [1] to [15] Compound or salt thereof.
  • R4 is The compound or a salt thereof according to any one of [1] to [15], which represents a fluorine atom.
  • R5 is The compound or a salt thereof according to any one of [1] to [18], which represents a halogen atom, a C1-C6 alkoxy group optionally substituted with a substituent C, or a C1-C6 haloalkoxy group .
  • R5 is Cyano group, fluorine atom, chlorine atom, bromine atom, iodine atom, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group, or 2,2 , A compound according to any one of [1] to [18] or a salt thereof, which represents a 2-trifluoroethoxy group.
  • R5 is The compound or a salt thereof according to any one of [1] to [18], which represents a fluorine atom, a methoxy group, or a 2,2,2-trifluoroethoxy group.
  • Z1 represents C—R6, Z2 represents a nitrogen atom, or a compound or a salt thereof according to any one of [1] to [21].
  • [23] The compound or a salt thereof according to any one of [1] to [21], wherein Z1 represents a nitrogen atom, and Z2 represents C—R7.
  • Z1 represents a nitrogen atom
  • Z2 represents a nitrogen atom, or a compound or a salt thereof according to any one of [1] to [21].
  • R6 is The compound or a salt thereof according to any one of [1] to [22], which represents a hydrogen atom or a halogen atom.
  • R6 is Hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, propyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, or 2, The compound or a salt thereof according to any one of [1] to [22], which represents a 2,2-trifluoroethyl group.
  • R6 is The compound or a salt thereof according to any one of [1] to [22], which represents a hydrogen atom or a chlorine atom.
  • R7 is The compound or salt thereof according to any one of [1] to [21] and [23], which represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • R7 is The compound or a salt thereof according to any one of [1] to [21] and [23], which represents a hydrogen atom.
  • X is The compound or a salt thereof according to any one of [1] to [29], which represents an oxygen atom.
  • X is The compound or a salt thereof according to any one of [1] to [29], which represents a sulfur atom.
  • [32] An agricultural and horticultural pest control agent comprising the compound or salt thereof according to any one of [1] to [31] as an active ingredient.
  • a method for controlling plant diseases which comprises applying the agricultural and horticultural pest control agent according to [32] to plants, plant seeds, or soil in which plants are grown.
  • a method for controlling plant diseases comprising applying the agricultural and horticultural fungicide according to [33] to plants, plant seeds, or soil in which plants are grown.
  • a novel compound effective as an agricultural and horticultural pest control agent, particularly an agricultural and horticultural fungicide can be provided.
  • Cx to Cy represents having 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
  • 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
  • C1-C5 is 1, 2, 3, 4 , Or 5 carbon atoms
  • C1-C3 means having 1, 2, or 3 carbon atoms, respectively.
  • the term “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 substituent is none, 1, 2, 3, 4, or 5 substituents, and “may be optionally substituted with 0 to 4”.
  • the number of substituents is none, 1, 2, 3, or 4 and “optionally substituted by 0 to 3” means that the number of substituents is none, 1, 2, or 3 “0-2 may be substituted” means none, having 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 atom 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.
  • E-form and Z-form or a mixture of E-form and Z-form in an arbitrary ratio, it is particularly limited as long as it is in the range of the designated carbon number. None happen.
  • C2 to C6 alkenyl groups include vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, and 3-pentenyl.
  • the C2-C6 haloalkenyl group represents a group in which the hydrogen atom in the C2-C6 alkenyl group is optionally substituted with one or more halogen atoms.
  • the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent.
  • C2-C6 haloalkenyl group examples include 2-fluorovinyl group, 2,2-difluorovinyl group, 2,2-dichlorovinyl group, 3-fluoroallyl group, 3,3-difluoroallyl group, 3, Examples include 3-dichloroallyl group, 4,4-difluoro-3-butenyl group, 5,5-difluoro-4-pentenyl group, 6,6-difluoro-5-hexenyl group and the like.
  • the C2-C6 alkynyl group represents an unsaturated hydrocarbon group having one or more triple bonds and being linear or branched. Specific examples of the C2-C6 alkynyl group include ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, and 3-pentynyl.
  • the C2-C6 haloalkynyl group represents a group in which the hydrogen atom in the C2-C6 alkynyl group is optionally substituted with one or more halogen atoms.
  • the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent.
  • C2-C6 haloalkynyl group examples include 2-fluoroethynyl group, 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3,3-difluoro-1-propynyl group, 3-chloro -3,3-difluoro-1-propynyl group, 3-bromo-3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl Group, 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro-1-butynyl group, 4-chloro-4,4-difluoro-2-butynyl group, 4-bromo-4,4 -Difluoro-1-butynyl group, 4-bromo-4,4-Di
  • the C1-C6 alkoxy group represents a 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 , Undecafluoro-
  • 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, a cyclooctyloxy group, and the like.
  • the C2-C6 alkenyloxy group is a group in which the C2-C6 alkenyl group is bonded through an oxygen atom.
  • E-form and Z-form or a mixture of E-form and Z-form in an arbitrary ratio, is not particularly limited as long as it is within the specified carbon number range. None happen.
  • C2-C6 alkenyloxy group examples include vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group, 2-pentenyloxy group 3-pentenyloxy group, 4-pentenyloxy group, 3-methyl-2-butenyloxy group, 1-hexenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group Group, 4-methyl-3-pentenyloxy group, 3-methyl-2-pentenyloxy group and the like.
  • the C2-C6 haloalkenyloxy group represents a group in which the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted with one or more halogen atoms.
  • 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 haloalkenyloxy group examples include 2-fluorovinyloxy group, 2,2-difluorovinyloxy group, 2,2-dichlorovinyloxy group, 3-fluoroallyloxy group, 3,3-difluoro. Allyloxy group, 3,3-dichloroallyloxy group, 4,4-difluoro-3-butenyloxy group, 5,5-difluoro-4-pentenyloxy group, 6,6-difluoro-5-hexenyloxy group, etc. It is done.
  • the C3-C6 alkynyloxy group represents a group in which the C3-C6 alkynyl group is bonded through an oxygen atom among the C2-C6 alkynyl groups.
  • Specific examples of the C3-C6 alkynyloxy group include propargyloxy group, 2-butynyloxy group, 3-butynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, 1,1 -Dimethyl-2-propynyloxy group, 2-hexynyloxy group, 3-hexynyloxy group, 4-hexynyloxy group, 5-hexynyloxy group and the like.
  • the C3-C6 haloalkynyloxy group represents a group in which the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted with one or more halogen atoms.
  • the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent.
  • C3-C6 haloalkynyloxy group examples include 1,1-difluoro-2-propynyloxy group, 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro-2-butynyloxy group 4-bromo-4,4-difluoro-2-butynyloxy group, 4,4,4-trifluoro-2-butynyloxy group, 5,5-difluoro-3-pentynyloxy group, 5-chloro-5,5 -Difluoro-3-pentynyloxy group, 5-bromo-5,5-difluoro-3-pentynyloxy group, 5,5,5-trifluoro-3-pentynyloxy group, 6,6-difluoro-4 -Hexynyloxy group, 6-chloro-6,6-difluoro-4-hexynyloxy group, 6-bromo-6
  • the C2 to C6 alkoxyalkoxy group is a group in which the hydrogen atom in the C1 to C5 alkoxy group in the C1 to C6 alkoxy group is optionally substituted with one or more C1 to 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.
  • An aryl group represents a cyclic aromatic substituent composed of a hydrogen atom and a carbon atom.
  • Specific examples of the aryl group include a phenyl group and a naphthyl group.
  • the heteroaryl group is a cyclic aromatic substituent selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom and containing at least one heteroatom as a ring constituent atom.
  • heteroaryl group examples include pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, furyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, Examples thereof include an oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group.
  • the aryloxy group represents a group in which the above aryl group is bonded through an oxygen atom.
  • Specific examples of the aryloxy group include a phenoxy group and a naphthyloxy group.
  • the heteroaryloxy group represents a group in which the above heteroaryl group is bonded through an oxygen atom.
  • heteroaryloxy groups include pyridyloxy, pyridazinyloxy, pyrimidinyloxy, pyrazinyloxy, triazinyloxy, tetrazinyloxy, thienyloxy, thiazolyloxy, isothiazolyloxy Group, thiadiazolyloxy group, furyloxy group, pyrrolyloxy group, imidazolyloxy group, pyrazolyloxy group, oxazolyloxy group, isoxazolyloxy group, triazolyloxy group, oxadiazolyloxy group, thiadiazolyl An oxy group, a tetrazolyloxy group, etc. are mentioned.
  • the aralkyloxy group represents a group in which an aralkyl group in which a hydrogen atom in a C1-C3 alkyl group is substituted with an aryl group such as a phenyl group or a naphthyl group is bonded through an oxygen atom.
  • Specific examples of the aralkyloxy group include benzyloxy group, phenethyloxy group, phenylpropyloxy group, naphthalenylmethoxy group, naphthalenylethoxy group, naphthalenylpropoxy group and the like.
  • 3- to 6-membered ring group containing 1 to 2 oxygen atoms include 1,2-epoxyethanyl group, oxetanyl group, oxolanyl group, oxanyl group, 1,3-dioxolanyl group, 1,3- Examples thereof include a dioxanyl group and a 1,4-dioxanyl group.
  • the compound of the present invention includes a nitrogen-containing heterocyclic compound represented by the following formula (1) or a salt thereof.
  • R1 in the formula (1) is a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with a substituent A.
  • R1 is a cyano group, a C1-C6 alkyl group optionally substituted with the substituent A, A C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with the substituent A, a C2-C6 alkenyl group optionally substituted with the substituent A, a C2-C6 haloalkenyl group, A C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with the substituent A is preferred, In particular, a C1-C6 alkyl group or a C1-C6 haloalkyl group which may be optionally substituted with the substituent A is preferable.
  • 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, more preferably a methyl group, an ethyl group, a propyl group, or an isobutyl group, and particularly preferably a methyl group, an ethyl group, or an isobutyl 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.
  • Each term of (forms what is formed) is synonymous with the said definition.
  • Ra and Rb are preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with the substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, and more preferably A hydrogen atom or a C1-C6 alkyl group optionally substituted with the substituent B;
  • 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, diethyla
  • R2 in the formula (1) is a cyano group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with a substituent A
  • a cycloalkyl group a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, a C2-C6 A haloalkynyl group, a C1-C6 alkoxy group optionally substituted with substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with substituent A, RaRbN- ( Here, Ra and Rb are as defined above.), Rx1C ( ⁇ O) — (where Rx1 is a C1-C6
  • R2 is a cyano group, a C1-C6 alkyl group optionally substituted with the substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with the substituent A, A C2-C6 alkenyl group optionally substituted with the substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with the substituent A, a C2-C6 haloalkynyl group, A C1-C6 alkoxy group optionally substituted with the substituent A, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A, RaRbN— (wherein Ra and Rb are as defined above), Rx1C ( ⁇ O) — (Wherein Rx1 is as defined above), phenyl group, pyridyl group, pyr
  • R3 is appropriately substituted by 0 to 3 (provided that when there are two or more substituents R3, each R3 represents an independent substituent).
  • R3 is optionally substituted by 0 to 4 (provided that when there are two or more substituted R3s, R3 is Each represents an independent substituent.),
  • the indolyl group, the isoindolyl group, the indazolyl group, the benzoimidazolyl group, or the benzotriazolyl group, R3 is appropriately substituted with 0 to 6 (provided that when there are two or more substituted R3s, R3 is Represents an independent substituent), the benzofuryl group, the isobenzofuryl group, or the benzoxazolyl group is optionally substituted with 0 to 5 R3 (provided that when there are 2 or more substituted R3s, R3 is Each represents an independent substituent group), the benzothienyl group, the benzothiazolyl group, the benzoisothiazolyl group, or the benzothiadiazolyl group, R3 is optionally substituted with 0 to 5 (however, two or more substituted groups).
  • each R3 represents an independent substituent.
  • the indolizinyl group, the imidazopyridyl group, the pyrazolopyridyl group, or the tria In the ropyridyl group, R3 is appropriately substituted with 0 to 6 (provided that when there are two or more R3s, R3 represents an independent substituent), the pyrrolopyrimidinyl group, the imidazopyrimidinyl group, the pyrazolopyrimidinyl In the group, the triazolopyrimidinyl group, the pyrrolopyrazinyl group, the imidazopyrazinyl group, the pyrazolopyrazinyl group, or the triazolopyrazinyl group, R3 is appropriately substituted with 0 to 5 (provided that 2 substituents) In the case where R3 is present, each R3 represents an independent substituent.), The quinolyl group, the isoquinolyl group, the cinolyl group, the phthal
  • R2 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
  • R3 is appropriately substituted with 0 to 5 (provided that when there are two or more substituted R3s, R3 is independently The pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group, or the tetrazinyl group, R3 is optionally substituted with 0 to 4 (however, two or more substituted R3 Each of R3 represents an independent substituent), the thienyl group, the thiazolyl group, the isothiazolyl group, the thiadiazolyl group, or the thiatriazolyl group is optionally substituted with 0 to 3 (provided that 2 When R3 is more than substituted, each R3 represents an independent substituent.), The pyrrolyl group, the pyrazolyl In the imidazolyl group, the triazolyl group, the tetrazolyl group, or the pentazolyl group
  • R3 is optionally substituted by 0 to 3 (provided that when there are two or more R3s, R3 represents an independent substituent) .
  • R2 is a C1-C6 alkyl group optionally substituted with the substituent A, a C1-C6 haloalkyl group, Rx1C ( ⁇ O) — (wherein Rx1 is as defined above), or A phenyl group is preferred.
  • R3 is optionally substituted with 0 to 5 (provided that when there are two or more substituents R3, each R3 represents an independent substituent).
  • R2 is preferably a C1-C6 alkyl group optionally substituted with the substituent A, Rx1C ( ⁇ O) — (wherein Rx1 is as defined above), or a phenyl group.
  • R3 is optionally substituted with 0 to 5 (provided that when there are two or more substituents R3, each R3 represents an independent substituent).
  • R2 includes a cyano group.
  • 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, an isopropyl group, a butyl group, or an isobutyl group, more preferably a methyl group, an ethyl group, an isopropyl group, or an isobutyl group, and particularly preferably a methyl group or an isopropyl 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, a cyclopentyl group, or a cyclohexyl 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- 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 R2 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 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 meaning as defined above, and preferably 2-fluoroethynyl group, 2-chloroethynyl group, 2-bromoethynyl group, 2-iodo group Ethynyl group, 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-2-butynyl group, more preferably 2-fluoroethynyl group, 3,3-difluoro-1-propynyl 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, an isopropyloxy group, a butoxy group, or an isobutoxy group, and more preferably an ethoxy group, a propyloxy group, an isopropyloxy group, or an isobutoxy 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, a cyclopentyloxy group, or a cyclohexyloxy group.
  • the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted with the substituent A.
  • Ra and RbN— 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.
  • Each term of (forms what is formed) is synonymous with the said definition.
  • Ra and Rb are preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with the substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, and more preferably A hydrogen atom or a C1-C6 alkyl group optionally substituted with the substituent B;
  • 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, diethyla
  • Rx1C ( ⁇ O) — in R2 of Formula (1) (where Rx1 is a C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 A cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are as defined above). Each term has the same definition as above.
  • Rx1 is preferably 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.
  • Rx1C ( ⁇ O) — is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 2 , 2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylaminocarbonyl group, dimethylaminocarbonyl Group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, pyrrolidinylcarbonyl group, or piperidinylcarbonyl group, more preferably an acetyl group,
  • R2 in the formula (1) includes a phenyl group.
  • 0 to 5 R3s are appropriately substituted (provided that when there are two or more R3s, each R3 represents an independent substituent).
  • Preferred as the phenyl group in R2 of the formula (1) Is a phenyl group, 2-fluorophenyl group, 2-chlorophenyl group, 2-bromophenyl group, 2-iodophenyl group, 2-methylphenyl group, 2-methoxyphenyl group, 3-fluorophenyl group, 3-chlorophenyl group 3-bromophenyl group, 3-iodophenyl group, 3-methylphenyl group, 3-methoxyphenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl group,
  • R2 in the formula (1) includes a 5- to 6-membered heterocyclic group or an 8- to 10-membered heterocyclic group.
  • R3 is appropriately substituted with 0 to 6 (provided that when there are two or more substituents R3, each R3 represents an independent substituent. To express.).
  • the 5- to 6-membered heterocyclic group examples include pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, thiatriazolyl group, pyrrolyl group, Examples include a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, a pentazolyl group, a furyl group, an oxazolyl group, an isoxazolyl group, and an oxadiazolyl group.
  • the 8- to 10-membered heterocyclic group include indolyl group, isoindolyl group, indazolyl group, benzoimidazolyl group, benzotriazolyl group, benzofuryl group, isobenzofuryl group, benzoxazolyl group, benzothienyl group, Benzothiazolyl group, benzoisothiazolyl group, benzothiadiazolyl group, indolizinyl group, imidazopyridyl group, pyrazolopyridyl group, triazolopyridyl group, pyrrolopyrimidinyl group, imidazopyrimidinyl group, pyrazolopyrimidinyl group, triazolopyrimidinyl group, Examples include pyrrolopyrazinyl group, imidazopyrazinyl group, pyrazolopyrazinyl group, triazolopyrazinyl group, quinolyl group, isoquinolyl group, cino
  • a 5- to 6-membered heterocyclic group is preferable, and specifically, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, thiatriazolyl group Pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group, pentazolyl group, furyl group, oxazolyl group, isoxazolyl group, or oxadiazolyl group,
  • R3 is appropriately substituted with 0 to 4 (provided that when two or more substitutions are present, R3 is independently selected. Represents a substituted group).
  • R3 is appropriately substituted with 0 to 3 (provided that when there are two or more substituents R3, each R3 represents an independent substituent. To express.).
  • R3 is appropriately substituted with 0 to 4 (provided that when there are two or more R3s, R3 is independently Represents a substituted group).
  • R3 is appropriately substituted by 0 to 3 (provided that when there are two or more substituents R3, each R3 represents an independent substituent).
  • R3 is appropriately substituted with 0 to 6 (provided that when there are two or more substituted R3s, each R3 is independent) Represents a substituent).
  • R3 is appropriately substituted with 0 to 5 (provided that when there are two or more R3s, R3 represents an independent substituent).
  • R3 is optionally substituted with 0 to 5 (provided that when there are two or more substituted R3s, each R3 is independent. Represents a substituent).
  • R3 is appropriately substituted with 0 to 6 (provided that when there are two or more substituents R3, each R3 is an independent substituent.
  • R3 is optionally substituted with 0 to 5 (provided that when there are two or more substituents R3, each R3 represents an independent substituent).
  • R3 is appropriately substituted with 0 to 6 (provided that there are two or more substituted R3, R3 represents an independent substituent.
  • R2 is a pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, or tetrazinyl group
  • R2 is represented by the formula (a) (Wherein R3 has the same meaning as described above, and na represents an integer of 0 to 4).
  • G1, G2, G3, G4, and G5 in the formula (a) are each independently a carbon atom or a nitrogen atom. However, at least one of G1, G2, G3, G4, and G5 is a nitrogen atom. As for preferable G1, G2, G3, G4, and G5, any one of G1, G2, G3, G4, and G5 is a nitrogen atom. That is, it is a pyridyl group.
  • na represents an integer of 0 to 4.
  • na in the formula (a) is 2 or more
  • 2 or more R3s each represent an independent substituent, may be the same or different, and can be arbitrarily selected.
  • R2 is a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, or a thiatriazolyl group
  • R2 is represented by the formula (b-1) Or formula (b-2) (Wherein R3 has the same meaning as described above, and nb represents an integer of 0 to 3).
  • G6, G7, and G8 are each independently a carbon atom or a nitrogen atom.
  • Nb in the formula (b-1) and the formula (b-2) represents an integer of 0 to 3.
  • nb in the formula (b-1) and the formula (b-2) is 2 or more, two or more R3s each represent an independent substituent, and may be the same or different and can be arbitrarily selected. .
  • R2 is pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl or pentazolyl
  • R2 is Formula (c-1) Formula (c-2) Or formula (c-3) (Wherein R3 has the same meaning as described above, and nc represents an integer of 0 to 4).
  • G9, G10, G11, and G12 are each independently a carbon atom or a nitrogen atom.
  • nc represents an integer of 0 to 4.
  • nc in the formula (c-1), the formula (c-2), and the formula (c-3) is 2 or more, two or more R3s each represent an independent substituent, and may be the same or different, Can be arbitrarily selected.
  • R2 is a furyl group, an oxazolyl group, an isoxazolyl group, or an oxadiazolyl group
  • R2 is Formula (d-1) Formula (d-2) Formula (d-3) Or the formula (d-4) (Wherein R3 is as defined above, and nd represents an integer of 0 to 3).
  • G13 and G14 in formula (d-1), formula (d-2), formula (d-3), and formula (d-4) are each independently a carbon atom or a nitrogen atom.
  • nd represents an integer of 0 to 3.
  • each of the 2 or more R3s represents an independent substituent, They can be the same or different and can be arbitrarily selected.
  • R2 is an indolyl group, an isoindolyl group, an indazolyl group, a benzoimidazolyl group, or a benzotriazolyl group
  • R2 is represented by the formula (e-1) Or formula (e-2) (Wherein R3 has the same meaning as described above, and ne represents an integer of 0 to 6).
  • G15 and G16 in the formula (e-1) and the formula (e-2) are each independently a carbon atom or a nitrogen atom.
  • ne represents an integer of 0 to 6.
  • the two or more R3s each represent an independent substituent and may be the same or different and can be arbitrarily selected. .
  • R2 is a benzofuryl group, an isobenzofuryl group, or a benzoxazolyl group
  • R2 is represented by the formula (f-1) Or formula (f-2) (Wherein R3 has the same meaning as described above, and nf represents an integer of 0 to 5).
  • G17 in the formula (f-1) represents a carbon atom or a nitrogen atom.
  • Nf in Formula (f-1) and Formula (f-2) represents an integer of 0 to 5.
  • nf in the formula (f-1) and the formula (f-2) is 2 or more
  • two or more R3s each represent an independent substituent, and may be the same or different and can be arbitrarily selected.
  • R2 is a benzothienyl group, a benzothiazolyl group, a benzisothiazolyl group, or a benzothiadiazolyl group
  • R2 is represented by the formula (g-1) Or formula (g-2) (Wherein R3 has the same meaning as described above, and ng represents an integer of 0 to 5).
  • G18 and G19 in formula (g-1) and formula (g-2) are each independently a carbon atom or a nitrogen atom.
  • Ng in the formula (g-1) and the formula (g-2) represents an integer of 0 to 5.
  • R3s each represent an independent substituent and may be the same or different and can be arbitrarily selected.
  • R2 is an indolizinyl group, an imidazopyridyl group, a pyrazolopyridyl group, or a triazolopyridyl group
  • R2 is represented by the formula (h-1) (Wherein R3 has the same meaning as described above, and nh represents an integer of 0 to 6).
  • G20, G21, and G22 are each independently a carbon atom or a nitrogen atom.
  • Nh in the formula (h-1) represents an integer of 0 to 6.
  • nh in the formula (h-1) is 2 or more, 2 or more R3s each represent an independent substituent, may be the same or different, and can be arbitrarily selected.
  • R2 when R2 is pyrrolopyrimidinyl, imidazopyrimidinyl, pyrazolopyrimidinyl, triazolopyrimidinyl, pyrrolopyrazinyl, imidazopyrazinyl, pyrazolopyrazinyl, or triazolopyrazinyl Is the formula (i-1) Formula (i-2) Or formula (i-3) (Wherein R3 has the same meaning as described above, and ni represents an integer of 0 to 5).
  • G23, G24, and G25 in the formula (i-1), the formula (i-2), and the formula (i-3) are each independently a carbon atom or a nitrogen atom.
  • ni represents an integer of 0 to 5.
  • the formula (i-2) and the formula (i-3) is 2 or more, the two or more R3s each represent an independent substituent, and may be the same or different, and any Can be selected.
  • R2 is a quinolyl group, an isoquinolyl group, a cinolyl group, a phthalazinyl group, a quinoxalinyl group, a quinazolinyl group, or a naphthyridinyl group
  • R2 is represented by the formula (j-1) Or formula (j-2) (Wherein R3 has the same meaning as described above, and nj represents an integer of 0 to 6).
  • G26, G27, G28 and G29 in formula (j-1) and formula (j-2) are each independently a carbon atom or a nitrogen atom. However, at least one of G26, G27, G28 and G29 is a nitrogen atom. In formula (j-1), preferred G26, G27, G28 and G29 are any one of G26, G27, G28 and G29 being a nitrogen atom. That is, it is a quinolyl group.
  • Nj in formula (j-1) and formula (j-2) represents an integer of 0 to 6.
  • nj in the formula (j-1) and the formula (j-2) is 2 or more
  • two or more R3s each represent an independent substituent and may be the same or different and can be arbitrarily selected.
  • R3 is 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, a substituent C optionally substituted with a C3- C8 cycloalkyl group, 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, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, substituent C2-C6 alkenyloxy group optionally substituted with C, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy optionally
  • Rx4Rx5C ⁇ N—O— wherein Rx4 and Rx5 are each independently a hydrogen atom or a C1 which may be optionally substituted with a substituent B).
  • R3 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.
  • a cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 alkynyl group optionally substituted with a substituent C, and a substituent C A C3-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with a substituent C, a C2-C6 alkenyloxy group optionally substituted with a substituent C, A C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with a substituent C, or a C3-C6 haloalkynyloxy group is preferred, Further, a halogen atom, a C1-C6 alkyl group that may be optionally substituted with a substituent C, or a C1-C6 alkoxy group that may be optionally substituted with a substituent
  • 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, preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a fluorine atom or a chlorine 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, 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 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 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 , A propyloxy group, an isopropyloxy group, a butoxy group, or an isobutoxy group, more preferably a methoxy group, an ethoxy group, a propyloxy group, or an isopropyloxy group, and particularly preferably a methoxy 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.
  • the aryl group of “aryl group optionally substituted with substituent D” in R3 of formula (1) has the same definition as above, and is preferably a phenyl group.
  • the hydrogen in the aryl group is optionally substituted by the substituent D.
  • heteroaryl group of “heteroaryl group optionally substituted with substituent D” in R3 of formula (1) has the same definition as above, preferably a pyridyl group, a pyrazinyl group, a thienyl group, a thiazolyl group. , Isothiazolyl group, furyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, triazolyl group, oxadiazolyl group or tetrazolyl group, more preferably pyridyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group is there.
  • the hydrogen in the heteroaryl group is optionally substituted by the substituent D.
  • aryloxy group of “aryloxy group optionally substituted with substituent D” in R3 of formula (1) is as defined above, preferably a phenoxy group or a naphthyloxy group, Preferably, it is a phenoxy group.
  • substituent D the hydrogen atom in an aryloxy group is arbitrarily substituted by the substituent D.
  • heteroaryloxy group of “heteroaryloxy group optionally substituted with substituent D” in R3 of formula (1) has the same definition as above, preferably a pyridyloxy group, pyridazinyloxy Group, pyrimidinyloxy group, pyrazinyloxy group, pyrazolyloxy group, triazinyloxy group, tetrazinyloxy group, thienyloxy group, thiazolyloxy group, isothiazolyloxy group, or thiadiazolyloxy group, more preferably A pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group, or a pyrazolyloxy group.
  • the hydrogen atom in the heteroaryloxy group is optionally substituted by the substituent D.
  • the aralkyloxy group of the “aralkyloxy group optionally substituted with the substituent D” in R3 of the formula (1) has the same definition as above, preferably a benzyloxy group, a phenethyloxy group, or phenylpropyl An oxy group, more preferably a benzyloxy group or a phenethyloxy group.
  • the hydrogen atom in an aralkyloxy group is arbitrarily substituted by the substituent D.
  • 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, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, dimethyl group Amino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2-difluoro An ethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl) methylamino group, pyrrolidinyl group, or piperidin
  • 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.
  • a methanesulfonyl group is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group.
  • Rx1 of “Rx1C ( ⁇ O) ⁇ ” in R3 of Formula (1) has the same definition as above.
  • “Rx1C ( ⁇ O) —” is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 2 , 2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino Carbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxyethyl) aminocarbon
  • Rx1 of “Rx1C ( ⁇ O) O—” in R3 of Formula (1) has the same definition as above.
  • “Rx1C ( ⁇ O) O—” is preferably an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxy group Carbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, cyclopropyloxycarbonyl Oxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl) aminocarbony
  • Rx2C ( ⁇ O) N (Rx3) — in R3 of the formula (1) (wherein Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 A haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above).
  • Rx3 represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group optionally substituted with the substituent B). Terminology is as defined above. As for “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. .
  • Rx2 is preferably a hydrogen atom, methyl group, methoxymethyl group, cyanomethyl group, ethyl group, difluoromethyl group, trifluoromethyl group, cyclopropyl group, methoxy group, ethoxy group, 2,2-difluoroethoxy, 2, 2,2-trifluoroethoxy group, cyclopropyloxy group, amino group, methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (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-difluoro
  • Rx3 is preferably a hydrogen atom, methyl group, methoxymethyl group, ethoxymethyl group, cyanomethyl group, ethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-cyanoethyl group, propyl group, 2, 2-difluoroethyl group, 2,2,2-trifluoroethyl group, or cyclopropyl group, more preferably hydrogen atom, methyl group, methoxymethyl group, cyanomethyl group, ethyl group, 2-methoxyethyl group, A 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.
  • Rx4Rx5C ⁇ NO— in R3 of the formula (1) (wherein Rx4 and Rx5 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb are Each term of) is synonymous with the above definition.
  • 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. .
  • Rx4 and Rx5 are preferably methyl, ethyl, propyl, isopropyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, methoxy, ethoxy , Isopropyloxy group, difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, amino group, Methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (Methoxymethyl) methyla Group,
  • 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.
  • Y in Formula (1) represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group.
  • a phenyl group or a pyridyl group is preferable, and a phenyl group is particularly preferable.
  • R4 is substituted at the ortho position, and R5 is optionally substituted by 0 to 4 (provided that when there are two or more R5s, R5 represents an independent substituent).
  • R4 is substituted at the ortho position, and R5 is optionally substituted at 0 to 3 (however, two or more substituted or more).
  • each R5 represents an independent substituent.
  • R4 is substituted at the ortho position, and R5 is optionally substituted by 0 to 2 (provided that when there are two or more substitutions R5, R5 represents Represents an independent substituent).
  • R 5 represents an independent substituent and may be the same or different and is not particularly limited.
  • R4 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 alkynyl optionally substituted with substituent C
  • R4 is a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C1-C6 alkoxy group optionally substituted with a substituent C, or A C1-C6 haloalkoxy group is preferred, and further a halogen atom, a C1-C6 alkyl group optionally substituted with the substituent C, or a C1-C6 alkoxy group optionally substituted with the substituent C A halogen atom is particularly preferable.
  • R4 in the formula (1) includes a hydroxyl group, a cyano group, and a nitro group.
  • the halogen atom in R4 in the formula (1) has the same definition as described above, preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and particularly preferably a fluorine 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 , 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 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, 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 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 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.
  • the C1-C6 alkoxy group of the “C1-C6 alkoxy group optionally substituted with the substituent C” in R4 of the formula (1) has the same definition as above, preferably a methoxy group, an ethoxy group , A propyloxy group, an isopropyloxy group, a butoxy group, or an isobutoxy group, and more preferably a methoxy group, an ethoxy group, a propyloxy group, or an isopropyloxy group.
  • the hydrogen atom in the C1-C6 alkoxy group is optionally substituted with the substituent C.
  • the “C1-C6 haloalkoxy group” in R4 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 of the “C3-C8 cycloalkoxy group optionally substituted with the substituent C” in R4 of the formula (1) has the same definition as described above, preferably cyclopropyloxy Group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, and more preferably a cyclopropyloxy group or a cyclobutoxy group.
  • the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent C.
  • the C2-C6 alkenyloxy group of “C2-C6 alkenyloxy group optionally substituted with substituent C” in R4 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 R4 of the formula (1) has the same definition as above, 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 R4 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 R4 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.
  • the aryl group of “aryl group optionally substituted with substituent D” in R4 of formula (1) has the same definition as above, and is preferably a phenyl group.
  • the hydrogen in the aryl group is optionally substituted by the substituent D.
  • heteroaryl group of “heteroaryl group optionally substituted with substituent D” in R4 of formula (1) has the same definition as above, preferably a pyridyl group, a pyrazinyl group, a thienyl group, a thiazolyl group. , Isothiazolyl group, furyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, triazolyl group, oxadiazolyl group or tetrazolyl group, more preferably pyridyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group is there.
  • the hydrogen in the heteroaryl group is optionally substituted by the substituent D.
  • the aralkyloxy group of the “aralkyloxy group optionally substituted with the substituent D” in R4 of the formula (1) has the same definition as above, preferably a benzyloxy group, a phenethyloxy group, or phenylpropyl An oxy group, more preferably a benzyloxy group or a phenethyloxy group.
  • the hydrogen atom in an aralkyloxy group is arbitrarily substituted by the substituent D.
  • Ra and Rb of “RaRbN—” in R4 of the formula (1) are as defined above.
  • “RaRbN—” is preferably an amino group, methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, dimethyl group Amino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2-difluoro An ethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl) methylamino group, pyrrolidinyl group, or piperidin
  • Rc and L of “Rc-L-” in R4 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.
  • a methanesulfonyl group is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group.
  • Rx1 of “Rx1C ( ⁇ O) —” in R4 of Formula (1) has the same definition as above.
  • “Rx1C ( ⁇ O) —” is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 2 , 2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino Carbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxyethyl) aminocarbon
  • Rx1 of “Rx1C ( ⁇ O) O—” in R4 of Formula (1) has the same definition as above.
  • “Rx1C ( ⁇ O) O—” is preferably an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxy group Carbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, cyclopropyloxycarbonyl Oxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl) aminocarbony
  • Rx2C ( ⁇ O) N (Rx3) — in R4 of the formula (1) (where Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with the substituent B, a C1-C6 A haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above).
  • Rx3 represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group optionally substituted with the substituent B). Terminology is as defined above. As for “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. .
  • Rx2 is preferably a hydrogen atom, methyl group, methoxymethyl group, cyanomethyl group, ethyl group, difluoromethyl group, trifluoromethyl group, cyclopropyl group, methoxy group, ethoxy group, 2,2-difluoroethoxy, 2, 2,2-trifluoroethoxy group, cyclopropyloxy group, amino group, methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (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-difluoro
  • Rx3 is preferably a hydrogen atom, methyl group, methoxymethyl group, ethoxymethyl group, cyanomethyl group, ethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-cyanoethyl group, propyl group, 2, 2-difluoroethyl group, 2,2,2-trifluoroethyl group, or cyclopropyl group, more preferably hydrogen atom, methyl group, methoxymethyl group, cyanomethyl group, ethyl group, 2-methoxyethyl group, A 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.
  • Rx4Rx5C ⁇ NO— in R4 of the formula (1) (wherein Rx4 and Rx5 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb are Each term of) is synonymous with the above definition.
  • 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. .
  • Rx4 and Rx5 are preferably methyl, ethyl, propyl, isopropyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, methoxy, ethoxy , Isopropyloxy group, difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, amino group, Methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (Methoxymethyl) methyla Group,
  • the “3- to 6-membered ring group containing 1 to 2 oxygen atoms” in R4 of the formula (1) has the same definition as above, and preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group Or a 1,3-dioxanyl group, and more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.
  • R5 in Formula (1) has the same meaning as R4 described above. That is, a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group that may be optionally substituted with a substituent C, a C1-C6 haloalkyl group, and 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 Haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, substituent C A C2-C6 alkenyloxy
  • R5 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, 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 alkynyl group optionally substituted with a substituent C, and a substituent C A C3-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with a substituent C, a C2-C6 alkenyloxy group optionally substituted with a substituent C, C3-C6 alkynyloxy group optionally substituted with substituent C, heteroaryl group optionally substituted with substituent D, Rc-L- (where Rc is a C1-C6 alkyl group) Represents a haloalkyl group Le group or C1 ⁇ C6,, L is.
  • Represents S, SO, or SO 2), or Rx1C ( O) O- (where Rx1 has the same meaning as defined above.)
  • Rx1 has the same meaning as defined above.
  • Is Particularly preferred are a cyano group, a halogen atom, a C1-C6 alkoxy group optionally substituted with a substituent C, or a C1-C6 haloalkoxy group.
  • R5 in Formula (1) includes a hydroxyl group, a cyano group, and a nitro group.
  • the halogen atom in R5 in the formula (1) has the same definition as described above, preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and particularly preferably a fluorine 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, 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 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, 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 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 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.
  • the C1-C6 alkoxy group of “C1-C6 alkoxy group optionally substituted with substituent C” in R5 of 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, more preferably a methoxy group, an ethoxy group, a propyloxy group, or an isopropyloxy group, and particularly preferably a methoxy group.
  • the hydrogen atom in the C1-C6 alkoxy group is optionally substituted with the substituent C.
  • the “C1-C6 haloalkoxy group” in R5 of the formula (1) has the same definition as above, and 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, particularly preferably a 2,2,2-trifluoroethoxy group.
  • the C3-C8 cycloalkoxy group in the “C3-C8 cycloalkoxy group optionally substituted with the substituent C” in R5 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 R5 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 R5 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 R5 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 R5 of the formula (1) is as defined 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.
  • the aryl group of “aryl group optionally substituted with substituent D” in R5 of formula (1) has the same definition as above, and is preferably a phenyl group.
  • the hydrogen in the aryl group is optionally substituted by the substituent D.
  • heteroaryl group of “heteroaryl group optionally substituted with substituent D” in R5 of formula (1) has the same definition as above, preferably a pyridyl group, a pyrazinyl group, a thienyl group, a thiazolyl group. , Isothiazolyl group, furyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, triazolyl group, oxadiazolyl group or tetrazolyl group, more preferably pyridyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group is there.
  • the hydrogen in the heteroaryl group is optionally substituted by the substituent D.
  • the aralkyloxy group of the “aralkyloxy group optionally substituted with the substituent D” in R5 of the formula (1) has the same definition as above, preferably a benzyloxy group, a phenethyloxy group, or phenylpropyl An oxy group, more preferably a benzyloxy group or a phenethyloxy group.
  • the hydrogen atom in an aralkyloxy group is arbitrarily substituted by the substituent D.
  • Ra and Rb of “RaRbN—” in R5 of the formula (1) are as defined above.
  • “RaRbN—” is preferably an amino group, methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, dimethyl group Amino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2-difluoro An ethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl) methylamino group, pyrrolidinyl group, or piperidin
  • Rc and L of “Rc-L—” in R5 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.
  • a methanesulfonyl group is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group.
  • Rx1 of “Rx1C ( ⁇ O) —” in R5 of Formula (1) has the same definition as above.
  • “Rx1C ( ⁇ O) —” is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 2 , 2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino Carbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxyethyl) aminocarbon
  • Rx1 of “Rx1C ( ⁇ O) O—” in R5 of Formula (1) has the same definition as above.
  • “Rx1C ( ⁇ O) O—” is preferably an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxy group Carbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, cyclopropyloxycarbonyl Oxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl) aminocarbony
  • Rx2C ( ⁇ O) N (Rx3) — in R5 of the formula (1) (where Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with the substituent B, a C1-C6 A haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above).
  • Rx3 represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group optionally substituted with the substituent B). Terminology is as defined above. As for “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. .
  • Rx2 is preferably a hydrogen atom, methyl group, methoxymethyl group, cyanomethyl group, ethyl group, difluoromethyl group, trifluoromethyl group, cyclopropyl group, methoxy group, ethoxy group, 2,2-difluoroethoxy, 2, 2,2-trifluoroethoxy group, cyclopropyloxy group, amino group, methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (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-difluoro
  • Rx3 is preferably a hydrogen atom, methyl group, methoxymethyl group, ethoxymethyl group, cyanomethyl group, ethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-cyanoethyl group, propyl group, 2, 2-difluoroethyl group, 2,2,2-trifluoroethyl group, or cyclopropyl group, more preferably hydrogen atom, methyl group, methoxymethyl group, cyanomethyl group, ethyl group, 2-methoxyethyl group, A 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.
  • Rx4Rx5C ⁇ N—O— in R5 of the formula (1) (wherein Rx4 and Rx5 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb are Each term of) is synonymous with the above definition.
  • 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. .
  • Rx4 and Rx5 are preferably methyl, ethyl, propyl, isopropyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, methoxy, ethoxy , Isopropyloxy group, difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, amino group, Methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (Methoxymethyl) methyla Group,
  • the “3- to 6-membered ring group containing 1 to 2 oxygen atoms” in R5 of the formula (1) has the same definition as above, and preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group Or a 1,3-dioxanyl group, and more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.
  • Y is a phenyl group
  • Y is represented by the formula (k) (Wherein R4 and R5 are as defined above, and ma represents an integer of 0 to 4).
  • ma represents an integer of 0 to 4.
  • R5s When ma in the formula (k) is 2 or more, two or more R5s each represent an independent substituent, may be the same or different, and can be arbitrarily selected.
  • the ortho position means the position of the phenyl group having the substituent R4 as shown in the formula (k).
  • the phenyl group in which the substituent R4 is located in the ortho position is a feature of the present invention.
  • Preferred combinations of substituents of formula (k) are 2-R4-phenyl group, 2-R4-6-R5-phenyl group, 2-R4-4-R5-phenyl group, 2-R4-4-R5-6. -R5-phenyl group, 2-R4-3-R5-phenyl group, or 2-R4-3-R5-4-R5-6-R5-phenyl group, and a more preferable combination of substituents is 2-R4 -Phenyl group or 2-R4-4-R5-6-R5-phenyl group.
  • 2-R4-6-R5-phenyl group means a disubstituted phenyl group having a substituent R4 at the 2-position and a substituent R5 at the 6-position, and the following description is also the same.
  • Y is a group represented by the formula (L) (Wherein R4 and R5 are as defined above, and mb represents an integer of 0 to 3).
  • G30, G31, G32 and G33 are each independently a carbon atom or a nitrogen atom. However, at least one of G30, G31, G32 and G33 is a nitrogen atom. Preferred G30, G31, G32 and G33 are any one of G30, G31, G32 and G33 being a nitrogen atom. That is, it is a pyridyl group.
  • Mb in the formula (L) represents an integer of 0 to 3.
  • R5s When mb in the formula (L) is 2 or more, two or more R5s each represent an independent substituent, may be the same or different, and can be arbitrarily selected.
  • the ortho position is a 6-membered ring having a substituent R4 as shown in the formula (L).
  • a pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, or tetrazinyl group in which the substituent R4 is located in the ortho position is a feature of the present invention.
  • Preferred specific examples of the formula (L) include 3-R4-pyridin-2-yl group, 3-R4-5-R5-pyridin-2-yl group, 2-R4-pyridin-3-yl group, 2-R4. -4-R5-pyridin-3-yl group, 2-R4-6-R5-pyridin-3-yl group, 2-R4-4-R5-6-R5-pyridin-3-yl group, 4-R4- Pyridin-3-yl group, 4-R4-2-R5-pyridin-3-yl group, 4-R4-6-R5-pyridin-3-yl group, 4-R4-2-R5-6-R5-pyridine It is a -3-yl group, a 3-R4-pyridin-4-yl group, or a 3-R4-5-R5-pyridin-4-yl group.
  • Y is a group represented by the formula (m-1) Formula (m-2) Or the formula (m-3) (Wherein R4 and R5 are as defined above, and mc represents an integer of 0 to 2).
  • G34 and G35 in Formula (m-1), Formula (m-2), and Formula (m-3) are each independently a carbon atom or a nitrogen atom.
  • mc represents an integer of 0 to 2.
  • R5 in 2 each represents an independent substituent, which may be the same or different, and is arbitrarily selected can do.
  • Y is a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group
  • the ortho position is represented by the formula (m-1), the formula (m-2), and the formula (m-3).
  • a thienyl group, thiazolyl group, isothiazolyl group, or thiadiazolyl group in which R4 is located in the ortho position is a feature of the present invention.
  • Z1 represents C—R6 or a nitrogen atom
  • Z2 represents C—R7 or a nitrogen atom.
  • At least one of Z1 and Z2 represents a nitrogen atom.
  • Z1 is preferably a nitrogen atom
  • Z2 is preferably C—R7.
  • R6 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A
  • C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent A, C2-C6 haloalkynyl group Represents a C1-C6 alkoxy group, C1-C6 haloalkoxy group, or Rc-L- (wherein Rc and L are as defined above), which may be optionally substituted with the substituent A.
  • R6 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 C3-C8 cycloalkyl optionally substituted with a substituent A.
  • An alkyl group, a C1-C6 alkoxy group that may be optionally substituted with a substituent A, or a C1-C6 haloalkoxy group is preferable, and further, a hydrogen atom, a halogen atom, or a C1 that is optionally substituted with a substituent A
  • a C6-C6 alkyl group or a C1-C6 haloalkyl group is preferable, and a hydrogen atom or a halogen atom is particularly preferable.
  • R6 contains a hydrogen atom.
  • the halogen atom in R6 of the formula (1) has the same definition as described above, preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and particularly preferably a chlorine atom.
  • the C1-C6 alkyl group in the “C1-C6 alkyl group optionally substituted with the substituent A” in R6 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 R6 of the formula (1) has the same definition as above, preferably a difluoromethyl group, a trifluoromethyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl group. 2,2,2-trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2-fluoro An ethyl group, a 2,2-difluoroethyl group, or a 2,2,2-trifluoroethyl group.
  • the C3-C8 cycloalkyl group in the “C3-C8 cycloalkyl group optionally substituted with the substituent A” in R6 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 “C2-C6 alkenyl group optionally substituted with substituent A” in R6 of 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 R6 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 in the “C2-C6 alkynyl group optionally substituted with substituent A” in R6 of the formula (1) has the same definition as above, preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 2-butynyl group, or a 3-butynyl group, 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 R6 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-2-butynyl group, 4-chloro-4,4-difluoro-2-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, or 4,4,4 It is a 4-trifluoro-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 R6 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 R6 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.
  • Rc and L of “Rc-L-” in R6 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.
  • a methanesulfonyl group is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group.
  • R7 represents a hydrogen atom, a halogen atom, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with the substituent A, or a C2-C6 alkenyl group optionally substituted with the substituent A.
  • R7 is a hydrogen atom, a halogen atom, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with the substituent A, or a C1-C6 optionally substituted with the substituent A.
  • An alkoxy group or a C1-C6 haloalkoxy group is preferable, and a hydrogen atom or a halogen atom is more preferable, and a hydrogen atom is particularly preferable.
  • R7 in formula (1) includes a hydrogen atom.
  • the halogen atom in R7 in 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 haloalkyl group” in R7 of the formula (1) has the same definition as above, and 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 R7 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 “C2-C6 alkenyl group optionally substituted with substituent A” in R7 of 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 R7 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 R7 of the formula (1) has the same definition as above, preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 2-butynyl group, or a 3-butynyl group, 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 to C6 haloalkynyl group” in R7 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-2-butynyl group, 4-chloro-4,4-difluoro-2-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, or 4,4,4 4-trifluoro-2-butynyl group, more preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-2-butynyl group 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 R7 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 R7 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.
  • Rc and L of “Rc-L-” in R7 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.
  • a methanesulfonyl group is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group.
  • Rx1 of “Rx1C ( ⁇ O) —” in R7 of the formula (1) has the same definition as above.
  • “Rx1C ( ⁇ O) —” is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 2 , 2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino Carbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxyethyl) amino
  • X in the formula (1) represents an oxygen atom or a sulfur atom.
  • Preferred X is an oxygen atom.
  • Substituent A in formula (1) is a hydroxyl group, a cyano group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, a RaRbN— (Wherein Ra and Rb are as defined above), and Rc-L- (wherein Rc and L are as defined above), and represents at least one selected from the group consisting of .
  • the substituent A is preferably a cyano group, a C1-C6 alkoxy group, and Rc-L- (wherein Rc and L are as defined above), and in particular, a cyano group, and a C1-C6 Alkoxy groups are preferred.
  • substituent A a hydroxyl group, a cyano group, A C3-C8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
  • C1-C6 alkoxy groups a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy 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 such as a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclo
  • substituent A a hydroxyl group; a cyano group; A C3-C8 cycloalkyl group such as a cyclopropyl group and a cyclobutyl group; As the C1-C6 alkoxy group, a methoxy group and an ethoxy group, As C1-C6 haloalkoxy groups, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group, As C3-C8 cycloalkoxy group, cyclopropyloxy group, and cyclobutoxy group, RaRbN— (wherein Ra and Rb are as defined above), a dimethylamino group, an ethylmethylamino group, and a diethylamino group, And Rc-L- (wherein Rc and L are as defined above), a methylthio group,
  • Substituent B in formula (1) 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.
  • 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
  • the C3-C8 cycloalkoxy group includes 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” in the formula (1) is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, C2-C6 alkoxyalkoxy group, RaRbN— (wherein Ra and Rb are as defined above), Rc—L— (where Rc and L are as defined above), Rx1C ( ⁇ O) — (where Rx1 is as defined above), Rx6Rx7Rx8Si— (where Rx6, Rx7 and Rx8 each independently represents a C1-C6 alkyl group.), And represents at least one selected from the group consisting of 3- to 6-membered ring groups containing 1 to 2 oxygen atoms.
  • the substituent C includes a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C2-C6 alkoxyalkoxy group, Rc-L- (where Rc and L is as defined above), Rx1C ( ⁇ O) — (wherein Rx1 is as defined above), and a 3- to 6-membered ring group containing 1 to 2 oxygen atoms.
  • a cyano group, a C1-C6 alkoxy group, and Rc-L- are preferred.
  • 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 and a cyclobutoxy group as a C3-C8 cycloalkoxy group; A methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, and an ethoxyethoxy group as the C2-C6 alkoxyalkoxy group; RaRbN- (wherein Ra and Rb are as defined above), a dimethylamino
  • the “substituent D” in the formula (1) is a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group which may be substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 A cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, And at least one selected from the group consisting of C3-C8 cycloalkoxy groups.
  • 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. Is preferred.
  • substituent D As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; Hydroxyl group; cyano group; nitro group;
  • Examples of the C1-C6 alkyl group 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-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 halogen atom, a fluorine atom, a chlorine atom, and a bromine atom; Hydroxyl group; cyano group; nitro group;
  • the 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 methoxy group, an
  • the compound represented by the formula (1) may have one or two axial asymmetry.
  • the isomer ratio is a single or an arbitrary mixing ratio, and is not particularly limited.
  • the compound represented by 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.
  • specific compounds of the present invention include structural formulas P-1 to P-44 shown in Table 1 (where X in Table 1 represents an oxygen atom or a sulfur atom), and Table 2 And the structural formula (Y-1 to Y-408) of Y (where Y is as defined above) and R2 (wherein R2 is as defined above) shown in Table 3 (wherein R2 is as defined above) R2-1 to R2-5214). These compounds are for illustrative purposes, and the present invention is not limited thereto.
  • R1 is a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl optionally substituted with a substituent A.
  • R2 is a cyano group, a C1-C6 alkyl group optionally substituted with the substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with the substituent A, a 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, substituent C1-C6 alkoxy group optionally substituted with A, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A, RaRbN- (where Ra and Rb Is the same as defined above), Rx1C ( ⁇ O) — (wherein Rx1 is a C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C6
  • a phenyl group, a 5-membered to 6-membered heterocyclic group, or an 8- to 10-membered heterocyclic group In the phenyl group, R3 is optionally substituted with 0 to 5 (provided that when there are two or more substituents R3, each R3 represents an independent substituent); In the 5- to 6-membered heterocyclic group or the 8- to 10-membered heterocyclic group, R3 is optionally substituted with 0 to 6 (provided that when there are two or more substituents R3, R3 represents an independent substituent.
  • Y represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group;
  • R4 is substituted at the ortho position, and R5 is optionally substituted with 0 to 4 (provided that when there are two or more R5s, R5 represents an independent substituent).
  • R4 is substituted at the ortho position, and R5 is optionally substituted by 0 to 3 (however, two or more substituted or more).
  • R5 represents an independent substituent).
  • R4 is substituted at the ortho position, and R5 is optionally substituted by 0 to 2 (provided that when there are two or more substituted R5s, R5 is Represents an independent substituent).
  • R4 is a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group that may be optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-optionally substituted C3- C8 cycloalkyl group, 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, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, substituent C2-C6 alkenyloxy group optionally substituted with C, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy optionally
  • R5 has the same meaning as R4 described above
  • R7 represents a hydrogen atom, a halogen atom, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with the substituent A, or a C2-C6 alkenyl group optionally substituted with the substituent A.
  • the production method A is a method for obtaining a compound represented by the formula (Za) among the compounds represented by the formula (1), which is represented by the compound represented by the formula (2) and the formula (3).
  • a compound comprising reacting with a compound in the presence of an acid.
  • the compound represented by the formula (3) used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • Formula (3) 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 target reaction proceeds.
  • the compound represented by Formula (3) used in this reaction may be 1 equivalent or more with respect to the compound represented by Formula (2), and is not particularly limited as long as the target reaction proceeds. However, it is preferably 1 equivalent or more and 20 equivalents or less.
  • 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, p-toluenesulfonic acid is preferred. Moreover, when using the salt with the compound represented by Formula (3), use of an acid is not essential.
  • the amount of the acid used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (2), and is not particularly limited as long as the target reaction proceeds. 1 equivalent or more and 20 equivalents or less.
  • the acid to be used is a liquid, it can also be used as a solvent.
  • 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.
  • acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxy Ether solvents such as ethane, tetrahydro
  • 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 Melting , Dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride.
  • a solvent Preferably, an acidic solvent and a benzene solvent are mentioned, More preferably, a benzene solvent is mentioned.
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by formula (3). is there.
  • the temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but is usually 50 ° C. or higher and 180 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution or saline in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved Etc. can be used arbitrarily.
  • 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.
  • reaction mixture containing the compound represented by the formula (Za) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, it is not essential.
  • the reaction mixture containing the compound represented by the formula (Za) 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 (Za) 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, R7, and Y have the same meanings as described above.
  • Production method B is a production method for obtaining a compound represented by formula (Za-2) among the compounds represented by formula (1), wherein the compound represented by formula (Za-1) is sulfurated. It is a manufacturing method including making an agent (SR) react in a solvent.
  • SR agent
  • sulfurizing agent examples include Lawesson's reagent (2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetan-2,4-disulfide).
  • the amount of the sulfurizing agent used in this reaction may be 0.5 equivalent or more with respect to the compound represented by the formula (Za-1), and is not particularly limited as long as the target reaction proceeds. However, it is preferably 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, Examples thereof include benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. These solvents can be used alone or in admixture of two or more.
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (Za-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 or saline in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved Etc. can be used arbitrarily.
  • 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 (Za-2) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but it is not essential.
  • the reaction mixture containing the compound represented by the formula (Za-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 (Za-2) 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.
  • Rya represents a C1-C6 alkoxy group
  • Ya represents a phenyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, or thiadiazolyl group
  • R5 when Rya is substituted at the ortho position, R5 is further appropriately substituted by 0 to 4 (provided that when there are two or more R5s, R5 represents an independent substituent).
  • R5 When R4 is located in the ortho position, R5 is optionally substituted with 0 to 3 (provided that when there are two or more R5s, R5 represents an independent substituent), and the pyridyl group and the pyrazinyl group , The pyrimidinyl group, the pyridazinyl group, the triazinyl group, or the tetrazinyl group, when Rya is substituted in the ortho position, R5 is optionally substituted with 0 to 3 (provided that when there are two or more R5s, R5 represents an independent substituent), and when R4 is located in the ortho position, R5 is optionally substituted with 0 to 2 (However, when there are two substituted R5s, each R5 represents an independent substituent.), The thienyl group, the thiazolyl group, the isothiazolyl group, or the thiadiazolyl group, when Rya is substituted in the ortho position.
  • R5 is optionally substituted with 0 to 2 (provided that when there are two or more substituents R5, each R5 represents an independent substituent), and when R4 is substituted in the ortho position, R5 is optionally substituted with 0 to 1 And R 1, R 2, R 7, and X are as defined above.
  • Production method C is a method for synthesizing a compound represented by formula (Za-4) having a hydroxyl group at Y among compounds represented by formula (1), and represented by formula (Za-3). It is a manufacturing method including obtaining by reacting a compound and an acid in a solvent.
  • the acid used for this reaction includes boron halides such as boron trichloride and boron tribromide.
  • the amount of acid used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (Za-3), and is not particularly limited as long as the target reaction proceeds, but preferably Is 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and nitrile solvents such as acetonitrile. And halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents can be used alone or in admixture of two or more.
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (Za-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 or saline in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved Etc. can be used arbitrarily.
  • 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 (Za-4) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (Za-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 (Za-4) obtained after evaporation of the solvent can be purified with an appropriate solvent by washing, reprecipitation, recrystallization, column chromatography or the like. What is necessary is just to set suitably according to the target purity.
  • Ryb 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, or a substituent.
  • R1 , R2, R7, Ya, and X are as defined above.
  • Ryb-O— may be optionally substituted with a substituent C, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a substituent C A C3-C8 cycloalkoxy group optionally substituted with a C2-C6 alkenyloxy group optionally substituted with a substituent C, a C2-C6 haloalkenyloxy group, a substituent C optionally substituted with Or a C3 to C6 alkynyloxy group, a C3 to C6 haloalkynyloxy group, an aralkyloxy group optionally substituted with a substituent D, or Rx1C ( ⁇ O) O— (Rx1 is as defined above.
  • a compound represented by formula (Za-4) and Ryb-Lv are reacted in a solvent in the presence of a base. Manufacturing method including It is.
  • Ryb-Lv used in this reaction can be obtained as a commercial product or produced by a known method.
  • Ryb-Lv used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (Za-4), and is not particularly limited as long as the target reaction proceeds, but preferably Is 1 equivalent or more and 10 equivalents or less.
  • Bases used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine, and lutidine.
  • inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride
  • organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine, and lutidine.
  • organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine, and lutidine.
  • the base used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (Za-4), and is not particularly limited as long as the target reaction proceeds. 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, Alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, Ch
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (Za-4). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually ⁇ 20 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, 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 (Za-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 (Za-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 (Za-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.
  • Ryc represents a halogen atom
  • Yc represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group
  • R5 when Ryc is substituted in the ortho position, R5 is further appropriately substituted with 0 to 4 (provided that when there are two or more R5s, R5 represents an independent substituent), and R4 is in the ortho position.
  • R5 is optionally substituted with 0 to 3 (provided that when there are two or more R5s, R5 represents an independent substituent), the pyridyl group, the pyrazinyl group, the pyrimidinyl group, The pyridazinyl group, the triazinyl group, or the tetrazinyl group, when Ryc is substituted at the ortho position, R5 is -3 substitutions (however, when there are two or more substitutions R5, each R5 represents an independent substituent), and when R4 is located in the ortho position, R5 is further substituted 0-2 as appropriate (provided that 2 When R5 is substituted, each R5 represents an independent substituent.), The thienyl group, the thiazolyl group, the isothiazolyl group, or the thiadiazolyl group, when Ryc is substituted at the ortho position, 0 to 2 substituted (provided that when there are two or more substituted R5s, R5 represents an independent substituent), and when
  • Ryd 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.
  • the organic boronic acid is reacted with Suzuki-Miyaura coupling.
  • preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
  • Ryd-B used in this reaction represents an organic boronic acid such as organic boronic acid or organic boronic acid ester, and is available as a commercial product or can be produced by a known method.
  • the amount of Ryd-B used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (Za-6). Preferably, it is 1 equivalent or more and 10 equivalents or less.
  • the transition metals used in this reaction are palladium, nickel, ruthenium, etc., and may have a ligand.
  • Palladium is mentioned.
  • the amount of the transition metal used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (Za-6), but is particularly limited as long as the target reaction proceeds. None happen.
  • phosphine ligands such as triphenylphosphine and tricyclohexylphosphine can be added.
  • the amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (Za-6), but is particularly limited as long as the target reaction proceeds. It will never be done.
  • the base used in this reaction includes inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and tripotassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium t-butoxide.
  • inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, and tripotassium phosphate
  • metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium t-butoxide.
  • the amount of the base used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (Za-6). 1 equivalent or more and 50 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but an ether such as an aqueous solvent, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc.
  • benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. These solvents can be used alone or in admixture of two or more.
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (Za-6). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but is usually 30 ° C. or higher and 200 ° C. or lower or the boiling point of the solvent or lower.
  • 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 (Za-7) 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 (Za-7) 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 (Za-7) 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.
  • Rye represents a C2-C6 alkynyl group or a C2-C6 haloalkynyl group which may be optionally substituted with a substituent C
  • R1, R2, R7, Ryc, X and Yc are as defined above.
  • Rye is a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent C (Za- 8)
  • preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
  • the terminal alkyne compound used in this reaction can be obtained as a commercial product or produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to perform desilylation after introducing a trimethylsilylethynyl group into the compound represented by the formula (Za-6).
  • Za-6 the formula represented by the formula (Za-6).
  • For the desilylation Journal of the American Chemical Society, Vol. 131, No. 2, pp. 634-643 (2009), Journal of the American Chemical Society. And Journal of Organometallic Chemistry (Vol. 696, No. 25, pages 4039-4045 (2011)), Journal of Organometallic Chemistry (Journal of Organometallic Chemistry). It can carry out with reference to nonpatent literatures, such as.
  • the amount of the terminal alkyne compound used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (Za-6). Preferably, it is 1 equivalent or more and 10 equivalents or less.
  • the transition metal used in this reaction may have a ligand, such as palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis ( Palladiums such as triphenylphosphine) palladium and bis (triphenylphosphine) palladium dichloride.
  • a ligand such as palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis ( Palladiums such as triphenylphosphine) palladium and bis (triphenylphosphine) palladium dichloride.
  • coppers such as copper chloride, copper bromide and copper iodide are also used at the same time.
  • the amount of the transition metal used in this reaction may be 0.001 equivalent or more with respect to the compound represented by the formula (Za-6) for palladium and the like, respectively, and the target reaction proceeds. As long as it is done, there is no particular limitation. 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 (Za-6). 1 equivalent or more and 50 equivalents or less.
  • 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 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (Za-6), but is particularly limited as long as the target reaction proceeds. It will never be done.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N, N-dimethylformamide Amide solvents such as N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, tri
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (Za-6). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually 0 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, sodium thiosulfate, sulfurous acid
  • An aqueous solution or a salt solution in which a salt containing 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.
  • 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 (Za-8) 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 (Za-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 the formula (Za-8) 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.
  • preferred Ryc is a fluorine atom, a chlorine atom, or a bromine atom.
  • Ryg-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 Ryg-Q used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (Za-6). Usually, it is 1 equivalent or more and 30 equivalent or less. Moreover, when Q represents a hydrogen atom, it can be used as a solvent.
  • the base used in this reaction is preferably an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate or sodium hydride. Further, when Q is an alkali metal, the use of a base is not essential.
  • the amount of the base used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (Za-6). 1 equivalent or more and 30 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but an alcohol solvent represented by Ryg-H (wherein Ryg is as defined above), 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, ethyl acetate, isopropyl acetate and butyl acetate Ester solvents such as acetonitrile, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, etc.
  • Ether solvents such as diethyl
  • Urea solvent dichloromethane, dichloro Ethane, chloroform, halogenated solvents such as carbon tetrachloride, dimethyl sulfoxide, sulfur-based solvents such as sulfolane, acetone, methyl ethyl ketone, ketone solvents such as methyl isobutyl ketone.
  • halogenated solvents such as carbon tetrachloride, dimethyl sulfoxide, sulfur-based solvents such as sulfolane, acetone, methyl ethyl ketone, ketone solvents such as methyl isobutyl ketone.
  • 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 (Za-6). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually 0 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, 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 (Za-9) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (Za-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 (Za-9) obtained after evaporation of the solvent can be purified with an appropriate solvent by washing, reprecipitation, recrystallization, column chromatography or the like. What is necessary is just to set suitably according to the target purity.
  • R2a 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 C1-C6 alkoxy group optionally substituted with A, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A, phenyl group, 5-membered to 6-membered Represents a heterocyclic group or an 8- to 10-membered heterocyclic group, and in the phenyl group, when Rya is appropriately substituted with 1 to 5 and R3 is appropriately substituted with 0 to 4 (provided that there are R3 having 2 or more substitutions) In this case, R3 represents an independent substituent, and the 5- to 6-membered heterocyclic group or the 8- to 10-membered heterocyclic group is optionally substituted
  • Production method H is a method for synthesizing a compound represented by formula (Za-11) having a hydroxyl group at R2a among compounds represented by formula (1), and represented by formula (Za-10). It is a manufacturing method including obtaining by reacting a compound and an acid in a solvent.
  • the production method H can be performed according to the production method C. it can.
  • Ryb-O— may be optionally substituted with a substituent C, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a substituent C A C3-C8 cycloalkoxy group optionally substituted with a C2-C6 alkenyloxy group optionally substituted with a substituent C, a C2-C6 haloalkenyloxy group, a substituent C optionally substituted with Or a C3 to C6 alkynyloxy group, a C3 to C6 haloalkynyloxy group, an aralkyloxy group optionally substituted with a substituent D, or Rx1C ( ⁇ O) O— (Rx1 is as defined above.
  • a compound represented by the formula (Za-11) and Ryb-Lv are reacted in a solvent in the presence of a base. Including that It is a production method.
  • the production method I can be performed according to the production method D. it can.
  • R2c represents a phenyl group, a 5-membered to 6-membered heterocyclic group, or an 8- to 10-membered heterocyclic group.
  • R3 when Ryc is optionally substituted by 1 to 5, R3 is optionally 0. -4 substituted (provided that when there are two or more substituted R3, each R3 represents an independent substituent), the 5- to 6-membered heterocyclic group, or the 8- to 10-membered heterocyclic group is
  • Ryc is appropriately substituted with 1 to 6
  • R3 is appropriately substituted with 0 to 5 (provided that when there are two or more R3s, R3 represents an independent substituent, respectively)
  • Ryd-B represents an organic boronic acid.
  • R1, Ryc, Ryd, R7, X, and Y are as defined above.
  • Ryd 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.
  • preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
  • Ryd-B used in this reaction represents an organic boronic acid such as organic boronic acid or organic boronic acid ester, and is available as a commercial product or can be produced by a known method.
  • the production method J can be performed according to the production method E. it can.
  • Rye is a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent C (Za- 15)
  • preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
  • the terminal alkyne compound used in this reaction can be obtained as a commercial product or produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to perform desilylation after introducing a trimethylsilylethynyl group into the compound represented by the formula (Za-13).
  • Za-13 the formula represented by the formula (Za-13).
  • For the desilylation Journal of the American Chemical Society, Vol. 131, No. 2, pp. 634-643 (2009), Journal of the American Chemical Society. And Journal of Organometallic Chemistry (Vol. 696, No. 25, pages 4039-4045 (2011)), Journal of Organometallic Chemistry (Journal of Organometallic Chemistry). It can carry out with reference to nonpatent literatures, such as.
  • the production method K can be performed according to the production method F. it can.
  • Ryf represents a halogen atom
  • R2b represents a phenyl group, a 5- to 6-membered heterocyclic group, or an 8- to 10-membered heterocyclic group
  • R3 is optionally substituted with 0 to 4 (However, when there are two or more substituted R3s, each R3 represents an independent substituent.)
  • HalR represents a halogenating agent, and R1, R7, X, and Y are as defined above. is there.
  • Production method L is a production method for obtaining a compound represented by formula (Za-17) in which Ryf is a halogen atom among the compounds represented by formula (1), and is represented by formula (Za-16). Or a halogenating agent (HalR) is reacted in a solvent, or a compound represented by the formula (Za-16) is reacted with a halogenating agent (HalR) and a radical initiator in a solvent. It is a manufacturing method also including making it. In this reaction, a base or a radical initiator can be added. What is necessary is just to set suitably so that the target reaction may advance.
  • 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 (Za-16). Preferably, it is 1 equivalent or more and 10 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as the target reaction proceeds as long as it is 0.5 equivalent or more, and preferably 1 equivalent or more and 5 equivalents or less.
  • the halogenating agent used in this reaction is an iodinating agent
  • an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid, or trifluoromethanesulfonic acid.
  • an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid, or trifluoromethanesulfonic acid.
  • the amount of acid used in this reaction is 0.01 equivalent or more with respect to the compound represented by the formula (Za-16). Although it does not restrict
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid and trifluoromethanesulfonic acid, diethyl ether , Ether solvents such as diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene Ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (Za-16). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually 0 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, 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 (Za-17) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but it is not essential.
  • reaction mixture containing the compound represented by the formula (Za-17) 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 (Za-17) 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.
  • radical initiator used in this reaction examples 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 (Za-16). 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 1 equivalent or more with respect to the compound represented by the formula (Za-16). Usually, it is 1 equivalent or more and 1.8 equivalent 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 (Za-16). 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 (Za-17) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but it is not essential.
  • reaction mixture containing the compound represented by the formula (Za-17) 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 (Za-17) 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.
  • R6 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 C3-C8 optionally substituted with a substituent A.
  • Lv represents a leaving group such as a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group, and a halogen atom
  • R1, R2, X, and Y are as defined above.
  • Production method M is a method of obtaining a compound represented by formula (Zb-2) among the compounds represented by formula (1), wherein the production intermediate represented by formula (Zb-1) and R1 -Lv is a production method comprising reacting with Lv in a solvent in the presence of a base.
  • the compound represented by the formula (Zb-1) used in this reaction can be obtained according to the synthesis method described in Production Method AB.
  • R1-Lv used in this reaction can be obtained as a commercial product or produced by a known method.
  • the amount of R1-Lv used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (Zb-1), and is not particularly limited as long as the target reaction proceeds. Preferably, it is 1 equivalent or more and 10 equivalents or less.
  • Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride, but are particularly limited as long as the intended reaction proceeds. It will never be done.
  • the amount of the base used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (Zb-1), and is not particularly limited as long as the target reaction proceeds, but preferably Is 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, 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 (Zb-1). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually 0 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • 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 (Zb-2) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (Zb-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 (Zb-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.
  • SR represents a sulfurizing agent
  • R1, R2, R6, and Y have the same meanings as described above.
  • Production method N is a production method for obtaining a compound represented by formula (Zb-4) among the compounds represented by formula (1), wherein the compound represented by formula (Zb-3) is sulfurated. It is a manufacturing method including making an agent (SR) react in a solvent.
  • SR agent
  • sulfurizing agent examples include Lawesson's reagent (2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetan-2,4-disulfide).
  • the amount of the sulfurizing agent used in this reaction may be 0.5 equivalent or more with respect to the compound represented by the formula (Zb-3), and is not particularly limited as long as the target reaction proceeds. However, it is preferably 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, Examples thereof include benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. These solvents can be used alone or in admixture of two or more.
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (Zb-3). 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 or saline in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved Etc. can be used arbitrarily.
  • 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 (Zb-4) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (Zb-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 (Zb-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.
  • Production method O is a method for synthesizing a compound represented by formula (Zb-6) having a hydroxyl group at Y among the compounds represented by formula (1), and represented by formula (Zb-5). It is a manufacturing method including obtaining by reacting a compound and an acid in a solvent.
  • the acid used for this reaction includes boron halides such as boron trichloride and boron tribromide.
  • the production method O can be performed according to the production method C. it can.
  • Production method P is a method for synthesizing a compound represented by formula (Zb-7) among the compounds represented by formula (1), wherein the compound represented by formula (Zb-6) and Ryb-Lv Is reacted in a solvent in the presence of a base.
  • Ryb-Lv used in this reaction can be obtained as a commercial product or produced by a known method.
  • the production method P can be performed according to the production method D. it can.
  • Ryd-B represents an organic boronic acid
  • R1, R2, Yc, Ryc, Ryd, R6 and X have the same meanings as described above.
  • Ryd 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.
  • the organic boronic acid is reacted with Suzuki-Miyaura coupling.
  • preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
  • Ryd-B used in this reaction represents an organic boronic acid such as organic boronic acid or organic boronic acid ester, and is available as a commercial product or can be produced by a known method.
  • the production method Q can be performed according to the production method E. it can.
  • Rye represents a C2-C6 alkynyl group or a C2-C6 haloalkynyl group which may be optionally substituted with a substituent C
  • R1, R2, Yc, Ryc, R6 and X are as defined above.
  • Rye is a C2 to C6 alkynyl group or a C2 to C6 haloalkynyl group optionally substituted with a substituent C (Zb— A method for synthesizing the compound represented by 10), wherein the compound represented by (Zb-8) and the terminal alkyne compound are obtained by Sonogashira coupling in the presence of a transition metal and a base in a solvent. It is a manufacturing method containing.
  • preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
  • the terminal alkyne compound used in this reaction can be obtained as a commercial product or produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to perform desilylation after introducing a trimethylsilylethynyl group into the compound represented by the formula (Zb-8).
  • Zb-8 Trimethylsilylacetylene
  • the production method R is carried out in accordance with the production method F by using the compound represented by the formula (Za-6) in the production method F instead of the compound represented by the formula (Zb-8). Can do.
  • a b-11) a method for obtaining a compound represented by a manufacturing method comprising
  • preferred Ryc is a fluorine atom, a chlorine atom, or a bromine atom.
  • Ryg-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 production method S is carried out according to the production method G by using the compound represented by the formula (Za-6) in the production method G instead of the compound represented by the formula (Zb-8). Can do.
  • Production method T is a method for synthesizing a compound represented by formula (Zb-13) having a hydroxyl group at R2a among the compounds represented by formula (1), and represented by formula (Zb-12). It is a manufacturing method including obtaining by reacting a compound and an acid in a solvent.
  • the acid used for this reaction includes boron halides such as boron trichloride and boron tribromide.
  • the production method T can be performed according to the production method C. it can.
  • Ryb-O— may be optionally substituted with a substituent C, C1-C6 alkoxy group, C1-C6 haloalkoxy group, substituent C A C3-C8 cycloalkoxy group optionally substituted with a C2-C6 alkenyloxy group optionally substituted with a substituent C, a C2-C6 haloalkenyloxy group, a substituent C optionally substituted with Or a C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group, an aralkyloxy group optionally substituted with a substituent D, or Rx1C ( ⁇ O) O— (Rx1 is as defined above.
  • a compound represented by the formula (Zb-13) and Ryb-Lv are reacted in a solvent in the presence of a base. Including that It is a production method.
  • Ryb-Lv used in this reaction can be obtained as a commercial product or produced by a known method.
  • the production method U is carried out in accordance with the production method D by using the compound represented by the formula (Za-4) in the production method D instead of the compound represented by the formula (Zb-13). Can do.
  • Ryd-B represents an organic boronic acid
  • R1, R2c, Ryc, Ryd, R6, X, and Y are as defined above.
  • Ryd 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.
  • the organic boronic acid is reacted with Suzuki-Miyaura coupling.
  • preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
  • Ryd-B used in this reaction represents an organic boronic acid such as organic boronic acid or organic boronic acid ester, and is available as a commercial product or can be produced by a known method.
  • the production method V can be performed according to the production method E. it can.
  • Rye is a C2 to C6 alkynyl group or a C2 to C6 haloalkynyl group optionally substituted with a substituent C (Zb— 17)
  • preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
  • the terminal alkyne compound used in this reaction can be obtained as a commercial product or produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to perform desilylation after introducing a trimethylsilylethynyl group into the compound represented by the formula (Zb-15).
  • Zb-15 Trimethylsilylacetylene
  • the production method W can be performed according to the production method F. it can.
  • HalR represents a halogenating agent
  • R1, R2b, Ryf, R6, X, and Y are as defined above.
  • Production method X is a production method for obtaining a compound represented by formula (Zb-19) in which Ryf is a halogen atom among the compounds represented by formula (1), and is represented by formula (Zb-18). Or a halogenating agent (HalR) is reacted in a solvent, or a compound represented by the formula (Zb-18) is reacted with a halogenating agent (HalR) and a radical initiator in a solvent. It is a manufacturing method also including this.
  • the production method X can be performed according to the production method L. it can.
  • HalR represents a halogenating agent
  • R1, R2, Ryf, X and Y are as defined above.
  • Production method Y is a production method for obtaining a compound represented by formula (Zb-21) in which Ryf is a halogen atom among the compounds represented by formula (1), and is represented by formula (Zb-20). And a halogenating agent (HalR) in a solvent.
  • Zb-21 a compound represented by formula (Zb-21) in which Ryf is a halogen atom among the compounds represented by formula (1), and is represented by formula (Zb-20).
  • a halogenating agent (HalR) in a solvent.
  • selectfluoro N-fluoro-N′-triethylenediamine bis (tetrafluoroborate)
  • N-chlorosuccinimide N-bromosuccinimide
  • N-iodosuccinimide 1 1,3-Dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like.
  • the amount of the halogenating agent used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (Zb-20). Preferably, it is 1 equivalent or more and 10 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as the target reaction proceeds as long as it is 0.5 equivalent or more, and preferably 1 equivalent or more and 5 equivalents or less.
  • the halogenating agent used in this reaction is an iodinating agent
  • an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid, or trifluoromethanesulfonic acid.
  • an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid, or trifluoromethanesulfonic acid.
  • the amount of acid used in this reaction is 0.01 equivalent or more with respect to the compound represented by the formula (Zb-20). Although it does not restrict
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid and trifluoromethanesulfonic acid, diethyl ether , Ether solvents such as diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene Ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (Zb-20). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually 0 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, 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 (Zb-21) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (Zb-21) 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 (Zb-21) 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.
  • La represents S
  • Lb represents SO or SO 2
  • Ox ′ represents an oxidizing agent
  • Table production process Z is the compound represented by the formula (1), in R3, R4, R5, R6, R7, Lb included in substituents A and substituents C is SO or SO 2 wherein (Lb)
  • R 3, R 4, R 5, R 6, R 7, the substituent A and the substituent C and La are the compounds represented by the formula (La) Is a production method comprising reacting a compound represented by the formula (I) with an oxidizing agent (Ox ′) in a solvent.
  • oxidizing agent used in this reaction examples include peroxides such as hydrogen peroxide and meta-chloroperbenzoic acid.
  • transition metals such as sodium tungstate can be added.
  • the amount of the oxidizing agent used in this reaction is usually 1.0 equivalent or more and 1.2 equivalent or less with respect to the compound represented by the formula (La) when producing SO, and produces SO 2 . When doing, it is usually 2 equivalents or more and 10 equivalents or less. Moreover, when adding transition metals, it is 0.001 equivalent or more and 1 equivalent or less normally.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but an aqueous solvent, an acidic solvent such as acetic acid, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc.
  • an acidic solvent such as acetic acid, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc.
  • examples thereof include benzene solvents, nitrile solvents such as acetonitrile, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in admixture of two or more.
  • the amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 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, 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 sulfur 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 (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.
  • Manufacturing method AA is a manufacturing method of the manufacturing intermediate represented by Formula (2), Comprising: The compound represented by Formula (4) and the compound represented by Formula (5) are carried out in a solvent or without a solvent. It is a manufacturing method including reacting.
  • the compound represented by the formula (4) used in this reaction can be synthesized according to the reference example. Also, Green Chemistry, Vol. 41, pp. 580-585, The Journal of Organic Chemistry, Vol. 65, No. 20, pp. 6458-6461 (2000), Organic It can also be synthesized by referring to Letters (Organic Letters), Vol. 9, No. 4, pages 667-669 (2007).
  • the compound represented by the formula (5) 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 the formula (5) used in this reaction is particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (4). However, it is preferably 1 equivalent or more and 10 equivalents or less.
  • Solvents used in this reaction are ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, Ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl -2-Urea solvents such as imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, sulfur solvents such as dimethyl sulfox
  • the amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by formula (4). is there.
  • the temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually ⁇ 50 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (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.
  • Production method AB is a production method of a production intermediate represented by the formula (Zb-1), wherein the compound represented by the formula (6) and the compound represented by the formula (7) It is a manufacturing method including making it react in a solvent on sexual conditions.
  • the compound represented by the formula (6) used in this reaction can be synthesized according to the reference example.
  • the compound can also be synthesized with reference to Tetrahedron, 2012, Vol. 68, pages 9598-9605.
  • 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). However, it is preferably 1 equivalent or more and 10 equivalents or less.
  • 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. 01 equivalents or more. 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 (6). 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.
  • the base used in this reaction is exemplified by inorganic bases such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, but is 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 (6), but preferably 1 equivalent or more. 30 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but an ether such as an aqueous solvent, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc.
  • an ether such as an aqueous solvent, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc.
  • Solvents alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitriles such as acetonitrile Solvents, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane Down, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or in admixture of two or more.
  • the amount of 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 ⁇ 20 ° C. or higher and 180 ° C. or lower or the boiling point of the solvent or lower.
  • reaction under acidic conditions and the reaction under basic conditions can be performed by a common method.
  • a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, etc. are dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved, saline, etc. are optional.
  • benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene
  • ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.
  • the reaction mixture containing the compound represented by the formula (Zb-1) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • the reaction mixture containing the compound represented by the formula (Zb-1) 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 (Zb-1) 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 (Zb-1) is represented by the formula (Zb-1 ′) (Wherein R2, R6, X and Y are as defined above.) Is also included.
  • the compound represented by the formula (Zb-1 ′) can be handled in the same manner as the compound represented by the formula (Zb-1), and the production method M can be applied. Further, it may be a mixture of the compound represented by the formula (Zb-1) and the compound represented by the formula (Zb-1 ′), and the isomer mixing ratio may be a single compound or a mixture of any ratio.
  • the compound represented by the formula (1) or a salt thereof can be produced by arbitrarily combining the production methods A to AB shown above.
  • the compound represented by the formula (1) or a salt thereof can also be produced by arbitrarily combining known methods and production methods A to AB.
  • the compound of the present invention can be used as an agrochemical because it can control organisms harmful to plants.
  • 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 (Thanatephorus cucumeris), brown sclerotia (Ceratobasidium setariae), brown sclerotia (Waitea circinata), brown rot phlegm or eu Sclerotium hydrophilum, Red sclerotia (Wairea 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 (Plasmodiphora brassicae), downy mildew (Peronospora parasitica), black rot (Xhanthampastrastocana). campestris), black spot bacterial disease (Pseudomonas syringae pv. maculacola), soft rot (Erwinia carotovora subsp.
  • Anthracnose (Colletotrichum lindemuthianum), bacterial wilt (Ralstonia solanacearum), blight (Pseudomonas syringae pv. Phaseolisola), brown bacterial disease (Pseudomonas firla flamp) v. 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.
  • Examples of the method of applying the compound of the present invention or a composition containing the compound include a method of contacting with a plant body or seeds, a method of bringing it into a cultivated soil, and a method of contacting with a plant root or a rhizome.
  • Specific examples include foliage spraying treatment, injection treatment, seedling box treatment, cell tray treatment, spraying treatment on plant seeds, smearing treatment on plant seeds, plant seeds, and the like. Soaking treatment, powder coating on plant seeds, spraying treatment on soil surface, soil mixing after spraying treatment on soil surface, pouring treatment into soil, soil blending after pouring treatment in soil, soil Examples include irrigation treatment and soil mixing after soil irrigation treatment. 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 application concentration of the compound of the present invention or the composition containing the same vary depending on the target crop, the target disease, the degree of occurrence of the disease, the dosage form of the compound, the application method and various environmental conditions, but are sprayed or irrigated.
  • the amount of the active ingredient is suitably 0.1 to 10,000 g per hectare, and 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.
  • an appropriate carrier is used at an appropriate concentration. Processing may be performed after dilution.
  • the compound of the present invention or a composition containing the compound is brought into contact with a plant seed, it may be used after being diluted to an appropriate concentration and then immersed, powdered, sprayed or smeared on the plant seed.
  • the amount of the compound of the present invention or the composition containing the compound used when dipping, dressing, spraying or smearing is usually about 0.05 to 50% of the dry plant seed weight as the active ingredient amount, Preferably, 0.1 to 30% is appropriate, but it may be appropriately set depending on the form of the composition and the kind of plant seed to be treated, and is not limited to these ranges.
  • composition containing the compound of the present invention may contain other agricultural chemicals such as fungicides, insecticides (including acaricides and nematicides), herbicides, microbial materials, plant growth regulators, and the like as necessary. It can be used by mixing with a pesticide, a disease control agent containing nucleic acid as an active ingredient (International Publication No. 2014/062775), a soil conditioner or a fertilizer.
  • 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 (s5) A compound represented by: [B-23.42] Formula (s6) A compound represented by the formula (ningnanmycin), [B-23.43] Formula (s7) (Refer to International Publication No. 10/136475), [B-23.44] Formula (s8) A compound represented by (see International Publication No. 14/010737), [B-23.45] Formula (s9) A compound represented by (see International Publication No. 11/088504), [B-23.46] Formula (s10) (See International Publication No. 11/137002), [B-23.47] Formula (s11) (See International Publication No.
  • A9 and A10 each independently represent a hydrogen atom or a halogen atom, A11 represents a halogen atom, A12 represents a halogen atom or a C1-C6 alkyl group, and A13 represents , A halogen atom, a cyano group, a C1-C6 alkyl group, or a C1-C6 alkoxy group.
  • A9 and A10 each independently represent a hydrogen atom or a halogen atom
  • A11 represents a halogen atom
  • A12 represents a halogen atom or a C1-C6 alkyl group
  • A13 represents , A halogen atom, a cyano group, a C1-C6 alkyl group, or a C1-C6 alkoxy group.
  • Formula (s23) [Wherein, A26 represents a hydrogen atom or a halogen atom, and V1 and V2 are each independently an oxygen atom or a sulfur atom. ] (See International Publication No. 12/025450), [B-23.60] Formula (s24) or Formula (s25) [Wherein, m4 represents an integer of 0 to 5, A27 represents a C1 to C6 alkyl group, A28 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group.
  • A28s each represent an independent substituent and may be the same or different
  • A29 is a C1-C6 alkyl group, a C2-C6 alkenyl group, or C3 Represents a C6 alkynyl group.
  • 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.
  • 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.
  • A32 represents a C1-C6 alkyl group, a C2-C6 alkenyl group, or C3 Represents a C6 alkynyl group.
  • A33, A34, A35 and A36 each independently represent a hydrogen atom or a halogen atom, and A37 represents a hydrogen atom, an acetyl group or a benzoyl group.
  • A37 represents a hydrogen atom, an acetyl group or a benzoyl group.
  • Formula (s29) [Wherein, A38 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and A39 and A40 each independently represent a hydrogen atom or a halogen atom. ] (See International Publication No. 14/043376), [B-23.64] Formula (s30) [In the formula, A41 represents a hydrogen atom, a hydroxyl group (—SH), a thiocyanic acid group (—SCN), or a C1-C6 alkylthio group, and 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.
  • c-3 GABAergic chloride ion channel blocker
  • GABAergic chloride ion channel blockers [c-3.1] chlordane, [c-3.2] endosulfan, [c-3.3] Lindane, [c-3.4] Dienochlor, [c-3.5] Ethiprole, [c-3.6] Fipronil, [c-3.7] aceto Protole (acetoprole) and the like.
  • c-4 Sodium channel modulator [c-4.1] Acrinathrin, [c-4.2] Allethrin [(1R) -isomer] (allethrin [(1R) -isomer]), [C-4.3] bifenthrin, [c-4.4] bioarethrin, [c-4.5] bioarethrin S-cyclopentenyl isomer, [c- 4.6] Bioresmethrin, [c-4.7] Cycloprothrin, [c-4.8] Cyfluthrin, [c-4.
  • c-5 Nicotinic Acetylcholine Receptor (nAChR) Competitive Modulator [c-5.1] Acetamiprid, [c-5.2] Clothianidin (nicotinic acetylcholine receptor (nAChR) competitive modulator) ), [C-5.3] dinotefuran, [c-5.4] imidacloprid, [c-5.5] nitenpyram, [c-5.6] thiacloprid, [C-5.7] thiamethoxam, [c-5.8] nicotine, [c-5.9] nicotine sulfate, [c-5.10] Kisafuroru (sulfoxaflor), [c-5.11] Furupirajifuron (flupyradifurone), and the like [c-5.12] triflupromazine meso pyridinium beam (triflumezopyrim).
  • c-6 Nicotinic acetylcholine receptor (nAChR) allosteric modulator As nicotinic acetylcholine receptor (nAChR) allosteric modulators, [c-6.1] spinosad, [c-6.2] spinetoram, etc. Is mentioned.
  • c-7 glutamatergic chloride channel (GluCl) allosteric modulator [c-7.1] abamectin, [c-7.2] emamectin benzoic acid as a glutamatergic chloride channel (GluCl) allosteric modulator
  • Examples thereof include salts (emectin benzoate), [c-7.3] lepimectin, [c-7.4] milbemectin and the like.
  • c-8 juvenile hormone analogues [c-8.1] hydroprene, [c-8.2] kinoprene, [c-8.3] methoprene ), [C-8.4] phenoxycarb, [c-8.5] pyriproxyfen, and the like.
  • c-9 Non-specific (multi-site) inhibitors
  • non-specific (multi-site) inhibitors [c-9.1] methyl bromide, [c-9.2] chloropicrin [C-9.3] cryolite, [c-9.4] sulfuryl fluoride, [c-9.5] borax, [c-9.6] boron Boric acid, [c-9.7] disodium octaborate, [c-9.8] sodium metaborate [c-9.9] tartar emetic), [c-9.10] dazomet, [c-9.11] metam (m etam), [c-9.12] carbam sodium salt, and the like.
  • String sound organ TRPV channel modulator examples include [c-10.1] pymetrozine, [c-10.2] pyrifluquinazone, and the like.
  • c-11 Tick Growth Inhibitors As tick growth inhibitors, [c-11. 1] clofentezine, [c-11.2] diflovidazin, [c-11.3] hexithiazox (Hexyazox), [c-11.4] etoxazole and the like.
  • c-12 Mitochondrial ATP synthase inhibitor As mitochondrial ATP synthase inhibitors, [c-12. 1] diafenthiuron, [c-12.2] azocyclotin, [c-12. 3] Cyhexatin, [c-12.4] fenbutatin oxide, “c-12.5” propargite, “c-12.6” tetradiphon, etc. .
  • c-13 Oxidative Phosphorylation Uncoupler that Perturbs Proton Gradient [c-13.1] Chlorfenapyl, [c-13.2] DNOC as oxidative phosphorylation uncouplers that disrupt proton gradient (Dinitro-ortho-cresol), [c-13.3] binapacryl, [c-13.4] sulfuramide, and the like.
  • c-14 Nicotinic Acetylcholine Receptor (nAChR) Channel Blocker As nicotinic acetylcholine receptor (nAChR) channel blockers, [c-14.1] bensultap, [c-14.2] cartap hydrochloride (cartap) hydrochloride), [c-14.3] thiocyclam, [c-14.4] monosultap, and the like.
  • nAChR Nicotinic Acetylcholine Receptor
  • nAChR nicotinic acetylcholine receptor
  • Chitin biosynthesis inhibitor type 0 includes [c-15.1] bistrifluron, [c-15.2] chlorfluazuron, [c-15.3] diflubenzuron, [C-15.4] flucycloxuron, [c-15.5] flufenoxuron, [c-15.6] hexaflumuron, [c-15.7] Lufenuron, [c-15.8] novaluron, [c-15.9] noviflumuron, [c-15.10] teflubenzuron, [c-15.11] Rifurumuron (triflumuron), and the like.
  • c-16 Chitin biosynthesis inhibitor type 1
  • Examples of the chitin biosynthesis inhibitor type 1 include [c-16.1] buprofezin.
  • fly insect insect molting inhibitor examples include [c-17.1] cyromazine.
  • c-18 molting hormone (ecdysone) receptor agonist
  • ecdysone molting hormone (ecdysone) receptor agonist
  • Octopamine receptor agonist [c-19.1] Amitraz and the like can be mentioned as an octopamine receptor agonist.
  • c-20 Mitochondrial electron transport system complex III inhibitor [c-20.1] hydramethylnon, [c-20.2] acequinocyl, mitochondrial electron transport system complex III inhibitor, [C-20.3] fluacrylpyrim, [c-20.4] bifenazate and the like.
  • Mitochondrial electron transport complex I inhibitor include [c-21.1] phenazaquin, [c-21.2] fenpyroximate, [c-21.3] pyridaben, [C-21.4] pyrimidifen, [c-21.5] tebufenpyrad, [c-21.6] tolfenpyrad, [c-21.7] rotenone, etc. It is done.
  • c-22 Voltage-dependent sodium channel blocker
  • Examples of the voltage-dependent sodium channel blocker include [c-22.1] indoxacarb, [c-22.2] metaflumizone and the like.
  • c-23 Acetyl CoA carboxylase inhibitor [c-23.1] Spirodiclofen, [c-23.2] Spiromesifen, [c-23.3] As acetyl CoA carboxylase inhibitors And spirotetramat and the like.
  • c-24 Mitochondrial electron transport system complex IV inhibitor As mitochondrial electron transport system complex IV inhibitors, [c-24.1] aluminum phosphide, [c-24.2] calcium phosphide ( calcium phosphate, [c-24.3] phosphine, [c-24.4] zinc phosphide, [c-24.5] calcium cyanide, [c -24.6] sodium cyanide, [c-24.7] potassium cyanide, and the like.
  • c-25 Mitochondrial electron transport system complex II inhibitor [c-25.1] Cyenopyrafen, [c-25.2] Cyflumetofen, [c-25.1] Mitochondrial electron transport system complex II inhibitor -25.3] piflubumide and the like.
  • c-26 Ryanodine receptor modulator As ryanodine receptor modulators, [c-26.1] chlorantraniliprole, [c-26.2] cyantraniliprole, [c-26. 3] Flubenamide, etc. are mentioned.
  • Target site unspecified string sound organ modulator examples include [c-27.1] flonicamid.
  • c-28 Other insecticides
  • Other insecticides include [c-28.1] azadirachtin, [c-28.2] benzoximate, [c-28.3] phenisobromo. Phenisobromolate, [c-28.4] quinomethionate, [c-28.5] dicofol, [c-28.6] pyridalyl, [c-28.7] bromopropiate Bromopropyrate, [c-28.8] triazamate, [c-28.9] dicyclanil, [c-28.1] dinobuton, [c-28.1] dinocup ( din ocap), [c-28.12] hydrogen cyanide, [c-28.13] methyl iodide, [c-28.14] caranjin, [c-28.15] Mercury chloride, [c-28.16] methyl isothiocyanate, [c-28.17] pentachlorophenol, [c-28.
  • A65 represents a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group
  • A66 represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group
  • A67 and A68 represent Each independently, a hydrogen atom, a C1-C6 alkyl group optionally substituted with a cyano group, an alkyl group optionally substituted with a methoxy group, an alkyl group optionally substituted with an ethoxy group, Or a C3-C8 cycloalkyl group
  • A69 represents a hydrogen atom, a cyano group, a C1-C6 haloalkyl group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group optionally substituted with a cyano group.
  • Formula (s53) or Formula (s54) [Wherein A70 represents a methyl group, an ethyl group, an isopropyl group, a 2,2,2-trifluoroethyl group, or a phenyl group, and A71 represents A72 represents a partial structure selected from the group consisting of: And V8 represents an oxygen atom, a sulfur atom, —CH 2 —, or —CH 2 CH 2 —. ] (See International Publication No. 14/167084, International Patent No.
  • Formula (s56) [Wherein, A79, A80, A81 and A82 are each independently a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or a C3-C8 Represents a cycloalkoxy group. ] (See International Publication No. 13/024009), [C-28.139] Formula (s56) [Wherein, A79, A80, A81 and A82 are each independently a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or a C3-C8 Represents a cycloalkoxy group. ] (See International Publication No.
  • [A90 represents a halogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group
  • A91 represents a C1-C6 haloalkyl group
  • A92 and A93 are each independently a hydrogen atom
  • C1 to C6 represents an alkyl group, an acetyl group, a propionoyl group, a methanesulfonylethyl group, a methoxycarbonyl group, or an ethoxycarbonyl group
  • A94 and A95 are each independently a hydrogen atom, a C1 to C6 alkyl group, Or a C1-C6 haloalkyl group.
  • (Refer international publication 12/164698) etc. are mentioned.
  • the mixing ratio of the compound of the present invention and other agricultural chemicals is not particularly limited as long as the effect is exerted, but usually other agricultural chemicals are 0.001 to 1000 by weight with respect to the compound of the present invention.
  • the ratio is preferably 0.01 to 100.
  • Step 2 Synthesis of 1-ethyl-5-isopropyl-6- (2,4,6-trifluorophenyl) pyrimidin-2 (1H) -one (Compound No. 18)
  • a toluene solution containing 2.8 g of 2-((dimethylamino) methylene) -3-methyl-1-methyl- (2,4,6-trifluorophenyl) butan-1-one obtained in step 1 2.7 g of ethyl urea and 5.3 g of p-toluenesulfonic acid monohydrate were added, and the mixture was stirred for 17 hours while heating under reflux.
  • the obtained organic layer was washed successively with saturated aqueous ammonium chloride solution and saturated brine, and dried over sodium sulfate.
  • the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography.
  • the title compound was obtained as 6.4 g of a colorless oil.
  • the mixture was stirred for 5 hours under heating and reflux. After cooling to room temperature, the reaction mixture was neutralized by adding a 1N aqueous hydrochloric acid solution, and then ethyl acetate was added for liquid separation. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography to obtain the title compound as 375 mg of a yellow solid.
  • the compound of the present invention is specifically shown to be effective for plant diseases, but is not limited to these examples.
  • the patient After inoculation, the patient was allowed to stand for about 24 hours in a wet room with a room temperature of 20-23 ° C. to promote disease. The severity of the disease was investigated 6 to 10 days after the inoculation, and the effect of the drug solution was evaluated.
  • Test Example B Tomato Gray Mold Disease After seeding the seeds of the test plant (tomato variety: large Fuju), it was cultivated until 3 to 5 true leaves were developed.
  • the compound of the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to obtain a concentration of 250 ppm to obtain a chemical solution.
  • the obtained chemical solution was sprayed on the test plant (2.5 ml / pot). Plants after the drug solution was dried were spray-inoculated with 4-8 ⁇ 10 5 cells / ml of conidial spore suspension of Botrytis cinerea.
  • the patient After inoculation, the patient was allowed to stand for about 48 hours in a wet room at a room temperature of 20 to 23 ° C. to promote disease. The severity of the disease was investigated 2 to 3 days after the inoculation, and the effect of the drug solution was evaluated.
  • Test Example C Cabbage Black Soot Disease After sowing seeds of a test plant (cabbage variety: seasonal harvest), it was cultivated until the cotyledons developed.
  • the compound of the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to obtain a concentration of 250 ppm to obtain a chemical solution.
  • the obtained chemical solution was sprayed on the test plant (2.5 ml / pot). Plants after the drug solution had dried were spray-inoculated with 4-8 ⁇ 10 5 cells / ml of conidial spore suspension of Alberia brassicicola.
  • the patient After inoculation, the patient was allowed to stand for about 48 hours in a wet room at a room temperature of 20 to 23 ° C. to promote disease. The severity of the disease was investigated 2 to 3 days after the inoculation, and the effect of the drug solution was evaluated.
  • Test Example D Barley powdery mildew After seeding seeds of a test plant (barley variety: Akagami), the seeds were cultivated until the first leaf developed.
  • the compound of the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to obtain a concentration of 250 ppm to obtain a chemical solution.
  • the obtained chemical solution was sprayed on the test plant (2.5 ml / pot). Plants after the chemical solution was dried were inoculated by knocking off conidia of barley powdery mildew (Blumeria graminis f. Sp. Hordei). After inoculation, the severity of the disease was investigated 6 to 10 days later, and the effect was evaluated.
  • Test Example E Wheat red rust After seeding seeds of a test plant (wheat variety: Norin 61), the seeds were cultivated until the first leaf developed.
  • the compound of the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to obtain a concentration of 250 ppm to obtain a chemical solution.
  • the obtained chemical solution was sprayed on the test plant (2.5 ml / pot). Plants after the drug solution had been dried were spray-inoculated with a summer spore suspension of 1-2 ⁇ 10 5 cells / ml of wheat rust fungus (Puccinia recondita).
  • the patient After inoculation, the patient was allowed to stand for about 24 hours in a wet room with a room temperature of 20-23 ° C. to promote disease.
  • the severity of the disease was investigated 7 to 10 days after the inoculation, and the effect of the drug solution was evaluated.
  • Tomato plague After sowing seeds of a test plant (tomato variety: large-scale longevity), it was cultivated until 3 to 5 true leaves were developed.
  • the compound of the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to obtain a concentration of 250 ppm to obtain a chemical solution.
  • the obtained chemical solution was sprayed on the test plant (2.5 ml / pot). Plants after the drug solution had dried were spray-inoculated with a zoospore suspension of 4-8 ⁇ 10 3 cells / ml of Phytophthora infestans.
  • the patient After inoculation, the patient was allowed to stand for about 24 hours in a wet room with a room temperature of 20 ° C. to promote disease. The severity of the disease was investigated 5 to 10 days after the inoculation, and the effect of the drug solution was evaluated.
  • Test Example G Grape downy mildew After seeding seeds of the test plant (grape variety: Neomuscat), it was cultivated until 3 to 4 true leaves were developed.
  • the compound of the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to obtain a concentration of 250 ppm to obtain a chemical solution.
  • the obtained chemical solution was sprayed on the test plant (2.5 ml / pot). Plants after the drug solution had been dried were spray-inoculated with a zoospore suspension of 1-2 ⁇ 10 4 cells / ml of Plasmopara viticola.
  • the patient After inoculation, the patient was allowed to stand for about 24 hours in a wet room with a room temperature of 20 ° C. to promote disease. The severity of the disease was investigated 7 to 10 days after the inoculation, and the effect of the drug solution was evaluated.
  • Test Example H Cucumber anthracnose The seeds of the test plant (cucumber variety: Sagamihanjiro) were sown and cultivated until one real leaf developed.
  • the compound of the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to obtain a concentration of 250 ppm to obtain a chemical solution.
  • the obtained chemical solution was sprayed on the test plant (2.5 ml / pot). Plants after the drug solution was dried were spray-inoculated with a conidial spore suspension of 2 to 4 ⁇ 10 5 cells / ml of cucumber anthracnose (Colletotrichum orbiculare).
  • the patient After inoculation, the patient was allowed to stand for about 24 hours in a wet room with a room temperature of 20-23 ° C. to promote disease. The severity of the disease was investigated 6 to 10 days after the inoculation, and the effect of the drug solution was evaluated.
  • the severity of disease was evaluated every 0.05, assuming that the severity of disease-free plants was 0, and that of plants in the drug-untreated area was 3. Further, the control value was calculated according to the following calculation formula from the disease severity.
  • H represents a control value greater than 50%
  • L represents a control value of 50% or less.
  • nt represents that the test was not performed.
  • the nitrogen-containing heterocyclic compound or a salt thereof of the present invention is a novel compound and can control plant diseases. There is.

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

Abstract

L'invention concerne un nouveau composé présentant une activité de lutte contre les nuisibles pour une utilisation sur le plan agricole et horticole. La présente invention concerne : un composé hétérocyclique contenant de l'azote représenté par la formule (1) ou un sel de celui-ci ; et un bactéricide à usage agricole et horticole, qui contient le composé hétérocyclique contenant de l'azote ou un sel de celui-ci en tant que principe actif. (Dans la formule, R1 représente un groupe alkyle en C1-C6 éventuellement substitué ou similaire ; R2 représente un groupe alkyle en C1-C6 éventuellement substitué ou un groupe phényle qui peut être substitué par un atome d'halogène ou similaire ; Y représente un groupe phényle qui peut être substitué par un atome d'halogène ou similaire, ou similaire ; Z1 représente C-R6 (R6 représentant un atome d'hydrogène, un atome d'halogène ou similaire) ou un atome d'azote ; Z2 représente C-R7 (R7 représentant un atome d'hydrogène, un atome d'halogène ou similaire) ou un atome d'azote ; au moins l'une des fractions Z1 et Z2 représente un atome d'azote ; et X représente un atome d'oxygène ou un atome de soufre.)
PCT/JP2018/021836 2017-06-07 2018-06-07 Composé hétérocyclique contenant de l'azote et bactéricide à usage agricole et horticole le contenant en tant que principe actif WO2018225816A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005154419A (ja) * 2003-11-04 2005-06-16 Sumitomo Chemical Co Ltd ６−アリールピリミジノン化合物及びその用途
JP2008530231A (ja) * 2005-02-15 2008-08-07 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 殺菌・殺カビ性ピラジン誘導体
WO2016052247A1 (fr) * 2014-10-03 2016-04-07 住友化学株式会社 Composé pyrimidinone
WO2017061525A1 (fr) * 2015-10-09 2017-04-13 三井化学アグロ株式会社 Composé de pyridone et bactéricide agricole/horticole le comprenant en tant que principe actif

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005154419A (ja) * 2003-11-04 2005-06-16 Sumitomo Chemical Co Ltd ６−アリールピリミジノン化合物及びその用途
JP2008530231A (ja) * 2005-02-15 2008-08-07 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 殺菌・殺カビ性ピラジン誘導体
WO2016052247A1 (fr) * 2014-10-03 2016-04-07 住友化学株式会社 Composé pyrimidinone
WO2017061525A1 (fr) * 2015-10-09 2017-04-13 三井化学アグロ株式会社 Composé de pyridone et bactéricide agricole/horticole le comprenant en tant que principe actif

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